This Might Not Work – A Manifesto For Modern Builders

“I’m not sure.”

How often have I said this to myself?
How often have I said it out loud?

Not being sure is the place where I live.

Am I right about the concept of “vibe content” (not sure… and the LinkedIn comments provide no additional guidance).
There’s a strange kind of panic that sets in when you’re not 100% sure what you’re doing.
Not clueless… just uncertain… unsteady.

I remember showing ThinkersOne to a very prominent Thinker, and they didn’t see the value. 

I reiterated back to them that they might be right.
This might not work… we’re not sure.
That this is the job of an entrepreneur to potentially… maybe… be right.
It’s like walking through fog but everyone else seems to have a map you didn’t get.

It happens to me more than I care to admit… mid-project… mid-decision… mid-conversation… mid-night.

But something Vicki Tan said in our conversation stuck with me…
She believes the best ideas come from that place… the not-sure place.
Not being sure isn’t a weakness… it’s a signal.
It’s the sound of something real taking shape… a form of tension… of ambiguity… of the space between what we know and what we’re about to discover… or create.

Business culture has fetishized certainty.

Make the plan… stick to the plan… move fast… correct course and don’t look back.
But the most meaningful work (the most honest ideas) don’t arrive in a flash of certainty.
They emerge slowly… they simmer… they detour.
They show up as fragments, doubts, scribbles and half-sentences you almost didn’t write down (or share in spaces like this).
And still… most of us apologize for them (I might be doing that right now).

We soften our language… we bury the unpolished stuff…

We try to sound thoughtful when maybe we should just be thinking… out loud… in the open.
It’s not easy to do.
Don’t believe me (scroll through the comments… it takes thick skin).

I’ve been sitting with this question all week:

What if not being sure is the point?
What if that friction you’re feeling (that hesitation to think out loud) isn’t a failure of clarity, but the very condition that makes clarity future-possible?

I needed that reminder… maybe you did too?

(Vicki’s a brilliant designer and Thinker. We talked about her book, Ask This Book A Question, on this week’s episode of Six Pixels of Separation – The ThinkersOne Podcast).

Before you go… ThinkersOne is a new way for organizations to buy bite-sized and personalized thought leadership video content (live and recorded) from the best Thinkers in the world. If you’re looking to add excitement and big smarts to your meetings, corporate events, company off-sites, “lunch & learns” and beyond, check it out.

 •  0 comments  •  flag
Share on Twitter
Published on July 28, 2025 13:36
No comments have been added yet.


Six Pixels of Separation

Mitch Joel
Insights on brands, consumers and technology. A focus on business books and non-fiction authors.
Follow Mitch Joel's blog with rss.