I’m 27. I had two paper-route-style jobs before I started college and did three internships. At age 23, I became a freelancer. That’s it. My entire “CV.”
Clearly, I know almost nothing about work. I’ve just gotten started. And yet, it feels like in those four years I’ve already done a lot of things. Maybe I have.
I worked at a tax consultancy for $15/hr. I did their marketing, corporate identity, even helped with accounting and re-did their website. I translated, interpreted, and wrote corporate blog content. I ghost-wrote articles for a high-profile SEO blog. I coached 300 people in various habits. I built an affiliate website. I edited the posts of a professional blogger. I made an online course, self-published a book on Amazon, and experimented with Patreon.
When I look back, not just on those four years, but on my relationship with work throughout all my life, I can point to various phases of how I thought about it. And while you’ll have to experience most of them for yourself in order to really learn, I can at least see one thing worth sharing. Here it is:
Your work should reflect who you are, not what you want your life to look like.
Let me walk you through three of those phases to explain what that means.
1. The Best Work Is No Work
Forgive me for quoting myself:
When my best friend and I graduated high school, we came up with “the List.”
We thought about our wildest dreams and put them on a timeline. Three months, one year, then five, then ten. There was only one problem: they were all stupid, greedy, selfish goals. Like, downright delusional.
For starters, our top priority was to become a billionaire. And it only got worse from there.
The reason we thought the only work worth doing was work that’d make us rich was that we didn’t think work could be inherently meaningful at all. It just didn’t register as a goal worth having.
And while I’d really like to punch 20-year-old me in the face, I can’t actually blame him all that much, because that’s the exact approach society teaches us.
We’re all raised to want money and nice things, which is why most people choose their work based only around those two.
If you do that and never look back, however, this is the kind of career planning that leads to the stories of people who “wake up” at 50, realize they’re profoundly unhappy, and frantically try to rebuild their life.
With this approach, the best you can hope for is that by the time that happens, it won’t be too late.
2. Freedom To Instead of Freedom From
As my friend and I set out on this wry road to riches, we both hit walls less than 100 days into college. We insta-doubted everything from workload to methods, from rightness to relevance.
In my fourth semester, I studied abroad in the US and caught a little break. I really got into blogs, life hacks, reading, and all these self-improvement gurus and movements. I say ‘little’ because once I had the realization I didn’t want to be a corporate consultant and build my own career instead, I thought I was “woke.” Out of the matrix, if you will.
Except now, all I was doing was chasing a different lifestyle. One that was optimized around freedom, rather than money. From the bible on this topic:
People don’t want to be millionaires — they want to experience what they believe only millions can buy. […] The question is then, How can one achieve the millionaire lifestyle of complete freedom without first having $1,000,000?
While I still value freedom a lot today, the lifestyle design philosophy, if driven by bucket lists, is only one step forward and two steps back. In the words of my favorite modern-day philosopher:
“My old definition was ‘freedom to,’ freedom to do anything I want. Freedom to do whatever I feel like, whenever I feel like. Now I would say that the freedom that I’m looking for is internal freedom. It’s ‘freedom from.’ It’s freedom from reaction. It’s freedom from feeling angry. It’s freedom from being sad. It’s freedom from being forced to do things. I’m looking for freedom from internally and externally, whereas before I was looking for freedom to.”
What used to be a backbreaking, mind-numbing job in Henry Ford’s factory now is a mind-breaking, soul-crushing job at Goldman Sachs. Both well paid, both leading to the same, gaping void, even if you managed to retire at 40.
When I first embraced lifestyle design, I was looking for freedom. Freedom to choose my work, freedom to travel, freedom to have amazing experiences. Nowadays, I’m mostly looking for freedom from stress, freedom from feeling an artificial need to travel or buy or do things, freedom from any other standards but my own.
If you choose the lifestyle career lens after a purely material one, you’re worse off than before. All you’re in is a different hamster wheel, but now you think you’ve solved the puzzle.
You might build something incredibly successful, but something that’s still completely out of line with who you are, which will leave you just as unhappy as chasing money for money’s sake alone.
3. The Perfect Workday
Since it’s much harder to get out of, I was stuck in the passive income bubble even longer than in the greedy, I-deserve-to-win-the-lottery one. But about two years ago, just as I started to make it work, my mindset shifted again.
The more I wrote and the better I got, the more fun it was. I learned that passion was something you could synthesize. And with that, the idea of retiring young or quitting work altogether became less and less important. I’d rather have a relationship with work that leaves me healthy and happy, but never ends, than one where work is always a means to some distant outcome.
So, about a year ago, I tried to design my perfect workday and then build towards a life where that kind of day was more likely to happen more often. What were the requirements? What the potential stressors? How could I make it flexible enough to adjust to unexpected problems? Flexible enough so it doesn’t get boring? And so on.
The perfect day exercise wasn’t so bad. It taught me a lot of things. The only thing I was wrong about was my source of inspiration. At the time, I thought you could just wish for any kind of work day and then work towards that. I now realize that might backfire.
In order for this exercise to work, you need to imagine a workday that reflects who you already are.
It needs to be built around your existing traits, values, and skills. Only then will you design your perfect workday in a way that actually makes you happy.
The Only Thing I Know About Work
I can’t tell you how many twists and turns I went through before I somehow stumbled into being a writer. Too many to count. Only in hindsight can I see that I enjoyed writing from day one because it fit who I already was.
I’ve always been introverted, creative, and living in my own head. I’ve always loved stories, fantasy, and putting things together in my mind. I don’t mind working a lot, I actually like it. But I do like working alone.
That’s why pursuing being a writer naturally made me happy. Because it allowed me to be myself.
To find work you love, learn to love yourself.
Because if you like who you are, you’ll naturally want a job that allows you to thrive. Regardless of what that job looks like, how hard it is, or how much money you make.
In order to want what makes us happy, we first have to accept who we are. Only then can we want the right things.
That’s the only thing I know about work. But I hope I never forget it.