Working For Myself: One Year In

Inventing Your Own Life's Meaning

One year ago, I quit my full-time job as a Head of Product to work for myself. It was scary because I was leaping into the unknown, unsure I could pull it off.

Reflecting on my journey one year later, was that fear justified?

What went well on my adventure, and what could I have done better?

What goals did I set, and did I achieve them? What was my motivation for setting those goals?

As you can already tell from how I’ve phrased these questions, I don’t believe my experience can be generalized to others. That doesn't mean sharing it won’t be helpful. I regularly get asked for advice on how to pull it off.

Answering messages to help others is not very scalable and time-consuming. That’s why I’ve decided to bundle everything I believe I know together in a single article. If this article doesn’t answer your specific question(s), please comment below, and I might update the article to answer it.

Before answering all these questions I’ve phrased, let’s start by setting the stage. I will explain my situation, my personal motivation for going solo, and all the things I did before starting out for myself.

WARNING: Please don’t try to follow my steps or conclude my journey is the way to go.

I hope sharing my journey might help you carve your own path or figure out where you want to go. The viewpoints in this article are deeply personal.

There is no right or wrong here. You have to decide what matters to you, which may differ greatly from what matters to me.

My Situation Before Starting For Myself

• I started writing articles and posts about Agile, Product Management, and Scrum around eight years ago. Nobody cared about my first articles, and they pretty much sucked. I loved writing so much that I continued. I was fine with sucking, and I was good at persisting. At some point, some people other than myself started to enjoy some of my writings, too.

• The more I wrote, the better I got at writing. The better I got at writing, the more people liked what I wrote. The more people liked what I wrote, the bigger my audience became. The bigger my audience became, the more feedback I received. The more feedback I got, the better my writing became. That makes the biggest difference between me and most people who begin writing: I stuck with it. You can be the most talented writer ever, but if you don’t persist, you won’t build an audience.

• At some point, I gained sufficient traction, and I was asked for podcasts, community events, and conferences. Once those doors opened, I began to be asked more frequently for podcasts, community events, and conferences. Getting your foot in the door is hard, but once you’re in, getting asked for more things is much easier.

• This work was mostly possible because I had a limited social life. My partner supported my writing by frequently taking care of our kids. She has a super successful business to boot, so I also benefited from all her knowledge and mistakes she had made to help hit the ground running. She alleviated my worries and told me it would all work out in the end.

Writing for seven years wasn’t glamorous or exciting; it was mostly monomaniacal. Picture me writing at night in my attic. I didn’t go out and meet a lot of people, many of my nights were lonely and filled with writing, podcasts and presentations.

I could do it because I loved the writing, and without any success, I would still keep on doing it.

When Exactly Did You Gain Traction?

That’s a difficult question to answer. Let’s use the following arbitrary definition: the time between my first article and the first time I was invited to speak on a podcast: around four years.

I don’t believe there is such a thing as an overnight success. Show me an overnight success, and there will be a story behind it that was many years in the making. We don’t see all the sweat that was necessary to get there. We only see the end result.

I want to stress, don’t let this scare you. I don’t believe 4 years is fast by any means, and I know many writers who had a far steeper trajectory than I did. I don’t care about being slow or fast. I care about doing what I enjoy.

Should I Start Writing Too To Gain Exposure?

The short answer is no, unless you like writing. Most people like the idea of writing, not doing the actual writing.

I always get messages from people who want to write. Far more people want to write than enjoy it enough to keep it up for many years. That’s the main challenge. That’s why my advice is always to write about what you care about. The most important thing is to keep it up for a longer period of time.

That’s why, if you don’t like writing, I would not recommend you to go for it. Do something else. Host a podcast like Mark Metze is doing, or start a channel on YouTube like Maria Chec. When you do what you love, it’s much easier to keep doing it and make someone else care too.

It’s hard enough to stick to something when you like it. Forget about doing it when you dislike it.

When Did I Decide to Become a Solopreneur?

At some point, it felt like I had two jobs: work and writing, together with a minuscule social life. Therefore, I decided to eliminate one of the two (no, not my social life! :)). I decided to take the plunge into solopreneurship.

Before doing so, we had saved enough money to survive without any income for at least a year. I’m not saying this is a prerequisite, but we wanted to play it safe. I wanted to feel comfortable to take the plunge, and I’m pretty risk averse.

Going solo was a carefully calculated move many years in the making.

My Motivation and Goals For Going Solo

I regularly read the commencement speech Bill Waterson gave at Kenyon College because for me, it stands out as a brilliant reminder of the things that truly matter:

“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, artist and writer of Calvin and Hobbes

I understand what I’m going to write next comes from a position of privilege - from my first job, I never had any monetary concerns or financial problems. I’m lucky to live in a country where healthcare isn’t tied to my job, and we have a strong social system for the unemployed. Even if everything backfired, we’d still be fine as a family.

That’s why starting for myself was never about the money. Not to say that money doesn’t matter, but my primary motivation was to have more flexibility and control over my time.

I want to carve out a life where I can do more of the things I like doing. I wanted to create a luxurious position where I could choose how I spent my time as much as possible because time is ultimately the most precious and scarce thing in your life.

“On a long enough timeline, the survival rate for everyone drops to zero.“

- Chuck Palahniuk in Fight Club

The clock is ticking and will run out, even if your money never runs out. The biggest risk is not doing what you love in the hope you buy yourself the time to do it later.

I love reading. I love writing. I love being with my family. I want a life that satisfies my soul. The more control I have over my time, the more control I have over a life that can satisfy my soul.

I believe I could achieve that best by becoming a solopreneur.

My Personal Goals

In short, my goal for starting for myself was the following:

• To make around the same money as I did when I was a full-time employee while having significantly more freedom and control over my time to do the things I love the most.

Money still matters, but the goal isn’t to make as much money as possible. This goal had the following implications:

• I should be comfortable saying no to things and getting rejected. As little cannibalization of joy as possible in exchange for more money. Beyond the point of living comfortably, it’s important to protect your time, happiness, and stress levels.

• I’m not trying to grow and make more money every year. I’d be perfectly cool with not growing and making around the same every year. I’m not trying to beat anyone or buy a bigger house. I’m content with the current situation, where I spend a lot of time with our family.

• The moment I do something that doesn’t grant me joy, I should wonder why I’m doing it.

I do want to stress that if I were to face financial hardship, this goal would immediately go out of the window. Food on the table and being able to pay the mortgage come first, and Bill Waterson followed in those same footsteps. Bill Waterson worked at an advertising agency - a job he truly hated - to make ends meet for many years until he became famous.

Here’s the story in his words:

“To endure five years of rejection to get a job requires either a faith in oneself that borders on delusion, or a love of the work. I loved the work.

Drawing comic strips for five years without pay drove home the point that the fun of cartooning wasn't in the money; it was in the work. This turned out to be an important realization when my break finally came.” - Bill Waterson, artist and writer of Calvin and Hobbes

The Main Challenges For Me

When I let the world know my services were available, I already had quite a large following and reader base. My inbox flooded with companies wanting to explore whether we could work together. All this means is that I could have started sooner because this was already seven years in the making.

I was wholly unprepared for this influx of requests. I had a website, but I had no sales pitch. I’ve never worked in consulting, and I’ve never done any sales. I was hopping on calls with companies who were used to working with big consulting companies like McKinsey or Deloitte. I was clueless and butchering calls.

During this period, I’m quite sure I destroyed many potential opportunities by my lack of experience and poor way of positioning myself and my services. I still don’t think I’m great, but I did receive some help from experts in sales on my journey (many thanks for that!).

What Would I Have Done Differently

It probably would have been wiser if I’d done more sales and consulting work before starting out for myself. I was in the fortunate position it didn’t matter, as I started too late, so there were enough opportunities I could lose and use to level up quickly in those areas.

What I Still Have To Figure Out

I work with companies and colleagues, but most of the time I do everything alone. Most of my income comes from fractional advisory work, presentations, trainings, and workshops in the realm of Agile and Product Management.

I miss the company and community of working at a company. This year, I’ll try to figure out a way to belong more somewhere instead of just being a solopreneur doing their own thing.

I have enough time to go to the gym, but I still don’t do that enough. I’m going to build more habits and routines so that it will become easier. It’s easy to go once you have the habit and routine, but once you break that habit chain, it becomes much harder again.

I love writing and reading so much that I sometimes forget to see more of my friends. I will need to make that more a priority, as it’s easy to get sucked in doing what you love and becoming a hermit living in their attic.

Being a Solopreneur Is Not The End Goal

If you remember one thing from this article, being a solopreneur is not the end goal. It’s figuring out how you want to spend your limited time on the planet earth.

Creating the conditions so you can do what you love as much as possible and choose to spend time in a way that makes you happy that’s what matters the most. And those are answers you have to seek within yourself which I won’t be able to provide.

Bill Waterson could have worked forever at an advertising agency, only making the comics he loved at night and in his spare time, without big success.

The success isn’t what matters. It’s spending the time doing what you like doing. And if you’re doing what you love, nobody can beat you, as there is no contest.