When Scaling Your Firm, Mindset Matters

Collective 54’s Greg Alexander frames the lifecycle of a professional services firm as a 15-year journey: 5 years of growth, 5 years of scale, and 5 years to exit. If I had followed that path, I’d be on my third company by now.

But my firm, Corporate Insight, is 33 years old. My dad founded it in 1992, and I joined him in 1997. For many of those years, it was run largely as a lifestyle business. That began to change about 10 years ago when my dad stepped back and I fully stepped into the CEO role.

That was when I saw how much more potential the firm had. I didn’t use the term “scaling” back then — Collective 54 didn’t yet exist — but that’s exactly what I set out to do. I told the team, “Let’s step on the gas and take it to the next level.” What I didn’t realize was how hard that would be — not just operationally, but mentally and emotionally.

Like any business, we’ve faced our share of challenges — growing pains, unexpected crises, even a global pandemic. But the biggest obstacle I’ve had to overcome wasn’t market conditions or competition. It was my mindset.

Business owners are naturally optimistic. We gather and talk about how great things are — even when they’re not. We’re competitive. We don’t want to look like we’re behind our peers, making bad decisions, or missing our targets. On the outside, I was projecting confidence. But on the inside, I was beating myself up.

Every time we hit headwinds, I’d question myself: Am I making the right decisions?
I’d think about the responsibility I carry and worry that I might be falling short.

Hearing the success stories from other Collective 54 members or business owners I admire, I’d sometimes wonder, Why haven’t I figured it out yet?

At times, the pressure felt overwhelming — I’d get stuck in indecision, overanalyzing every move. It was exhausting.

But recognizing those moments for what they were — just moments — helped me step back, reset, and keep moving forward.

Then about a month ago, I was watching one of Greg’s Boutique in Theory webinars when he said something that stuck with me:
“Scaling is hard.”

At first, it seemed obvious. But the words echoed in my head. They reminded me that this process — this struggle — is normal. That I wasn’t failing. I was scaling. And scaling is hard.

That moment helped me zoom out, reframe where I was, and give myself something I hadn’t offered in a long time: grace.

In the weeks since, I’ve started to understand how deeply mindset shapes the experience of scaling a business. And how the right mindset can create not only better outcomes — but also freedom and peace of mind.

Here are a few things I’ve learned (and continue to re-learn):

• Notice the story you’re telling yourself. We all create internal narratives — about our worth, our competence, our trajectory. When things go wrong, that story can quickly turn destructive: “I’m not cut out for this.” “I’m screwing everything up.” Start catching those thoughts. Ask: Would I say this to a friend in the same position? Probably not. Rewrite your internal story to reflect truth and perspective — not fear or perfectionism.
• Comparison is a trap. It’s easy to measure yourself against the highlight reels of others — especially in groups like Collective 54, where the success stories are inspiring but sometimes intimidating. But no one shares the full picture, and every firm has a different context, team, client base, and market. Stay focused on your Progress isn’t linear — and it certainly isn’t universal.
• Be kind to yourself. Scaling is a long game. You will make mistakes. You will have off weeks, bad hires, underwhelming launches, and tough quarters. Self-compassion isn’t weakness; it’s fuel for resilience. The more grace you give yourself, the more stamina you’ll have to keep going.
• Celebrate progress, not just milestones. It’s tempting to delay satisfaction until you hit a big goal — a revenue target, a headcount, a liquidity event. But if you don’t learn to appreciate the small wins, you’ll burn out before you get there. Look back every so often and say, We’ve come a long way.
• Don’t isolate. When things feel heavy, the instinct is to retreat. But those are the moments when you most need connection — with peers, mentors, even your team. Vulnerability is hard, but it’s what unlocks real conversations and unexpected support. You’re not the only one feeling stuck or overwhelmed — and you don’t have to figure it out alone.

  Collective 54 has been a great community for this. I’ve made it a point recently to reach out and connect with peers I’ve met — and every time, I walk away feeling less alone and more energized.

• Lead yourself before you lead others. Your mindset sets the tone. If you’re operating from fear or frustration, it seeps into the culture — whether you intend it or not. I was reminded of this recently during a tough day when I walked out of my office visibly stressed. My Integrator gently pointed out that my mood was rippling through the team.

  That was a wake-up call. Even when you don’t have all the answers, showing up with calm, curiosity, and confidence can be powerful. That energy is contagious — in the best way.

Final thought:

Scaling isn’t a straight line. It’s a test — of strategy, leadership, and mindset. But when you start with the right mindset, the rest becomes more manageable. Give yourself grace. Keep showing up. And know that if it feels hard… you’re probably doing it right.