Growing pains

Hello my friend,

From $25k/month to $3M/month in less than three years.

That's the rocket ship I've been on at beehiiv for nearly three years now. It's been incredible, but there’s something about this nobody tells you in these situations. The company you ‘grew up’ with isn’t company you work for anymore. At least I’m feeling that way.

About three years ago, we were 10 people in a room working absurdly hard for what seemed like endless days and nights. We'd huddle up for last-minute fixes, swarm Twitter when users tagged us, and literally sit together grinding through thousands of emails to find and fix issues. When someone asked how we did it, my colleague Daniel Berk put it best:

"We all worked like complete psychopaths."

It was chaotic. It was exhausting. And I loved every minute of it. I know I sound like a total nerd, but it’s true.

Now we're 90+ people building processes, hierarchies, and strategic planning. People work hard, but we can't all be everywhere anymore.

The wild west days are over, and honestly? I miss them.

But missing how things used to be can kill your career if you're not careful.

Between AI transforming work, companies scaling faster than ever, and all the change, most of us are facing some version of this. The skills that got you here might not get you to the next stage of your career. The company culture you thrived in might be evolving past you.

Handle the transition badly, and you become the person longing for "the good old days" while everyone else moves forward. Handle it well, and these growing pains become your biggest career accelerator.

So today, let's talk about adapting when things you loved about work change, and how to thrive instead of just survive the transition.

The pains nobody talks about

Here's what's hard to admit: I really struggle with and often resist the new processes.

When I see a Slack thread with 15 people debating something we used to decide in 30 seconds, I find myself wanting to just handle it the old way. When there's an issue affecting users and I have to "follow the proper channels" instead of just fixing it right away, it feels inefficient.

I've caught myself saying things like "we decided that (more or less) randomly, why can’t we just change it now?" or "this would have taken us five minutes before." It’s not a good look. And it’s hard to deal with potentially being that guy that’s stuck in the past while the company’s trying to move forward.

When companies change this fast, it can feel like saying goodbye to a version of the company that meant a lot and was a big part of my life and career. Statistically, we probably spend more time at work than with our friends over a lifetime. It’s hard to say goodbye.

There was a time when I knew every customer by name. When a single Slack message could rally the entire company. When my opinion mattered on everything because there were only 10 of us.

Now? I'm one voice among 90+. My style of being scrappy, moving fast, wearing every hat isn’t necessarily as valuable anymore. The company needs different things now: systems, processes, specialization.

And that's terrifying in many ways. Does it mean I’m starting from step 1 again? No, but it feels freaky when to me in general. What if I'm not good as good a fit when we’re 90 people compared when we were 10?

I’ve reflected on all this a lot. Whether your company is changing because it’s growing, or because leadership wants to go through ‘change management,’ work is a big part of a person’s life and change in a big part of life can be tricky.

The real cost of fighting change

Over the past few weeks, I've made some mistakes that all trace back to one thing: trying to work like it's still the wild west when it's not.

A "simple" update actually had third and fourth-degree impacts I missed because we rushed it when it needed more thought. I said yes to changes I should have said no to because I was thinking like a 10-person company, not a 90+ person one.

But here's the kicker: these weren't just my mistakes. They became everyone's problem.

One bug that used to affect 300 users now affects 3,000. When we work in isolation, it takes 20 people to clean up a mess an extra hour could have avoided. Attachment to the old ways was creating real friction for people who never experienced them.

That's when it hit me: the company that got us to $3M/month isn't the company that'll get us to $30M/month. And if I keep trying to be the employee from three years ago, I'll become a liability instead of an asset.

So, how do I find my place in this new version of the company I helped build?

Finding a new way to matter

After a few weeks of bruising my ego (and probably pissing off my teammates), I reflected HARD. I realized I had two choices: keep mourning what we used to be, or figure out how to be valuable in what we're becoming.

I chose the latter. Here's what's working:

1. Hunt for the gaps that nobody owns

Growing companies always have gaps. Things that fall between departments, processes that don't exist yet, problems everyone assumes someone else is handling.

Instead of trying to recreate my old role, I started looking for these gaps. What's not getting done that could have a massive impact if someone just... did it?

Our CEO helped me with this a lot. Last week, I noticed we were getting bug reports across five different channels—Slack, email, customer support tickets, the in-app-reporting, even Twitter DMs. We have people on this, but we weren’t necessarily connecting the dots to see patterns or prioritize fixes.

So I’ve been collecting every single bug report, organizing them by severity and frequency, writing up impact reports, and planning out fixes for the engineering team. It's a few extra hours of work, but it's having a massive impact because bugs are critical in a software company.

Seeking out specific ways to add value that leverage both my context and the new tools available (AI helps enormously with organizing and analyzing all this data) is key.

If you’re in a growing company, I can’t recommend this enough. It’ll be tough at first, but the long-term improvements are massive.

2. Become the bridge between old and new

One advantage of being here since the early days is understanding both versions of the company.

I know why we made certain decisions when we were small. I remember the context behind features that seem random to new employees. I can translate between "how we used to do things" and "how we need to do things now."

This means over-communicating everything, but strategically. In Slack, I try to share not just what's happening, but why it matters and how it connects to other parts of the business:

• Connecting a churning users’ history (product analytics, support tickets, etc) to how we can reduce churn.

• When someone suggests a change, I provide historical context about what we've tried before

• When new processes feel frustrating, I help explain the problems they're solving citing how chaotic it used to be

It's not about being the company historian. It's about helping everyone make better decisions by understanding the full picture.

3. Help others navigate their own transitions

Realistically, I’m probably not the only one struggling with change. Instead of just delegating work I don't want to do, I've started deliberately working with people who want to grow into areas where I have experience (product).

When someone in customer success expressed interest in product work, I offered to walk them through how I prioritize bug fixes and gather user feedback. When a new hire seemed overwhelmed by our pace, I shared what I learned about managing up in a fast-moving environment.

Helping people level up, if they’re willing, can have massive impacts across the overall business.

Choices in these moments can define a career

How would we replace the energy, closeness, and the feeling that we were that small, powerhouse unit?

Wrong question.

It's not about replacing what we had. It's about building something better with what we have now.

We got to $3M being that scrappy startup that turned on a dime. We’ll get to $30M a month as a systematic, process-driven company that’s built on that scrappy, fast-paced culture.

Now, I’m not a leader in the business. I don’t manage people. My job is to push to make this successful, not just because I have a stake in the business, but because the nerd in me wants to know what it feels like to get to $30M a month.

All I can share is what I’ve learned reflecting on this in the last month. The people who thrive during growing pains aren't the ones who adapt fastest or resist least. They're the ones who find new ways to be indispensable.

When your old style’s not as relevant, you develop a new way. When the company structure changes around you, you build your place in the new architecture. When processes replace instinct, you become the person who bridges both world to keep the great things and fill the gaps.

This applies whether you're at a rocket ship startup, a corporate job being transformed by AI, or anywhere the rules of the game are changing faster than you'd like.

The companies that survive rapid change are the ones with employees who see growing pains as growing opportunities. The employees who advance their careers during transitions are the ones who help their companies navigate them successfully.

Change is still annoying. I still miss the wild west days sometimes. But I'm not the same person who joined a 10-person company three years ago, and that's exactly the point.

The question isn't whether things will keep changing. Change is guaranteed. It’s going to happen whether we like it or not. The question is whether you'll change with them, or get left behind wondering what happened to the good old days.

And if you’re reading this newsletter, I know the choice you’d make. You know mine.

Thanks again for reading!

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