When to Let Go and When to Dig In

Howdy! In today’s blog, I want to talk about something almost every founder will encounter, but not enough of us have spoken about honestly: when to pivot and when to push through.

It’s almost guaranteed that when you’re building something, there will come a point where the path forward gets muddy.

You might hit a plateau.
Or lose traction.
Or realize you’re spending more time trying to force momentum than create it.

It’s in these types of moments where you’ll ask yourself:
Should I keep going? Or is it time to move on?

Pushing through isn’t always the answer.

But pivoting is not necessarily the answer, either. 

I’ve had ideas I believed in that never took off. I’ve launched products that were too early, too late, or just… not enough.

I’ve also had projects that looked shaky at first but, with time and persistence, became some of the best decisions I’ve ever made.

The difference wasn’t luck. The difference always came down to one thing: opportunity cost.

Here’s how I think about it:

At any given time, I can only focus on two things. Max. Not ten. Not five. Two.

That means every “yes” I give is a “no” to something else.

So when I’m deciding whether to pivot or push through, I ask:

Is this still the best use of my time, energy, and capital?

Is this idea still aligned with what matters most?

Or am I clinging to it because I don’t want to be seen as “quitting”?

Here’s what I’ve learned:

You push through when:

The problem is real—but the timing or approach needs adjustment

The core mission still fuels you

You’re evolving, not just treading water

You pivot when:

You’re spending more time maintaining than building

The opportunity cost is too high

You’re afraid to let go because of how it might look

At the end of the day, you need to be honest to yourself, and to your team. Sometimes the most strategic thing you can do… is stop.

Letting go of what’s not working creates space for what will.

Important question to ask yourself this week:

Where in your business are you holding on too tightly? What might open up if you made room for something new?