I’m 30

Every year, for the last twelve years, I’ve done a birthday post. These posts summarize what’s happened in my life over the last year, as well as my thoughts about the future.

This year was a big one for me, more than just rolling into a new decade. I got married. I signed a book deal. I spent ten days at a silent meditation retreat. My team and I developed a new course, which should be ready in September.

More than just these milestones, however, this year has taught me quite a few things, as well as shown me how much more I still have to learn.

Things I’ve Learned (and am Still Learning)

1. Anxiety and Perfectionism with High-Stakes Creative Projects

The major project for me this year was writing a book. I had wanted to write a book about ultralearning for a few years, and now finally felt like the right time.

I knew from the start that I wanted to do something different from my previous self-published ebooks. I wanted it to be driven more by stories other than my own, and be backed up by more scientific research and less my own experiences and opinions.

On the one hand, this is good. The higher standards have pushed me in a lot of ways to produce better writing, that I wouldn’t have gotten on its own.

The downside was also that I felt a lot of anxiety about my own performance at times. I often got stuck, either because I wasn’t sure what direction to take, or because my own fears about how the book would turn out meant it was easy to avoid working on it.

This was a new experience for me. In the past, whenever I’ve felt pressure on projects, they’ve tended to push me forward rather than hold me back. In the beginning of the MIT Challenge, when I was most uncertain about meeting the deadline, the pressure forced me to work very hard to make it. Similarly, when studying languages, any doubts I had about reaching the goals I had set made me want to work even harder.

I think the difference owes to the different dynamics of the tasks. With many learning goals, the solution to anxiety about performance is simply to do more practice. Same is true with a lot of business goals, where worries about meeting a target are best soothed by working harder at it.

In creative tasks, however, there’s a risk that making an early mistake in how you structure something, or choices about how to handle certain things, can become embedded into the structure later. In these situations, the result can be paralyzing because added anxiety forces you to stop and think rather than push forward bravely.

My previous ebooks and courses rarely felt this level of pressure, because in my mind, I was mostly writing to my own audience, with no real expectations of mainstream success. However, with an agent, advance, publisher expectations and my own internal ideas of what I wanted to accomplish, it was harder to de-escalate those expectations that led to feelings of perfectionism.

I’m not sure I have a solution to this issue yet, but I suspect as I go further, and the stakes become higher for projects I’m working on, it’s going to be a problem that will get worse if I don’t find a good workaround.

2. Switching From Solo to Team

In the past, I did nearly everything by myself. That meant, when I started a big project, I simply stopped doing a lot of other work. It might require some choices, but coordination was fairly easy because things simply had to be done in sequence.

Now, my business has grown and there are around a dozen people I work with regularly, including a few full-time employees. On the one hand, this is an amazing benefit. I can focus on the things I’m good at, and not need to worry about being great at the things I’m not.

On the other hand, individual productivity is different from team productivity. It’s no longer simply a matter of picking projects and working through them sequentially, but trying to time my involvement in multiple, concurrent projects. This is a lot trickier to do, and I’m still figuring it out.

One of the big mistakes I made this year was a failure to organize these schedules. In addition to writing my book, my team and I also developed a new course. The downside was that the busy periods for the book and course often coincided. This meant periods where it was difficult to decide where to focus because both were demanding my attention.

In the future, I’m going to have to be more careful about scheduling projects so that the intense times for projects don’t overlap so much.

What’s Next?

I still have a month to go before I hand in my manuscript for my book. After that, there will be at least a year of editing, finalizing, printing and marketing. So, in some senses, the major efforts of my next year or so have already been decided.

However, I expect that once the full-time writing stretch ends, my life is going to be a little more open, so there’s going to be more opportunities for new things. Here are some of the things I’ve been thinking about that I want to work on:

1. Flexible Habits

The busyness of the past year have pushed me to explore different ways of thinking about my habits and the ways I want to do things in my life.

In the past, if I wanted to set up a good habit—say going to the gym, meditating or learning Chinese—I’d simply put effort into making that my priority and including a chunk of time each day towards it. Going to the gym 3-4x per week for an hour or so has been a long-term habit for me for a decade or more.

However, lots of large, clunky habits can be difficult to fit into my schedule. This creates inconsistencies with how those habits are applied, and sometimes, can lead to them slipping.

These days, I’ve found a lot of success with setting up quite minimal habits. Things that are probably insufficient for my goals, but if done every day as a background activity, they also prevent things from getting too out of hand if the clunkier habits slip a little.

Six months ago, for instance, I set the habit of doing fifty push-ups a day. I’m happy to say that in that time period, I’ve only missed one day of the habit.

The habit works well because it works in almost any circumstances. I even did some after my wedding because I had forgotten to finish them in the morning. Going for a workout in the gym, in that case, would have become incredibly difficult.

The success of this habit and a few others I had started, have made me think more about establishing a few baseline habits for areas of life which are important to me, and can run in the background essentially forever, no matter how busy I am, where I am in the world or how I’m feeling.

2. Making Travel a Priority

I’ve traveled quite a bit, and in the past, travel has been something I’ve done in bursts, for long stretches of a time. I did one year in France in university. I did another year around the world, several years ago. Between those times, I’ve been on plenty of month-long or multi-week trips.

These days, long bursts of travel are harder to schedule. This is going to be even more true if my business grows or I have kids.

Yet, travel is something that’s important to me. Not as a vacation, but as a goal of expanding my understanding of the world, different cultures and ideas. I see travel, done properly, as being akin to reading books in offering windows into different aspects of life and the world. Just as reading is important to me, beyond just leisure, so is travel.
The solution here is that I need to start planning for trips longer in advance, and fitting them into my schedule ahead of time. Waiting until I have some downtime was an approach I used to take, but as my work has expanded, those downtime moments evaporate much more rapidly.

3. New Ultralearning Projects

Although I don’t always write about it, I’m always spending time learning new things. The ultralearning projects I’ve done are something different, investing a focused burst of time to accomplish something big. 

I like the ultralearning projects because they allow me to make progress on something I care about but haven’t been able to devote enough time to. They are also helpful for pushing through obstacles that make casual practice less enjoyable. A big motivation for my most recent portrait drawing challenge was that I was too bad at it to enjoy it in the beginning, yet it was a skill I thought I’d like to develop.

I’d like to do another ultralearning project, but I haven’t decided on exactly when or what topic.

Some ideas I’ve had include:

  • Trying to deeply learn some professional skill, with perhaps the side-goal of turning it into a functioning freelance business by the end.
  • Chess. In particular, I thought this might be interesting because the whole process could be live-streamed, unlike my previous projects which function with semi-regular updates.
  • Art or music. Painting, guitar, photography, animation or something similar might be interesting skills to work on. They also are easier to demonstrate, which makes them more fun as a project.
  • Something academic. There’s a lot of academic topics I’ve wanted to build skills in. Statistics, machine learning, quantum physics and neuroscience are all possibilities.

The only project I’ve contemplated seriously yet is trying to combine an extra push of language learning with the release of my book. I was thinking about possibly going to some of the countries where the book is being translated and released, and give some speeches about it and answer questions in those languages.

This last goal is a tricky one though, because if I limit myself just to rehearsing a prepared speech, this is something I can almost certainly do with enough practice in any of the languages. However, responding to live Q&A is quite difficult, even in languages I’m best at, so defining the scope of the challenge will be tricky.

Final Thoughts

I’ve been writing for a long time, so in many ways my writing here is a less a snapshot of my opinions, but an evolution from who I was when I was 17 until today.

In some ways, I feel like time has vindicated some of my philosophy. I managed to build a successful business, marry the woman of my dreams, have adventures and live a happy and comfortable life. Those things weren’t true when I started, so in some ways, it has felt good that some of my original ideas turned out to be good ones, even if that wasn’t clear at the time.

In other ways, though, my views on anything being the right “answer” for how to live life have become a lot more tenuous. I used to hold fairly rigid opinions about what was the right way to approach things. Now, I’ve come to see that there are many different ways one can approach life, quite different from how I approach mine, that are also valid. Different perspectives have their own benefits and disadvantages, but I’m less inclined to believe mine is the only way, or necessarily the best for everyone.

This fact itself puts me in an interesting place with my writing. On the one hand, I feel like I have some useful strategies and approaches to life to share. On the other, I’m more aware of the diversity of different ways to live and how those might involve doing the exact opposite of what I suggest for certain people in certain situations.

I guess I feel that the value of my writing is that, for those who feel that the approach resonates with them, that I can offer some thoughts on how to get more of it. For those taking a different path, there’s no problem with not following my approach.

Thanks for reading this past year, I look forward to sharing more with you in the next one!

On Keeping Your Word

Most people are pretty good at keeping promises to others.

When I make an appointment with a busy person, even just for something as simple as a call, they almost never cancel on me. If they do have to, they almost always apologize and work to reschedule.

This is true even if I don’t know the person. Even if the call was just a friendly chat, not something incredibly important.

There are exceptions, of course. But the fact that they feel so rude is evidence itself that broken promises to other people are quite rare. If they happened often, they would just feel normal, not like an insult.

Promises to Yourself

Yet, how often do you break promises to yourself?

You tell yourself you’ll stick to a new diet… and give up after one week.

You tell yourself you’ll start a business and never get past printing the cards.

You tell yourself you’ll make a change, but nothing ever comes from it.

We break promises to ourselves all the time. Unlike when others break their commitments to us, these are so common, that, for most of us, they don’t even feel disappointing. They’re just “part of life.”

The Value of Promises

Maybe the reason we break our own promises is that it doesn’t feel like it has a cost. If I break a promise with you, you’ll be mad at me and trust me less. If I break a promise with myself, there’s nobody to get mad at.

But this is just an illusion.

Breaking promises to yourself has the same costs as breaking it to other people. Except the person you trust less is you.

When you trust yourself less, you treat the future-you as being inherently less reliable, less responsible, less likely to commit to the things current-you says you’ll do.

Without trust, you take your own plans less seriously. Take your own plans less seriously, and you’ll be less likely to commit to them in the future. A dangerous circle develops where you fail at your goals not because they were impossible, but because you simply didn’t think somebody like you would be able to stick to them.

Make Fewer Promises; Keep All of Them.

I don’t make many promises. Reality can change, so if I’m not sure I can make a party, or have time for a call, or help with a chore, I won’t commit. Better to disappoint someone early, than betray a trust later.

But the promises I do make, I keep. Sometimes they cost more than I had expected. Sometimes plans change and the reasons I promised them no longer make sense. But I keep them because, if I didn’t keep my promises, what kind of colleague, friend or husband would I be?

In the same way, I don’t make many promises to myself. I make few commitments, but I stick with them. I don’t always expect to be successful, or that life will always go according to plan, but I trust that the failure won’t be because I didn’t decide it was worth sticking with.

If you haven’t kept your promises in the past, rebuilding that trust takes time. It starts with small promises and keeping them even if they don’t feel like they matter.

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