💙 Dispatch #10: One Year Later

3 Lessons I've Learned After One Year of Self-Employment

In February 2024, I experienced no less than four life altering events.

1. I separated from my then-wife,

2. moved across the country to the East Coast to lick my wounds, in what would be my 2nd cross country move in a single year and not my last move,

3. was laid off from a job I had held for five years,

4. and started an intensive coach training program called Aletheia.

Someone “normal” may have gone on a job hunt and searched for stability with so much in flux, but I’m not a normal person and I’m not sure normal people exist, anyhow.

Instead I took on my first contract role with a startup, helping them discern the services they would bring to market and put together the foundations of their business.

In June 2024, someone asked to pay me for coaching, and I started that business too, which is growing into a full-on leadership and organizational development firm.

I left the startup gig six months later to go all in on my business, and I’ve been fully self-employed since.

One year later feels like a good time to reflect and share some things I’ve learned.

Here are 3.

Lesson #1: Solo, Not Alone

Being self-employed is great fun. It can also be a lonely endeavor if you’re used to how a 9-5 working situation can provide most of your social connections.

I’m grateful that I’d already invested a lot of time in building an international network by the time I started building my business in earnest. Some of those connections have become my closest friends. Many of them have been sources of coaching leads, collaborators, and have coached me through all of the ups and downs of this path.

When you unplug from the confines of a single organization, you have the opportunity to plug into a whole ecosystem of fellow visionaries, risk takers, heart breakers, and room shakers. You just have to be intentional about plugging in. And do it before you need anything from that ecosystem.

I love being in this ecosystem of weirdos. And it is a weird thing, to be an entrepreneur. You have to live in this reality shifting field with an unquestioning belief in your own ability to make this work, despite great statistical evidence that it probably won’t.

It helps to be surrounded by other people who understand that field and live it every day too.

Oh, and you want to meet big hearted people? Find the coaches, healers, shamans, change makers, and other helpers who decide to take this path of birthing a practice to offer their medicine directly to those who need it.

I’m still blown away by the types of people I get to meet day in, and day out.

A scene from a recent trip to Amsterdam.

Lesson #2: The Greatest Personal Development Lab

Self-employment is the world’s greatest personal development lab. When you get hired for a specific set of skills by a company, you have the luxury of both staying in your lane and also being able to pass the buck or bash management for their perceived fallacies.

If you are management - well, you take the abuse and move on with your life.

Either way, you do the job, and you leave. You’re not sales? Well, let’s hope sales does their job well so you can keep eating. Not your problem.

Self-employment is different. To use a crude metaphor, you have to kill everything you eat. You can’t hide from sales conversations. You have to market yourself to be visible enough to attract people who can pay for your services. You have to manage your books, and understand your tax situation with way more nuance.

Oh, and you should be damn good at what you do, too. If I throw a rock from my balcony, right now, I will guaranteed hit another leadership coach in the face as they walk down the sidewalk. The market is saturated. Mediocrity simply won’t do.

Being self-employed has forced me to look at a whole lot of uncomfortable truths about myself.

How I haven’t valued myself, and my time.

How I have avoided conflict.

How I’ve stayed in the poetic and abstract to avoid the tangible and concrete.

How I overcommit and overwork for very little in return.

And so forth.

Thankfully, I believe in coaching, so I also get coached. A lot.

It helps to do hard things that bring up all of that crap that I’ve been supported in working through.

There was probably a gentler way to do all of that, but again - not a normal person.

This jazz singer’s poster is all over my neighborhood here in Berlin. His vibe tickles me. I saw him in person at a cafe a few weeks ago and it made my year.

Lesson #3: Health is Wealth

Want to know what really sucks?

When your livelihood depends on your ability to talk to people,

and you can’t talk because you’re so sick that every other sentence is a cough.

That was my entire month in March 2025.

I had moved to Berlin a few months before, and I was now several German doctors into a bacterial infection that kicked my ass six ways to Sunday.

I could not take time off from work and expect to get paid.

No billed client work, no income.

So I made trade offs,

cancelled the unnecessary,

shifted plans,

and gutted through coaching calls with a cough drop rattling around my cheeks - just quiet enough to not be picked up on the AirPod microphones.

This reality has forced me to take a good look at my health at every angle.

That’s a positive from a lot of angles, but it did take seeing this direct relationship between my vitality and my business activity to finally take it seriously enough to start making changes. This is an ongoing edge. Thank goodness it’s happening at age 38 and not age 58.

Not to say that missing work when you’re an employee is awesome either.

Which leads me to a bonus lesson.

A typical scene on the canals of Berlin. There’s a makeshift spirit here that I both love and hate depending on my mood.

Lesson #4: It’s All Tradeoffs, Baby

I remember dreaming about freelancing years ago.

The flexibility.

The autonomy.

Only doing the work I wanted to do,

answering to myself only.

A tale as old as time, right?

If I could go back in time several decades and slap that guy a few times,

I think he’d benefit from the splash of direct contact with reality.

Often, this dream we have of working for ourselves is born from an avoid-dance with ourselves when we come into contact with the friction of trying to make it work in organizations with others.

I traded all that drama in - and received a new context in which to meet parts of myself that I would rather have avoided.

Wherever you go, there you are.

The truth is, I can’t imagine doing anything else than being an entrepreneur.

I do have dreams for this business.

I do believe they can come true.

But one year in, I no longer believe what I used to believe about this path.

It’s all tradeoffs, all the way down.

You want flexibility?

Great, but you have to get your own ass out of bed to put the hours in.

Nobody will yell at you if you don’t.

You lose the social accountability force field that holding down a job offers.

You want autonomy?

Great, but how do you decide what to do if you could do literally anything?

And oh yeah, you’re a chronic people pleaser who doesn’t say no without immense inner friction?

Cue “Welcome to the Jungle” by Guns n’ Roses.

So yeah, I love this life.

It’s afforded me the flexibility to travel the world, meet interesting people, and breathe in exotic tree sperm that shows the body all sorts of allergies it didn’t know was possible.

But I do know more about what I don’t know about the tradeoffs.

Maybe that’s wisdom?

Understanding European history more deeply has been a highlight of living here. For example, the town of Bath in the UK was founded by the Roman Empire, and you can find evidence of their influence all over the architecture there.

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Thanks for reading and reflecting with me.

The last year has been interesting.

I wonder what I’ll write about one year from now.

I guess we’ll see, huh?

Take care of each other out there.

💙

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PS - if you’re a professional coach or people leader who is Generative AI-curious but unsure of whether or not it can be useful to you outside of basic research and content creation, I’m holding a workshop on June 18th from 3PM to 4:30PM Central European Time where I’ll share a system I’ve developed using client session transcripts, Claude.ai, and other useful knowledge sources to help me deepen my relationships with those I lead in 1:1 conversations.

If you’d like to learn more and register, the link to do so is 👉🏼 here.

I’m keeping it small because I’d like to learn with the people who attend and open space for better conversation around the shifts we’re seeing in our world as GenAI tools become better and more ubiquitous.

Cheers! 🍻