Most of the founders and leaders I work with are looking for certainty.
They want more data.
More validation.
I understand that. Certainty feels like solid ground.
But here’s what I’ve learned after years of working with people who build things: the ones who wait for certainty are still waiting. Not because they’re weak or fearful – but because the sign they’re looking for doesn’t exist.
In year two of Gotcha Covered, the international wholesale linens company my partner and I built and exited, Tempur-Pedic came to us needing sheets for a national promotion. There was one problem. At that time, we only made pillowcases specifically for their memory foam pillows.
My partner and I freaked out a bit – and said yes anyway.
We both knew we couldn’t grow a company selling pillowcases exclusively. This was our chance.
We committed to producing sheets for the first time.
No guarantee of the outcome. No roadmap for how to do it.
The promotion flopped. We were left with a warehouse full of unsold sheets.
And then something shifted. Instead of a liability we saw an asset. Those sheets became the foundation of an entirely new product line – one that eventually became our number one seller.
A failed promotion handed us our next chapter.
That experience is where I started to understand that not all certainty is the same.
What looks like certainty when you’re starting out is something else entirely.
It’s really clarity – knowing what you want and being willing to move before you’re ready.
Not certainty about the how or the outcome. Just a yes.
What feels like certainty after years of success is something different. It’s the moment you stop questioning what you already know – and start assuming that what worked before will work again.
Adam Grant calls this out in Think Again – the more successful people become, the more they rely on what has already worked rather than questioning whether it still applies.
Success doesn’t just bring confidence. It often replaces curiosity with conviction.
And most people don’t notice it happening.
What I’ve learned – from building something from nothing and watching others do the same – is that the yes has to come before the how.
That’s never felt comfortable. It’s always been worth it.
Which kind of certainty is running you right now?
The kind that’s pulling you toward something new – uncomfortable, uncharted, alive with possibility?
Or the kind that’s keeping you exactly where you are, protected by everything you already know?
Both feel like solid ground. Only one of them is moving forward.
Until next time, Margalit