The Loneliest Lesson I’ve Learnt as an Entrepreneur
I never imagined I would write this.
A few weeks ago, I was at the point of registering the business. The paperwork was in front of me.
The business was growing. Clients trusted us. The team was expanding. For the first time in a long time, it felt like years of uncertainty were beginning to make sense. Then, one conversation after another, that feeling disappeared.
I won’t pretend it didn’t sting.
People I’ve invested in chose to leave. Some resigned over WhatsApp. And if I’m honest, that hurt more than the resignations themselves.
It wasn’t until they gave notice that I understood what I’d actually built. I thought I’d built a system. I’d built a set of dependencies with names.
This isn’t a post to blame anyone. People leave jobs. They should. They have every right to choose what’s best for them. It wasn’t about people leaving. It was realizing we were never building the same thing.
Looking back, I realise the mistake I made wasn’t teaching people, paying them fairly, or opening doors for them. I hope I never stop doing those things.
My mistake was expecting that investment will create loyalty.
Businesses don’t work like that. People aren’t indebted to you because you believed in them. That’s a difficult lesson when you’ve paid salaries from your own savings because clients delayed payments. When you’ve spent evenings teaching someone skills they never had. When you’ve introduced them to opportunities you wished someone had given you.
None of it was a contract. It was a series of choices I made as a leader. And leadership means accepting that people may still choose a different path.
For a long time, I treated my company like a family. Today, I think that’s the wrong metaphor. A company isn’t a family. It’s a shared mission that lasts only as long as everyone’s goals align. The moment those goals change, people move on. That doesn’t make them villains. It also doesn’t make my disappointment any less real.
I’ve also realised something uncomfortable.
I’ve been a better entrepreneur than a manager. Vision comes naturally to me. Boundaries don’t. Sometimes people confuse entrepreneurship and the manager role. They are not the same.
The part of Entrepreneurship
There is another part of entrepreneurship that people rarely talk about. The part that doesn’t show up on LinkedIn posts or podcasts.
While reading “The Hard Thing About Hard Things“, I came across a few lines that captured this feeling.
The hard thing isn’t setting up an organizational chart. The hard thing is getting people to communicate within the organization that you just designed.
The hard thing isn’t dreaming big. The hard thing is waking up in the middle of the night in a cold sweat when the dream turns into a nightmare.
It’s waking up on a Saturday already thinking about Monday. Client reports, campaigns, invoices, payroll, the next lead, the next opportunity. Nobody asks you to carry those thoughts. You just do.
When a client trusts me with their business, I can’t stop at posting content or running ads. I want to understand how the business works, why customers choose them, where they’re struggling, and how we can genuinely help them grow. Sometimes that means reading more, testing ideas, or lying awake because I know we can do better. And that’s what made me who I am today. A responsible person who takes ownership by myself without asking. And that’s how this entrepreneurship was born for me.
It was so natural that I now remember my first-ever manager. He (I will talk about him in another post) made me a manager when I was 21 years old. It was a small start-up; we were kind of doing odd jobs in the IT world. Some did data entry, some did HTML coding, some worked in ERP. I was part of the EPUB work. And managing 4-5 people at 21 years old, even though it’s a small business, scared the hell out of me. And what did I do? I tried to perfect the work that I ended up doing myself after they completed it, and got shouted at, which I will never forget. All I remember was – BS said again and again. I cried my eyes out.
Employment Role: Don’t mistake it for ownership or loyalty.
Most people come to work to do their job well, earn a living, and go home. There is nothing wrong with that. They are doing exactly what they signed up for.
I expected ownership from people who had signed up for employment.
What surprised me wasn’t that everyone around me didn’t think this way. Looking back, that wasn’t their mistake. It was that I expected them to.
I celebrate with my team. I mentor them. I invest in them emotionally. Somewhere along the way, I started expecting the relationship to mean the same thing to everyone involved.
If there’s one lesson I’ll carry forward for the rest of my life, it’s this:
Care deeply. Teach generously. Pay fairly. Help people grow.
But don’t confuse kindness with an agreement that they’ll stay.
Build systems, not dependencies. Build teams, not heroes.
Never let your business rest on one or two people, no matter how talented they are. Because the business has to survive even when people move on.
My Takeaways
And maybe this is the biggest lesson of all:
If your vision is bigger than your team’s, don’t resent them. Not everyone is supposed to carry your dream.
It’s yours. Your responsibility is to find people who genuinely want to build it with you, for however long that journey lasts.
I still believe people are good. I still believe mentoring people is worth it. I still believe businesses should create opportunities. But I’ll build differently now.
With clearer boundaries. With better systems. With fewer assumptions.
This chapter stings.
I’m not ashamed to admit that. But if entrepreneurship has taught me anything, it’s that every difficult season eventually becomes part of the story you needed to live before you could tell it.
So I’ll keep going.
A little wiser.
A little less naïve.
And hopefully, a much better leader than I was yesterday.
It’s alright, you made it this far…..
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