Growing Pains

You knew growth wouldn’t be easy. But you didn’t expect it to feel like this.

Your company is bigger than it was a year ago—maybe twice as big, maybe more. And yet, instead of feeling rock-solid, everything feels a little... wobbly. The thrill of acceleration hasn’t disappeared, but it’s been joined by something else: friction.

People are stressed. Processes are cracking. The pace that once felt exhilarating now feels—let’s be honest—a little unsustainable.

Congratulations. You’ve made it to the in-between.

The Messy Middle of Growth

The leap from Acceleration to Maturation isn’t a straight line. It’s a chaotic, awkward transition where your company feels caught between what it was and what it’s becoming. It’s exciting. It’s exhausting. It’s completely normal.

But normal doesn’t mean easy. If you’re feeling the pain, here’s why—and what to do about it.

1. Your Relationships Will Be Tested

Growth applies pressure. And pressure exposes cracks.

The co-founder you once brainstormed with over beers? He might resent the need for structure. The early employees who thrived in the chaos? Some will struggle when it’s time to play by new rules.

Some won’t like the shift. Some won’t make it. And that’s okay.

The companies that survive don’t cling to relationships that no longer serve their future. Growth isn’t just about hiring new people—it’s about knowing when to let go.

2. Time Will Start Playing Tricks on You

One day, you’re moving too slow. The next, everything’s changing too fast.

This phase distorts time. You’ll feel like you’re perpetually five minutes away from leveling up—for years. Small decisions will drag on forever. Crucial systems will take twice as long to implement.

And then, suddenly, it happens.

The companies that make it don’t wait for the transition to feel natural. They prepare before they feel ready.

3. You’re Playing a Different Game Now

You were great at playing the startup game: spotting gaps, taking risks, moving fast.

Bad news: that game is over.

Mature companies don’t win by being scrappy. They win by executing at scale. By making smarter decisions with bigger stakes. That means different skills, different leaders, different mindsets.

Some founders make the transition. Many don’t.

4. “Busy” Isn’t the Same Anymore

In the early days, “busy” meant sprinting between crises. Chasing new ideas. Putting out fires.

Now? That’s a liability.

In this phase, “busy” should mean working on the business, not in it. Strengthening teams. Fixing inefficiencies before they become disasters.

And, maybe hardest of all? Learning to say no. Not every opportunity is worth chasing anymore.

5. Success Will Feel… Boring

Remember when everything felt like a win? Every new hire? Every funding round? Every client deal?

That phase is over.

Mature companies don’t win by chasing highs. They win by delivering—consistently, efficiently, predictably.

And predictability? Doesn’t feel exciting.

This is where companies panic. They assume they’re losing their magic. But real success isn’t about being exciting. It’s about being effective.

Want to win? Get comfortable with consistency. Build systems that repeat success. And don’t mistake stability for stagnation.

6. You Can’t Keep Winging It

In the startup phase, experimentation was a luxury. Pivoting was normal. You were still figuring out who you were.

Not anymore.

Mature companies commit. To a strategy. To an identity. To a way of operating.

That doesn’t mean losing agility. It means gaining clarity.

Because if you don’t commit? The market will decide who you are, for you. And you might not like its answer.

The Hardest Part of Growth

Nobody warns you about this part of the journey.

And here’s the truth: This is where most companies fail. Not because they weren’t smart enough, or talented enough. But because they weren’t prepared for what growth actually demands.

So, ask yourself:

Are you just getting bigger?

Or are you growing up?

Because the companies that survive don’t just scale.

They evolve.