What No One Tells You About Pivots

A story about clarity, grief, and what it really takes to change direction.

Everyone loves the pivot story: the startup that changed lanes and struck gold. You know the type:

“We realized the market wasn’t right, so we shifted to something better.”

“We listened to customers, made the switch, and 10x’d growth.”

It sounds clean. Strategic. Like an act of genius.

But what no one tells you is that real pivots feel like grief.

Before the clarity comes the chaos.

I’ve lived through three different pivots that tore through everything we thought we knew.

It didn’t come as a brilliant idea in a strategy session. It came after months of tension, user confusion, stalled numbers, and hard conversations with my co-founders.

We had built something we believed in. We’d spent years on it. Raised thousands of dollars.

But somewhere along the way, the data and the truth started whispering different things.

What we were building, at least in its current form, wasn’t going to work.

Not because we didn’t care.

Not because we weren’t smart.

But because the market had shifted, or we misunderstood something core, or we were just… early.

For one of those times, I still remember clearly, it was because COVID struck, our product had to do with people getting online to have calls with each other, what we didn’t envisage was that our target audience (black professionals) was going to be dealing with something called “Zoom Fatigue.”

And that’s when the real pain sets in.

Pivots don’t start with new ideas.

They start with letting go.

Letting go of the product you loved.

Letting go of your past roadmap.

Letting go of your ego (this is one of the biggest battles you’d have to deal with as a first-time founder).

Sometimes, they also mean letting go of team members.

Or watching a co-founder lose belief.

Or realizing you’ve spent the last 6 months avoiding the truth because it was too painful to admit.

And the worst part? You won’t always be sure the new direction is better.

You’ll be staring at a half-built bridge, wondering if there’s land on the other side.

Every time we’ve had to pivot, it was never really a moment of glory or this insane clarity; it was about taking a hard bite with as much conviction as you can muster. It was a long, murky stretch of half-belief and heavy responsibility.

My last venture was a pivot of a pivot, and guess what: it doesn’t matter.

What I’ve learned is this:

• Pivots are emotional, not just strategic.

  You’re not just changing the business. You’re breaking an identity and trying to rebuild one in real time.

• Pivots test everything.

  Your team’s trust. Your intuition. Investor patience. Your ability to hold tension without flinching.

• The “new direction” won’t always be the right one.

  But not pivoting? That might kill you faster.

• You can pivot too late. Or too early.

  The difference is usually found in painful, clear conversations, not brainstorming.

• Sometimes, pivots break things that can’t be fixed.

  And sometimes, they’re the only thing that lets something better emerge.

If you’re in the middle of one right now…

I see you. I know how disorienting it can be.

You’re probably getting advice from people who only see the surface.

You’re carrying more uncertainty than anyone outside your team realizes.

And you’re probably grieving a version of your dream that didn’t make it.

But here’s the thing:

Just because something didn’t work, doesn’t mean you didn’t.

The courage to pivot isn’t about quitting something.

It’s about choosing to adapt while it still hurts, rather than waiting until it’s too late.

It’s about moving forward, even when the map is blurry, because staying put means sinking.

Final thought:

This might sound cliche at this point, but I’d like to say:

You’re not starting from scratch.

You’re starting from experience.

If you’ve ever pivoted or are considering one now, just know I am rooting for you.

Until next time,

Jephtah