How to Find What You Actually Love
Avoiding spending too much time lusting over things you don't actually enjoy
Disclaimer: This article is a bit of a mess. I’m going to consider it a draft, but I also am trying very hard to stick to a publishing deadline. The most valuable lesson to come out of this newsletter is making sure to properly flesh out my outlines earlier!
“Do what you love and you’ll never work a day in your life”.

For the past couple of decades, the advice to follow your passion has grown from something your parents or guidance counselor told you to a million-dollar guru/life coach industry. We have people all around us telling us how important it is to follow your passion, or how valuable passion is to success. They offer courses littered with platitudes about how everyone can turn their passions into side hustles. #hustleporn #pleasestopit
But there really are two main issues I have with this advice.
Not all passions can provide a living wage.
How do you even decide what you love doing?
The first problem is something that cannot really be controlled and can safely be ignored. If you are lucky, your passions and the value they hold in the world will end up combining at some point. But success isn’t always monetary and following your passion may lead you to a successful life in many other ways. So stop thinking about following your passion to success as purely monetary.
But the second problem, the one about deciding what you love, is what we’re going to focus on. Some people are lucky and they just seem to know. It’s infuriating at times. For the rest of us, we bumble through life, moving from hobby to hobby, in search of that deep, visceral passion that those lucky ones were seemingly born with. Unfortunately, when you don’t have something you are passionate about, it’s hard to be honest with yourself about why you aren’t finding success in your hobbies.
Luckily, it’s almost certainly true that you have a passion, even if you haven’t admitted it to yourself. And the really good news is that you can start eliminating things you’ve been fooling yourself about by asking one question:
Would you still do the thing if more barriers prevented you from getting started on it?
There are thousands of things that I enjoy doing. Deciding on what to do at any given point in the day is really the root cause of most of my anxiety. Playing video games? Let’s do it. Sailing? Anchors away! Axe-throwing? Watch your fingers, but count me in.
If you ask me to do or try something, the answer is almost always yes. And while we are doing the thing, I’ll probably really enjoy it.
But, when left alone, thinking about how I should do said thing, without the assistance of someone who has already taken care of all the barriers to enjoyment, I’ll never go do it. Doesn’t matter how much fun it was in the moment, the fact that there are barriers between the enjoyable part and the necessary parts, means I’m not going to bother.
And that feeling, the ability to dismiss doing something you enjoy because of an added barrier to starting, is what we should be looking out for to help us decide what our passions truly are.
An example. I really enjoy playing golf. When I’m out on the golf course, I don’t want to be anywhere else. No matter how well I end up playing I always leave feeling great and thinking about how I should definitely golf more.
But for years, I didn’t have a set of clubs. An easily surmountable barrier to playing a round of golf and yet, for years I just didn’t play. The additional task of sourcing a set of clubs to play with was enough to keep me off the course for quite some time. For me, this happens all the time with so many activities or hobbies I enjoy; things that other people are definitely passionate about.
Sailing is another faux passion. It was an activity I was lucky enough to grow up being able to do. Out on the boat, the wind lifting the side of your hull and carrying you across the water is an absolutely wonderful feeling. But there are so many tasks required for maintaining the boat or my absolute dislike of getting chucked into cold, seaweed filled water that the enjoyment I get from the actual sailing isn’t enough to make the rest worth it. Some of my best childhood friends, on the other hand, would put up with almost anything to find time to get in the boat.
On the flip side, I’ve recently accepted that I am truly passionate about writing and sharing stories. Putting words to pages, having people read them, and even better, having people enjoy them, is something that I have always come back to doing. No matter how many barriers get thrown my way, I keep trying to write. When I have spare minutes in my day, I write down ideas or paragraphs or bulleted lists for an outline. If I’m watching a movie, I’m thinking about how if I could write better dialogue or a better twist.
Kids and a full-time job are a massive barrier to writing because they take up large swaths of time and yet, I always make the time to write.
I wrote recently about the enjoyment of being a generalist and how trying out many things is great. But it’s really easy to feel FOMO when it comes to watching others be successful doing something they are deeply passionate about. You see them and say, “I love doing that, I could be successful if I just had the time.” Then an opportunity to put time into it comes up and you exacerbate the smallest barrier to prevent yourself from getting started. It’s a pretty useful self-sabotage to avoid doing things you don’t really love doing.
Personally, though, I don’t believe there is nothing wrong with this. You can’t be all-in on everything, but if you listen to yourself in these moments, you can stop feeling bad about not committing to succeeding at things you aren’t all that passionate about.
The next time you have a spare minute, pay attention to what you choose to do and see if you can find a recurring theme. Then, drop the stigma of feeling like you need to hustle your passion into a career and just keep doing it. Maybe you’ll get lucky and the winds of change will blow in your favor, but if not, hopefully, you’ll see yourself as being successful just because you love what you do.