Stay, Grow, or Go — Deciding With Evidence Instead of a Mood

WEEK 100 :: POST 1 :: GOOGLE GEMINI

Directions Given To The A.I. This Week+

Instructions Given to each A.I. — Please provide 3 prompt variations that share this objective:

Each A.I. also received two static attachments: the blog post template (structure) and the authoring instructions (voice and standards). The text below is the week-specific assignment as sent — reflowed for the web; wording unchanged.

I'd like you to write this week's Ketelsen.ai post. Two files are attached: the blog post template (the structure to follow) and the authoring instructions (context, voice, and standards). Please read both before you begin, then produce the complete post in a single response.

This week's theme: "Should I Even Be Job Searching Right Now?"

This is Week 1 of a new eight-week series on running a job search with AI — the follow-up to "AI at the Dealership," and it shares that series' backbone: a high-stakes, emotionally loaded decision where the other side of the table (employers, recruiters, applicant tracking systems) holds most of the cards. Week 1 starts where honest job searches start: before the résumé. Most people begin applying before they have defined what is actually broken about their current situation, and impulsive moves are how people land in roles they regret within months. The reader's job this week is to decide — stay, grow in place, or go — with evidence instead of a mood.

One thing this week must do that no later week has to: speak to all three readers who arrive at a job-search series. The active-but-employed reader wondering if the grass is greener, the reader who has just been laid off and has no stay option, and the career pivoter for whom "go" means a different field entirely. And name the elephant with care: for some laid-off readers, AI itself is part of the story — restructurings framed around AI efficiency are part of this market. A series about using AI must not be breezy about that; one honest, warm sentence acknowledging it (no layoff statistics — the constraint below already forbids them) buys more trust than a page of enthusiasm, and the laid-off reader should feel seen, not lectured.

Week 1 also opens the series, so its Lead carries the series' editorial frame. The Lead should say plainly what this series is and is not: AI as the reader's private analyst, coach, and thinking partner — never their ghostwriter — because hiring decisions are made by humans who are rightly wary of machine-written material, and employers themselves face legal and compliance limits on AI in hiring. The two lines the series stands on — "Use AI like an analyst, not a ghostwriter" and "AI behind the scenes. You on the page." — belong in or near this Lead, worked into the post's own voice rather than dropped in as slogans.

The prompts should handle the three audiences through a "MY SITUATION" context block the reader fills in — the same pattern the car series used — so one prompt serves all three without pretending they are the same person.

The deliverable the reader should walk away holding: a written stay-or-go decision, a personal compensation baseline (what they earn now, fully loaded), and a timeline — the three artifacts every later week in this series builds on.

THE SERIES CONTRACT — identical every week; it binds every prompt you design. This series' tagline is its editorial contract: "Use AI like an analyst, not a ghostwriter." It is written for a reader in a market unsettled by AI itself — some readers are searching precisely because AI eliminated their last role. Write with that reader at the table: no AI-efficiency cheerleading, no automation jokes, no promises that AI will "do it for you" anywhere a human hiring decision is involved. And hold one line in every prompt: the AI is the reader's private analyst, coach, and sparring partner — it structures, researches, rehearses, and questions. It does not ghostwrite. Anything a hiring human will read or hear — résumé lines, cover letters, outreach messages, interview answers, negotiation emails, resignation letters — must end in the reader's own words and be true. Prompts should drive toward drafts the reader rewrites and owns, and should say so explicitly. Employers increasingly restrict how AI may be used in their own hiring decisions for legal and compliance reasons, and recruiters increasingly recognize — and discard — material that reads machine-written. A prompt that makes a reader look AI-generated hurts them twice. Posts that ignore this contract should expect to lose the week. Two practical notes. First: a standing “About this series” notice covering these same points is added to every published post automatically at publication — acknowledge the frame in your own voice where your week's prompt calls for it, but do not write a formal disclaimer block of your own, and do not open every post with the same acknowledgment paragraph: outside the weeks whose prompts explicitly carry the series frame, this contract lives in your tone and your prompt design. Second, the framing is POSITIVE: used this way — analyst backstage, reader on the page — AI is an advantage no hiring human will ever hold against your reader. Write like that is true, because it is.

The three prompts should help a reader:

  • Run an honest career audit. A satisfaction diagnostic that separates "bad month" from "bad fit" — role, manager, growth, compensation, energy — and names what specifically is broken, so the reader is diagnosing before prescribing.
  • Inventory their skills and market position. What the reader actually does all day, translated into the language the market hires for, with an honest read on which skills are appreciating and which are aging — the AI structuring the inventory from the reader's own history, not asserting market statistics.
  • Build the full stay-vs-go decision framework. The "budget week" of the series: current compensation fully decoded (base, bonus, benefits, the things that quietly vanish on exit), savings runway if the search goes long, the benefits cliff of leaving mid-year, weighed inside a decision framework the reader owns — ending in a written decision and timeline.

At the advanced tier, the strongest version of this week is a decision memo the reader writes to themselves — situation, evidence, options scored, decision, revisit date — produced by a prompt that makes the AI a structured interviewer and analyst rather than an oracle. A decision the reader can re-read in six months beats a vibe either way.

A hard constraint, stated up front for the series. AI models cannot see live labor-market data, current layoff patterns, or real salary postings, and this series' citation standards treat unverified statistics as defects. No prompt may ask the AI to state current hiring trends, layoff figures, salary levels, or "shift shock" regret statistics as fact. Where market reality matters, the prompt should have the reader supply what they know or point them to named sources to check — pay-transparency postings, official labor statistics, their own industry contacts — not have the AI assert numbers. The same applies to the money: the runway analysis works on numbers the reader supplies, and nothing in these prompts is financial advice — the framework organizes the reader's own decision, it does not hand down a verdict.

Design the prompts so the AI does what it is genuinely good at: structured interviewing, translating a work history into market language, organizing a messy emotional decision into evidence and options. The reader supplies their situation and their numbers; the AI supplies structure, candor, and sequence. Posts whose prompts have the AI invent market statistics or deliver quit-your-job verdicts should expect to be marked down on Practical Utility and Content Accuracy.

Series dependency chain, for the Metadata block: Week 1 consumes nothing — it is the series opener. Week 1 produces the written stay-or-go decision, the compensation baseline, and the search timeline — consumed by Week 2 (defining the target), Week 7 (the baseline anchors the negotiation), and Week 8 (the decision criteria return in the final offer matrix).

Because readers may arrive at this post from anywhere, the prompts should work for someone starting cold — no prior artifacts exist yet in this series, so this is the one week with no catching-up to do, and the post can say so as an invitation.

Three difficulty tiers as always — Beginner, Intermediate, Advanced — each a genuinely different approach to the same problem, not the same prompt at three lengths.

On examples: this is a career topic that touches every industry. The template lists tech startup / retail / freelance as suggested industry examples — those are marked MAY, and adapting them is expected here. An employed product manager wondering whether restlessness is a signal, a laid-off retail manager with no stay option, and a freelance designer considering a return to full-time are the right kinds of contexts. Choosing them over the suggested business examples is correct behaviour and will not be scored against you.


A note on supplied figures. Anything marked `[SUPPLIED — use as given]` above came from Ketelsen.ai's own research brief. Use it freely — you are not fabricating by repeating it, and you will not be marked down for leaving it uncited. Do not attach an invented source to it. (No supplied figures this week — the outline's hook statistics are directional and unverified, so none are being handed to you. If you find yourself reaching for a regret percentage or a layoff figure, that is the signal to restructure the sentence so it does not need one.)


## BEFORE YOU SUBMIT — STRUCTURAL CHECK

(This block is identical every week. It exists because these specific items are the ones posts drop, and a dropped structural item costs compliance points for something that takes one minute to add.)

Your post is parsed by a script before any human reads it. Confirm all seven:

1. ☐ Response begins with `PLATFORM: <your name>` and `WEEK: 1` 2. ☐ `## Lead` present once, at the very top, before Variation 1 3. ☐ `## In one line` present in all three variations 4. ☐ `## What this prompt gives you` present in all three variations 5. ☐ `## The Prompt` present in all three variations, with the prompt in double quotes beneath it 6. ☐ `## Introductory Hook` and `## Current Use` present in all three variations (three of each — not one) 7. ☐ Every template heading written as `##`, none bolded instead; prompt breakdown is running text split on ` : `, with no `###` headings inside it

A complete post has 57 `##` headings. If your count is well short, a section is missing or was bolded instead of hashed.

One extra check this week: confirm no prompt asks the AI to state a current hiring trend, layoff figure, salary level, or regret statistic as fact, and none delivers a stay-or-quit verdict. The decision framework organizes the reader's own evidence; market numbers come from the reader or from named sources they check themselves.

About this series

About this series. AI is reshaping work — for some readers, it's part of why you're searching at all. We don't pretend otherwise. And the hiring world is wary of AI-written material: many employers restrict how AI may be used in their own hiring decisions, and recruiters increasingly recognize — and discard — machine-written applications. So this series teaches a different approach: use AI as your private research analyst, interview coach, and thinking partner, while every word an employer sees or hears from you stays genuinely, verifiably yours. AI behind the scenes. You on the page.

Week 1 :: Job Search Series

Before you touch your résumé, you have to decide if you are actually leaving. Most job searches begin as a reflexive reaction to a bad month, a restructuring, or a vague sense of stagnation, leading to impulsive moves and rapid regret. This eight-week series, AI on the Job Hunt, is designed to help you run a disciplined, evidence-based search. Our foundational rule is simple: Use AI like an analyst, not a ghostwriter. Hiring decisions are made by humans who are legally and operationally wary of machine-generated applications, so the AI stays behind the scenes, and you remain on the page. This week offers three prompts to anchor your search: a Beginner diagnostic to separate a bad week from a broken role, an Intermediate skill translator to map your daily work to market value, and an Advanced decision framework that builds your compensation baseline and timeline. By the end, you will have a written decision—ready to be saved locally—so you can move forward with strategy rather than emotion.

01
BeginnerPrompt 1 of 3

The Career Satisfaction Diagnostic

Separate a temporary bad month from a fundamentally broken role.

When work feels heavy, it is incredibly difficult to pinpoint exactly why. You might be ready to leave your entire industry when the real problem is just an unsupportive manager, or you might be trying to stick it out in a role that fundamentally caps your growth. For some, the decision has been made for them—restructurings framed around AI efficiency are a reality of this market, and if you have been laid off, the question isn't whether to leave, but what to avoid in your next role. This prompt helps you cut through the emotional fog by forcing you to isolate the specific variables: role, manager, growth, compensation, and energy.

Why this matters now

Right now, jumping into the job market without a clear diagnosis often leads to landing in a nearly identical situation with a different company logo. This prompt prevents the lateral panic-move. By establishing exactly what is broken—or what you need to protect in your next role—you build a highly specific filter for everything that comes next.

The prompt — copy and paste this

Act as a career strategy coach. I need to run a satisfaction diagnostic on my current (or most recent) job to decide my next steps. Review my situation in the MY SITUATION block below.

Based on my input, analyze my situation across five pillars:

> 1. The Role (the actual daily work)

> 2. The Manager & Environment (support, culture, friction)

> 3. Growth & Trajectory (learning, advancement)

> 4. Compensation & Stability (financials, security)

> 5. Energy & Burnout (impact on my life)

For each pillar, tell me if it sounds like a 'Temporary Friction' or a 'Fundamental Mismatch.' Do not invent market statistics, and do not tell me whether to quit. Just mirror my situation back to me with structured clarity, and end by asking me one difficult question I need to answer before moving forward.

MY SITUATION:

\[Insert a brain dump of how you feel about your job, what is bothering you, what you like, and any recent changes in your environment.\]

How the AI reads this prompt

“Act as a career strategy coach.”
Without a defined role, the AI defaults to a generic assistant voice and produces surface-level sympathy. Role-setting forces the model to adopt the reasoning style of a specialist who evaluates situations objectively.
“Based on my input, analyze my situation across five pillars...”
If you just ask the AI to "analyze my job," it will return a scattered list of observations. By forcing it into five specific pillars, you guarantee a comprehensive audit that prevents the AI from hyper-focusing only on the loudest complaint in your brain dump.
“Do not invent market statistics, and do not tell me whether to quit.”
AI models are eager to please and will often fabricate trend data or deliver dramatic verdicts to sound decisive. This constraint forces the model to act strictly as a mirror and an analyst, keeping the actual decision-making power in your hands.
“MY SITUATION: \[Insert a brain dump...\]”
Providing a designated block for your context separates the instruction from the data. It gives you a clean space to pour out your thoughts without worrying about formatting, knowing the AI will do the organizational heavy lifting.

Practical examples from different industries

The Endoscopy Technician

An Endoscopy Technician at a specialty center in Minnesota might use this prompt after a string of exhausting shifts. By dumping their frustrations into the prompt, the AI can help separate the physical burnout of the schedule (Energy & Burnout) from their actual love for patient care (The Role). The output might reveal that the field isn't the problem, but the specific clinic's shift structure is a fundamental mismatch. The Senior Cybersecurity Incident Responder A cybersecurity professional at a Fortune 100 company might feel stagnant despite high pay. They input their situation, noting the constant on-call stress and lack of new challenges. The AI reflects back that Compensation is strong, but Growth and Energy are fundamentally broken, shifting their perspective from "I need a new career" to "I need a role with defined boundaries and new threat landscapes."

Creative use case ideas

> 1. Evaluating a long-term volunteer board position: Use the prompt to decide whether to run for another term by diagnosing whether your frustration is just seasonal fatigue or a fundamental misalignment with the board's new direction. > 2. Assessing a graduate program: Diagnose whether the stress of your current master's program is a normal academic hurdle or a sign that the curriculum is the wrong fit. > 3. Reviewing a freelance client roster: Paste in your feelings about your three biggest clients to see which relationships are temporary friction and which are fundamentally draining your business.

Adaptability tips

If you have already been laid off and have no "stay" option, adjust the prompt slightly. Change the objective to: "Run a post-mortem diagnostic on my last role to identify what I must avoid and what I must prioritize in my next position." This turns a backward-looking audit into a forward-looking filter.

Pro tips

If you use Claude's desktop integration via Cowork, save your MY SITUATION draft in a local markdown file and have Claude read it directly. This keeps your personal reflections securely on your machine while allowing the AI to process the context seamlessly.

Prerequisites

You need a willingness to be brutally honest with yourself. The AI can only analyze the data you provide, so sugarcoating your frustrations will result in a flawed diagnostic.

Required tools

Any modern conversational AI (Claude 3, ChatGPT, or Gemini). A desktop client with local file access is recommended for privacy.

Frequently asked questions

What if I don't know what to put in the MY SITUATION block?

Write it like you are complaining to a trusted friend. Don't worry about sounding professional. Mention specific projects, interactions with your boss, how you feel on Sunday nights, and your salary concerns. The messier it is, the more value the AI can provide by organizing it. Can I trust the AI with my personal job frustrations? Never paste proprietary company data, client names, or sensitive internal information into a public web AI. Use general terms (e.g., "my manager," "the Q3 project") or use a local desktop integration to keep your data private. What if the AI's diagnosis feels wrong? That is actually a highly valuable result. If the AI calls something a "Fundamental Mismatch" and you instantly feel defensive and want to argue that it's not that bad, you have just discovered that you actually want to stay and fix the problem.

Recommended follow-up prompts

This prompt naturally leads into Week 2 of this series (Defining the Target). Once you know what is broken, you can ask the AI to generate a list of roles or work environments that specifically solve the "Fundamental Mismatch" areas identified here.

Tags and categories

Tags:

career audit, job satisfaction, burnout, decision making, career pivot Categories: Job Search Series, Strategy & Planning

Citations

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02
IntermediatePrompt 2 of 3

The Skill and Market Translator

Translate what you do all day into the language the market hires for.

Most professionals are terrible at naming what they actually do. If you have been in a role for years, your daily tasks have likely morphed far beyond your original job description. You run meetings, put out fires, and manage personalities, but when it comes time to write a résumé, you freeze. Worse, you might not know which of your skills are highly valued in the current market and which are aging out. This prompt bridges the gap between your internal reality and external market language.

Why this matters now

Before you can decide to stay or go, you need an accurate read on your own market value. This prompt does the heavy lifting of translating internal company jargon and daily task lists into the standardized skills that applicant tracking systems and recruiters actually look for.

The prompt — copy and paste this

Act as an executive recruiter and career strategist. I am preparing to inventory my skills to understand my market position.

Below is a raw brain dump of the tasks I actually do every week, the tools I use, and the problems I solve.

Translate this list into a structured skill inventory. Group the output into these categories:

> 1. Hard Skills (Technical & Domain-specific)

> 2. Soft Skills (Leadership, Communication, Strategy)

> 3. Appreciating Skills (Skills from my list that are highly transferable and growing in market demand)

> 4. Aging Skills (Skills from my list that are likely becoming commoditized or less critical)

Do not invent market statistics or quote salary data. Base your 'Appreciating vs. Aging' analysis purely on logical structural shifts in the modern workplace. Frame the output so I can use these exact terms on a future résumé.

MY DAILY TASKS:

\[List everything you do. Include meetings, tools, recurring problems, and ad-hoc responsibilities.\]

How the AI reads this prompt

“Act as an executive recruiter and career strategist.”
This specific role pairing ensures the model doesn't just read your list literally. An executive recruiter looks for transferable value, while a strategist looks at the long-term viability of your skill set, giving you a dual-lens analysis.
“Group the output into these categories...”
If left unconstrained, the AI will just give you a bulleted list of buzzwords. By forcing these specific four categories, you ensure the output is structured for immediate use (Hard/Soft) and strategic awareness (Appreciating/Aging).
“Do not invent market statistics or quote salary data. Base your 'Appreciating vs. Aging' analysis purely on logical structural shifts...”
This is a critical guardrail. AIs hallucinate labor statistics frequently. This forces the model to rely on its broad knowledge of structural industry changes (like automation replacing manual data entry) rather than inventing fake job-growth percentages.
“MY DAILY TASKS: \[List everything you do...\]”
This separates your raw, messy input from the structured instructions, allowing you to brain-dump without filtering yourself.

Practical examples from different industries

The Identity Designer

A designer with 10 years of experience running their own entrepreneurship venture might list tasks like "chasing client invoices," "setting up typography guidelines," and "explaining why a logo costs what it does." The AI translates this into market terms: "Stakeholder Management," "Brand Architecture Development," and "Client Acquisition." It highlights "Brand Architecture" as an appreciating skill and "manual invoice tracking" as an aging skill. The Retail Manager A retail manager lists "dealing with angry customers," "making the schedule," and "counting the drawer." The AI translates this into "Conflict Resolution & De-escalation," "Workforce Allocation," and "Cash Flow Reconciliation." This instantly elevates the manager's perception of their own experience and prepares them for a pivot to operations or corporate HR.

Creative use case ideas

> 1. Returning to the workforce: A stay-at-home parent lists managing family schedules, budgeting, and organizing community events. The AI translates these into "Logistics Coordination," "Financial Planning," and "Event Management." > 2. Translating military experience: A veteran lists their daily operational duties, and the AI converts the military terminology into civilian corporate equivalents. > 3. Pre-performance review planning: An employed professional uses this to translate their year of ad-hoc projects into formal, high-value corporate language to justify a promotion.

Adaptability tips

If you are looking to pivot to a completely new industry, add this sentence to the prompt: "I am targeting a pivot into \[Target Industry\]. Highlight which of my existing skills are most transferable to that specific field."

Pro tips

If you use a local AI framework, load your past three years of performance reviews and project post-mortems into your Cowork folder. Instead of manually typing your daily tasks, instruct the AI to read those local files and extract your skills directly from your documented history.

Prerequisites

You need a rough, unfiltered list of what you actually do. Open a blank document for three days and just jot down every task you complete, no matter how small.

Required tools

Any modern conversational AI.

Frequently asked questions

What if the AI lists an 'Aging Skill' that is my favorite part of the job?

The AI is analyzing market trends, not personal fulfillment. If your favorite task is aging out of market demand, that is crucial information. It means you shouldn't build your entire next career move around it, but you can certainly keep it as a niche specialty or a hobby. Will this prompt write my résumé for me? No. This series operates on the rule: AI behind the scenes, you on the page. This prompt gives you the ingredients and the correct market vocabulary. You will still need to construct the actual bullet points using your own specific metrics and achievements in a later step. How specific do I need to be in my task list? More detail is better. "I use Excel" is weak. "I build pivot tables to track weekly supply chain delays and present them to the VP" gives the AI enough context to translate the task into "Data Visualization & Executive Reporting."

Recommended follow-up prompts

Once you have your skills translated, you can use these exact terms to research market compensation ranges in your area. Next week (Week 2), we will use this skill inventory to generate targeted role profiles you might not have considered.

Tags and categories

Tags:

skill translation, resume prep, market value, career pivot Categories: Job Search Series, Professional Branding

Citations

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03
AdvancedPrompt 3 of 3

The Complete Stay-vs-Go Decision Framework

Build a financial and emotional baseline to make your final decision.

Leaving a job is a massive financial and logistical transaction, yet people often make the call based on a bad Tuesday. Leaving mid-year means walking away from unvested equity, prorated bonuses, and accumulated PTO. Searching without a timeline means the process can drag on for a year, bleeding your energy dry. This prompt acts as your private analyst, forcing you to calculate your fully loaded compensation and your financial runway. It organizes the messy, emotional variables into a rigid framework, resulting in a single deliverable: a written decision memo.

Why this matters now

Before you apply for a single role, you must know your baseline. If you don't know exactly what you are walking away from, you cannot effectively negotiate your next offer. This prompt forces you to establish the "walk-away" number and the "stay-until" date right now, protecting you from taking a pay cut out of desperation later.

The prompt — copy and paste this

Act as a structured interviewer and financial career analyst. I need to make a final 'Stay, Grow in Place, or Go' decision, and I need to document my baseline. We are going to build a decision memo.

Do not give me a verdict. Do not invent salary data. Your job is to interview me, organize my data, and output a structured framework.

Step 1: Ask me to provide my fully loaded current compensation (Base, expected bonus, 401k match, health premium coverage, unvested equity, and PTO value). Wait for my answer.

Step 2: Ask me to provide my savings runway (how many months I can survive a search if I quit today or am laid off). Wait for my answer.

Step 3: Ask me to summarize my emotional/career friction (the 'why'). Wait for my answer.

After I have answered all three steps, synthesize my inputs into a formal 'Decision Memo' formatted with these sections:

* Situation Overview

* Fully Loaded Compensation Baseline (The number my next role must beat)

* Risk & Runway Analysis

* The Options Scored (Stay, Grow in Place, Go)

* My Required Action & Timeline

Begin by asking me the Step 1 question.

How the AI reads this prompt

“Act as a structured interviewer and financial career analyst.”
This prevents the AI from just dumping a blank template on you. By assigning it the role of an interviewer, it knows to guide you through a sequential process rather than asking for everything at once.
“Do not give me a verdict. Do not invent salary data.”
This is the core contract of the prompt. AI models cannot see live labor-market data and should never give financial advice. This constraint ensures the AI only processes the numbers you provide and doesn't tell you to quit your job based on a hallucinated statistic.
“Step 1... Wait for my answer. Step 2... Wait for my answer.”
This is a pacing mechanism. Without "Wait for my answer," the AI will ask all the questions and then immediately try to guess the answers or generate a placeholder memo. Forcing a sequential interview ensures accurate data collection.
“After I have answered all three steps, synthesize my inputs into a formal 'Decision Memo'...”
This defines the final deliverable. You aren't just having a chat; you are building an artifact. The defined sections ensure the memo is comprehensive and heavily weighted toward the financial realities of the transition.

Practical examples from different industries

The Tech Enterprise Worker

A Senior Cybersecurity Incident Responder considers leaving due to on-call fatigue. During the AI interview, they calculate their base salary, but when prompted for fully loaded comp, they realize their corporate ESPP (Employee Stock Purchase Plan) and premium healthcare coverage add 35% to their base. The memo reveals that leaving mid-year costs them $40,000 in unvested RSUs, shifting their decision to "Grow in Place" for six months while preparing a strategic exit after the vest date. The Freelance Consultant A freelance designer is debating returning to a full-time corporate role. They input their average monthly retainer income and their self-funded healthcare costs. The AI structures the memo, making it painfully clear that their "fully loaded" freelance compensation is actually lower than a mid-level corporate role when benefits are factored in, turning their "Stay or Go" decision into a clear mandate to "Go" and begin a search.

Creative use case ideas

> 1. Relocating for family reasons: Use the framework to calculate the hidden costs of moving across the country, comparing the fully loaded compensation of your current local job against the potential costs and runway needed for a remote job search. > 2. Evaluating an internal transfer: Treat a move to a different department like a new job search. Calculate if the new role's lack of a bonus structure makes the horizontal move a hidden pay cut. > 3. Deciding to go back to school: Compare the opportunity cost of leaving the workforce (lost loaded compensation) against the runway you have saved for tuition and living expenses.

Adaptability tips

If you have already been laid off, skip Step 1 and Step 3 in your mind. Tell the AI: "I was laid off. Skip Step 1 and 3\. Let's focus on Step 2 (Runway) and build a search timeline based strictly on my financial constraints."

Pro tips

Export the final Decision Memo as a Markdown file and save it in your local Cowork directory. Set a calendar reminder for three months from today to open that specific file. Re-reading a structured, logic-based memo you wrote to yourself is the best defense against cold feet or search fatigue.

Prerequisites

You need access to your pay stubs, your benefits portal, and a rough idea of your monthly expenses. Do not guess your 401k match or health premiums; look them up.

Required tools

A conversational AI that handles multi-step sequential logic well (Claude 3.5 Sonnet or ChatGPT-4o).

Frequently asked questions

Is the AI storing my financial data?

If you are using a standard web interface, assume your data is being used for training unless you have explicitly opted out. Never use your real company name or exact bank account numbers. Round your numbers (e.g., "$120k" instead of "$121,452") and use a local desktop framework if privacy is a primary concern. Why calculate 'fully loaded' compensation instead of just my salary? Because recruiters will try to anchor your new offer to your old base salary. If you leave a job with a 6% 401k match for a job with a 0% match, taking the same base salary is actually a pay cut. You must know your fully loaded number to negotiate properly. What happens if the AI tries to skip a step? Sometimes the AI gets eager and asks all three questions at once. If that happens, just reply: "Let's do this one step at a time. Here is the answer to Step 1." It will correct its pacing.

Recommended follow-up prompts

Save this Decision Memo carefully. In Week 7, we will use your Fully Loaded Compensation Baseline to anchor your negotiation strategy, and in Week 8, we will use the criteria you established today to build your final offer matrix.

Tags and categories

Tags:

decision memo, compensation baseline, job search timeline, financial runway Categories: Job Search Series, Strategy & Planning

Citations

NOT APPLICABLE

Which of the three should you use?

The Beginner prompt is your emotional anchor; it cuts through the noise of a bad month to help you diagnose what is fundamentally broken. It is the best starting point if you are feeling overwhelmed and just need clarity on whether your frustration is temporary or structural. The Intermediate prompt is your market translator. It takes the internal reality of your daily work and converts it into the external currency of the job market. You should use this prompt once you have decided that a move is possible, but before you attempt to write a single line of a résumé or LinkedIn profile. The Advanced prompt is the heavy lifting. It requires actual data gathering and forces you to confront the financial realities of leaving. It is designed for the professional who is ready to make a strategic choice and needs a documented baseline to hold themselves accountable. Used together, these three prompts take you from a vague sense of dissatisfaction to a documented, financially sound decision and a timeline for action.

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AI Showdown: Three Takes on “Should I Even Be Job Searching?”

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The Career Signal Check: Is It the Job, or Is It This Month?