The Stay-or-Go Decision Framework

You're not lazy. You're not ungrateful. You're facing a decision that will shape the next chapter of your career—and you deserve a clear way to think about it.

Not sure where you stand? Take the Stay-or-Go Calculator — a 2-minute quiz that scores your situation and gives you a personalized recommendation.

The Problem With How We Usually Make This Decision

Most people spend months or years stuck in a loop: some days convinced they should leave, other days talking themselves into staying. They poll friends, read job listings at 2 AM, and oscillate between panic and paralysis.

This isn't a character flaw—it's a structural problem. The stay-or-go decision is genuinely hard because:

1. The information is incomplete. You can't know what the new job will actually be like until you're in it.
2. The emotions are loud. A bad week can make everything feel unbearable; a good week can make you forget why you wanted to leave.
3. The stakes feel enormous. And they are—your income, your identity, your relationships are all on the line.

What you need isn't more courage or less fear. You need a framework that separates signal from noise.

The Stay-or-Go Framework

This framework breaks the decision into three distinct questions. Answer them honestly, and the right path usually becomes clear.

Question 1: Is the core problem fixable—and are you willing to do the work?

Before you start job searching, you need to know whether the thing that's making you unhappy is something that could change without you leaving.

• A specific difficult relationship with your manager (often improvable with direct conversation)
• Unclear expectations or scope (can be negotiated)
• Insufficient resources or headcount (sometimes solvable with a business case)
• Missing skills or experience (often addressable with training or stretch projects)
• Boredom from having mastered your role (might be solved with a scope expansion or internal move)

• Fundamental values mismatch with the company
• Industry decline or company trajectory you can't influence
• A culture of fear, blame, or dishonesty
• Systemic underinvestment in your function
• Your manager's manager is the problem

The key question isn't just "is it fixable?" but "am I willing to invest 3-6 months trying to fix it?" If not, you have your answer.

Question 2: What does staying actually cost?

People underestimate the cost of staying because it feels like the "safe" choice. It isn't. Staying has compounding costs:

• Skills atrophy if you're not learning
• Your network stagnates if you're not moving
• Market value declines if your title or compensation lags
• You miss windows of opportunity (certain roles, certain companies, certain markets)

• Chronic stress affects your health and relationships
• Cynicism seeps into how you show up
• You model stuckness for your team or your kids
• The opportunity cost of your limited energy

The question isn't "am I unhappy enough to leave?" It's "what is the cost of another year of this—and is that cost acceptable?"

For many people, the honest answer is: the cost of staying is higher than the cost of the uncertainty of leaving.

Question 3: What would make you confident enough to decide?

You will never have perfect information. The goal isn't certainty—it's having enough clarity that you can commit to a path and stop second-guessing.

• You've had at least one honest conversation with your manager about what would need to change
• You've tested the external market enough to know your realistic options
• You've identified the 2-3 things that matter most to you in your next role
• You've talked through the decision with someone who isn't emotionally invested in the outcome
• You've set a deadline for deciding (without one, you'll loop forever)

If you haven't done these things, you're not ready to decide—you're ready to gather information.

The Three Biggest Mistakes People Make

Mistake 1: Waiting for the "right time"

There's never a perfect time to leave a job. There's always a project to finish, a bonus to vest, a transition to manage. The right time is when you've done your due diligence and the cost of staying exceeds the cost of uncertainty.

Waiting for the right time is often code for "I'm scared to make the leap." Which is understandable—but it's not a strategy.

Mistake 2: Making the decision alone

The stay-or-go decision involves identity, money, and relationships. No one thinks clearly about all three at once. You need at least one person who can help you separate what's true from what feels true.

This isn't about getting permission or being told what to do. It's about having someone ask the questions you're avoiding.

Mistake 3: Optimizing for the wrong thing

Many people focus on salary or title when those aren't actually their biggest sources of dissatisfaction. They take a higher-paying job that has the same problems as the one they left.

Before you start looking, get clear on what's actually broken and what success would look like in the next role. Usually it's something like: "a manager who advocates for me," "the ability to make real decisions," or "a product people actually want."

A Real Example

The situation: A Director of Product at a mid-stage startup. Two years in. Frustrated because the CEO kept overriding product decisions and the roadmap felt reactive rather than strategic. Considered leaving multiple times but worried about looking like a "job hopper" (this was her third role in 5 years).

The framework applied:

1. Is it fixable? She hadn't had a direct conversation with the CEO about decision-making authority. She assumed it would be dismissed. We worked on a specific ask: "I need to own the roadmap for [specific initiative] end-to-end, with weekly check-ins rather than daily overrides. If that works, we expand it."

1. What's the cost of staying? She'd stopped learning. Her best PMs had left. She was spending 40% of her energy managing around the CEO instead of building. At this rate, she'd be less hireable in a year than she was now.

1. What would make her confident enough? She needed to have the conversation with the CEO and see if he was willing to try a different dynamic. And she needed to know what her external options looked like—she'd been heads-down for two years and had no idea.

What happened: She had the conversation. The CEO said all the right things but nothing changed after 6 weeks. Armed with that clarity—she'd done the work to fix it and it hadn't worked—she started looking. She had an offer within 10 weeks at a company where the CPO explicitly structured the role to give her the autonomy she needed.

She didn't leave because she was unhappy. She left because she'd done the analysis and the math was clear.

What You'll Walk Away With

When you work through this decision systematically—whether on your own or with a coach—you end up with:

• A clear recommendation: stay, go, or pivot internally, with the reasoning laid out
• A risk map: what could go wrong with either choice, and how you'd handle it
• Conversation scripts: exactly what to say to your boss, your partner, your recruiter
• A 14-day action plan: concrete next steps, not vague intentions

The goal isn't to make the "right" decision. It's to make a good decision well—so that whatever happens next, you don't waste energy second-guessing yourself.

A Note on Timing

If you're reading this, you've probably been thinking about this for a while. The question isn't whether you're ready to decide. It's whether you're ready to stop circling and start moving.

The framework above works. The mistakes are common but avoidable. The only thing you can't get back is time.

Ready for Personalized Guidance?

Every situation is different. If you want help thinking through yours—with someone who's seen hundreds of similar cases—consider working with a coach.

• A structured conversation to clarify your situation
• Frameworks tailored to your specific circumstances
• Scripts you can actually use
• A clear action plan

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