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Dave Kang spent years trying to figure out his “one thing.” You know the drill: find your purpose, your passion, your Ikigai. That one perfect intersection of what you love, what you’re good at, what the world needs, and what you can get paid for.
It was frustrating. And it didn’t work. And it’s not even the original meaning of Ikigai!
So instead, he’s embraced life as a CEO. No, not that kind. A Chief Exploratory Octopus.
Living as a generalist with multiple interests (aka tentacles) reaching in different directions, without forcing it all to converge into one neat identity.
Now he writes about this on his Substack, helping other multi-talented, multi-interested people break free from the pressure to pick just one thing. As another identity-struggled creative generalist, that’s exactly how I found his work, and it was a huge relief to realise there were others like me and a mental model for thinking about it.
Chatting with Dave was an absolute joy, and I left feeling inspired and reassured about being someone with “too many” interests. Here’s a few highlights from our conversation.
Highlights from my chat with Dave Kang
1. The Ikigai diagram you know isn’t actually Japanese
That famous Venn diagram with four overlapping circles is not part of the original Japanese concept of Ikigai. The diagram was created by a Spanish astrologer in 2011, then a British blogger relabeled it “Ikigai” in 2014 after watching a TED Talk.
The original Japanese concept, researched by psychiatrist Mieko Kamiya in 1966, had nothing to do with finding "your one thing." It was about everyday joys and small life-affirming moments. Dave wrote about this and it went viral because it hit a nerve: people are tired of forcing themselves into frameworks that force them to find their “one true purpose”. Which leads us onto…
2. You don’t have to do just “one thing”
For multi-interested people, the pressure to find one calling is exhausting and often counterproductive. Dave realized he didn’t have one thing, couldn’t figure out what it was, and finally gave up trying. That’s when things got interesting. If you’re a “jack of all trades” or an “octopus” person who likes doing lots of different things, you don’t have to fight this part of yourself. You can invent your own framework instead of squeezing yourself into someone else’s box.
3. Embarrassment is often the price of entry for an interesting life
Most good things are on the other side of embarrassment. Starting a podcast. Sharing your work. Being passionate about eight things instead of one. Quitting your job to try something new. People worry about what others will think. In reality, nobody cares as much as you think they do. You care a hundred million times more than anyone else. And even if they do judge you, so what? The alternative is living your entire life based on imagined criticism from people who aren’t even paying attention.
If anything, you probably need to lean into the cringe if you want to do something interesting.
4. Play like an octopus
Octopuses have eight tentacles, three hearts, and brain cells in their arms. They’re constantly exploring with their tentacles, picking things up, examining them, and dropping them if they’re not interesting. They don’t always deploy all eight tentacles at once. They don’t have a rigid schedule. They’re organic, fluid creatures who have survived for millions of years with this approach. It’s a fun metaphor, and it works. Be like an octopus.
5. Your tentacles don’t have to be equal
You don’t need eight equally-weighted interests. Maybe you’re a three-tentacle octopus. Maybe one tentacle is way stronger than the others. Maybe you deploy two tentacles intensely for a while and let the rest dangle. The point isn’t balance in the traditional sense, but instead giving yourself permission to engage with multiple things in whatever proportion feels right at the time.
6. You don’t have to win Wimbledon
Roger Federer dedicated 40 years to tennis and became the best in the world. Leonardo da Vinci had a dozen interests and was fantastic at most of them. Both had meaningful lives. You don’t need to aim at being either of them. You don’t need a Wikipedia article. You don’t need to win Wimbledon. You just need to be true to yourself, deploy your gifts, and live in a way that feels authentic. That’s enough.
7. Stop optimizing your calendar like a factory worker
Calendars, clocks, time blocking, Pomodoro timers - these are all artifacts of industrial work culture. They evolved because factories needed to track when workers punched in and out. Not all cultures are obsessive about time. Many treat it far more fluidly. Dave doesn’t use rigid schedules anymore. He follows his energy and intuition.
8. Leave room for serendipity
If you pre-optimize your entire week, you’ve already decided what you’ll do before you’ve felt what you actually want to do. You’ve blocked out all the white space where accidents, inspiration, and discovery happen. Scheduling everything “perfectly” means you’ll have zero room for serendipity, play, and chance encounters, and that is exactly where the interesting stuff usually happens.
9. It’s okay to quit. In fact, it’s good for you.
We stigmatize quitting, but life is full of it. Kids quit activities all the time, and good parents let them. Quitting helps you figure out what you don’t like, which is just as valuable as knowing what you do like. Dave quit football after a week and a half in high school. Quitting gives you data. It helps you discover yourself. Go ahead and quit things. It’s good for you.
10. “Why not?” is more useful than “Why?”
Simon Sinek says “start with why.” Dave says start with “why not?” Finding your why is hard. It requires sitting around thinking about your life’s purpose. Why not just try things instead? Experiment. See what sticks. You might discover your why by accumulating a lot of “why nots.” Action beats contemplation. You’ll learn by doing and experimenting, not by challenging yourself with a big “why” before you even start. Rarely is something so serious that you can’t give it a go. So why not?
11. Overthinking is an illusion of control
Overthinking can feel productive and safe. If you just think through every scenario, maybe you can prevent bad outcomes. That’s an illusion. No amount of thinking prepares you for reality. And while you’re overthinking, you’re not doing anything. That’s why the cure for overthinking is just doing things. Action gives you information and feedback that thinking never will.
12. Not everything needs to make money
It’s easy to let every hobby become “how do I turn this into a side hustle?” But most things are worth doing just for the joy of it. Dave played pickleball recently. He’s not making money from it. It’s just fun. If you try to monetize everything you love, you risk killing what made it enjoyable in the first place. Protect some tentacles from commerce.
Resources Mentioned
Dave’s Substack: Dave Kang's Octopus Life
Dave’s book recommendations:
The Pathless Path by Paul Millerd
The Great Work of Your Life by Stephen Cope
Range by David Epstein
Four Thousand Weeks: Time Management for Mortals by Oliver Burkeman
Full transcript available here.
