The Hardest Part of Scaling: Letting Go of What Worked
Hustle got you here. Systems will take you the rest of the way.
Everyone wants to build a dream team.
But very few talk about what it actually takes.
Getting started is hard. But scaling? That’s a whole different kind of hard.
What worked in the early days won’t take you where you’re trying to go next.
You have to think like an operator.
And operating is hard.
It’s not just about execution. It’s about trust.
And the twist? You often have to trust new people, not the folks who were in the trenches with you at Day 1.
Not your ride-or-dies from the garage days.
But the people who know how to run systems. Build process. Multiply effort.
They’re not there to prove themselves through grit.
They’re there to build a machine.
And trusting them isn’t easy.
Because it feels like letting go of the past version of yourself that got you here.
But if you want to grow in a meaningful way, you have to change.
You need people who scale.
People who force you to operate differently.
Who help you become a better version of yourself, a version you probably didn’t even know you were capable of being.
And like all things worth doing… it’s awkward.
It’s uncomfortable.
Honestly?
It’s business puberty.
Yes, I said it.
Just like teenagers’ voices crack as they figure out who they’re becoming, startups go through this messy middle phase.
One day you sound like a Fortune 500, the next you’re yelling across Slack about broken onboarding emails.
Welcome to the awkward stage.
Let me put it another way.
I loved my first car.
It was a Mitsubishi Outlander.
I drove it everywhere.
It was reliable, scrappy, and perfect for a younger version of me.
But then I grew up. Had a family. Needed something bigger.
My needs changed.
The Mitsu? It just didn’t fit my life anymore.
It was great for short trips and quick errands, but it wasn’t built for the long hauls.
And startups are the same way.
The team that got you from zero to one?
They’re like that first car. They’re fast, flexible, and know how to hustle.
But once the trips get longer, the stakes get higher, and the load gets heavier, you start to realize it might be time for a different kind of car. Or at least a few upgrades.
And look, it’s hard to let go.
I held on to my car way longer than I should have.
It was sentimental. I loved it.
But eventually, I passed it on to someone in my extended family who really needed it.
At some point, I had to accept it wasn’t the right fit for where I was headed.
What does that mean for your startup team?
It means you have to be honest.
About what kind of skills are needed now.
About whether your current team can scale with you.
And about whether you are ready to become an operator yourself.
Getting things done on your own is one skill. Leading through others and building systems? That’s something else entirely.
You can absolutely make that leap.
But it requires humility. And discipline.
Here are 3 hard-learned lessons if you’re trying to evolve from startup jack-of-all-trades to trusted operator:
1. Be around people smarter than you
The early team thrives in ambiguity.
But scaling requires expertise - and that often means hiring people who are 10x better than you in their domain.
This is where ego gets tested.
You have to hire people who might make you feel a little dumb.
Who challenge your thinking.
The ones who challenge your patterns and raise your standards.
“If you’re the smartest person in the room, you’re in the wrong room.”
– Attributed to various thought leaders (and every decent executive coach)
Matt Mochary, in The Great CEO Within, talks about how founders must bring in world-class operators before they feel ready. Not just to offload work, but to learn from them.
Surrounding yourself with better people is the fastest way to scale yourself.
2. Invest in Thought Leadership That Challenges You
It’s easy to read content that confirms your instincts.
It’s much harder to seek out material that challenges your operating assumptions.
But that’s where the growth happens.
Want to scale? You need to break your mental models.
You need to learn from operators who’ve done it before, especially in different industries or stages.
Start with these:
Scaling People by Claire Hughes Johnson - a masterclass on building structure early so you don’t pay for chaos later.
High Output Management by Andy Grove - the blueprint for operational execution through systems and teams.
Turn the Ship Around! by L. David Marquet - all about empowering your team through decentralized decision-making.
Claire Hughes Johnson’s work at Stripe is a blueprint in itself. She helped Stripe bring rigor to its operations before most startups even think about process, and that’s exactly why they scaled so well.
The point? Don’t just learn what supports your bias.
Learn what pushes you into new ways of thinking.
3. Track your progress
You can’t scale yourself if you don’t measure your own growth.
Growing into an operator means holding yourself accountable to more than output.
Track how you lead.
Track how you show up in cross-functional work.
Track what you’re learning and what’s still unclear.
Julie Zhuo, in The Making of a Manager, says it best:
“Leadership growth should be treated with the same discipline as product growth.”
Some ideas to start:
Ask 2–3 people every quarter: “What’s something I could be doing better?”
Keep a running doc of decisions you’ve made and what you learned from them.
After major meetings or planning cycles, do a quick retro. What worked? What didn’t?
And if you can swing it - get a coach.
Not because you're broken, but because you’re ready to evolve faster than your own self-assessments can carry you. Someone who has no stake in your politics or promotion. Someone who will tell you the truth.
These are the ABCs of becoming an operator.
Not everyone wants to. That’s okay.
But if you’re leading a startup and wondering whether your day-one hustlers are ready to scale with you, run them through this list.
If they resist feedback?
Can’t admit weaknesses?
Only operate in chaos?
Then you’ve got your answer.
Not everyone will make the leap.
And that’s not a betrayal. It’s just growth.
Sometimes, the best thing you can do for your team, and yourself, is to trade the Mitsu in.