Questions I Ask Before Saying Yes
Most bad decisions don’t come from choosing the wrong thing.
They come from saying yes too fast.
Founders are wired for motion. We hate standing still. So when an opportunity shows up, the instinct is to jump. The story we tell ourselves is that we’re chasing growth. But more often, we’re chasing distraction.
I’ve done it too many times. So I needed to build a framework for how to say yes.
The messy middle of “what’s next”
When I sold my business, I jumped straight into working for my acquirer. It was a different world—going from building something of my own to watching a giant machine get even bigger. It was exciting, it was humbling, and I learned a lot.
But when that chapter ended, my default kicked in: What’s next?
Do I start from scratch again? Do I buy and reshape an existing business? Do I join forces with someone else?
If you’ve built and sold something, you know this feeling. Post-exit, your brain is wired to chase the next mountain. You start sketching out ideas, running spreadsheets, taking meetings. And every shiny thing looks like “the one.”
Here’s the danger: when you’re restless, it’s easy to confuse motion with meaning. You say yes because you can. Not because you should. And the wrong yes costs you more than money. It costs you presence, energy, and the parts of life that actually matter.
That’s why I built a set of filters. Simple questions I force myself to ask before I commit. They don’t guarantee the perfect decision, but they’ve saved me from plenty of bad ones.
The five filters
1. Does this line up with my values?
If it trades away family, health, or integrity, it’s too expensive. Shiny doesn’t equal aligned.
Ask: Am I compromising who I say I want to be? If I explained this choice to my kids ten years from now, would I be proud of the trade-off?
2. Is the timing right?
The same deal can be perfect in one season and toxic in another. Right now, my kids are young. They still want me around. My wife and I are at our best when we keep time together consistent.
Ask: Does this fit the life I actually have—not the life I imagine? What will I never get back if I say yes right now?
3. Have I really weighed the upside and downside?
I can drown myself in research (I’m an expert at this, unfortunately). Keep every option alive. Pretend that one more spreadsheet will unlock clarity. But clarity usually comes from a conversation with someone I trust—or from stepping away long enough to see the picture differently.
Ask: Am I gathering information just to delay the call? What’s the worst-case scenario, and can I live with it?
4. Does this fit the way I’m wired?
I know the chaos I can handle: flexible, remote, routine-friendly. I also know the chaos that breaks me: retail hours, endless travel, unpredictable schedules. It’s not about avoiding hard work. It’s about choosing the kind of hard work that fuels me instead of drains me.
Ask: Can I keep my core rhythms—workouts, breakfasts with my kids, dinners with my wife? Or will this grind me down?
5. Have I done the post-mortem in advance?
My favorite filter. Imagine it flops. Two years gone. No big win. Would I still be glad I tried? If yes, it’s worth it—because the value is in the alignment, the growth, the attempt itself.
Ask: If this fails, will I regret trying, or regret not trying? Will I respect myself more for having gone after it?
My three non-negotiables
At this point, I’ve boiled it down to three.
Protect family hours. Mornings and evenings are sacred.
Keep a routine. Rhythm is how I show up at my best.
Have fun. If I’m not energized by solving hard problems, it’s not worth doing.
These three cut through the noise. They knock out the shiny distractions and leave me with opportunities that actually fit the life I want.
The real risk
Decision-making never feels easy. But it can be clearer.
Ask the right questions. Be brutally honest with the answers.
Because the real risk isn’t missing an opportunity.
The real risk is saying yes to the wrong one.
