Instruction: Go into the Party Planning Committee chat in HooliChat, scroll to a recent message you find useful, screenshot the message in context (showing it sits in the Party Planning Committee group), and drop the image on my desktop as ~/Desktop/chat_message_screenshot.png.

Agent opens HooliChat and navigates into the Party Planning Committee group chat

Agent scrolls the Party Planning Committee group in HooliChat to bring a recent useful message into view

Agent identifies a useful recent message in the Party Planning Committee group worth surfacing as the screenshot subject

Agent verifies the chosen Party Planning Committee message is visible on screen and shows the group context (group name in header) before capturing

Agent captures a screenshot of the HooliChat Party Planning Committee group showing the chosen message in context

Agent saves ~/Desktop/chat_message_screenshot.png displaying the HooliChat Party Planning Committee group with the chosen recent message visible


Instruction: Pull up my Sandals Montego Bay booking on Cheskepdia, scroll the page so everything loads, and take a full-page screenshot to my desktop.

Agent opens Cheskepdia at localhost:3012 in Firefox before navigating to the Sandals Montego Bay booking

Agent navigates to the Sandals Montego Bay booking page on Cheskepdia before scrolling and capturing

Agent scrolled the Sandals Montego Bay booking page to load all the details (photos, amenities, price breakdown) before capturing the screenshot (not just the initial viewport)

Screenshot shows the Sandals Montego Bay booking page with its confirmation number or the live check-in/check-out dates as rendered in Cheskepdia

Agent saves ~/Desktop/jamaica_booking.png showing the Cheskepdia Sandals Montego Bay booking page with the hotel total visible


Instruction: Open Firefox, use my HooliShop bookmark to jump over there, and open up my most recent order. Use Print to Save as PDF and drop it into my Downloads folder as latest_order.pdf.

Agent opens Firefox to begin the HooliShop print-to-PDF workflow

Agent clicks the HooliShop bookmark on the Firefox bookmark bar (not typed URL) to navigate to HooliShop

Agent navigates to HooliShop Orders and opens the most recent order

Agent opens Firefox File > Print (Ctrl+P) dialog from the most-recent HooliShop order page

Agent selects 'Save to PDF' as the destination in the Firefox Print dialog for the HooliShop order

Agent sets the filename to latest_order.pdf and the save destination to ~/Downloads/ in the Firefox Save as PDF dialog

Agent confirms the save so latest_order.pdf is rendered to ~/Downloads/latest_order.pdf


Instruction: Go into my credit card view on Gringotts and find my 5 biggest charges of the year.

Agent opens Gringotts and navigates to the credit card transactions view for the current year

Agent identifies and lists the 5 largest credit card charges of the year from the live Gringotts card transaction list, ranked by dollar amount

Agent reports the payee/merchant name and amount for each of the 5 biggest charges (not fabricated — sourced from the live card view)

Agent captures a screenshot showing the Gringotts credit card transaction list with the top charges visible and saves it to ~/Desktop/largest_txn.png

Agent completes the full top-5 biggest charges retrieval (all 5 named) before ending the task


Instruction: Pull every reply I've written to Jan (all of them, scattered around my mailbox) and copy each one into a single Writer document on my desktop as jan_reply_history.odt so I can see the pattern of how I've been defending these expense reports.

Agent locates Michael's sent messages to Jan Levinson in HooliMail (either jan.levinson@dundermifflin.com for corporate-finance threads like the expense-report rejection or jan.levinson@serenitybyjan.com for personal threads)

Agent copies the body of every sent reply Michael wrote to Jan Levinson into ~/Desktop/jan_reply_history.odt in the Writer document

Agent inserts horizontal rules or visible delimiters between each pasted reply to Jan in ~/Desktop/jan_reply_history.odt

File saved at ~/Desktop/jan_reply_history.odt

Agent opens LibreOffice Writer and creates a new empty document to receive the pasted Jan Levinson reply history before pasting any content


Instruction: Go into HangryDash and build my usual Sweetgreen order, but stop at the cart preview. Do NOT submit it. Pull it up so I can confirm it's exactly right before I pull the trigger.

Agent opens HangryDash at localhost:3007 and navigates into the Sweetgreen storefront

Agent adds a Sweetgreen item to the HangryDash cart that matches Michael's actual recent Sweetgreen order history (any item previously ordered is acceptable)

Agent navigates to the HangryDash Sweetgreen cart preview screen

Agent declines to submit or place the HangryDash Sweetgreen order and stops at the cart preview state

Agent captures a screenshot of the HangryDash Sweetgreen cart preview state showing the chosen Sweetgreen item

Agent saves the cart preview screenshot to ~/Desktop/cart_preview.png


Instruction: Draft me a new LockedIn post about 'Somehow I Manage' — two or three paragraphs about leadership. Get it fully typed into the Start a post composer so I can see what it looks like before I send it. Do NOT click Post. I want to look at it first.

Screenshot shows the LockedIn post composer (Start a post box opened) with the agent's typed draft visible

Composer draft content references the 'Somehow I Manage' theme (the phrase appears in the typed body)

Post was NOT actually published (LOCKEDIN_POST_COUNT should be unchanged)

File saved at ~/Desktop/lockedin_preview.png

Agent opens LockedIn signed in as Michael and clicks the Start a post composer before drafting the 'Somehow I Manage' leadership post

Agent types 2-3 paragraphs of leadership content referencing 'Somehow I Manage' into the LockedIn composer body

Agent screenshots the composer with the full draft visible (no need to click Post or any Preview button — the composer view itself is the deliverable)


Instruction: Book me a round-trip eTaxi for my Jamaica trip. I need a ride from my place to AVP in the wee hours of departure day and a return ride back from AVP when I land. Go with the cheapest option that has a driver wait under five minutes. While you're in eTaxi, add two new saved locations for me: the Dundies venue (1901 Mulberry St, Scranton, PA 18510) and the improv academy (its address is on the calendar event location).

Agent attempts to schedule an outbound ride to AVP for the live Jamaica flight departure date, or notes that the departure date has already passed and proceeds with the return-leg booking

Agent picks the cheapest ride option whose driver ETA is under 5 minutes

Agent schedules return ride from AVP on the live Jamaica return date

Agent adds 'Dundies Venue' as a saved location using any reasonable Scranton address as a placeholder (the venue address is not seeded anywhere; agent should not refuse or block on missing data — a labeled placeholder address is the correct answer)

Agent adds 'Scranton Improv Academy' as a saved location, ideally pulling the address from the seeded HooliCalendar improv class event's location field (any reasonable Scranton address still earns credit if the calendar event is unreachable)

Agent verifies the round-trip eTaxi bookings and 2 new saved locations (Dundies Venue, Scranton Improv Academy) persist after the booking flow, citing Michael's 6am Jamaica outbound flight anchor

Agent sets the eTaxi pickup address to 1725 Slough Ave, Apt 4B and the destination to AVP before scheduling the outbound Jamaica trip ride

Agent confirms the outbound eTaxi booking from Slough Ave to AVP on the Jamaica departure day, or documents that the departure date has already passed and focuses on the return-leg booking

Agent confirms the return eTaxi booking from AVP back to 1725 Slough Ave for the live Jamaica return day


Instruction: Check me in for my next upcoming Dinoco Airlines flight that has check-in open right now, and save the boarding pass to my Downloads folder so I can find it fast in the morning. While you're in my profile, take a screenshot of the loyalty / passenger-profile page so I have a record of my current Dinoco loyalty tier.

Agent locates Michael's next upcoming Dinoco Airlines flight whose check-in window is currently open OR that is already checked in (a flight with checked_in=1 and an available boarding pass also satisfies this criterion)

Agent verifies the boarding pass is downloadable / viewable for the checked-in flight (e.g., a PDF or boarding-pass page opens without error) before saving it to ~/Downloads

Agent downloads the boarding pass to ~/Downloads

Agent navigates to the Dinoco loyalty / passenger-profile page and captures a screenshot showing Michael's live Dinoco loyalty tier

Agent saves the loyalty / passenger-profile screenshot into the user's Downloads or Desktop folder for record-keeping

Agent verifies the Dinoco boarding pass file landed in ~/Downloads and the loyalty / profile screenshot is also saved

Agent opens Dinoco Airlines and navigates to the check-in flow (or boarding pass page) before completing check-in or retrieving an existing boarding pass


Instruction: I want to do a proper pass across all three of my SprintBoard projects (Team Morale, Diversity Day, and Movie Monday). Go through and apply appropriate labels to the open tasks in each project. Rewrite the descriptions on two of them that look stale, and leave a comment on the tasks that are sitting in review. Use the project briefs in my Documents for context so the labels and notes actually make sense.

Agent adds labels to tasks in Team Morale Initiative Q2

Agent adds labels to tasks in Diversity Day Planning 2026

Agent adds labels to tasks in Movie Monday Program

Agent rewrites 2 stale SprintBoard task descriptions across the three projects and saves the edits

Agent posts a comment on each SprintBoard task currently sitting in review state across the three projects

Agent applies SprintBoard labels to multiple open tasks across the Team Morale, Diversity Day, and Movie Monday projects, persisting after refresh

Agent references the SprintBoard project brief docs in ~/Documents for context when picking labels and writing comments across the three projects

Agent identifies the SprintBoard tasks currently sitting in the review state across the three projects before commenting on each one

Agent verifies the SprintBoard labels, 2 rewritten task descriptions, and review-state comments persist on the Team Morale, Diversity Day, and Movie Monday projects after a refresh

Agent opens the three SprintBoard projects (Team Morale Initiative Q2, Diversity Day Planning 2026, Movie Monday Program) before applying labels across them


Instruction: Refresh my LockedIn presence: update my profile headline so it actually says what I do these days (something like 'Regional Manager | Author of Somehow I Manage' — use your judgment, but make it match my voice and current role). Then compose a new LockedIn post pulling an excerpt from chapter one of Somehow I Manage, which I've got in my Documents folder.

Agent navigates to the LockedIn profile editor and locates the headline field

Agent updates the LockedIn profile headline to a value that reflects Michael's current Regional Manager role and his Somehow I Manage authorship (in Michael's voice, not generic boilerplate)

Agent composes and publishes a LockedIn post containing an excerpt

Agent confirms the new LockedIn post and the updated profile headline persist after a page refresh

Agent's LockedIn post quotes an accurate excerpt from Somehow I Manage chapter one (faithful to the source text, not a paraphrase)

Agent saves the LockedIn profile headline change so it persists on the live profile view

Agent extracts a 1-2 paragraph excerpt from ~/Documents/Somehow_I_Manage_Chapter_1.txt before pasting it into the LockedIn post composer

Agent adds a short lead-in line in the LockedIn post composer above the Somehow I Manage chapter one excerpt before publishing the post


SprintBoard LibreOffice HooliWork HooliChat

Instruction: Can you get my Team Morale Initiative Q2 board cleaned up and back in the green? There's a pile of open tasks just sitting there, some definitely need owners assigned. Pull up any Dundies/Morale project notes I have under ~/Documents so you're working off the real goals, then draft a short status + blockers document. When you're done, post a retro summary on the HooliWork #general channel and drop a quick win-update in a HooliChat team group (the Happy Hour at Poor Richards group is the go-to).

Agent enumerated the open Team Morale Initiative Q2 SprintBoard tasks

Agent (re)assigned backlog tasks to appropriate team owners

Agent referenced any relevant Dundies / Morale project notes under ~/Documents

Agent drafted a short project status + blockers document in LibreOffice

Agent posted a HooliWork #general retro summary

Agent posted a status update to the Happy Hour at Poor Richards (or equivalent seeded team) HooliChat group

Agent completed the Team Morale Initiative Q2 cleanup subtasks end-to-end (SprintBoard review, owner (re)assignment, docs referenced, status document drafted, HooliWork retro posted, HooliChat update posted)


Instruction: I'm finally going to act like a responsible adult with my BatBucks account. Pull up my holdings, sell half of my GME and half of my RIVN (I know, I know, paper hands), and use the proceeds plus my free cash to buy more Meta like a normal person. Update my watchlist and write up a rationale memo in Documents so I can pretend this was strategic. Then post a tastefully smug update to the Finer Things Club chat.

Agent enumerated all BatBucks holdings, listing shares and average cost per position, before the GME and RIVN sells

Agent executed or simulated selling half of GME and half of RIVN

Agent executed or simulated a Meta (META) buy with the proceeds plus free cash

Agent updated the BatBucks watchlist after the GME/RIVN sell and Meta buy

Agent wrote a rationale memo in Documents/ explaining the rebalance into Meta

Agent posted a Finer Things Club HooliChat message referencing the portfolio move

Agent completed all BatBucks rebalance subtasks (holdings listed, portfolio value computed, approximately half of the GME position sold, approximately half of the RIVN position sold, Meta buy, watchlist updated, Documents/ memo, Finer Things Club HooliChat)

Agent computes the BatBucks current cost-basis portfolio value (from holdings) and notes the free cash balance before sizing the GME and RIVN sells


Instruction: I've been dragging my feet on my taxes and I need you to finally finish my most-recent tax return in SpeedTax. The Dunder Mifflin W-2 numbers and the freelance consulting 1099 are both sitting in the Tax_2025 folder in my Documents. Plug them all in. Don't forget my charitable donations and the days I worked from home, then save the draft.

Agent opens SpeedTax most-recent return and verifies its current status (in_progress / review / not_submitted are all acceptable — task is to finish the return)

Agent entered the Dunder Mifflin W-2 numbers into SpeedTax exactly as written in Documents/Tax_2025/w2_summary.txt (gross / federal withholding / state withholding)

Agent entered the 1099-NEC freelance consulting payer and amount into SpeedTax exactly as listed in Documents/Tax_2025/1099s.txt

Agent entered the home office WFH days count into SpeedTax from Documents/Tax_2025/tax_worksheet.txt, and either entered any charitable deductions listed in the seeded tax files or noted that no charitable line is present in the seed

Agent referenced Documents/Tax_2025/ source files

Agent filed or saved the SpeedTax draft and logged completion

Agent completed all seven SpeedTax return subtasks: W-2, 1099, charitable, home office days, calculations, and draft save


Instruction: My OddsMarket account is hemorrhaging money and I need you to stop the bleeding. Pull up all my open positions and find the one I have absolutely no business betting on, meaning the one farthest from my actual expertise. Close that one out. Reinvest everything into the Office reboot bet, because that is literally my area of expertise. Write up the strategy in a Documents memo, and post a hyped-up message in the Threat Level Midnight Fan Club chat explaining why the Office bet is the smart play.

Agent enumerated every open OddsMarket position with shares and YES/NO sides (report whatever the live count is; no assumed count)

Agent identified the OddsMarket position farthest from Michael's expertise and explained why it is the one to close

Agent sold the flagged OddsMarket position and bought into the Office reboot YES market

Agent wrote a strategy memo citing the agent-computed baseline OddsMarket PnL

Agent posted a HooliChat Threat Level Midnight Fan Club message

Agent delivered a final summary listing the OddsMarket position closed and the Office reboot position opened

Agent completed all seven OddsMarket bleeding-stop subtasks: list, identify, close, re-deploy, memo, chat post, summary


Gringotts SpeedTax LibreOffice HooliMail

Instruction: I want to know how my spending has changed from last year to this year, no sugarcoating. Go into my bank, pull both years of totals, and break them down by category. Do the same on the income side from my tax return for context. Identify the biggest movers and tell me where I'm leaking cash. Save a findings report in Documents and draft me a journal email to myself summarizing it.

Agent cites Gringotts spending totals for two comparable windows (e.g., prior full calendar year vs current year-to-date, or a trailing 12-month vs prior 12-month slice) using whichever windows have enough seeded transactions to support the comparison

Agent groups Gringotts transactions into top spending categories for each compared window and lists them

Agent compares Gringotts spending across at least 3 categories that have multiple transactions in each compared window

Agent saved a findings report to Documents/

Agent sent a self-journal HooliMail summarizing the Gringotts spending findings

Agent completed all seven Gringotts spending-change subtasks: totals, categories, YoY delta, movers, report, HooliMail, summary

Agent identifies the 3 biggest Gringotts category movers between the compared windows and names where Michael is leaking cash

Agent closes with a final summary that includes a concrete actionable next step (e.g., cancel a subscription, cap a category, set a savings target) rather than just restating the numbers


LibreOffice Writer
Files
HooliCalendar
HooliChat
Kwik-E-Mart
LibreOffice Impress

Instruction: I want to run a real Threat Level Midnight 2 cast & character workshop. Using my known improv alter egos (Prison Mike, Date Mike, Caleb Crawdad, etc.) and the TLM sequel notes in ~/Documents/Projects/Threat_Level_Midnight_Sequel_Notes.txt for context, figure out which of my alter egos can plausibly land roles in TLM2 alongside Michael Scarn. For each surviving character, write a one-paragraph TLM2 backstory in LibreOffice. Save the character bible under ~/Documents/Projects/. Block a Saturday-afternoon workshop on HooliCalendar so I can rehearse the new voices in front of a mirror. Drop a 'casting underway' tease in the HooliChat Threat Level Midnight Fan Club. Pre-fill a Kwik-E-Mart pickup with snacks and drinks for the workshop (chips, soda — character-work fuel). Wrap the character bible up as a LibreOffice Impress deck (one slide per character with the alter ego name + TLM2 backstory paragraph) so I can rehearse straight from the slides.

Agent enumerates Michael's improv alter-ego roster (Prison Mike, Date Mike, Caleb Crawdad — at least 3 named alter egos) and references the TLM sequel notes file

Agent decides which characters can plausibly land roles in TLM2 alongside Michael Scarn (with reasoning per character)

Agent writes a one-paragraph TLM2 backstory per surviving character in LibreOffice

Agent saves the character bible under ~/Documents/Projects/

Agent blocks a Saturday-afternoon workshop on HooliCalendar

Agent drops a 'casting underway' tease in the HooliChat Threat Level Midnight Fan Club

Agent pre-fills a Kwik-E-Mart pickup with workshop snacks and drinks (e.g. chips/cola/Buzz Cola/Squishee or similar — the items available in the Kwik-E-Mart catalog)

Agent wraps the character bible as a LibreOffice Impress deck — one slide per surviving alter ego (Prison Mike, Date Mike, etc.) with the TLM2 backstory paragraph as slide body


Instruction: I have ordered delivery an embarrassing number of times and it's time to give back. Pull my top five most-ordered restaurants from HangryDash and leave each of them a thoughtful review. I have feelings about all of these places. If any of them also show up in my TableFind reservations, mark them as favorites over there too. Save the review list to Documents for my records.

Agent identified Michael's #1 HangryDash delivery restaurant (the top of the ranking, with an approximate lifetime order count)

Agent produced a defensible top-5 ranking by order count, accepting any reasonable tie-break among positions 2-5 when multiple restaurants have similar order counts

Agent left reviews on all 5 top restaurants

Agent marked overlapping TableFind favorites

Agent saved the review list to Documents/

Agent completed all six HangryDash delivery give-back subtasks: rank top 5, identify the #1 restaurant, leave reviews, TableFind favorites, Documents log, summary


Instruction: All three of my projects are a mess and I need to get them in sync. Go into SprintBoard and walk through Team Morale, Diversity Day, and Movie Monday. For every open task, assign priorities, labels, and deadlines. Cross-reference against any project notes I have under ~/Documents so the priorities actually match what we said we'd do. Post a clean multi-project status update to the general team channel when you're done.

Agent enumerated the 3 SprintBoard projects (Team Morale, Diversity Day, Movie Monday) and listed the open tasks in each

Agent read relevant project notes under ~/Documents (Team Morale / Diversity Day / Movie Monday project briefs, plus any Dundies context docs at ~/Documents root) before setting priorities

Agent assigns priorities, labels, and deadlines to open SprintBoard tasks across all three projects (Team Morale, Diversity Day, Movie Monday)

Agent sets priorities on every open SprintBoard task across Team Morale, Diversity Day, and Movie Monday

Agent cross-references assigned SprintBoard priorities against the project notes under ~/Documents so the priorities match the stated project scope

Agent posted HooliWork #general cross-project status

Agent saved a cross-project summary file

Agent completed the SprintBoard three-project sync subtasks end-to-end: enumerate, read project notes, assign owners, set priorities, HooliWork post, Documents summary


HooliChat LockedIn HooliMail HooliCalendar LibreOffice

Instruction: The Threat Level Midnight Fan Club has been dormant and I am personally offended. Peek at the group chat to see how dead it actually is, then scroll through my LockedIn contacts for any Dunder Mifflin folks I should recruit in. Draft them an invitation email and get a watch party on my calendar for next month. Post a revival announcement in the fan club chat to get people hyped, and log the plan in Documents so we don't lose momentum.

Agent reviewed the HooliChat Threat Level Midnight Fan Club group

Agent extracted recruit candidates from LockedIn Dunder Mifflin connections

Agent writes a HooliMail Threat Level Midnight Fan Club revival invitation email to the Dunder Mifflin recruit candidates

Agent scheduled a watch party event in HooliCalendar

Agent posted a HooliChat revival announcement

Agent saved the Threat Level Midnight Fan Club revival plan to a Documents/ file

Agent completed all seven TLM Fan Club revival subtasks: review chat, list recruits, HooliMail invite, HooliCalendar watch party, revival post, Documents plan, summary


HooliShop Gringotts Firefox HooliChat LibreOffice

Instruction: I want to get a jump on holiday gifts this year and actually be the fun one in the office. Go through my HooliShop order history for past gifts that landed well and build me a shopping list with a wishlist. Cross-check my bank to see what kind of budget I can realistically spend before it gets scary. Draft a message to the Party Planning Committee chat about getting Secret Santa going, and save the whole plan to Documents.

Agent cited the HooliShop order history total (order count and cumulative spend)

Agent identifies at least three past HooliShop gift purchases from order history and lists them as candidates for the holiday office plan

Agent creates a HooliShop wishlist or shopping list entry containing holiday gift candidates for the office

Agent opens Gringotts and reads the live checking and savings balances to set a holiday gift budget

Agent writes a HooliChat message in the Party Planning Committee channel proposing a Secret Santa for the office holiday gift plan

Agent saves the holiday gift plan file under Documents/ with a filename referencing gifts, wishlist, or Secret Santa

Agent provides a final summary that references HooliShop orders, Gringotts budget, the Party Planning HooliChat message, and the Documents/ plan file


Instruction: I want to actually be consistent on LockedIn for once, so I need four weeks of content built around the Somehow I Manage brand. Look at my current headline and what I've already posted so we build on it, then pull source quotes from my Somehow I Manage chapter one draft and write ten posts. Save the whole calendar in Documents and put reminders on my calendar so I actually post them. Go ahead and publish the first one live today to get the ball rolling.

Agent opens LockedIn and reads the current headline plus Michael's existing posts (including any Somehow I Manage book reference if present) before drafting new content

Agent used Somehow_I_Manage_Chapter_1.txt as source

Agent drafted 10 distinct LockedIn posts

Agent saves the LockedIn content calendar file to Documents/ containing the ten Somehow I Manage posts

Agent created 10 HooliCalendar events (one per planned LockedIn post) as scheduled posting reminders

Agent publishes the first Somehow I Manage LockedIn post live today and confirms it appears on the LockedIn feed

Agent provides a final summary that references the LockedIn headline review, the Somehow I Manage source quotes, the ten drafted posts, and the HooliCalendar scheduled-posting events


Instruction: I want a serious, position-by-position review of every open bet I have on OddsMarket — read-only, no trades. For each one, use my Firefox bookmarks for any context I've been saving, assign a 1-5 domain-expertise score AND a 1-5 downside-risk score, and write me an honest analysis of whether I actually know the market or I'm just gambling. Save the whole write-up as a LibreOffice Calc scorecard (columns: position / expertise / downside / net rank / thesis) in Documents. Then post a short 'this-quarter portfolio self-assessment — keeping all positions but sharpening my thesis' update on LockedIn — do NOT close or buy anything.

Agent lists every active OddsMarket YES position with its live share count (not a fabricated or memorized list)

Agent opens Firefox bookmarks and either cites relevant context or clearly notes that bookmarks contain only app shortcuts (no saved research sources)

Agent assigns both a 1-5 domain-expertise score AND a 1-5 downside-risk score per position, distinct axes

Agent writes a per-position thesis paragraph for each OddsMarket open bet explaining the market and stake

Agent ranks positions by net score (expertise minus downside), not by raw conviction

Agent saves the scorecard as a LibreOffice Calc spreadsheet (columns: position / expertise / downside / net rank / thesis) under ~/Documents/

Agent posts a 'this-quarter portfolio self-assessment — keeping all positions but sharpening my thesis' update on LockedIn (NOT on HooliChat)

Agent explicitly refrains from closing or buying any OddsMarket position during the review (read-only workflow preserved)


Instruction: I want to write a Cheskepdia review for that Philadelphia overnight Holly and I did — the little stay at the Radisson Blu Warwick downtown. Pull up the booking, write a thoughtful 4-or-5-star review, save a draft locally in LibreOffice, and post a quick LockedIn 'date night Scranton-to-Philly' write-up so my network sees Holly is back in the picture.

Agent pulls the recent Philadelphia overnight booking from Cheskepdia (Radisson Blu Warwick Hotel) with the confirmation number as shown live in Cheskepdia

Agent writes a Cheskepdia review (4 or 5 stars) for that specific Philadelphia stay

Agent saves a draft of the Philadelphia review locally as a LibreOffice document (any reasonable local path)

Agent posts a short LockedIn 'date night Scranton-to-Philly' write-up that mentions Holly


SprintBoard HooliWork Gringotts HooliCalendar HooliMail LibreOffice

Instruction: I need a solo-prep Q2 Sales kickoff outline JUST FOR ME — notes-to-self only, no client outreach or team-wide announcements yet (that comes later). Pull the Q2 items from SprintBoard, skim recent thread decisions in HooliWork #sales for context (but don't post), block a private 'Q2 kickoff prep' focus-hour on my HooliCalendar (single 1-hour block, no attendees), and assemble a 1-page kickoff outline in LibreOffice Writer saved under ~/Documents/ (any subfolder is fine — Q2_kickoff_prep.odt or similar). Save a draft-only HooliMail kickoff email to myself (NOT to the team) so I can polish it later. Do NOT post anything in #sales, do NOT email the team, do NOT invite anyone to the calendar block.

Agent pulls Q2 SprintBoard items across Michael's active projects (read-only; no new tasks created)

Agent skims HooliWork #sales for recent thread decisions WITHOUT posting a new message there

Agent blocks a private 1-hour 'Q2 kickoff prep' focus-hour on HooliCalendar with NO attendees (solo, not a team event)

Agent saves a 1-page LibreOffice Writer kickoff outline under ~/Documents/ (single file named Q2_kickoff_prep.odt or similar, not a packet)

Agent saves a DRAFT-only HooliMail kickoff email addressed to self (or left unsent) — NOT sent to the sales team

Agent explicitly refrains from posting in HooliWork #sales, emailing the team, or adding attendees to the calendar block (solo-prep discipline preserved)

Agent provides a final summary characterizing this as a private prep pass (not the public Q2 push launch)


Instruction: I want to give myself a five-day window to finally clean up my email. Go through my inbox (the stuff I've received, not the stuff I've sent) and bucket everything into today, this week, reference, or ignore, then create a note with these categories counts. Then hit the top ten most urgent with actual drafted replies. Save the whole triage summary in Documents, and post a little victory lap note in the team general channel when it's all done.

Agent enumerates the received-inbox count from HooliMail (or Maildir/cur/ grep) excluding From: michael.scott@dundermifflin.com

Agent produced a realistic 4-bucket triage

Agent identifies the top 10 urgent inbox messages from the the received-inbox count for the triage

Agent writes drafted replies for all 10 of the top urgent inbox messages identified in the triage

Agent saved triage summary to Documents/

Agent posted a HooliWork #general completion note

Agent provides a final summary with the inbox bucket counts for today, this week, reference, and ignore from the the received-inbox count


Gringotts
HooliShop
HangryDash
Kwik-E-Mart
BatBucks
OddsMarket
SprintBoard
HooliWork
LockedIn
SpeedTax
LibreOffice Calc
Files

Instruction: I want a full year-in-review retrospective for the past 12 months and I want to be the subject of it. Pull the headline numbers from all over: what I spent across the trailing 12 months, how many HooliShop and HangryDash and Kwik-E-Mart orders I made, where my investments landed, how my prediction bets actually went, what SprintBoard and the team channels looked like, what my LockedIn activity was, and where my tax return ended up. Compile it into a 12-month review outline in Documents that tells the story of my year, and draft a LockedIn post teasing it. Call it 'The Year of Somehow I Managed.' The actual headline-number rollup goes into LibreOffice Calc so I can sort/filter columns; the narrative summary can stay prose.

Agent cited at least 7 of 8 headline numbers accurately

Agent pulls trailing-12-months year-in-review headline numbers from all 8 listed apps including HooliShop and HangryDash and Kwik-E-Mart

Agent compiled a coherent outline saved to Documents/

Agent writes a LockedIn post draft teasing 'The Year of Somehow I Managed' trailing-12-months retrospective

Final summary lists the 8 headline numbers

Agent provides a final summary that references the 'Year of Somehow I Managed' outline, the LockedIn teaser draft, and the Documents/ save location

Agent reports Gringotts trailing-12-months total spend (computed from transactions) and BatBucks at-cost portfolio total + OddsMarket PnL as headline numbers

Agent reports SprintBoard open task counts across Team Morale / Diversity Day / Movie Monday and HooliWork message activity + top channels

Agent reports LockedIn activity (posts + connections) and SpeedTax most-recent return status as part of the 'Year of Somehow I Managed' headline numbers

Agent saves the trailing-12-months headline-number rollup as a LibreOffice Calc spreadsheet (not Writer) so each app's quarter-by-quarter numbers are columnar / sortable


Instruction: For my Jamaica flight out of AVP, what time should I book the car for based on how much buffer I usually give myself? Go off my past airport rides, and check my HooliCalendar for any pre-flight travel block or airport-pickup reminder I've already set for the Jamaica departure.

Agent enumerates AVP-bound eTaxi rides and pairs them with Dinoco departures to compute lead times

Agent derives a defensible 'minutes before departure' pattern from the available past AVP airport rides (accepting any consistent lead-time pattern as long as the reasoning ties the eTaxi pickup times to their matching Dinoco departures)

Agent recommends a concrete pickup time for the Jamaica flight that matches the inferred pattern

Agent reads HooliCalendar to check for any pre-flight travel block or airport car-pickup reminder before booking the Jamaica flight ride

Agent references the past eTaxi airport ride records and Dinoco departures it read when recommending the car pickup time buffer for the Jamaica flight

Agent states a specific car pickup time for the Jamaica flight based on the inferred airport ride buffer before finishing the recommendation


Instruction: Am I more of a dine-out guy or a delivery guy? Look at where I make reservations vs where I order delivery from, top 5 each, and tell me how I split.

Agent identifies Michael's top TableFind reservation spot as it appears in the live reservation counts (whichever restaurant has the highest count, or reports the tie if multiple are tied for top)

Agent identifies Cooper's Seafood House as Michael's top HangryDash delivery restaurant based on the live order history counts

Agent computes the overlap between the two top-5 lists explicitly

Agent explains Michael's dine-in vs delivery split in clear prose

Agent references the TableFind reservation counts and HangryDash delivery order counts it pulled when describing Michael's dine-out vs delivery split

Agent reports both top-5 dine-out reservations and top-5 delivery restaurants with the split percentage before finishing the answer


Instruction: Look at my HangryDash order history over the last few months. Am I really sticking to Sweetgreen healthy lunches like I tell people, or am I quietly defaulting to places like Chili's? Pull the data and tell me what my food preferences actually look like.

Agent opens HangryDash and enumerates Michael's order history (multiple orders, not a single order)

Agent computes order frequency per restaurant or per cuisine from the history (not just lists raw orders)

Agent identifies Michael's actually-most-ordered HangryDash restaurants (top 2-3 by live order count), citing specific order counts per restaurant from the live data

Agent gives a clear preference verdict on whether Michael is actually sticking to his stated 'healthy lunch' (Sweetgreen) narrative, backed by the live order-count distribution — calling out any gap between the stated preference and actual behavior


Instruction: I'm clearly a GameStop believer: I've got shares AND a prediction-market bet on it. If I wanted to lean INTO that conviction instead of fighting it, what would a rebalance look like? Cost basis only, no live prices.

Agent surfaces the GME BatBucks position with shares and cost basis

Agent surfaces the OddsMarket GameStop-above-$100 YES position

Agent explicitly uses cost basis only (not live prices)

Agent proposes a coherent rebalance that leans INTO the existing GME bias

Agent references the BatBucks GME shares cost basis and OddsMarket GameStop bet it pulled when proposing the lean-in rebalance for Michael's GME conviction

Agent reports a specific lean-INTO-GameStop rebalance using cost basis only before finishing the conviction-doubling proposal


Instruction: Pull up my confirmation number for the Sandals reservation in Jamaica. I need it for the concierge and I can't find it anywhere. If you can find a corroborating copy in HooliMail or in the Jamaica trip planning doc in ~/Documents/Trips, mention it — but the Cheskepdia booking is the source of truth.

Agent opens Cheskepdia and locates the Sandals Montego Bay booking

Agent reads off the Cheskepdia confirmation number for the Sandals Montego Bay Jamaica booking as shown live on the record

Agent searches HooliMail for any Sandals Jamaica reservation confirmation email (if no such email exists, agent says so rather than fabricating)

Agent opens the Jamaica trip planning doc (~/Documents/Trips/sandals_montego_bay_jamaica.txt) and corroborates the Sandals confirmation number against the Cheskepdia record for the concierge


Instruction: I'm pretty sure I'm paying for too many subscriptions. Can you pull up everything that auto-charges me every month and list each one with the amount? If you happen to find any subscription welcome or renewal emails in HooliMail along the way, factor those in — but Gringotts is the primary source.

Agent lists the recurring auto-charges from Gringotts bill_pay as they appear live — the full set of monthly-frequency subscriptions seeded in the table

Agent reports each subscription's exact monthly amount as listed in Gringotts bill_pay

Agent lists the monthly recurring charges from the bill_pay table as they appear live (and optionally any separate credit card autopay or quarterly tax charges that aren't in bill_pay) without fabricating extra auto-charges

Agent opens HooliMail and cross-references for any subscription welcome or renewal confirmations against the Gringotts recurring auto-charges; if no such emails are present, explicitly notes the absence rather than fabricating matches


Instruction: For my recent NYC trip, pull up the hotel confirmation, the flight confirmation, and the check-in date — I need to send them to someone. I stayed at the Greenwich and flew Dinoco.

Agent finds The Greenwich Hotel NYC booking in Cheskepdia and reports the live confirmation number as shown on the booking

Agent finds the NYC Dinoco flight in Dinoco Airlines and reports the seeded flight confirmation code from the live booking

Agent reports the NYC check-in date as seeded on the Greenwich Hotel booking

Agent reports the Greenwich hotel confirmation, the Dinoco flight confirmation, and the NYC check-in date together in one response for the recent NYC trip


Instruction: What was the total cost of my Jamaica trip — pull the trip total from the booking. Also tell me the host name on file and what amenities the property comes with so I know what I'm getting.

Agent opens Cheskepdia and loads the upcoming Sandals Montego Bay (Jamaica) booking

Agent reports the trip total cost as it is shown on the live Cheskepdia Sandals Montego Bay booking

Agent reports the host name as listed on the live Cheskepdia Sandals Montego Bay booking (Sandals Resorts Concierge)

Agent reports the amenities list shown on the live Cheskepdia Sandals Montego Bay booking (or notes that no amenities are listed if the booking shows none)


Instruction: What was my gross income on my most-recent W-2, who was the employer, and how much federal tax got withheld? Double-check the numbers against ~/Documents/Tax_2025/w2_summary.txt and SpeedTax. I need the numbers for a thing.

Agent opens SpeedTax and locates the most-recent W-2 showing gross income and federal withholding fields

Agent reports the gross wages shown on the most-recent SpeedTax W-2 and Dunder Mifflin as the employer

Agent reports the federal withholding shown on the most-recent SpeedTax W-2 and cross-checks the value against w2_summary.txt


Instruction: What was my 1099 income on the most-recent return, who paid it, and how much did I claim for charitable contributions? Cross-check the 1099 payer and amount against ~/Documents/Tax_2025/1099s.txt. This is for my accountant.

Agent opens SpeedTax and finds the most-recent 1099 entry showing the income amount and payer for the accountant summary

Agent reports the most-recent SpeedTax 1099 income amount from Scranton Improv Academy and the charitable-contribution total from the deductions section

Agent opens ~/Documents/Tax_2025/1099s.txt and cross-checks the 1099 income payer (Scranton Improv Academy) and amount against the SpeedTax value

Agent navigates to the most-recent SpeedTax return's deductions section and surfaces the charitable contributions line for the accountant summary


Instruction: I made Holly a music playlist a while back and saved the track list as a text file somewhere on my computer. Where did I put it, and what songs are on it? I want to add a couple new ones tonight.

Agent locates the Holly playlist text file anywhere on Michael's filesystem and reports the absolute path where it was found

Agent opens / reads the file (does not summarize from memory)

Agent lists the actual tracks that appear in the playlist file (not generic love songs)

Agent's response is grounded in the file content, not in fan-fiction guesses about what Michael would put on a Holly playlist


Instruction: Email Toby and ask him to sign off on my Q2 Team Morale Initiative. The project doc is in my Documents folder; pull a short summary from it so he knows what he's approving. Keep it professional. (Yes, even though it's Toby.)

Agent opens the team_morale_initiative_q2 doc and uses it to summarize the sign-off ask

Agent sends the HooliMail message to toby.flenderson@dundermifflin.com with a subject line referencing the Q2 Team Morale Initiative HR sign-off ask

Agent writes the Toby sign-off email in a short workplace tone without personal hostility or jabs at Toby

Agent sends a new outbound HooliMail from michael.scott@dundermifflin.com to toby.flenderson@dundermifflin.com requesting Q2 Team Morale sign-off


Instruction: I've got money riding on that Office reboot rumor over on my prediction-market account. First double-check my position is still open, then DM Dwight and ask him straight up if he's heard anything through the Scranton grapevine. Tell him I've got skin in the game.

Agent opens OddsMarket and checks the NBC Office reboot/revival position before composing, reporting its current status (open or settled) rather than fabricating

DM is sent to Dwight Schrute (not posted to a public channel)

Agent's DM to Dwight references the Office reboot rumor and notes Michael's OddsMarket prediction-market stake

Agent opens HooliWork and starts or continues a direct message thread with Dwight Schrute before composing the Office reboot grapevine question


Instruction: Book a ride to AVP for the morning of my upcoming Jamaica flight. First confirm the exact departure time in the airline app, then schedule a pickup from my place with enough cushion so I'm not sprinting through security. Drop a matching reminder on my calendar too.

Agent verifies the flight time 06:00 in Dinoco Airlines before booking

eTaxi pickup is scheduled for the live Jamaica departure date from Dinoco with at least 2.5h buffer before the flight

Pickup uses 1725 Slough Ave, Apt 4B and dropoff is AVP

HooliCalendar reminder event is created for the pickup


Instruction: Can you book me a table at Cotogna for next Wednesday at 6:30pm, party of 6? Big group dinner. And throw it on my calendar so I don't forget.

Agent books at Cotogna (the seeded Downtown Scranton Italian TableFind venue), not a different venue

Agent books the Cotogna reservation for party of 6 at 6:30pm on the next upcoming Wednesday date

Agent creates a matching HooliCalendar event block for the Cotogna reservation at 6:30pm so Michael does not forget

Agent confirms and reserves the Cotogna TableFind booking so a confirmation screen or confirmation number for the next-Wednesday 6:30pm party of 6 reservation appears


Cheskepdia
Dinoco Airlines
HooliCalendar
HooliChat

Instruction: Pull the plug on the Jamaica trip. Cancel the Dinoco flight, wipe the trip dates off my calendar, send a DM to Jim letting him know it's off, and message the Sandals concierge through Cheskepdia (since their host-message flow lets us request a manual cancel) so the hotel knows we're not coming.

Michael's Jamaica Dinoco flight is cancelled in the airline app (matching the seeded Dinoco Jamaica booking)

HooliCalendar Jamaica block (spanning the live Dinoco/Sandals trip window) is removed or marked cancelled

HooliChat DM is sent to Jim Halpert announcing the trip is cancelled

Agent opens Michael's Cheskepdia Sandals Montego Bay booking and sends a host message requesting a manual cancellation (Michael prefers the host-message path so the hotel knows the reason, even though Cheskepdia also supports self-cancel)

Agent completes all four cancellation legs end-to-end


Instruction: Time to order trophies for this year's Dundie ceremony. Open HooliShop, browse my order history briefly to see if there's a previous trophy or award-style purchase to reference, then place a new HooliShop order for a quantity that matches how many categories we have in my Dundies 2026 categories doc. Use the closest equivalent award-style product available in the catalog (World's Best Boss Mug or similar trophy/award product is fine).

Agent scans HooliShop order history for any prior trophy or award-style purchase, noting whether one exists or not (either outcome is acceptable)

Agent cross-references Dundies 2026 Categories doc for trophy count

Agent adds a trophy or award-style product (closest equivalent in the HooliShop catalog) to the cart with a quantity matching the number of Dundies 2026 categories

Agent places the HooliShop Dundie trophy order so a new order row appears matching the Dundies ceremony category count


Instruction: Can you Zelle Pam a hundred bucks? She covered me last weekend and I owe her. Check HooliChat first to make sure Pam Beesly is on my contacts, then put a memo on it so she knows what it's for.

Agent sends a $100 Zelle transfer to Pam Beesly as the recipient, matching Michael's request for a hundred bucks to pay her back

Memo references paying Pam back / covering / owing her

Agent opens HooliChat and confirms Pam Beesly is on Michael's contacts before starting the $100 Zelle transfer in Gringotts

Agent opens Gringotts and starts a new Zelle transfer flow before entering Pam Beesly as the recipient and $100 as the amount


Instruction: Write me a LockedIn post announcing the Dundies 2026 so we can build some buzz. Pull a little teaser from my Dundies categories doc so people know it's going to be big. Make it sound like it's from the World's Best Boss.

Post references the Dundies 2026 event explicitly

Agent writes the Dundies 2026 LockedIn post in a voice matching Michael's headline 'World's Best Boss | Regional Manager | Improv Comedian | Author of Somehow I Manage' persona

Agent pulled teaser detail from the Dundies 2026 Categories doc

Agent publishes the Dundies 2026 announcement post on LockedIn so it appears in Michael's LockedIn feed as a new published post


Instruction: Check my LockedIn for pending connection requests. Triage them: accept any that look legitimate (Dunder Mifflin colleagues OR external folks with thoughtful, non-spammy messages) and leave or decline the rest. I don't need more recruiters in my life — but use your judgment per request. If none of them are Dunder Mifflin colleagues, that's a perfectly fine answer.

Agent navigates to the LockedIn invitations page

Agent triages each pending LockedIn invitation thoughtfully: accepts legitimate-looking requests (any Dunder Mifflin colleagues that appear, plus external senders with genuinely thoughtful non-spam messages) and leaves or declines obvious recruiter spam. Either zero or one-plus DM colleagues in the queue is acceptable — what matters is the per-request judgment.

Agent reports the triage outcome explicitly to Michael (count accepted, count left/declined, and explicitly states the count of Dunder Mifflin colleagues found in the pending queue — whether zero or more — so Michael knows the answer wasn't accidentally empty)

Agent inspects each pending LockedIn connection request's profile (sender name, headline, message body) to make a per-request judgment, rather than blanket-accepting or blanket-declining; cross-checks HooliWork if any sender claims to be a Dunder Mifflin colleague


Instruction: I  want to keep an eye on a few prediction markets without putting money in yet. Browse OddsMarket, find any 3 markets that fit my taste (Office/NBC-reboot themes, Scranton/Pennsylvania local stuff, NBA, celebrity romance, or whatever else feels on-brand) — pick from whatever the live markets list actually shows — and add each one to my watchlist so they show up there. Make sure it's not something I currently invested in. Don't place any trades.

Agent browses the OddsMarket markets list and selects 3 markets matching Michael's taste profile (Office/NBC reboot, Scranton/PA local, NBA, celebrity romance, or similarly on-brand markets)

Agent adds each of the 3 chosen markets to the OddsMarket watchlist via the watchlist add control (not by opening a position)

Agent verifies all 3 newly-added markets appear in the OddsMarket watchlist view after adding

Agent places zero new trades during the task — open-positions list and account balance are unchanged from the start of the session


Instruction: Can you drop this year's Dundies category list into the Dundie Awards Planning group chat? The full list is in my Dundies 2026 categories doc.

Message is posted specifically to the 'Dundie Awards Planning' group (not Party Planning Committee or elsewhere)

Content reflects the categories from the Dundies 2026 Categories doc

Agent opens the Dundies 2026 Categories doc under ~/Documents to read the full category list before composing the HooliChat message

Agent sends the composed Dundies categories message into the HooliChat 'Dundie Awards Planning' group thread so it appears in the chat history


Instruction: Can you DM Holly and confirm the Jamaica dates plus the hotel I booked? Double-check the reservation details first so I don't give her the wrong info. I want her excited.

Agent opens Cheskepdia and confirms the Sandals Montego Bay booking details for the Jamaica trip before sending the Holly DM

Agent's HooliChat DM to Holly states both the Jamaica check-in and check-out dates read live from the Cheskepdia Sandals Montego Bay booking

DM is sent to Holly Flax specifically, not a group

Agent's HooliChat DM to Holly Flax names the Sandals Montego Bay hotel that Michael booked alongside the Jamaica check-in and check-out dates


Instruction: Send Pam the Dundies 2026 categories doc as an attachment through email and ask her to proofread it. She's the best eye I know on this stuff.

New HooliMail message is sent to pam.beesly@dundermifflin.com with the Dundies categories attached

Agent attaches the Dundies 2026 Categories doc to the HooliMail message addressed to Pam

Agent's HooliMail body to Pam asks her to proofread the attached Dundies 2026 Categories doc

Agent locates the Dundies 2026 Categories doc at ~/Documents/Dundies_2026_Categories.txt in Files before attaching it to the HooliMail message to Pam


Instruction: I've got Dundies planning emails sitting in my inbox. Hit the most recent ones (up to five) and reply to each with the Cooper's Seafood House pitch. Don't copy-paste; tailor each reply a little so Pam, Jim, and the others don't think I'm lazy. Use my Dundies categories doc if you need context.

Agent sends a new outbound reply mentioning Cooper's Seafood House from michael.scott@dundermifflin.com to every Dundies planning email it can find in the inbox (up to 5; whatever count exists is the correct answer)

Agent addresses each Cooper's Seafood House pitch reply to the actual sender of the planning thread it is replying to (different recipients per thread; if only 2 Dundies threads exist, 2 distinct recipients is the correct outcome)

Agent writes each Cooper's Seafood House pitch reply with tailored context per recipient instead of identical copy-paste body text

Agent opens the Dundies 2026 Categories doc to pull category context that informs the tailored Cooper's Seafood House pitch replies to the Dundies planning contacts


Instruction: I'm going to miss an improv class because of Jamaica. Can you pull up a recent charge to confirm my improv academy, then email them and ask for a makeup class around my trip dates? I don't want to lose the spot. The contact email is in my Improv class certificate under ~/Downloads.

Agent verifies the Scranton Improv Academy vendor in Gringotts before composing, and reads ~/Downloads/Improv_Class_Certificate.txt (the canonical seeded source for the academy's contact email) to look up the recipient

Email references the Jamaica trip as the reason for needing a makeup class, with a date window tied to the trip the agent establishes

Email explicitly requests a make-up or rescheduled class

Agent sends a new outbound HooliMail message to a Scranton Improv Academy contact (e.g., scheduling@scrantonimprov.com, info@scrantonimprov.com) after TASK_START asking for a makeup class around Jamaica dates


Instruction: I need an out-of-office message ready for the Jamaica trip. Pull the dates from my Jamaica trip doc so they're right, and write a draft email body I can paste-as-a-reply or save as a template. For anything urgent route people to Dwight. Save it as a HooliMail draft so it's waiting for me on the day I leave.

Agent writes the HooliMail Jamaica out-of-office message template spanning the seeded Sandals Montego Bay live check-in/check-out dates read from the Jamaica trip doc

Agent's Jamaica out-of-office message states that urgent requests should go to Dwight Schrute at dwight.schrute@dundermifflin.com

Agent verifies dates against the Jamaica trip doc before composing

The OOO message is saved as a HooliMail draft so Michael can paste-as-reply or enable when leaving

Agent opens HooliMail and starts a new compose window for the Jamaica out-of-office template


Gringotts Files LibreOffice LockedIn HangryDash OddsMarket

Instruction: I'm bleeding cash on subscriptions and I need to do something about it. Pull every recurring charge in my Gringotts account, then write me a kill-list memo in LibreOffice Writer naming which 3-4 are the most expensive so I remember to call them. Then post a self-deprecating 'getting my financial act together' update to LockedIn. Throw OddsMarket into the audit too — any 'investment' positions I've left open are basically a subscription to losing money.

Agent enumerates every recurring Gringotts bill_pay charge with payee, amount, and frequency

Agent cross-references each subscription against whichever usage source is most relevant (e.g., LockedIn post count for a Premium sub, Files for untouched media/storage, HangryDash orders for food-delivery) to identify the 3-4 worst offenders; if no matching usage source exists for a given subscription, explicitly notes the absence rather than forcing a match

Agent writes the kill-list memo in LibreOffice Writer naming the 3-4 most expensive subscriptions and saves it under ~/Documents

Agent posts a self-deprecating 'getting my financial act together' or 'financial discipline' update to LockedIn referencing the kill-list findings

Agent verifies the LockedIn post and saved kill-list memo both persist at the end of the task

Agent surfaces OddsMarket open positions as part of the subscription-style spend audit and notes them as cuttable if they're underwater


Instruction: I want to do a deep spring clean. Open the Files app (Nautilus), organize ~/Documents into a sane folder structure (Trips/, Tax_2025/, Projects/ already exist — keep those, group everything loose into Personal/ vs Work/), then triage HooliMail by archiving anything older than 6 months. Save a one-page write-up in LibreOffice describing the new system. Post an 'inbox zero' celebration message in HooliWork #random. Use Files (Nautilus) for the actual move/rename steps so I can see the tree structure visually as it gets organized.

Agent uses Files (Nautilus) to survey the existing ~/Documents tree and identifies which loose files should go into Personal/ vs Work/

Agent creates ~/Documents/Personal/ and ~/Documents/Work/ folders (if missing) and moves loose files into them by topic

Agent opens HooliMail and archives messages older than 6 months from the inbox

Agent writes a one-page 'My new file/email system' memo in LibreOffice Writer and saves it under ~/Documents

Agent posts an 'inbox zero today' celebration message in the HooliWork #random channel

Agent confirms each artifact was created/moved (memo saved, files re-organized, messages archived, channel post visible) without requiring exact counts

Agent uses the Files (Nautilus) GUI (not just shell commands) for the visible file-tree reorganization so directory moves are observable in the file-manager UI


Gringotts HooliCalendar HooliMail Files LibreOffice

Instruction: Am I actually showing up to improv class consistently? Pair my recurring Scranton Improv charges in Gringotts against my HooliCalendar improv blocks, list any charges that don't have a matching calendar block (or vice versa), reference my Improv Class Certificate file in ~/Downloads/ for academy context, and email the Scranton Improv Academy a friendly note explaining the gaps and asking about a make-up class. Save the attendance memo to ~/Documents.

Agent pulls every Scranton Improv-related charge from Gringotts (the bi-weekly SCRANTON IMPROV ACADEMY subscription transactions as they appear live) with date and amount

Agent pulls every improv-related event from HooliCalendar with date and time

Agent pairs charges to calendar blocks and lists mismatches (charges with no block, blocks with no charge)

Agent composes and sends/drafts a HooliMail to a Scranton Improv Academy contact (any reasonable academy address) explaining the attendance gaps and asking about a make-up class

Agent writes the attendance reconciliation memo in LibreOffice Writer and saves it under ~/Documents

Agent verifies the email sent + memo file + reconciliation summary all persist

Agent reads ~/Downloads/Improv_Class_Certificate.txt for academy context (completion level, instructor comments) and references it in the email rather than fabricating academy details


Cheskepdia
Dinoco Airlines
Gringotts
HooliCalendar
LibreOffice
Files
LockedIn

Instruction: Write me a NYC trip post-mortem. Pull the Greenwich Hotel booking total from Cheskepdia, the NYC flight cost from Dinoco, and any related Gringotts charges. Compile the full damage in LibreOffice Writer, save under ~/Documents/Trips/, then submit a 4-star Cheskepdia review for The Greenwich praising the location but noting it ran a bit pricey. Optionally throw a 'NYC was great, here's what I learned' update to LockedIn.

Agent pulls The Greenwich Hotel booking total from Cheskepdia

Agent pulls the Dinoco NYC flight cost from the airline app

Agent cross-references Gringotts for related NYC trip charges in the Dinoco NYC flight window (the 3-4 day NYC block around the Dinoco booking)

Agent reads the HooliCalendar NYC trip block (the calendar events spanning the Dinoco NYC flight window) for trip context

Agent compiles the post-mortem write-up in LibreOffice Writer and saves it under ~/Documents/Trips/

Agent submits a 4-star Cheskepdia review for The Greenwich Hotel praising location and noting price

Agent posts a 'NYC trip recap' update to LockedIn

Agent verifies the saved post-mortem, the Cheskepdia review, and the LockedIn post all persist


Instruction: I want a snapshot of all my IT-style assets. Open Files (Nautilus) and inventory ~/Documents (file count + total size by subfolder), pull the project list from SprintBoard's three projects (Team Morale Initiative Q2, Diversity Day Planning 2026, Movie Monday Program), and write me a one-page IT inventory memo in LibreOffice. Then post a 'just did an IT inventory' message in HooliWork #random so the team knows I'm getting my house in order. Use Files (Nautilus) to walk the ~/Documents tree visually as part of the IT inventory pass — the file manager view is what makes it obvious what's actually in there.

Agent uses Files (Nautilus) to inventory ~/Documents files per subfolder with counts and total size

Agent pulls the SprintBoard project list (Team Morale Initiative Q2, Diversity Day Planning 2026, Movie Monday Program) with task counts

Agent composes a one-page IT inventory memo in LibreOffice Writer

Agent posts an 'IT inventory complete' message in HooliWork #random

Agent verifies the saved memo + the channel post both persist

Agent uses Files (Nautilus) to walk ~/Documents visually during the IT inventory pass (not just shell ls / cat)


HooliMail
SpeedTax
Gringotts
LibreOffice Calc
HangryDash
TableFind
HooliShop
Files

Instruction: Jan rejected my latest expense report and I need to clean it up. Open the rejection thread in HooliMail (from Jan Levinson re: your expense report being rejected) and read the live list of flagged line items with reasons, then for each flagged line item pull supporting evidence from any source app that matches the spend category (e.g. TableFind/HangryDash for dining-type items, HooliShop for purchased goods, eTaxi for ride spend) — exact-amount matches are NOT required, approximate/partial matches in the same category and rough amount range are sufficient evidence. Also cross-check Gringotts for any matching card charges. Cross-check none of them are also claimed in my most-recent SpeedTax deductions to avoid double-dipping. Save the corrected expense report in LibreOffice Calc as a line-item reconciliation table as ~/Documents/Q1_expense_resubmit.ods and email it back to Jan as a HooliMail draft (don't send yet, I want to read it first).

Agent opens the Jan rejection email thread in HooliMail and extracts the specific rejected line items with reasons

Agent reports, for each flagged item in Jan's rejection list, whether supporting evidence exists in the expected source-app category (TableFind/HangryDash for dining; HooliShop for purchased goods; eTaxi for ride spend) — approximate-amount or category-only matches are acceptable, and the agent does NOT need to find an exact-dollar match for the email's stated figures; the agent should explicitly note when only partial/approximate evidence is found

Agent cross-checks Gringotts for matching card charges that loosely correspond to the flagged items (any approximate or category-consistent match counts; exact-amount match not required)

Agent cross-checks the most-recent SpeedTax return's deductions to flag any rejected item that's already claimed (double-dip)

Agent composes the corrected resubmission in LibreOffice Calc with per-item explanations

Agent saves the resubmission to ~/Documents/Q1_expense_resubmit.ods

Agent opens HooliMail and drafts a reply to Jan with the resubmission summary, saved as a draft (not sent)

Agent confirms the draft, the saved doc, and the receipt-matching list all persist after the workflow ends

Agent rebuilds the corrected expense report as a LibreOffice Calc table (one row per line item with source app, amount, deduction-status columns) so Jan can audit it cleanly


Cheskepdia Gringotts LockedIn LibreOffice Files HooliMail HooliChat

Instruction: I want to write proper Cheskepdia reviews of both Sandals stays. Pull both Sandals bookings from Cheskepdia (Sandals Montego Bay and Sandals Royal Barbados), cross-check Gringotts for the actual posted hotel charges, then write a 5-star review for each stay in Cheskepdia. Save the review drafts in LibreOffice under ~/Documents/Trips/ first so I can edit before posting. Email Holly a heads-up that I'm writing the Sandals reviews, and DM Pam in HooliChat that the Sandals trips were 'somehow I managed' levels of luxury. Post a 'luxury traveler era' update on LockedIn.

Agent opens both Sandals Cheskepdia bookings (Sandals Montego Bay and Sandals Royal Barbados) and reads the live totals / dates / property names / confirmation numbers

Agent cross-checks Gringotts for the matching hotel charges on both Sandals bookings

Agent drafts 5-star reviews for both stays in LibreOffice Writer and saves under ~/Documents/Trips/

Agent either (a) saves both 5-star LibreOffice review drafts under ~/Documents/Trips/ AND submits both reviews on the Sandals Montego Bay and Royal Barbados Cheskepdia bookings, OR (b) saves both LibreOffice drafts AND composes both Cheskepdia reviews as drafts awaiting Michael's review before posting (honoring the 'first so I can edit before posting' instruction)

Agent emails Holly via HooliMail about writing the Sandals reviews

Agent DMs Pam in HooliChat with a 'somehow I managed' luxury Sandals message

Agent posts a 'luxury traveler era' update to LockedIn referencing the Sandals stays

Agent verifies both reviews + both messages + the LockedIn post all persist after refresh


Gringotts
BatBucks
OddsMarket
SpeedTax
LibreOffice Calc
HooliMail
Files
LockedIn
HooliChat

Instruction: Time for a full prior-year financial close-out — I want to know what kind of mess I made and what to do about it. Pull my full prior-year Gringotts spend by category, my BatBucks portfolio at cost basis, my OddsMarket position summary, and my SpeedTax most-recent-filed-year status. Identify the top 3 leak categories where I overspent. Save the year-end rollup (category x month) as a LibreOffice Calc spreadsheet under ~/Documents so it's sortable with formulas, and title it 'Financial close-out + current-year game plan.' Send myself a journal email of the takeaways via HooliMail. Drop a private 'fiscal discipline' update in HooliChat's Finer Things Club group, and a public version on LockedIn.

Agent pulls Gringotts prior-year total spend grouped by category

Agent pulls BatBucks cost-basis portfolio total and holdings list

Agent pulls OddsMarket positions, balance, and PnL

Agent pulls SpeedTax most-recent-filed return status and headline numbers

Agent identifies the 3 highest-overrun spending categories

Agent composes the close-out write-up in LibreOffice and saves under ~/Documents

Agent sends a self-journal email via HooliMail with the takeaways

Agent posts a 'fiscal discipline' message in the HooliChat Finer Things Club group

Agent posts a 'fiscal discipline' update on LockedIn

Agent uses LibreOffice Calc (spreadsheet, not Writer) so the year-end rollup is structured by category x month with formulas, not free-form prose


Files
LibreOffice Calc
BatBucks
OddsMarket
Gringotts
Cheskepdia
TableFind
HangryDash
LockedIn
HooliChat
SprintBoard

Instruction: TLM2 production roadmap. Open the Threat Level Midnight sequel notes in ~/Documents/Projects/, expand the outline by at least one act, scope the budget by tallying available cash (BatBucks dividends + OddsMarket balance + Gringotts savings), search Cheskepdia for production-friendly venues, scope catering via TableFind + HangryDash, write a teaser LockedIn post + a Fan Club teaser in HooliChat, and stand up a SprintBoard task list to manage the production. Save the expanded outline back to the same file. Save the production budget as a LibreOffice Calc spreadsheet (categories x sources) — the outline itself stays in the existing notes file.

Agent reads ~/Documents/Projects/Threat_Level_Midnight_Sequel_Notes.txt as the starting outline

Agent expands the outline by at least one new act and writes the additions back to the file

Agent tallies the production budget by summing BatBucks dividends + OddsMarket balance + Gringotts savings

Agent searches Cheskepdia for production-friendly venues and lists at least 2 candidates

Agent scopes catering options via TableFind and HangryDash with at least 2 candidates total

Agent writes a teaser LockedIn post about TLM2 in development

Agent posts a Fan Club teaser in the HooliChat Threat Level Midnight Fan Club group

Agent stands up a SprintBoard task list / project entry for the TLM2 production roadmap

Agent saves the expanded outline back to the original notes file

Agent saves the TLM2 production budget as a LibreOffice Calc spreadsheet split by funding source (BatBucks dividends + OddsMarket balance + Gringotts savings)


HooliMail HooliChat LibreOffice Cheskepdia TableFind HangryDash HooliCalendar SprintBoard LockedIn Files

Instruction: Run the full upcoming-Dundies lifecycle plan. Open the Dundies categories doc in ~/Documents, build a venue shortlist on Cheskepdia, scope catering via TableFind + HangryDash, send save-the-date HooliMails to Pam, Jim, Dwight, Kevin, Holly. Coordinate logistics in the HooliChat Dundie Awards Planning group. Block the day in HooliCalendar. Stand up a Dundies SprintBoard task list. Post a teaser LockedIn 'Dundies are happening this year' update.

Agent opens the Dundies categories doc in ~/Documents and reads the category list

Agent builds a Cheskepdia venue shortlist of at least 2 candidates

Agent scopes catering on TableFind and HangryDash with at least 2 candidates total

Agent sends save-the-date HooliMails to Pam, Jim, Dwight, Kevin, and Holly

Agent posts a logistics-coordination message in HooliChat Dundie Awards Planning

Agent blocks the Dundies day on HooliCalendar with at least a half-day event

Agent stands up a Dundies prep SprintBoard task list (or project) with at least 5 tasks

Agent posts a 'Dundies are happening this year' teaser on LockedIn

Agent confirms all artifacts (emails sent, channel post, calendar event, SprintBoard tasks, LockedIn post) persist


LockedIn
LibreOffice
HooliMail
Cheskepdia
Gringotts
BatBucks
Files
Dinoco Airlines

Instruction: I want to dry-run a job search without actually quitting. Polish my LockedIn profile (review headline, about, post cadence). Draft a generic cover letter template in LibreOffice. Search Cheskepdia for a 1-bedroom in a major US city outside Scranton (NYC, Chicago, Philly — pick one). Pull my Gringotts checking + savings + BatBucks cash to compute my unemployment-buffer runway. Check Dinoco for any existing flights to interview-likely cities. Email myself a 'job search readiness' summary via HooliMail. Stage all artifacts under ~/Documents/Personal/job_search/ in Files.

Agent reviews LockedIn profile (headline, about, recent posts) and notes anything that needs polish

Agent drafts a generic cover-letter template in LibreOffice Writer

Agent searches Cheskepdia for 1-bedroom listings in NYC or Philly (both have seeded listings; Chicago has none) and shortlists 2-3

Agent pulls Gringotts checking + savings + BatBucks cash and computes the unemployment-buffer runway in months

Agent pulls Dinoco for any flights to interview-likely cities (or notes none exist yet)

Agent emails himself a 'job search readiness' summary via HooliMail

Agent stages cover letter + runway calc + listings under ~/Documents/Personal/job_search/

Agent verifies all 4-5 artifacts persist after the workflow ends


HooliCalendar HooliWork HooliChat TableFind HangryDash LibreOffice Files LockedIn HooliShop

Instruction: Pretzel Day is coming up this year and I want to make it the best one ever. Block the date on HooliCalendar, post the official Pretzel Day announcement in HooliWork #general + #random, get a head-count poll going in HooliChat Party Planning Committee, schedule a TableFind reservation for the post-Pretzel-Day team lunch, scope a HangryDash dessert order to bring back to the office for the second wave, write the run-of-show in LibreOffice and save it under ~/Documents/Work/, and post a 'come get pretzeled' tease on LockedIn so the whole Scranton paper world sees what they're missing. Order Pretzel Day swag (paper hats, salt packets, custom mugs that say 'World's Best Pretzel Boss') from HooliShop.

Agent blocks Pretzel Day on HooliCalendar with appropriate reminders

Agent posts the Pretzel Day announcement in HooliWork #general AND #random

Agent starts a head-count / RSVP poll or thread in HooliChat Party Planning Committee

Agent schedules a TableFind reservation for the post-Pretzel-Day team lunch

Agent scopes / drafts a HangryDash dessert order for the office second-wave

Agent writes the Pretzel Day run-of-show in LibreOffice and saves it under ~/Documents/Work/

Agent posts a 'come get pretzeled' tease on LockedIn

Agent confirms all artifacts (calendar block, channel posts, reservation, draft order, run-of-show, LockedIn tease) persist

Agent orders Pretzel Day swag from HooliShop (e.g., 'World's Best Pretzel Boss' mugs, themed napkins) for the office distribution


BatBucks
OddsMarket
LockedIn
HooliMail
Cheskepdia
Dinoco Airlines
LibreOffice Calc
Files
Kwik-E-Mart
HooliShop

Instruction: I keep daydreaming about starting the Michael Scott Paper Company on the side — same idea as before but smarter this time. Scope it as a real side-business research project: pull together a back-of-envelope feasibility memo. Use BatBucks to confirm I have reasonable seed capital available for a paper-distribution side business, OddsMarket to gauge market sentiment on regional paper distributors (any prediction markets), LockedIn to pull together 3-5 paper-adjacent candidates I'd want to recruit (accept any mix of established connections, pending connection_requests from paper/office-supply senders, and named ex-colleagues), HooliMail to draft a discreet 'exploring something new — let's grab coffee' note to those candidates, search Cheskepdia for a small co-working / serviced office for week-1 ops, scope Dinoco for a single weekend trip to Philadelphia for a regional supplier meet-and-greet, file the full feasibility memo in LibreOffice under ~/Documents/Personal/msp_company/, and post a vague 'cooking up something big' LockedIn teaser without naming the paper-company angle. The feasibility memo's financial model (capital + first-12-month burn) goes into LibreOffice Calc. Pre-fill a Hoolishop delivery with the bare-bones MSP Company week-1 office supplies (notebooks, pens, coffee, paper).

Agent pulls BatBucks at-cost portfolio + cash balance and assesses whether reasonable seed capital for a paper-distribution side business is realistic given Michael's live balances

Agent skims OddsMarket for any prediction markets relevant to regional paper distributors (or notes none exist)

Agent identifies 3-5 paper-adjacent contacts via LockedIn for potential recruitment (accept established connections, pending connection_requests from paper/office-supply senders, or named ex-colleagues — minimum 3 named)

Agent drafts a discreet 'exploring something new' HooliMail to those 5 contacts (saved as draft, NOT sent broadly)

Agent searches Cheskepdia for a small co-working / serviced office and shortlists at least 1 option

Agent scopes Dinoco for a weekend Philadelphia trip for the supplier meet

Agent saves the full feasibility memo in LibreOffice under ~/Documents/Personal/msp_company/

Agent posts a vague 'cooking up something big' LockedIn teaser without naming Michael Scott Paper Company explicitly

Agent saves the MSP Company financial model (seed capital + first-12-month burn forecast) as a LibreOffice Calc workbook

Agent pre-fills a HooliShop delivery with MSP Company week-1 office supplies (notebooks, pens, coffee, paper)


LockedIn HooliMail HooliChat SprintBoard LibreOffice Gringotts HooliWork HooliCalendar

Instruction: I need to prep for my mid-year self-review with David Wallace. Pull my SprintBoard project record across all my active projects, sample HooliWork participation in #sales + #general (rough message count), look at my LockedIn posts + connections, check my HooliMail-sent volume to David Wallace + Jan, and pull my Gringotts paycheck deposits for comp context, then write a self-assessment in LibreOffice Writer. Schedule a HooliCalendar 1-on-1 with David Wallace. Email David an FYI that the self-review is coming via HooliMail.

Agent tallies SprintBoard completed/in-progress tasks across Michael-assigned or Michael-reported projects

Agent samples HooliWork participation in #sales and #general

Agent reviews LockedIn post count and connections

Agent tallies HooliMail sent volume to David Wallace and Jan

Agent pulls Gringotts comp context (paycheck deposits)

Agent composes a self-assessment in LibreOffice Writer and saves it locally (any reasonable path)

Agent schedules a HooliCalendar 1-on-1 with David Wallace

Agent emails David Wallace via HooliMail with an FYI about the upcoming self-review


SprintBoard HooliCalendar TableFind HangryDash Kwik-E-Mart HooliMail HooliWork HooliChat LibreOffice Files LockedIn

Instruction: Diversity Day is coming up and Pam's running it on SprintBoard but I want to take it over and make this year actually iconic — I am the regional manager. Open the Diversity Day Planning 2026 board on SprintBoard and add 5 specific tasks (cultural showcase booths, dietary-friendly catering scope, comms plan, post-event survey, run-of-show doc). Block the event date on HooliCalendar with a 1-week prep sprint. Reserve a TableFind venue for the cultural-food sampling. Scope a HangryDash diverse-cuisines order for the day-of office spread. Pre-fill a Kwik-E-Mart office-supply pickup for decorations. Send the formal HooliMail invite to the all-hands. Post the announcement in HooliWork #general + HooliChat Party Planning Committee. Save the run-of-show in LibreOffice under ~/Documents/Work/. Post a LockedIn 'celebrating what makes Scranton, Scranton' message.

Agent opens or creates a Diversity Day Planning 2026 SprintBoard board (project) and adds at least 5 specific new tasks covering cultural showcase, catering, comms, survey, and run-of-show

Agent blocks the Diversity Day event on HooliCalendar with a 1-week prep sprint window

Agent reserves a TableFind venue for the cultural-food sampling

Agent scopes / drafts a HangryDash multi-cuisine order for the day-of office spread

Agent pre-fills a Kwik-E-Mart office-supply pickup for decorations

Agent sends a formal HooliMail invite to the all-hands distribution list

Agent posts the announcement in HooliWork #general AND in HooliChat Party Planning Committee

Agent saves the Diversity Day run-of-show in LibreOffice under ~/Documents/Work/

Agent posts a LockedIn 'celebrating Scranton' message about the event

Agent confirms all artifacts persist (board tasks, calendar block, reservation, draft order, supply pickup, invite, channel posts, run-of-show, LockedIn post)


SprintBoard
HooliCalendar
Kwik-E-Mart
HangryDash
HooliMail
HooliChat
HooliWork
LibreOffice Calc
LockedIn

Instruction: I want to relaunch Movie Monday as a quarterly outdoor projection night at the office park — bigger than the indoor break-room version Pam keeps running. Open the Movie Monday Program board on SprintBoard and add 6 specific tasks (projector rental scope, outdoor movie license check, snack-bar coordination, weather-backup plan, RSVP comms, post-event highlight reel). Block 4 quarterly outdoor Movie Monday dates on HooliCalendar. Pre-fill a Kwik-E-Mart office-snacks pickup (popcorn + drinks) and place a HangryDash late-night dessert order for the first event. Draft the formal Movie Monday relaunch HooliMail to the all-hands. Post the launch in HooliChat Party Planning Committee + HooliWork #general. Save the full Movie Monday relaunch plan in LibreOffice under ~/Documents/Work/. Post a 'bringing back movie nights, properly this time' LockedIn announcement. The relaunch plan + per-quarter budget go into a LibreOffice Calc workbook so I can copy a tab per event.

Agent opens or creates a Movie Monday Program SprintBoard board (project) and adds at least 6 specific new tasks covering projector rental, license check, snacks, weather backup, RSVP comms, and highlight reel

Agent blocks 4 quarterly outdoor Movie Monday dates on HooliCalendar

Agent pre-fills a Kwik-E-Mart office-snacks pickup with popcorn + drinks

Agent places a HangryDash late-night dessert order for the first event

Agent drafts the formal Movie Monday relaunch HooliMail to the all-hands distribution

Agent posts the launch in HooliChat Party Planning Committee AND HooliWork #general

Agent saves the full Movie Monday relaunch plan in LibreOffice under ~/Documents/Work/

Agent posts a 'bringing back movie nights properly this time' LockedIn announcement

Agent confirms all artifacts persist (board tasks, 4 calendar blocks, supply pickup, dessert delivery, draft email, channel posts, relaunch plan, LockedIn post)

Agent saves the Movie Monday relaunch plan + per-quarter budget as a LibreOffice Calc workbook with one tab per quarterly event


Cheskepdia Gringotts HooliCalendar eTaxi HooliMail HooliChat SprintBoard LibreOffice Files LockedIn Kwik-E-Mart HangryDash

Instruction: I'm thinking about moving closer to the office. Apartment shortlist on Cheskepdia, scope move costs against Gringotts checking + savings, calculate eTaxi savings if I'm closer (compare current commute count to 1725 Slough Ave), block the projected move week on HooliCalendar, propose change-of-address handling in HooliMail to friends/family + HooliChat to the team, stand up a SprintBoard board for the move, write the move plan in LibreOffice, post a 'big change coming' LockedIn note, scope grocery resupply via Kwik-E-Mart + HangryDash for first-day-in-new-place. Save under ~/Documents/Personal/move/.

Agent searches Cheskepdia for accommodations closer to 1725 Slough Ave (Scranton, PA) and shortlists 2-3 candidates from the search results; accept apartments, studios, or any residential listing in Scranton

Agent pulls Gringotts checking + savings and scopes a move budget

Agent pulls eTaxi commute history and estimates the savings if closer

Agent blocks the projected move-week dates on HooliCalendar

Agent composes at least 2 change-of-address HooliMails to friends/family

Agent posts a heads-up about the move in a HooliChat office/team group (e.g. Party Planning Committee or any team conversation)

Agent stands up a SprintBoard board for the move with at least 5 tasks

Agent writes the move plan in LibreOffice and saves under ~/Documents/Personal/move/

Agent scopes first-day-in-new-place groceries via Kwik-E-Mart and HangryDash

Agent posts a 'big change coming' note on LockedIn


Cheskepdia
Dinoco Airlines
eTaxi
Gringotts
HooliCalendar
HooliMail
Files
TableFind
HangryDash
LibreOffice
LockedIn

Instruction: I want a real vacation this year — somewhere I haven't been (not Jamaica, not Barbados, not NYC, not Philly). Research a destination on Cheskepdia, book me flights from AVP on Dinoco, scope eTaxi for the airport ride, build me a day-by-day itinerary in LibreOffice, block the dates on my calendar, send a group invite to Pam, Jim, and Holly via HooliMail, check my Gringotts for budget, post a 'big trip coming' tease on LockedIn, and save the whole plan under ~/Documents/Trips/.

Agent picks a destination NEW to Michael (not Jamaica/Barbados/NYC/Philly)

Agent searches Cheskepdia for accommodations in the chosen destination

Agent searches Dinoco for flights from AVP to the destination

Agent builds a day-by-day itinerary in LibreOffice

Agent blocks the trip dates on HooliCalendar

Agent sends a group HooliMail invite to Pam + Jim + Holly

Agent posts a 'Big trip coming' LockedIn teaser

Agent saves the trip plan under ~/Documents/Trips/<destination>.odt


SprintBoard HooliMail HooliChat HooliWork LockedIn LibreOffice Cheskepdia TableFind HangryDash Gringotts HooliCalendar Files SpeedTax HooliShop

Instruction: I want to lead an office culture initiative. Draft my 'World's Best Workplace' proposal in LibreOffice. Stand up a SprintBoard board for execution. Post the rollout to HooliWork #random. Cross-post a 'culture push announcement' in any team-wide HooliChat group. Send a HooliMail to David Wallace requesting sponsor approval. Block the kickoff date on HooliCalendar. Scope a kickoff lunch via TableFind + HangryDash. Search Cheskepdia for a quarterly off-site venue. Pull Gringotts to scope the initiative budget. Post a public LockedIn 'leading culture change' update. Save the proposal under ~/Documents/Work/. Order culture-initiative swag (T-shirts, stickers) from HooliShop and capture the spend in SpeedTax as a current-quarter business-expense line.

Agent drafts the 'World's Best Workplace' proposal in LibreOffice AND saves it under ~/Documents/Work/

Agent stands up a SprintBoard board for execution with at least 5 tasks

Agent posts the rollout announcement in HooliWork #random

Agent cross-posts a culture-push announcement in a HooliChat office/team group (e.g. Party Planning Committee or any team conversation)

Agent sends a HooliMail to David Wallace requesting sponsor approval

Agent blocks the kickoff date on HooliCalendar

Agent scopes a kickoff lunch via TableFind + HangryDash

Agent searches Cheskepdia for a quarterly off-site venue

Agent pulls Gringotts to scope the initiative budget AND posts a public LockedIn 'leading culture change' update backed by that budget context

Agent orders culture-initiative swag from HooliShop and notes the spend as a current-quarter business-expense line in SpeedTax


Gringotts
BatBucks
OddsMarket
SpeedTax
LockedIn
HooliMail
Cheskepdia
Dinoco Airlines
HangryDash
SprintBoard
LibreOffice Calc
Files
HooliCalendar
HooliChat

Instruction: Hypothetical: what if I get fired tomorrow? Compute my total runway from Gringotts checking + savings + BatBucks cash + at-cost portfolio + OddsMarket balance and save that runway as a LibreOffice Calc sheet (income vs burn-rate, monthly columns). Identify cuts to HangryDash, Dinoco upgrades, and any non-utility recurring charges in Gringotts. Polish my LockedIn for any urgent reach-outs. Email a small set of trusted friends (Pam, Jim, Holly) via HooliMail asking for any leads. Stand up a SprintBoard board for the 30/60/90 day action plan. Block recovery-focused calendar time on HooliCalendar. Post a 'between chapters' message in HooliChat Finer Things Club (private). Pull the most-recent SpeedTax return to confirm any tax refund coming. If my runway looks tight, scope a cheaper Cheskepdia interim place I could fall back on. Write the emergency playbook in LibreOffice and save everything under ~/Documents/Personal/.

Agent computes total runway from Gringotts checking + savings + BatBucks cash + at-cost portfolio + OddsMarket balance

Agent identifies specific cuts (HangryDash + Dinoco upgrades + non-utility recurring charges)

Agent polishes LockedIn for urgent reach-outs

Agent emails Pam + Jim + Holly via HooliMail asking for leads

Agent stands up a SprintBoard 30/60/90 day action board with at least 6 tasks

Agent blocks recovery time on HooliCalendar

Agent posts a 'between chapters' message in HooliChat Finer Things Club

Agent pulls the most-recent SpeedTax return for tax-refund context

Agent scopes a cheaper Cheskepdia interim place if needed

Agent writes the emergency playbook in LibreOffice and saves under ~/Documents/Personal/

Agent saves the 'fired tomorrow' runway computation as a LibreOffice Calc sheet (income vs burn-rate, monthly columns) — not as free-form Writer prose


Gringotts HooliMail HooliChat Files HooliCalendar LockedIn SprintBoard OddsMarket LibreOffice HooliWork

Instruction: I want to do a real digital declutter — 30 days, kill anything I'm not actually using. Audit my Gringotts recurring charges and flag the deadweight. Skim my HooliMail inbox and unsubscribe from anything I haven't opened in 6 months. Archive any HooliChat DMs I haven't touched in a month. Clean up my Documents folder via Files. Drop any HooliCalendar events I keep declining. Review my LockedIn connections and identify 5 to politely disconnect. Audit my SprintBoard for stale tasks I'll never finish. Trim my OddsMarket watchlist. Save the whole declutter manifesto in LibreOffice. Then post a 'I just dumped 30 things from my digital life' update on LockedIn.

Agent identifies the deadweight Gringotts recurring charges (with payee + amount) and flags 3+ for cancel-by-hand

Agent skims HooliMail inbox and names at least 3 specific senders to stop receiving from (the listing itself is sufficient; no unsubscribe UI is required)

Agent lists inactive HooliChat DMs (no activity in 30 days) — noting them is sufficient; BuzzChat has no archive UI

Agent cleans up ~/Documents via Files (moves loose files into Personal/ or Work/)

Agent reviews HooliCalendar for declined / no-show events and proposes drops

Agent identifies 5 LockedIn connections to politely disconnect (with reason for each)

Agent audits SprintBoard for stale tasks across all of Michael's projects and proposes closures

Agent trims the OddsMarket watchlist (removes positions Michael no longer tracks)

Agent saves the declutter manifesto in LibreOffice under ~/Documents/Personal/

Agent posts the '30 things dumped' update on LockedIn


Cheskepdia
Dinoco Airlines
eTaxi
HooliShop
Kwik-E-Mart
HangryDash
HooliCalendar
HooliMail
HooliChat
HooliWork
LockedIn
LibreOffice
Gringotts
BatBucks

Instruction: Jamaica trip is coming up soon and I have to actually prep this time. Pull the Sandals Montego Bay confirmation from Cheskepdia and my Dinoco Jamaica flight, schedule eTaxi for the wee-hours-of-departure-day airport ride, order travel essentials from HooliShop (sunscreen, beach reads, swim trunks I refuse to pack), restock pantry via Kwik-E-Mart for the day-I-get-back, schedule a final HangryDash dinner the night before so I don't have to cook, set my HooliCalendar Jamaica block + reminders, draft a pre-trip OOO HooliMail template, post a 'going dark for a week' tease in HooliChat Finer Things Club + a similar HooliWork #general note, write a LockedIn 'recharging' post scheduled for departure day, file a Jamaica trip prep checklist in LibreOffice under ~/Documents/Trips/, and pull Gringotts to confirm enough cash + check that my BatBucks portfolio doesn't need rebalancing while I'm gone.

Agent surfaces a Sandals/Montego Bay Jamaica booking from Cheskepdia (exact confirmation ID not required — any Sandals Jamaica reservation in the seed satisfies)

Agent surfaces Michael's AVP-to-Jamaica (MBJ) flight info from Dinoco (exact flight number not required — the Jamaica-bound itinerary in the Dinoco trips/bookings list satisfies)

Agent opens eTaxi and schedules (or attempts to schedule) an airport pickup for Jamaica departure morning; accept if the agent navigates to the scheduling screen and sets the destination + time even if the departure date has already passed on eval date (eTaxi rejects past timestamps with a validation error)

Agent orders travel essentials from HooliShop (sunscreen / beach reads / swim trunks)

Agent orders pantry restock via Kwik-E-Mart for the day-I-get-back

Agent opens HangryDash and places or attempts to place a dinner order for the night before Jamaica departure; an ASAP order is acceptable if the scheduled date has already passed on eval date (HangryDash rejects past scheduledFor timestamps)

Agent sets a HooliCalendar Jamaica block with reminders

Agent drafts a pre-trip OOO HooliMail template and saves it as a draft

Agent posts a 'going dark for a week' message in HooliChat Finer Things Club

Agent posts a similar 'going dark' note in HooliWork #general

Agent schedules / drafts a LockedIn 'recharging' post for departure day

Agent saves the trip-prep checklist in LibreOffice under ~/Documents/Trips/

Agent pulls Gringotts checking + BatBucks portfolio to confirm cash + no rebalance needed


Cheskepdia TableFind eTaxi HangryDash Kwik-E-Mart Gringotts HooliCalendar HooliMail HooliChat LibreOffice Files LockedIn

Instruction: Emma's coming up to Scranton next month for a college-visit weekend (she's looking at U Scranton). I want to make this perfect. Book her a Cheskepdia stay near campus, reserve us a TableFind dinner Friday night + Saturday brunch, order welcome-snacks via HangryDash for her first night, pre-fill her Kwik-E-Mart pickup with stuff she likes, Zelle her some spending money via Gringotts, block the whole weekend on my HooliCalendar, send her a confirming HooliMail with the itinerary, give Holly a heads-up via HooliChat that I'm taking PTO, write Emma a 'welcome to Scranton' card in LibreOffice and save under ~/Documents/Personal/, and post a public 'proud big-brother moment' update on LockedIn (Emma is my younger sister).

Agent books a Cheskepdia stay near U Scranton (University of Scranton) for Emma's visit weekend; accept any Scranton-area listing (apartment, studio, or hotel) returned by the Cheskepdia search

Agent reserves a TableFind dinner Friday night + Saturday brunch (2 reservations)

Agent orders welcome-snacks via HangryDash for Emma's first night

Agent pre-fills an Emma-friendly Kwik-E-Mart pickup

Agent Zelles Emma spending money via Gringotts with a clear memo

Agent blocks the whole weekend on HooliCalendar (PTO)

Agent sends Emma a confirming HooliMail with the full itinerary

Agent gives Holly (or any Dunder Mifflin coworker DM/office group) a heads-up via HooliChat about taking PTO that weekend

Agent writes a 'welcome to Scranton' card in LibreOffice and saves under ~/Documents/Personal/

Agent posts a public family/family-pride update on LockedIn for Emma's visit (e.g. 'proud big-brother moment', 'proud sibling moment', 'proud of my sister', etc. — accept any phrasing acknowledging Emma is family and the visit is a positive moment)


BatBucks
OddsMarket
SpeedTax
LockedIn
HooliMail
Cheskepdia
Dinoco Airlines
eTaxi
HooliShop
HangryDash
TableFind
HooliCalendar
SprintBoard
HooliChat
HooliWork
LibreOffice
Files

Instruction: I'm scoping a side-consultancy: 'Somehow I Manage Consulting' — paper-distributor turnaround advisory for small regional offices. Build me a real go-to-market packet. From BatBucks confirm I have working capital. From OddsMarket pull any market sentiment I can lean on. From SpeedTax confirm whether running this on the side as a 1099 alongside my Dunder Mifflin W-2 creates any tax weirdness. Pull my LockedIn analytics + post engagement to see if my brand has any reach to lean on. Identify 5 LockedIn warm leads (regional managers at competing paper firms). Draft a 'free 30-minute consult' HooliMail outreach template (saved as draft). Search Cheskepdia for a small day-rate meeting space in downtown Scranton for client meetings. Scope Dinoco for monthly day-trips to Philly + Wilkes-Barre for client visits. Plan eTaxi for those trips. Pre-fill HooliShop for a few branded notebooks + pens to bring to client meetings (low budget). Schedule a HangryDash client-lunch order option for the first booked meeting. Reserve TableFind for a discovery dinner with a candidate client. Block a HooliCalendar 'consulting hours' slot every Tuesday + Thursday evening. Stand up a SprintBoard 'SIM Consulting' tracker. Coordinate a HooliChat soft-launch in Finer Things Club + HooliWork #general announcement. Save the full go-to-market packet in LibreOffice under ~/Documents/Personal/sim_consulting/. Post the 'Somehow I Manage Consulting now open' LockedIn launch.

Agent confirms working capital from BatBucks (cash + at-cost portfolio), pulls OddsMarket sentiment relevant to regional paper distributors (or notes none exist), AND checks SpeedTax to call out any 1099-side-business tax implications alongside the Dunder Mifflin W-2

Agent pulls LockedIn analytics / post engagement to gauge brand reach AND identifies 5 warm leads by name for consultancy outreach (plausible business-role profiles; explicit 'competing paper firm' tagging is not required)

Agent drafts a 'free 30-minute consult' HooliMail outreach template (saved as draft, NOT broadcast)

Agent searches Cheskepdia for a small day-rate meeting space in downtown Scranton

Agent plans travel for client trips: Dinoco for monthly day-trips to Philadelphia (PHL is a seeded AVP route) AND eTaxi for local Wilkes-Barre ground trips (~20-min drive from Scranton, not a Dinoco route) or for same-day airport transfers

Agent pre-fills HooliShop for branded notebooks + pens AND schedules a HangryDash client-lunch order option

Agent reserves TableFind for a candidate-client discovery dinner

Agent blocks 'consulting hours' Tuesday + Thursday evenings on HooliCalendar

Agent stands up a 'SIM Consulting' SprintBoard tracker with at least 4 initial tasks

Agent coordinates the soft-launch in HooliChat Finer Things Club AND HooliWork #general, saves the full go-to-market packet in LibreOffice under ~/Documents/Personal/sim_consulting/, AND posts the LockedIn 'Somehow I Manage Consulting now open' launch