How I Choose What Hobbies to Pursue

I’ve tried so many hobbies in the past like pole dancing, stand up comedy, basketball, badminton, table tennis, tennis, cross country, swimming, chess, Yu-Gi-Oh, volleyball, acro yoga, bouldering, you name it. Some lasted for years and others for a few weeks.

I knew intuitively why I didn’t go deeper in some hobbies but never put it into words until now. Why did I quit basketball after devoting my life to it my entire childhood? This is what I realized about myself.

The hobby must have unlimited potential to grow

I pole danced for a year and a half. It was very fun in the beginning, as with most hobbies, but there came a point where my body’s limitations started to show. My flexibility was nowhere near where it needed to be. It hurt to simply sit straight up with my legs spread out, my weight made me lean back because my inner hip is just not built for that.

I told myself that I have a growth mindset and that I could still do it. But even after stretching every day for a year straight, my flexibility improved, but barely to the “starting point” as most of the other dancers in my class. This was very discouraging because my results were disproportionate to the amount of effort I wanted to put in.

On top of flexibility, my body didn’t move in the fluid motion that I desired so much to have. My only slight advantage was my upper body strength but in order to progress to the next levels of pole, I needed to lose a ton of fat while gaining muscle (gymnast body) and that by itself was a whole other goal on top of stretching, and dancing. That’s a ton of work for very little reward.

This reminds me of when I used to play basketball growing up. I was actually good up until about 14 or so. I studied Pete Mavarich’s DVDs and practiced dribbling all around my house, the streets, and even to a church retreat. I was average height and everyone else had a similar build so having skills and basketball IQ was had a lot of weight instead of pure genetic athletic ability.

But when I got to high school, I made the freshman team as the last guy, the 13th pick. Our team was one of the best in the league so simply making it was a reward on its own. But holy crap, playing with the sophomores who are not only more skilled, but more athletic, taller, and stronger. They could have horrible basketball IQ but still dominate me in practice because I couldn’t compete.

There was one player on the team who I admired growing up. He was a short baller who had mad hops and speed. I looked up to him in the basketball world because he was living proof that quite possibly, I could do it too. But he too struggled while on the team. He was no longer the starting point guard as he was a liability on defense. He didn’t have the best 3 point shot, decent at best, and even with his playmaking abilities… his height served to be a huge issue as he went up from JV to Varsity, to the point where he just simply compete.

One could argue that I could have worked harder. I could have lifted more weights, studied more film, practiced extra hours before and after our workouts. But it goes back to stretching analogy, the more I would have worked would be disproportionate to the results I would have actually got. Also I was 14, I didn’t want to make basketball my entire life to make it as a consistent benchwarmer.

This is why I turned back to chess. I was an average chess player in high school (1400 ELO for you nerds out there) and when I took a sabbatical to study chess for 9 months, my rating shot up to 2000 ELO which is equivalent to a chess expert. People in this range are the top 96% of chess players on Chess.com (largest chess network in the world) or top 90% of registered chess players in the United States Chess Federation.

I loved studying chess because you can learn one concept and immediately use the lesson in your future games. I had unlimited potential to grow because unlike a physical sport, I didn’t need to be born tall or fast, I just needed to study hard and smart. The more hours I put in, the better results I achieved. It felt amazing to see your hard work paying off with such a rapid feedback loop.

However, to go from 2000 ELO to 2200 ELO which is chess master level is more difficult than going from 1400 ELO to 2000 ELO since the learning curve is getting incredibly steep. I would actually not mind fighting to go further but this leads to my next point on why I stopped playing chess ultra competitively.

The hobby must have community you enjoy being around

Studying chess was incredibly isolating and at times, tedious. I actually enjoy the study sessions and found it to be exciting. Staring at a chessboard for hours on end never seemed to phase me. It was just the loneliness that really bugged me.

Once you’re closer to the top, you need to find people at your level to “spar” with you, similar to a boxer or tennis player. Unfortunately, most people in the chess world that are experts or better are young kids with tiger parents or old retired White men. I would have to make a serious effort to bond with these players and ask if they wanted to spend a whole day studying grandmaster games together which is doable, but not that fun, as the only commonality we have is chess.

This is why I pay Eric Rosen to coach me in chess. He’s a 26-year old International Master living in Chicago who I think is not only a stellar teacher but someone who I can connect with. It’s genuinely enjoyable to learn chess.

In an ideal world, I would have a few friends locally to meet up once a week for study sessions and blitz game to level up our games. We’d travel to tournaments together and trade secrets just like in my competitive Yu-Gi-Oh games. Or it would be cool to go to the All-American leagues or Lebron James’ basketball camp where they bring together the top high school athletes to play ball 24/7. But there is no community like that for chess which discourages me to keep going at an ultra-competitive level.

Enjoy the process

Standup comedy seemed like it was going to be both terrifying and exciting. My first time performing was actually very fun and I wanted to do more of it until it finally hit me how hard it was to write original funny jokes.

The process of waking up every morning to a blank page writing dozens of jokes and being satisfied with one joke a week (if I was lucky) was just a pain in the butt. Then you would have to go to open mics to test your material in front of empty crowds or other comedians, night in and night out, for deliberate practice. Sometimes, you would have to show up two hours before the open mic just to sign up, and then won’t get called on until two hours after the show starts to get three minutes of stage time.

I loved the result of trying to be this charismatic and hilarious comedian but the process to get there was not fun at all.

Pole dancing has an incredibly supportive community but with limited potential to shine. Chess had such a high ceiling with plenty of potential to grow, and I really enjoyed the process of getting better, but the loneliness of studying solo and not having people to train seriously with got to me.

I needed a combination. I needed hobbies that gave me the unlimited potential to grow, a community that I really vibe with, and one where I really enjoyed the process of getting better.

I think I might have found my answer.

My new hobbies for 2019

I started dancing Bachata in January 2019 when I made a New Year’s resolution to do an activity that scares me.

Partner dancing, in general, intimidated me. I took a salsa class two years prior and remember not knowing anyone there, stepping on the other person’s shoes, putting my hand too low on their back accidentally and having them to correct me, and felt off-rhythm because I had never danced before (this was before pole).

I begged my best friend Chloe to go to a class with me so I don’t feel alone. My first couple of classes were actually very positive and I started to go to more without Chloe as I got more comfortable.

At my dance studio, they had a “social dance” once a month where the DJ plays music for the rest of the night and anyone can ask anyone to dance Bachata. I still didn’t feel comfortable to participate because I didn’t want to embarrass myself. Once the first social happened, I called my Uber when every single person started dancing, and booked it.

I stopped dancing because I was heads down in job hunting. But when I moved to Toronto, I wanted to go to my first social dance and I am incredibly lucky that I knew someone there that was deep in the dance scene. I met Amber for 30 seconds at a business conference in Chicago (my notes from Forefront) and now we are best friends dancing every week together.

She told me to just feel the music and to have fun. Those were my only two things that I needed to think about. It sounds simple and easy for her to say, but it actually worked.

But baby steps. The first social I went to, I danced to one song and Amber, and left. The second social I went to, I danced for 30 minutes. The third social, 1 hour. The 4th social, 2.5 hours. Yesterday might have been my 10th social and I stayed for 3.5 hours! I could have stayed longer if the length was my goal but being on your feet for that long is actually pretty tiring. ;)

You also didn’t need to be tall, fast, in shape, attractive, or whatever to dance. Dance welcomed everyone. There was no ceiling. Dance is so cool because the more moves you learn, the more you can instantly put it to use on the dance floor. Rapid feedback just like chess.

I also found a small community through dance. I am so grateful for Amber being my sherpa and introducing me to a bunch of her friends. Plus, after you go social dancing a few times, you see many familiar faces and make friends there and through my dance classes.

I enjoy the process so much because I love listening to Bachata songs. It’s my playlist for working, walking, and dancing in the kitchen. You also get to have fun and mess up with other people.

On top of dance, I’m just starting to learn Spanish because (1) it’s fun and I enjoy the process (2) unlimited potential (3) people speak Spanish.

I like going all-in on hobbies that reward me for going all-in.

I still play basketball, chess, badminton, and several other activities but know that it’s only for pure joy.

Now everything above is just my mental models of hobbies today. Maybe in 2021, I’ll discover a new need of mine and pursue another hobby, or change my environment to meet all these conditions, but in the meantime, I feel pretty proud and aligned with my decisions.