The Stay-or-Go Framework
Before making any decision, separate the fixable from the fundamental. This framework helps you cut through the noise.
Step 1: Name What's Actually Wrong
Write down your top three frustrations. Be specific. "I hate my job" isn't useful. "My manager undermines my decisions in front of the team" is.
Step 2: Test for Fixability
For each frustration, ask:- Has this changed in the last 12 months? (Direction matters)
- Is it within someone's power to fix it?
- Would fixing it require you to become someone you're not?
Step 3: Calculate Your Real Runway
Don't romanticize leaving. Know your numbers:- Months of expenses covered by savings
- How long your job search will realistically take
- What you'd accept vs. what you're hoping for
Step 4: Make the Call
If the problem is fixable and you have the energy to fight for it, stay and fight. If it's fundamental or you're already depleted, start planning your exit. There's no shame in either choice—only in staying stuck.
What This Looks Like in Practice
The Scenario: Alex, a first-time founder who had built a company from zero to $5M ARR, was exhausted. The board wanted to bring in an experienced CEO to scale to the next level. Alex wasn't sure if this was a vote of no confidence or a natural evolution—and whether stepping aside meant failure.
What He Did: Instead of reacting emotionally, Alex created space for clarity:
- He talked to three other founders who had gone through similar transitions
- He worked with an executive coach to separate his identity from the company
- He explored what role, if any, he wanted in the company's next chapter
The Outcome: The conversations revealed that bringing in a scaling CEO was common and often the right move—it wasn't about Alex's abilities, but about matching skills to stage. He negotiated a transition to Chief Product Officer, where he could focus on what he loved (building product) without the CEO responsibilities that drained him.
Two years later, the company hit $20M ARR. Alex was energized again, and glad he didn't let ego drive a reactive exit.
The Lesson: Founder transitions aren't failure—they're evolution. The question is whether you're in the driver's seat of that transition.
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What You'll Walk Away With
Our structured session produces concrete artifacts, not just conversation.
Decision Snapshot A clear-eyed assessment of your current situation—what's true, what's not, and what actually matters for your decision.
Fork Recommendation A specific direction (stay, go, or pivot) with the reasoning behind it, so you understand not just what to do but why.
Risk Map Everything that could go wrong with your chosen path, and how to mitigate each risk before it materializes.
Conversation Scripts Exact language for the hard conversations you need to have—with your boss, your partner, recruiters, or anyone else.
14-Day Action Plan The specific steps to take immediately after our session, so momentum doesn't stall.
30-Day Roadmap The longer-term plan for executing your decision, with milestones and check-in points.
These aren't templates—they're customized to your specific situation, role, and constraints.
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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.
What you get:- A structured conversation to clarify your situation
- Frameworks tailored to your specific circumstances
- Scripts you can actually use
- A clear action plan