Freedom Wasn't the Hard Part

Chào các bạn, hello friends!

In 2020, Contentful laid me off.

I called it the best thing that could have happened to me.

I had been burning out. I was drinking a lot, smoking weed every day and travelling every few months. My job paid well and I still had fun doing it, which made it easy to ignore how little room was left around it.

Then the job disappeared. For the first time in years, nobody needed me to be anywhere on Monday morning.

I picked up my bicycle.

I had always wanted to ride more, but I kept waiting for someone to join me. Once I stopped waiting, cycling became the thing that got me moving again. It was simple: choose a road, start pedalling, feel whatever turned up.

That part felt like freedom.

The part I did not understand was what to do with it once the ride was over.

This is about the gap between getting your time back and knowing what that time is for. I confused those two things for much longer than I realised.

Without a job, an older version of me started coming back. Before the partying and the career ladder, I had built an electric Bobby car, tinkered with electronics, organised festivals and hosted dinners. I liked making things and bringing people together. Suddenly I had room for all of it again.

So I tried things.

I almost bought an old hotel near Berlin with my dad and a friend. I resold USM Haller furniture. I looked at importing cycling products from Indonesia into Europe.

There had been ideas before that too. I brewed kombucha and wondered if I could sell it. My dad once had an opportunity to import sugar cane, and I imagined turning it into a soda. Friends and I had talked about a business in Delivery Hero’s territory.

Each idea reached the same invisible border. Regulation. Bottling. Funding. Competition. Permission.

I knew how to enter an unfamiliar technical system and figure it out. Business still looked like a country where I needed the right visa before I was allowed to begin.

From the outside, I was doing exactly what people dream about after leaving a job. I had time. I was riding, travelling, experimenting and saying yes to possibilities.

I was having a great time.

I was not content.

That was difficult to admit because nothing obvious was wrong. The calendar was mine. The old pressure was gone. I had escaped the thing I thought was making me unhappy, and the space it left behind did not come with instructions.

Freedom removed the structure. It did not replace it with direction.

So I kept filling the space. Another ride. Another idea. Another version of a life that might fit. Activity made the blank page less visible, but it did not tell me what belonged on it.

Eventually I decided I would freelance.

Then Workpath called.

The role was remote. The salary was big. I could build a team, and the person who would become my boss was someone I wanted to work with. I was on Tenerife when I signed the contract.

Going back to a job did not feel like failure. I wanted the work. I wanted the people. I also wanted a structure I knew how to stand inside.

It took another layoff three years later for me to see the pattern. Leaving had given me options both times. It had not made any of them meaningful. That part only came through trying things, talking to people and staying with the uncertainty long enough for a direction to emerge.

I used to think freedom was the destination. It was only the empty plot of land.

What are you doing with the space you asked for?

I didn’t need more freedom. I needed someone who could look at what I already had and tell me, honestly, what it was actually for.

If something in here landed — there’s probably a real thing underneath it. I run 90-minute Founder Bottleneck Diagnostics. DM me “diagnostic” on LinkedIn.

Keep it simple, keep it fresh, smile and let it go. — Yours truly, Trung