Lessons Learned: Working For Myself - 3 Years In

Start Climbing the Ladder of Your Soul

I’ve reached a crazy milestone:

I’ve worked for myself longer than I’ve ever worked at any other company.

The last 3 years have been a wild ride with speaking engagements, advisory work, and workshops all over the world.

What are the most important lessons I’ve learned from working for myself?

Let’s dig in!

1. Don’t Obsess Over More Money

As Yew Jin Lim expressed beautifully:

“Don’t trade money you don’t need for time you don’t have.” - Yew Jin Lim

Time is the most scarce and precious thing we have.

We don’t know how much time we have. You might get sick one year from now. Time also speeds up as we age. One of the reasons is because we’re no longer experiencing as many new things as when we’re young. This is especially true for people who are stuck in a corporate routine doing the same thing every day.

I remember seeing this picture in the early 2000s already:

Don’t risk spending your life not doing what you want on the bet you can buy yourself the freedom to do it later. Later is highly uncertain. Especially today, in the age of AI.

I’m not busy climbing any imaginary career ladder or trying to maximize my earnings. I already have everything I want from a material perspective, even before I started working for myself more than three years ago.

I want to live a fulfilling life, one that satisfies my soul. I want to spend lots of time reading, writing and being around my family. Those are the things I enjoy the most, besides being obsessed about helping organizations to deliver more value.

I understand I’m writing this from a position of privilege. Every month I get requests for engagements because of my articles. In the Netherlands, even if I earn nada, I will still have access to great healthcare.

This not something trivial.

If I didn’t have access to this healthcare system, I would be chasing more money to guarantee good healthcare no matter what happens for our family. If necessary, I will flip burgers to make ends meet.

I could easily maximize earnings by saying yes to everything, which is what I did in the beginning, but I realized that left me miserable.

Saying yes to chase more money means:

• More stress

• Worse sleep

• Worse health

• Less time with my family and kids

• Less time to read

• Less time to exercise

• Less time to write

• Less time to meet friends (to be frank, I still suck at this)

The ultimate luxury isn’t being able to buy anything you want, but being able to choose how you spend your time.

Freedom and flexibility is what I’m optimizing for, not a bigger house or a fancier car. Remember your life as a student? Were you happy back then? Did you have lots of fancy material possessions? Probably not.

I was already extremely happy as a student in a tiny room eating crappy food, because of all the freedom and flexibility I enjoyed.

That’s what I’m aiming for, not more money. I want to write and help people all over the world, even if it doesn’t directly earn me any money.

2. Follow Your Curiosity, Listen to Your Heart

Try out many different things and see how they make you feel. Work with big companies. Work with small companies. Do advisory work. Work as an individual contributor. Figure out what makes YOU happy.

What is the best way you can spend your precious and limited time on this planet?

As an example, I’ve (mostly) stopped doing Product Management coaching, because I don’t believe it’s the most effective way to spend my time. If I write one article in a few hours, I will help far more people than when I help a single person in a coaching session. Even if writing doesn’t bring in any money, at least directly, I much prefer doing that.

I sometimes still do coaching sessions, mostly when I feel a strong connection with someone. Otherwise, I’d much rather be spending time reading and writing. Even if I earn less money.

Through my writing I would be helping more people, and I’d be enjoying it more too.

3. Be Okay With Not Scaling

I’m intentionally not scaling anything I do, except through my writing. I could easily develop an online course or workshop, but currently I don’t want to spend my time doing that. Creating a course or workshop to scale and earn while I sleep, sounds incredibly boring to me.

I’d much rather be writing another book, even if it doesn’t bring in much money. Or help a company with a workshop that doesn’t scale, because it helps them with their unique situation.

As an example, I haven’t even made my newsletter paid, because I don’t want to waste my time figuring out and complying to EU VAT regulations. More importantly: I want everyone to be able to read my newsletter, even if I lose potential money.

I’m not scaling, because I already have enough. Money isn’t the point for me. I’m not trying to create a business to maximize profits, I’m trying to create a life where I maximize my enjoyment and flexibility.

Money Isn’t the Point

You might be surprised when you read this article: where are the business lessons from 3 years of working for yourself? Maybe you were expecting some article where I explain how I scaled to 300K per year in 12 months?

Well, tough luck! There are more than enough of those kinds of shallow articles out there. I’m writing this, so hopefully someone reconsiders what they’re currently doing. Why do you keep on chasing more? How much money will be enough?

I want to create as much value as possible by doing what I love, and capture enough value so that I can keep on doing that. The key word here is enough.

That’s all. I’m not chasing more.

Creating value is more important to me, e.g. through writing frequently, rather than squeezing every penny out of the value I’m creating. I don’t want to run my life as a business where I’m running in a hamster wheel to chase ever-increasing amounts of money.

Because, what’s the point? Just to buy a more expensive watch or a bigger house?

Before someone misreads what I’m writing, I’m not saying that you shouldn’t have ambitions. I’m saying you should have the right ambitions. Climbing the imaginary career ladder dictated by society, is a shallow ambition to me.

I’m filled with ambition. I’m obsessed with my work and constantly thinking about how to do things better.

Climbing the ladder means you’re settling for what the outside world decides as what being successful looks like. If the imaginary career ladder perfectly coincides with what your soul craves, go ahead and climb the imaginary career ladder.

But if the imaginary career ladder doesn’t coincide with the ladder of your soul, then it’s a terrible deal.

In the words of Bill Waterson, creator of Calvin and Hobbes:

“But having an enviable career is one thing, and being a happy person is another.

Creating a life that reflects your values and satisfies your soul is a rare achievement. In a culture that relentlessly promotes avarice and excess as the good life, a person happy doing his own work is usually considered an eccentric, if not a subversive.

Ambition is only understood if it’s to rise to the top of some imaginary ladder of success. Someone who takes an undemanding job because it affords him the time to pursue other interests and activities is considered a flake. A person who abandons a career in order to stay home and raise children is considered not to be living up to his potential-as if a job title and salary are the sole measure of human worth.

You’ll be told in a hundred ways, some subtle and some not, to keep climbing, and never be satisfied with where you are, who you are, and what you’re doing.

There are a million ways to sell yourself out, and I guarantee you’ll hear about them.

To invent your own life’s meaning is not easy, but it’s still allowed, and I think you’ll be happier for the trouble. - Bill Waterson, commencement speech Kenyon College”

Don’t sell yourself out. You don’t have to prove anything to anyone expect yourself.

Stop climbing the imaginary career ladder when you have enough. More isn’t better, in fact it comes at a significant cost. Especially for your loved ones.

Start climbing the ladder of your soul. Decide what matters the most to you, even if other people will ridicule you for it.

You’ll be much happier for it. In the words of the famous physicist Richard Feynman:

“What do you care what other people think?”