The Inconvenient Secret To Finding Purpose

As I mentioned before more than once, I did every exercise under the sun to discover what I wanted to do in my life. This gave me some great ideas and clues, but the only way to truly discover “my purpose” was to experiment. In practice. A lot. With more ideas than I can remember. I’m sharing a partial list, along with my learnings, to prompt you to start your own explorations. After all, you can’t possibly abandon more ideas than I have.

I started writing a book about machine learning (a subset of artificial intelligence) for non-technical people. A few posts I wrote on the subject went viral and I thought I could expand on that. O’Reilly, a big publisher in the technology space, even wanted me to partner with them on some content. I took classes in machine learning, involving subjects I haven’t touched since college like algebra (don’t be afraid to dust off those brain cells). I was bored out of my mind and gave up after a few months. This was me hanging on to the idea of building on the success I already had rather than listening to my intuition.

I looked into starting a high-quality clothing company. This sounds out of left field, but I did spend half my childhood drawing clothes and obsessively reading old Vogue issues (the other half was spent drawing and reading other things). I was so frustrated by today’s clothes getting holes after a few washes that I even took a garment manufacturing course to learn how to create something better. It was interesting, but I realized the operational component—my least favorite part—would dwarf the things I did like doing.

I started a lifestyle blog. I was curating for myself a lot of art / design / lifestyle / creative content and thought I’d share that with the world. I set up the blog, wrote 10 posts, and published none. I learned I’m not as interested in writing about other people’s creations as I was in creating something myself.

I started a company to provide internal social networks to connect employees in remote companies. This was pre-pandemic, and I probably could have raised $100M and grown this idea to a billion-dollar company in 2020 alone. Sadly after working on it for months I knew my heart wasn’t in it anymore for reasons I couldn’t explain. Now I know it was because I didn’t really want to build or run a huge tech company (which I knew this had the potential to be), but at the time it wasn’t something I was able to consciously see. I just knew this idea wasn’t “it” and I listened to my intuition rather than forcing it.

I wrote a detailed plan for a co-working space where people connect as if they worked for the same company (yes there’s a theme here). I finally figured it was a business I would have loved as a customer (I still would) but not a life I would love as the founder running it.

I started a blog on the “people side” of technology product management. I set up a blog and a mailing list, wrote many posts, and published two. This held my interest, but I soon had the epiphany that what I had written applied to most professions, not just product management. It was an early iteration of this blog.

I took a portrait painting class. I didn’t like anyone telling me what to paint and didn’t even finish it. That nixed the idea of going to art school “to become a professional artist”. I realized I didn’t need permission from anyone to do that.

I started putting together a book of writings and drawings. It felt like I was forcing it and maybe these creations weren’t ready to be combined in that way.

…and these are the ones I remember. I’m sure I missed a few. 

There were some common themes: Things I obsessed over in childhood. Ideas I wanted to see in the world like connecting people in non-standard work environments. Areas I had work experience in like machine learning and product management. Things I loved doing like sharing my knowledge with people.

I started all these thinking they might be interesting to pursue, not knowing how to do them or where they’d lead. Most led nowhere. But I noticed things I loved and found themes I went back to over and over again in various forms. I noticed things I didn’t love and didn’t want to go back to in any form. I did enough personal development work throughout to eventually get over enough fear to see what I truly wanted: To do the things that make people starve and open themselves up to painful criticism, like art and writing.

You see, I believe we all know what we truly want to do. We just take a lot of time, experimentation, and unlearning to admit it to ourselves.

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