People who’ve successfully figured out how to do what they love for a living are always telling others to do it. As a 20-something entrepreneur who escaped the shackles of salary servitude to attempt to do something I enjoy (and am finally achieving some of the success I’d hoped for), I often feel tempted to tell other people to do the same. But it’s more complicated than that, as everything always is.
To do what you love every day, you must figure out what you love. To figure that out, you must a. know yourself and b. try a bunch of different things on for size. And you have to dig as deep as you can within yourself.
‘Doing what you love’ doesn’t mean saying, “I like to play drums! Therefore I will devote the rest of my life to doing it and getting paid to do it!” I thought that would work for me (along with journalism, art sales, and marketing, among other foregone pursuits); turns out I hated everything about the music business besides playing drums, and, as in any entertainment career, most of one’s time as a performer is not spent performing. You have to love all the other stuff to enjoy yourself. That’s why a pop star who loves the hustle but has mediocre talent has more upward mobility than a one-in-a-million talent who just wants to play the blues. Just doing what you like, or what you’re good at, works for some people, sure. But here’s the tricky part:
Our passions are often more nuanced than we realize. What we ‘like’ can be hidden in the details of what we have to do to maintain longevity in a given space. Conversely, what we ‘dislike’ can be hidden in the details of what we think our ideal life is.
The solution is some creative experimentation, as well as embracing risk.
For 3 years, I’ve run a company that sells limited edition artist-designed fashion stuff to teenagers and hipsters— not something I ever thought I’d do every day. On the surface, I’d look at what I do now 5 years ago and say, “What the hell? That doesn’t interest me.” But I have always loved doing these things:
- Devouring images and studying art
- Building creative relationships with talented people
- Curating imagery to fit a particular aesthetic
- Social media growth strategies (see: @dailyzen’s Twitter following— it didn’t grow by accident)
- Accounting (I didn’t learn this until I realized how much I like balancing my books compared to my friends and colleagues)
- Talking to customers (I learned from Daily Zen that I love responding to emails from strangers interested in what I do)
There are plenty more, but this isn’t my life’s story. I get to do all of these things every day. And, despite the final product not being something I had ever expected to love, I love the process. This love translates into lots of confidence and hard work, which over the past few years has translated into far more success and freedom than I could have achieved if I’d kept toiling at entry-level jobs at galleries and magazines, or playing bar gigs with fame-thirsty bandmates.
So, if you’re pondering over the questions of “what do I love?” or “can I do what I love?” or “why is my boss such an asshole?”, the answers could be hidden a few layers deep. When I felt this dissatisfaction a few years ago, I started taking my meditation practice really seriously. I started reading a ton and journaling in a way that was almost interrogational, drafting questions to myself and answering them:
- What do I want from my ‘work life’?
- What do I want from my ‘life life’?
- What are my day-to-day needs and responsibilities?
- Where do they all overlap?
- Why do I want these things?
- Theoretically, what would my ‘ideal path’ be?
- Realistically, how would it feel to ‘arrive’?
- What are my surface-level passions?
- What are my more detailed / nuanced skills?
- What are my core values?
- What are my biggest strengths / weaknesses?
You can go as deep down this self-inquiry rabbit hole as you want; the more you probe, the more you uncover.
The biggest issue is that, when we feel unhappy or dissatisfied, we start to paint the world in broad strokes. We think in abstract concepts, when the devil’s always in the details. If you start with those broad strokes but then break them down into their elementary particles, you can start to figure out your real passions, motivations, and the roots of your discontent.
The major thing people overlook when discussing this, at least in my experience, is that, even if you magically find yourself on a path that’s perfect for you, some days are still going to suck. That’s life. There’s no avoiding it. And it’s ok; you learn from whatever stresses you out, and you overcome it. But the secret to actually living the life you want is to be honest with yourself about these facts and not fantasize. And that’s the thing we love to do most when we feel down: fantasize. All it does is confuse us further. “If only ___”. There’s no use in thinking this way.
Instead, try to dig deep into yourself. Let the questions, answers, and follow-ups pile up in a massive document or notebook until you feel you’ve gone somewhere. It’s very therapeutic. It applies to things outside of your career; this is just a practical example of how self-inquiry can bring out the best you have to offer. You never know what you might find, and, more importantly, how you can act on what you find. It’s never too late.
If you liked this, I wrote some follow-up journal questions for workshopping this post. They’re available here for premium subscribers.