What I Ought To Be Doing: Planting and Growing
How to find your life's work
Starting new projects is one of my favorite things to do, I love to plant things.
There is something about the era we are in that introduces a sort of paradox around this. We now have access to unbounded information and content, and that makes it easier than ever to get inspired and to track down the resources needed to get going and start planting new seeds. I feel the benefits of this fact. I've begun to internalize the feeling that I can learn anything if I sincerely want to learn it. I am doing this with programming. I built a Chrome Extension in a few hours and had it in the web store in a week or two, even though I'd never programmed a browser extension and never written software for more than a few users. I taught myself guitar and got decent pretty quickly in 2019. I have read countless books and watched countless videos and listened to countless podcasts about how to write well that have helped me to. I believe with the tools today, nearly anyone can learn the things they want to learn1.
But I said there was a paradox, and the other fact that feels true is that because I encounter so many cool people and so many cool projects on the internet or otherwise, I can get overwhelmed by the possible paths my life could take. When I read a perfect book, I am reminded I want to be a writer2. When I hear a beautiful song, I am reminded I want to be a musician. When I find a creative product, I am reminded I want to be an inventor. All of these things pop into my life every day, and I become the different selves inside of myself every day too. This is a wonderful thing, but it means I am always starting things, always trying something new. After only ten minutes I can be on a new trail of curiosity and before I know it I have a new page in my "side-projects" notion folder. New ideas grow like weeds, or wildflowers if we want to be romantic about it, and now my garden is full of them. I've heard that responsible gardeners prune their gardens. They wander around and find the flowers that matter most to them and they nurture those ones and don't spend their water on the others, beautiful as they may be. Should I be doing this? I think about it, but my answer always seems to be no. I always think I ought to keep exploring because curiosity is a gift and I've spent periods of life in its absence. So when I have it, I should trust it right?
But I worry that I am planting too many seeds, that I haven't grown the muscles necessary to cultivate something from infancy to maturity. Do I have what it takes to grow the seeds I've planted into beautiful flowers and tall Magnolias? I honestly don't know3. I've launched a ton of projects recently, and my only goal has been to "do cool things". To try things I am sincerely interested in or curious about. Isn't it odd that finding those things is much tougher than you'd expect?
When we all took those career aptitude tests in elementary school they presented us with the kind of society where people were meant to do certain things and they told us they could help us find the thing we were meant to do. This vision of finding purpose in work looked like the society from The Giver, which I had just read for the first time around taking my first career aptitude test. But that isn't how our society works really. Over the last few years I've started to wonder if letting go of this idea of career matching is essential to finding the right career.
The first part of the vision is probably true: people are better suited for certain kinds of work than others. If you doubt this, just think about the most miserable job you've ever had. The fact that you can rank your misery by jobs you've had, and the fact that your ranking would not align with someone else who had the same jobs proves it is true. So the first half is valid. But it is important to realize, and I've come to realize, that a single person is more than likely suited for a couple of different kinds of work. In other words, it isn't likely you are well suited for a single job, so you must revise the way you search for the path best suited for you based on that fact. Given that there may be several types of work we are best suited for, how do we start looking for them? Sure, hunting for a few candidates is slightly better than hunting for one, but not by much. My solution has been to aim for optimizing towards things I enjoy doing over time. To do this, I rely on the feeling I get while working on certain things. Do I feel energized having spent two hours on something or drained? Another trick I've used is to reflect on past projects. When in my life did I feel most like myself in work? These are helpful at getting you closer to the kind of work best suited for you, but they won't help you have certainty about the work you should devote your life to and they won't identify which of the many candidates you ought to be doing.
Just typing that sentence inspired shouting in my head, the shouting voice said "IT ISN'T LIKELY YOU WILL DEVOTE YOUR LIFE TO ONLY ONE TYPE OF WORK!"
I hear ya.
But did Newton not do that? Didn't Mozart do that? But most people don't I guess. I am not sure if that is good or bad, but my guess right now is that it is probably fine. The important thing isn't "are you sticking to the work you thought you should devote your life to", but something closer to "are you continuing to find work that is better suited for you over time?" I think that I am. Also, maybe it is that a specific job (or jobs) or "career" is not what matters, but the type of thinking and style that you apply to those specific mediums. It is like if a specific job is just one instrument, and the thing you are actually searching for is the kind of songwriter you want to be. So the solution to finding what you ought to be doing is to start looking for feelings rather than a job. If you are sufficiently attuned to how certain activities make you feel, then you will certainly know when you've found your perfect match. And relatedly, you will be alert if you stop feeling great doing a certain job over time. I am reminded of the famous Steve Jobs exercise. Apparently Steve would look in the mirror each morning and ask himself if he'd be glad to do the things he was going to do that day if he found out he only had a few months left to live. Anytime there were too many "no" days in a row, he knew it was time to change things up.
Anyway, back to the second half of the vision presented by career aptitude tests: that other people can tell you what you are meant to do. This is basically a lie. Other people can't tell you what you are meant to do. They can tell you what they think you might like based on their experience of you. They can tell you what careers they think are high status and well-paid and least likely to make people similar to you miserable or be disrupted violently by the impending AI revolution. And those are helpful, truly. But they can't do the important thing for you.
Why not? Why is it nearly impossible to assign people to work that is best suited for them? You'd think we could see how good someone is at math, science, writing, research, computers, public speaking, explaining things to others, team work, how long they can focus, how they get if they aren't moving around after too long, how they get from being inside too much, how they feel when given an undefined problem or creative freedom, and on and on and then based on that match them to a job. And many of us would be delighted if society could do this reliably for us. Why can't we do this? Is it that we can't measure how good people are at these sort of things? Or is that we can't measure how much these things matter in specific jobs? Or is it that 1) we can measure how good people are at these things and 2) we can measure how much these things matter in specific jobs, but being good at these things isn't what matters for determining "well-suitedness" for work? It has got to be that.
There are people naturally gifted at mathematics who would despise being a theoretical mathematician. There are people naturally gifted at public speaking and teaching who would much prefer to focus on writing, where they are alone most of the time.
This is because finding the work you are suited for isn't just about finding the things you are good at.
It is also because many jobs that are vastly different in practice require similar skill sets, so simply knowing what you are good at only narrows the potential set down rather than pointing to a specific job.
And also because most people are good at many things, even if they don't feel that they are. Things like a hierarchy of what you are good at, and the things you like doing, and what kind of impact you want your work to have all matter too.
I am now thinking of the modern framing for finding the work you should do, where the goal is to find the overlap of 1) things you are good at, 2) things that are in-demand / will make you money, and 3) things that you enjoy doing.
You could add 4) things that align with your desired amount of impact on the world. For example, someone might be great at guitar, love playing the guitar, and be offered a record deal, but if they want to ensure humanity stops climate change then it might not be the right path for them. I mean they could write environmental protest songs but is that really the most effective tool at their disposal? Suppose they are also a great venture capitalist and love investing; VC might be their top choice since they can invest in carbon capture and other climate startups that measurably reduce our climate impact. This is making me want to point out that this is where hobbies get introduced to the conversation. It is ok to love and be good at many things without monetizing them all or devoting your life to them all. It is also ok to "hop" from one to the next as your values, curiosities, and goals shift over your lifetime. In fact, count yourself lucky if you find yourself in this situation.
Where am I in this process? I certainly feel "closer" to finding what I ought to be doing in life than I did a few years ago. I always valued finding a path that truly aligned with my interests, values and skillsets. I was mostly able to avoid the social or familial pressure of choosing a path simply because it was high status, valued by a group whose opinion mattered to me, or paid a lot. Of course all of those things motivated me to get where I am today, but they didn't take the driver's seat. I don't feel I've found "the thing" yet though.
What clues have I found that may point me closer to the answer to "what I ought to be doing"? I love writing songs and making music and always have. I love writing fiction and posts like these and was always drawn to the idea of being a writer. I love tinkering and trying to build fun products or solutions to minor and major problems. I love listening to technical thinkers trying to solve big issues, and truly care about positively impacting the world through technology or otherwise. I am an optimistic person by nature and love when humanity tackles generational issues smartly. I am drawn to inventors and people "in the arena" and want to balance my love of music and writing with that fact.
What do these three things have in common? They are all immensely creative or generative. I go from having fragments of ideas to a whole that is greater than the sum of its parts. Relatedly, they are expressive. No writer, songwriter, or inventor would make the same essay, song, or invention as another. My personality, style, taste, and perspective all matter. They all involve time alone and then a time for sharing what I've done with the world. They are all unbounded, each time I set out to do them I experience them differently. There is a freshness and novelty to them, each song or piece of writing or product interfaces with the world and myself differently. I love that about them. They are also all at a kind of intersection of art and science. Music requires taste and style of course, but it also involves technical refinements and precision with things like structure, arrangement, and production. Writing is artful but requires truth and rigorous technical thinking to be good. Invention utilizes technology and the principles of science to create beautiful products that solve problems elegantly. What other things share these aspects? I will leave that for another day.
So right now I basically think of my life (as far as careers go) as a constant overlapping of these three areas: writing, music, and invention. I can't imagine any of those three things going away in the next decade or two. Let's think through those three categories with our lens of: things I am good at, things I love doing, things I can make money doing, and things that align with the amount of impact I want to have on the world.
First, let's start with the clearest of those criteria: things I love doing. The list of writing, music, and invention is the list of things I love doing. So all three pass that round. And for a moment I just want to pause for a moment of gratitude that I have that list. I do not want to take it for granted because as silly as it sounds, finding things you sincerely love is very difficult. It requires exploration and honesty with yourself and I am happy to have found at least three things that I truly love to do.
Next up is evaluating how good I am at these things.
How good someone is at music is toughest to determine I'd say. You can narrow it to technical proficiency on the level of instruments, theory, or production but that is clearly not what makes a musician live a successful and happy life (Paul McCartney can't read music, etc). Though I will say I am definitely not first rate in terms of technical or theoretical proficiency in music. I am nowhere near the top when it comes to playing guitar, piano, or production. What else can we use to determine how "good" I am at music? How many people listen to my tunes? How many people get my melodies stuck in their heads? What is the feedback from trustworthy and unbiased people who hear my stuff? All of those questions point in the same direction: share your music more Jake. And that, happily, is one of my goals this year. So I feel good about the music category when it comes to the "things you are good at" filter for now.
How good am I at writing? That is a bit more objective than music but not world's apart. Writing and music are both art, and "bad" writing (like "bad" music) can generate a huge audience. I will spare you the paragraph where I try to explain that I am a good writer. For now, suffice to say you can use the same criteria we talked about for music, for writing. Do you have readers, do they love what you write, does an exterior unbiased person or persons tell you that you are good at writing? Those are the sign posts. Publication and readership (over time of course, because the best writer alive right now may only have a handful of Substack subscribers, that is our era).
How good am I at inventing? Another strange and awkward question. Easier to evaluate though. Do I invent useful things when I try to? Do people want the things I make. This one depends on what sorts of things you make. If you are inventing software then what matters for this question could be "how good of a programmer are you?" But hack-y code that solves a great problem well or is useful to people is still a win in my book. And there are certainly top programmers who won't invent anything great in their lifetimes (that is a sad thought)4. I am not personally aiming for being an objectively "great programmer" or "great machinist" or "great Computer Assisted Drawer". It's not gonna happen and I don't enjoy the pursuit of it. I value insights and creativity aimed at impactful problems. But, perhaps for another post, I will leave this question here: how can I measure the value of my insights and creativity, and how well I aim them? For now, I will stick with: do they solve what they are meant to and do people value the solution?
Now, we turn to money, the dreaded paper. This one is actually pretty easy in my opinion because you can make a living doing anything today because of the internet. End of story! Just be smart about how you try to do that, because there are many paths to that destination. It also doesn't mean it is easy to do this, I don't think it is. For the practical thinkers out there I will say this: inventing probably has the most direct path to money. Writing and music are tougher but entirely possible now that they don't depend on traditional institutions (but the traditional institutions offer another path that is still viable).
Finally, it is time to wonder how music, writing, and invention align with the amount of impact I'd like to have on the world. As I've alluded to, impact is important to me. Valuing true usefulness is hardwired in me, so I wouldn't be content just writing poems or little love songs for (god willing) a small but financially viable audience. I need whatever itch invention scratches scratched. So whatever path I land on has to have it. Music and writing can have tremendous impact, I don't mean to imply they can't, but that sorta impact is much harder with music and writing than it is with invention or some related unnamed fourth thing.
All three of the things I love are viable candidates for what I ought to be doing. And I plan to keep doing them and listening to how they make me feel. I plan on being honest about how well I am doing them and how in demand the results are. Is there some fourth thing that miraculously combines the best parts of each of these three things under one clean career? I doubt it will turn out that simple. This was a useful exercise for me, hopefully you got something out of it too. I've wandered my garden and found the three things I am most interested in growing right now. Within those three garden beds, I can plant many seeds. I will write many songs, write many essays and short stories, and build many prototypes and MVPs. Can I grow any of them into maturity? Maybe trying to do that is my life’s work.
Our world is changing in a way that most people don't appreciate. Software has already drastically shaped our world, so we know this kind of change is possible even on a smaller scale. With the current batch of AI tools, I think our world will be drastically reshaped, in much more noticeable and stranger ways. Anyone will be able to create beautiful graphic design, new typefaces, personal websites, apps and other software products, music, digital art, and more*. This reality will make the paradox even more drastic: when you can do anything you want, deciding what you should do is harder and more important. AI will basically remove the requirement of picking things you are good at when searching for the work best suited for you, because if you aren't good at something but love doing it and can make money doing it then you just need the AI to do it well. One thought here is that things like painting and sculpture are currently "safe" from AI. Art that requires interaction and manipulation of the physical world might momentarily be considered the "truest art" for the early AI era. Theater might even have a boom era. Comedy is already experiencing a boom, but improv and standup will probably be even more popular in the next decade or so. Ditto for live music.
I routinely have this sort of experience; I am reading a book and find myself entering a flow state. The book is so good, the writing is so clear, and ideas start popping on like lights in the distance. I put down the book and smile to myself. I begin writing notes on my phone and capturing the idea chain that is forming in real time.
What is the harm of too many projects? In other words, why even worry about this tendency in myself? It is what Bilbo said, the feeling of being butter too thinly spread over toast. If your attention is divided too many times, nothing will get enough of it.
I wonder if this is true actually. I assume it is because there are so many talented people who do not apply their talents impactfully. But it would be interesting to explore this more deeply and identify why this happens.