It hits you in the weirdest places. In the Uber after your Series A celebratory dinner. On a Zoom call surrounded by 20 people, all waiting for you to speak. In the middle of a Monday all-hands that you scripted, edited, rehearsed-and suddenly can’t hear yourself in.
That low-grade hum of disconnection?
That’s loneliness. Not the “I don’t have friends” kind. The “everyone needs something from me and no one really knows what I’m carrying” kind.
Welcome to the CEO of a scaling company. You’ve got employees now. A board. A Slack full of emojis. But no real room to say: “I have no idea if this is working.”
“Leadership is the art of getting someone else to do something you want done because he wants to do it.”
– Dwight D. Eisenhower
(Eisenhower had a war. You have OKRs. Close enough.)
Why Scaling Is So Damn Isolating
In the early days, it was you and your co-founder eating Ramen and debating Figma fonts at 2AM. Now? Everyone’s specialized. The culture is shifting. You’re managing managers of managers. And the only people who truly understand your role either work for you, report to your board, or are your competitors.
Tip: How to Stay Sane (And Human)
- Find an external brain trust. Not your team. Not your investors. Think: other weirdos doing what you do. CEO dinners. Founder circles. Honest group chats. One therapist.
- Say the quiet part out loud-to someone. “I’m worried I’m faking it.” “I feel like I don’t matter anymore.” These thoughts lose power when shared.
- Design your own feedback loop. You won’t get raw feedback unless you beg for it. Or pay for it.
- Create rituals that aren’t performative. Morning walks. Journaling. Screaming into a pillow. (Yes, really.)
Table: Early-Stage Vibes vs. Scaling-Stage Reality
| Stage | How It Felt | What It Became |
| 0-10 employees | Tribe | Org chart and HR policies |
| 10-50 | Team standups in a circle | Standups that need decks |
| 50-200 | Everyone knows you | Most employees think you’re a meme |
| 200+ | You know the culture | The culture now knows you |
FAQ
Q: Should I admit to my exec team that I’m struggling?
A: Yes-with nuance. Honesty builds trust, but panic spreads fast. Say, “I don’t have all the answers, but I’m here to find them with you.” Not “I’m falling apart, send memes.”
Q: How do I stay connected to the team without faking it?
A: Skip the performative empathy. Just be visible. Listen more than you talk. Join the product demo. Send weird birthday gifs. Presence beats perfection.
A Little Joke (Dark, But Real)
What’s the difference between a scaling CEO and a submarine captain?
The captain gets regular sonar.
An Open Question
What part of this job still makes you feel alive?
Is it the people? The product? The problem space?
Or are you just performing leadership because everyone expects you to?
Scaling is supposed to be thrilling. But it can also be a mirror-and not always a flattering one. You see your limits. Your blind spots. The pieces of you that don’t scale.
But you’re not broken. You’re evolving. Slowly, messily, and sometimes painfully.
Just don’t do it alone.
