My Yes Addiction
Why I can't say no—and what it's actually costing me
The Yes Addiction
Why I can’t say no — and what it’s actually costing me
My friend Chris Marr runs The Question First Group. He wrote something last week that stopped me mid-scroll.
An opportunity landed on his desk. The kind his company would have said yes to a month earlier, no questions asked. This time, one of the owners turned it down. Wrong fit. Not the niche. Not the direction they’d chosen.
One sentence. And I couldn’t stop thinking about it.
Because I can’t do what that owner did.
I say yes to everything. And I know exactly why.
Today I called my friend Tom. Thirty seconds in, I could hear it — that low-grade burnout hum in his voice. I asked what was going on. He described his week like a man trying to grab six things falling off a shelf at once. Arms everywhere. Nothing caught.
I wasn’t in a position to help him. I was living his week.
That same morning, I’d admitted something to myself. Again. For maybe the tenth time this year.
I can’t say no.
The sabbatical that lasted three weeks
Back in June, I published an essay announcing my summer side-hustle sabbatical. It’s my normal summer break to step back, simplify, breathe.
This one lasted three weeks.
Three genuinely great weeks. Calm. No inbox anxiety. No “just one more opportunity.”
Then I got restless, and restlessness always disguises itself as productivity. So I did what any founder with an addiction to the chase does — I called it “strategic planning” and got back to work.
I looked at where my side-hustle income actually came from. 95% of it traced back to two channels. Two. Out of a dozen things I was spending time on.
The math was obvious: stop touching the other ten. Go all in on the two that work.
So naturally, the next day, I got offered a $5K/month opportunity built entirely on one piece of unrelated content.
I canceled the sabbatical. I said yes.
And within 48 hours, I regretted it.
Regret isn’t about the work. It’s about the mismatch.
Here’s the part that took me two phone calls and an email to actually understand: I didn’t regret the work itself. I regretted being untrue to what I’d previously decided mattered.
The first call was from my friend Todd. He wanted to walk me through his new venture — the one he’s actually passionate about, not the big agency he’s spent a years building. He was lit up in a way I hadn’t heard from him before.
Normally, in our friendship, I’m the one chasing the thing that energizes me — writing, ideas, ownership over my time. Todd’s the empire builder. This time the roles flipped, and it rattled me enough to ask myself why.
Then Tom, days later. Same conversation, different words.
Then Chris’s email hit my inbox. About saying no.
Three signals in a short period, pointing at the same blind spot.
Where the “yes” actually comes from
I know exactly where mine started.
I’ve been laid off multiple times. The last time, our daughter was nine months old. We had zero saved. No side income. No cushion. Just a mortgage and a newborn and a very bad month.
I told myself, never again. And I spent the next decade building like it was still that month — every “no” felt like the version of me standing in that kitchen with an empty bank account.
Here’s the uncomfortable part: we’re not wealthy, but we’re financially secure now. We could absorb a real income gap without blinking.
The threat is gone. The reflex isn’t.
That’s the trap. The behavior outlives the reason for the behavior. You keep running from a fire that’s already out, and you call it ambition.
Saying no is a business decision before it’s a personal one
Chris’s co-owner didn’t turn down that opportunity because he was disciplined. He turned it down because he knew, with precision, what his business was and wasn’t — and he trusted that clarity more than the dollar signs in front of him.
That’s not a personality trait. It’s a filter. And you can build one even if, like me, your default setting is yes.
Before I say yes to anything now, I’m forcing myself through three questions:
Does this touch one of the channels that actually drives results — or does it just feel productive? Doing something creative because I want to is one think. Doing something just to feel productive is a yes that should be a no.
Would I have said yes to this a month ago, before I knew what I know now — or am I only saying yes because it showed up fast?
Am I solving a real problem, or am I still responding to a threat that isn’t there anymore? I love this question in particular. It makes me think of my MMA days. When judging between an opponent’s faints and real attacks was second nature.
If I’d asked myself those three questions before that $5K/month call, I already know the answer.
The personal reasons you can’t say no and the professional reasons you keep taking the wrong prospects aren’t different conversations. They’re the same conversation, wearing different clothes.
So — what old threat are you still running from that isn’t actually chasing you anymore?
P.S. This post may not feel GTM advice. But it is. Look deep. What clients are you saying yes to where they aren’t your ICP?