If your life experiences have been anything like mine (e.g., growing up in collectivist culture, a formal education in business, working in professional services), they may have conditioned you to understand what other people wanted. Your own inclinations may appear less clearly to you because you haven’t paid attention to them in a while.

Maybe you compromise, twisting yourself into fitting the opportunities in front of you that you see; you want to start a new independent project—maybe a business—but you’re looking for new jobs instead. 

Or you chase whatever’s exciting to you in the present moment, because the feeling of validation is very rewarding. 

Or you decide to simply want whatever other people want; either in the mimetic sense of copying other people’s desires and adhering to convention, or simply supporting them to achieve their goals. If they’re happy, you’re happy. 

But, you tell yourself, not everybody gets to do what they want.

As a result, you’ve fallen out of tune with yourself; you’re not sure what you want. You trust other people more than you trust yourself.

If any of this sounds familiar, I want to suggest a moment of mindfulness. If you’re used to talking yourself out of what you want, or not even considering it, you may find yourself waking up one day to find yourself living a life you didn’t imagine for yourself. (The phenomenon of a mid-life crisis comes to mind.) One way to step off of this default path, and in pursuit of a meaningful life, is to build self trust.

The latest edition of my newsletter, Three Thought Starters, explores this topic and asks the following three questions:

What does freedom mean to you?

What did you leave too early?

Where can you show up as yourself? How can you sustain it?

You may read the edition here, and subscribe here.

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A pet is essentially part of a person’s family. Dogs and cats don’t need to help make money in order to earn their spot; they just need to be loved. When one passes away, it can feel as painful as losing a family member. It’s personal.

These two classifications—livestock and pets—tell entirely different stories about animals. It’s why the idea of eating dogs can seem disgusting, and the idea of having a pet cow seems so whimsical. It’s also a useful metaphor for thinking about your creative projects.

For example, if you’re an author working on your book with a publisher, don’t be surprised if they treat it like livestock. It’s just another book to them, and it’s how they make a living.

If you want to make a business out of your own creative projects, it may be more useful for you to learn how to treat them more like livestock than pets. And vice versa if you want to get more fulfillment from your creative projects; you want to treat them more like pets than livestock.

From this perspective, it’s easier to understand disagreements in perspective. Some people vehemently disagree with using AI in creative work, because to them, creative work is like a pet. Other people think it’s silly to not tap into such a powerful technology because it’s livestock. Nobody’s wrong; they each have different goals and purposes for their creative work.

This contrast is also useful for being flexible. For example, I treat every blog post like a pet, so I type everything by hand. That’s the point. However, if there’s a project I’m working on to promote my work, or to support a client, I will use AI as a tool if it helps make the work better; it’s livestock.

A good way to balance this could be to treat one project like livestock—e.g., purely commercial interests, etc.—and then to treat the next one like a pet—e.g., as a passion project. You can keep alternating and build a balanced portfolio of projects, with a half sustaining profit and the other sustaining passion. The old Hollywood saying goes, “One for them, and one for you.”

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In Welcome to the Hyunam-dong Bookshop, a high school student asks this question to a character named Seungwoo who works as an employee at a big corporation and also writes a blog. Does this person enjoy work more, or writing and editing more? 

Seungwoo had worked his dream job at a corporation, but was constantly working late into the night and travelling. He decided to switch to a division with more reasonable hours, even though it meant giving up his dream job. With the time he got back, he started writing and editing for fun. He responds:

“Doing what you like doesn’t guarantee happiness. Unless you’re also in an excellent environment, then maybe. Sometimes, it’s the environment that’s more important. If you’re in an ill-suited environment, what you enjoy can become something you want to give up.”

What Seungwoo suggests is whatever you’re doing is less important than the environment you’re actually doing the work in. If you have trouble finding a supportive environment, it’s useful to remember you can create one yourself.

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Let’s imagine that your dream is to hit the NYT bestselling list. If you want to improve your odds, you’ll need to get familiar with their rules, including the sales venues they consider, finding a traditional publisher, and sell over 5,000 copies in a week. If, all of a sudden, they do it less often, your odds decrease accordingly. 

That’s a lot of power to give someone else (and, potentially, a lot of time not spent writing!). And, oftentimes, it’s in these parties best interests—the NYT bestseller list, the Grammys, the Met Gala, the Fortune 100, the recruiters at your dream company, an investor or venture capitalist, etc.—to maintain that power.

There’s no conspiracy happening; they work hard to create a consensus that they’re the gold standard. If you buy into that, and they want to make a change, then you will need to follow. If someone powerful decides to blacklist you, then you’re out of luck.

It’s useful to remember that these achievements are gratifying, but you can seek other sources of validation, purpose, and meaning.

You can, always, choose to give your dream its own intentional shape. If you don’t, it’s very easy for someone else, or the perceived majority, to make the default decision for you.

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I’ve since returned to working independently. While I remember this lesson clearly, and been going through the motions of asking for help, I still find it really difficult to practice interdependence. I recently came across a blog post by Visakan Veerasamy who’s aiming to focus on providing more for his family and being present for them. He describes a cycle he’d previously gotten stuck into it before:

    I fixate on trying to provide more

    I struggle and fail at it

    I feel guilt and shame about the failure

    The shame constricts me into feeling unworthy and/or incapable of presence

    Lack of presence makes me more anxious, despairing

    I resort to various unhealthy coping mechanisms with a cover story of “this will distract me from the pain and then I can provide more”

    Fail to provide more, fail to be present, cycle keeps getting worse

The last time this spiral reached its worst, I crashed out really badly, and my wife graciously pulled me back into reality by pointing out how badly I was failing, and how selfish I was for shutting her out of it. I logged off the internet for about 6 months (anybody who knows me knows how insane that is– I used to post even when I was sick) and spent a lot of time staring at trees. I came to see that these patterns of avoidance go all the way back to my early childhood, and I also saw very clearly that if I didn’t find a way to disrupt this pattern, my wife and children were going to pay the price for it.

I’ve since made it a habit to prioritize presence and connection with my family over everything else. I see now that I was even using “I just gotta provide more” as a kind of anxious bullshit cover story to avoid the discomfort of connection, of being vulnerable, of acknowledging my failures. I suspect this must be a pattern for a lot of absent workaholic dads around the world, and witnessing a version of that pattern in myself has, annoyingly, made me feel less righteously indignant about all those shitty dads out there. There’s some of that in me too. I could be that guy. I’m trying to be different. But I could be that guy. I have been that guy in some moments. The challenge is to be different.

Reading about Visa’s struggle with this, and the “cover story” metaphor, was very useful for me. I have my own cover stories which sound more like, “I need to provide for myself and my wife,” as well as, “I need to future proof my career,” and “I need to feel creatively fulfilled.” They all could benefit each other, and instead, sometimes it feels like each one is pulling me further from the others. 

As for what they’re covering up: the pain of failure and doubt, the effort required to start and maintain, and the need for more business to sustain the journey. The even smarter ways of saying this is, “There’s so much to feel grateful for, I feel silly for even complaining,” or, “This is all a distraction and I should just put my head down and work.” And yet.

I started writing every day to make it harder for me to avoid telling the truth. Today, there was a window for me to give you a piece of it, so I did. There is no happy ending—not yet!—and I’m learning to make peace with it.

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The music I listened to in high school, the language I spoke, my interests and friends, none of them suggested to him that I would make a decision to move to Hong Kong. It was entirely improbable to him.

One of the most useful things you can do as a creative person, especially as a writer, is to live an interesting life. Often, that means doing things that are improbable. Friends and family may not understand the decision very well, expect it from you, or be able to relate.

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When the technician came, he saw the loose arm and said he’d start with what he saw first. I was about to tell him the dishwasher worked fine with the loose arm the whole time, to troubleshoot the error code instead. But, he was the expert, so I said nothing.

After a few minutes of properly tightening the arm and setting it back up, he ran it. Over 40 minutes later, it was still going. It was clearly fine, and I was surprised that the fix was so simple. In my very brief search for the error code, I never saw that as a possible answer. When I told him about it, he laughed and reminded me that he did this every day. I really appreciated his expertise.

He left once he felt confident the dishwasher was all good, which it was, though he still checked in with me after to confirm.

I believe in practice, expertise, and people. This experience reminded me why.

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Each condition helps you achieve something different. Is your goal to get as high as possible, as steadily as possible or to create the safest landing?

As you’re reading this, there’s a good chance that you’re already trying your best. Of course, you see ways you can improve, but you’re not sure how you can get there yet. Here are some conditions that can help you make your efforts go further:

Stories: There is always more than one side to a story. How can you tell a useful story about your experience? When you’re getting closer to a useful story, you’ll know it because you’ll feel more open-minded, energized, light, expansive, and action-oriented. You can’t change the facts about a situation, or other people’s opinions of it, however you can change what it means to you. Sometimes, a good first step is finding a better question to ask.

Focus: Once you’ve found a useful story, how can you remind yourself of it? If you’re mindful, you can choose what to focus on. Even just a few seconds of space can snap you out of distraction, and into focus. Bonus: One way to snap into focus is to change your physical environment.

Agreements: What agreements have you explicitly and implicitly made with the people around you? What have each of you trained the other to do? The more intentional you are with the agreements you make and re-make with other people, the more things will start to work. For example, deciding to work as a full-time employee or as an independent contractor are two different agreements. 

Systems: What rituals, routines, and practices do you maintain? What work relies on you to get done, and what doesn’t? How can you get other people involved to help you? What tools are you using? How can you increase the output with the same input, or achieve the same output with less input? How can you feel more energized? A chore’s only a chore until you tell a useful story about it.

Relaxation: What can you do to push yourself to the limits as little as possible (i.e., create more slack)? Stress is inevitable, how can you find and practice a sense of calmness? Fear, anger, and paranoia are not sustainable sources of fuel. When in doubt, bring yourself to the present moment, and focus on what is in front of you.

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This stands out in contrast to my own words from last year, “Take fewer photos. Be intentional about the moments you want to take photos of, and trust your brain to remember the rest of it.”

I assumed that taking a photo would take you out of the moment. Let’s flip that on its head: what if the need to take a photo encouraged you to be more present? The need to find an interesting scene could encourage you to look around more, make a decision to focus on something in your environment, and remember it.

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“JOMO,” which stands for, “Joy of Missing Out,” is a fulfilling experience. The reward of JOMO is the feeling of purpose you earn by behaving in a way that’s true to yourself. It’s the same feeling of fulfillment you feel when you behave with integrity.

JOMO comes with a price, of course: you’ll need to miss out and develop the courage to commit to that.

Here are some questions worth asking: 

Do I actually want the thing? Or do I just want to keep up? 

Do I want to avoid not having the thing just because I want to keep up? 

Can I “win” by keeping up, or am I trying to “win” by going further? Is this achievable? 

Can I be the one people keep up with? What will it cost me to keep up? 

Will the reward of keeping up be worth the effort, time, and money?

Many of my friends are starting to have children, so that’s the main example that comes to mind. My partner and I are still deciding; however if we decide to sit it out, we will both need to accept the cost that comes with sitting out. We will miss out on the parenting experience, as well as a chance to get to watch children grow up. The friends that choose to have children will inevitably drift much closer together and away from us.

Funny enough, this wouldn’t be the first time I’ve missed out on something. Here are a couple of “important” things I have missed out on:

The 2010s Toronto condo boom: Many of my friends bought condos in Toronto during the 2010s, as prices were increasing year after year. Some made a tidy profit from it. At the time, I was working independently and didn’t want to overextend myself, and I didn’t feel as much conviction that the prices were going to keep going up. I didn’t doubt it, I just didn’t accept the reasoning of, “It’s gone up every year!” I feel glad I questioned the assumption, now that we are in the so-called Toronto condo recession of the 2020s, but I had no idea it was going to happen.

If I committed to a condo and a mortgage, I would need to take less risk with my career and personal life. I took a year off to write Creative Doing. I ended up moving to Hong Kong and New York City in the early 2020s. I’m sure I could’ve sold my condo or rented it out, but that commitment would’ve created a greater sense of inertia. Maybe I wouldn’t have written or moved at all. 

Instead of investing in a condo, I invested my cash in stocks and ETFs. However, I’m not able to feel the pride of saying, “I’m a homeowner.” I thought, for sure, I’d feel inferior to my friends, but this hasn’t been the case; maybe because now that I’m in a position to buy, I intentionally choose not to. 

My friends started a business together: In the mid-2010s, my friends started a company and I was invited to join. My plate was very full at the time, and the company wasn’t able to afford my rates, so I declined, though I pitched in efforts as a friend would.

For my friends, this company was their primary focus, work inevitably came up during the time we all spent together. Because I wasn’t a part of the company, I couldn’t really contribute. They shared inside jokes that I had no idea about. They also shared personal life updates in the company Slack, which I didn’t have access to. Friendships come in seasons, and this was the company’s season, which I wasn’t a part of. Even though it was my decision, I felt completely iced out, and it was very painful. I handled this as gracefully as I could.

As I reflected, I realized that monetary compensation and stock equity—the professional rewards—were just a part of the experience. Getting to know each other better as people was another part of this. I wasn’t comfortable with the business terms being offered, though, so I needed to miss out. A few years later, the company was acquired, and everyone moved on to the next part of their careers. It felt natural to drift together and be friends again as each of us explored what was next. In the meantime, since I moved, I also made new friends.

There’s a lot more I could write about here, like declining an opportunity to interview at Shopify in the 2010s, missing out on the 2010s crypto run, etc. 

What I choose to take away is that while missing out felt painful, it was very recoverable, and those tradeoffs also provided me with the fertile ground I needed to do what I’m doing today. I got to live in three different countries. I wrote Creative Doing, I’m about to publish The Consistency Journal, and I continue to work independently with tech companies on business writing.

The courage to miss out could also be rephrased as, “The courage to commit.” There’s no life without missing out.

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