Hi, this is Ray.

A confession to start. In the past 15 years, I have started learning (and quit) the following: oil painting, classical guitar (the second time, after also quitting the first time), woodworking, three different programming languages, two different martial arts, sourdough baking (got somewhere with this one), Mandarin, Korean, the actual Hebrew alphabet (twice, somehow), beekeeping (just the research phase, no actual bees were involved or harmed), poker, and at one point I ordered a starter kit for blacksmithing that arrived and is still, as of this moment, sitting in my garage in its original box. Hello, blacksmithing kit. We will meet someday. Probably.

The pattern, looking back, is humbling. I'd get hit with an enthusiasm wave, throw money and time at the new thing, then watch my motivation evaporate somewhere around week 3-5. I'd blame myself. "Maybe I just don't have the discipline." "Maybe I'm one of those scattered people who can't commit." "Maybe I'm Gimli, easily distracted by shiny things and small adventures." (Gimli would have been great at poker, actually. Different newsletter.)

What I eventually realized (after far too many abandoned hobbies) is that I wasn't picking BADLY because I lacked discipline. I was picking badly because nobody had ever taught me HOW to pick. The cultural advice on this is genuinely terrible. "Follow your passion" is a recipe for chasing dopamine spikes. "Learn what's marketable" is a recipe for grinding through things you'll quit. The actual science of motivation (which has been steadily building for 50 years now) offers something more useful than either. It tells you what conditions need to be met for you to actually stick with a thing long enough to get good at it. Once you know those conditions, you can evaluate any potential learning project against them BEFORE you commit. Which is much smarter than what I did, which was buy a blacksmithing kit on a Tuesday at midnight.

Today's newsletter is the framework I wish I'd had 15 hobbies ago. Whether you're picking a college major, a side hobby, a career pivot, or just figuring out what to do with your evenings… this is how to choose well.

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Let's start with the foundational research. Most of what's known about human motivation comes from a body of work called Self-Determination Theory (SDT), developed primarily by Richard Ryan and Edward Deci over the past 50 years. It's one of the most-replicated frameworks in all of psychology, and its core finding is simple: humans have three basic psychological needs that determine whether we'll engage with something deeply or bail on it.

Those three needs are autonomy (feeling like you genuinely chose the activity), competence (feeling like you can actually make progress at it), and relatedness (feeling connected to others through it). According to Simply Psychology's overview of the theory, Self-Determination Theory holds that students are most intrinsically motivated to learn when their environment satisfies the fundamental psychological needs for autonomy, competence, and relatedness, and improving self-determination means intentionally creating the conditions under which these three needs can be satisfied. When all three are met, you keep showing up. When one or more is missing, you eventually stop. That's not a character flaw. That's how human motivation works at the cognitive level.

Here's why this matters for choosing what to learn. Most people pick learning projects based on whether the OUTCOME sounds good… being a doctor, being fluent in Spanish, having a sourdough Instagram. Almost nobody evaluates whether the actual DAILY EXPERIENCE of learning the thing will satisfy these three needs. That's why so many ambitious learning projects die. The outcome was attractive. The path to the outcome failed to meet your basic psychological needs, so your motivation drained out, so you quit. You didn't fail. The selection failed. Big difference.

The neuroscience backs this up. Research on intrinsic motivation has identified specific brain mechanisms. As one neuroscience review noted, intrinsically motivated exploratory and mastery behaviors are subserved by dopaminergic systems, and intrinsic motivation is associated with patterns of activity across large-scale neural networks, including those that support salience detection, attentional control, and self-referential cognition. Translation: when a learning project genuinely meets your three needs, your brain gives you free dopamine for engaging with it. When it doesn't, you're trying to push uphill against your own neurochemistry. One of these is sustainable. The other is not.

Quick detour to dismantle the most common piece of life advice you'll get on this question. "Follow your passion" sounds wise. It is, in practice, often disastrous. Here's why.

Passion in the moment of choosing is usually based on the imagined OUTCOME, not the actual daily experience. When I bought my blacksmithing kit, I was imagining the moment when a beautiful hand-forged knife would emerge from my forge and someone would say "wow, you made that?" I was not imagining the actual hours of arm-aching, sweaty, repetitive hammering required to produce one mediocre knife. The fantasy was about being a blacksmith. The reality was about doing blacksmithing. These are different products.

A study reviewing intrinsic versus extrinsic goal framing found that intrinsic goal framing (relative to extrinsic goal framing and no-goal framing) produces deeper engagement in learning activities, better conceptual learning, and higher persistence at learning. Note what's NOT on the list: "feeling passionate about the outcome." The variable that predicts persistence isn't passion intensity. It's whether the framing of the goal itself is intrinsic (meaning the doing matters to you) versus extrinsic, meaning only the having or the appearing matters to you. Many "passion" choices are actually extrinsic in disguise. You don't want to be a writer. You want to BE SEEN AS a writer. Different motivational fuel. The first sustains. The second runs out almost immediately the moment writing turns out to be hard.

The other common piece of advice (learn what the market will pay for, regardless of your interest) has the opposite failure mode. It's autonomy-poor. You're choosing something because someone else (the labor market, your parents, a TikTok careers influencer) has told you to. That violates the autonomy condition right out of the gate.

The research on this is clear. SDT studies have consistently found that when learning is driven primarily by external pressure (pure marketability, parental expectations, social comparison), the motivation tends to be brittle. As one major review of the theory in education noted, both intrinsic motivation and well-internalized (and thus autonomous) forms of extrinsic motivation predict positive outcomes, but motivation driven primarily by external pressure or controlling mandates is associated with worse persistence, lower wellbeing, and less effective learning. Translation: you CAN make extrinsic motivation work, but only if you internalize it… meaning you find your own reasons to care, beyond the external reward. "I should learn coding because it pays well" rarely sustains motivation. "I should learn coding because I want financial autonomy AND I find the problem-solving genuinely interesting" might.

So pure passion fails because the daily experience doesn't match the fantasy. Pure pragmatism fails because you didn't really choose. The sweet spot is the overlap: things you find genuinely engaging in the doing, that ALSO have value to you in the broader world, that you've actually chosen.

Here's the framework I use now, post-blacksmithing-kit. Before I commit to any new learning project, I run it through five questions. If I can't answer "yes" to most of them, I don't start. This has saved me a LOT of money on starter kits.

This is the single most important question. Most learning failures happen because we wanted the destination but didn't realize the road would be 90% hammering hot metal in the heat. So before committing, do a "daily reality check." What does an HOUR of doing this thing actually look like? Not a peak moment… an average Tuesday at 7pm when you don't feel like it.

For language learning: it's flashcards, repetition, awkward conversations where you sound like a toddler. For programming: it's hours of staring at error messages that say "syntax error" with no further explanation. For drawing: it's bad sketches that you have to do anyway because that's the only way to get to good ones. If you can't get excited about the UNGLAMOROUS daily reality, the project will die. Not maybe. Will.

A trick I use: spend 60 minutes doing the actual activity at amateur level before committing. One hour of bad guitar playing. One hour of failing at chess puzzles. One hour of squinting at Korean alphabet drills. If you're miserable in that hour, that's the hour you'd be doing every day. Listen to the data.

This is the autonomy question. Are you learning Spanish because YOU want to, or because your partner wants to travel to Spain, or because LinkedIn says it's marketable, or because everyone in your family is bilingual and you feel ashamed not to be? You can still proceed with externally-suggested options, but you need to convert them into genuine choice first.

The conversion process: imagine a world where nobody knew or cared whether you did this. No external rewards. No social approval. No parents judging. Would you still want to do it? If yes (even a little), you have something workable. If you genuinely wouldn't, you're choosing something that won't sustain itself when motivation gets hard. Save yourself the inevitable abandonment.

A concept from SDT that's helpful here: research on autonomy-support found that a manageable number of choices, roughly six rather than thirty, prevents the paralysis and ego depletion that can accompany excessive optionality. Don't try to evaluate every possible thing you could learn. Narrow to a shortlist of five or six options that genuinely appeal to you. Then choose. Choice paralysis is real. Don't let it stop you from picking anything at all.

This is the competence question. Some skills have terrible early-game experiences. You start, you suck, you keep sucking for months, you quit. Other skills give you small wins early that sustain you through harder later stages.

This isn't about avoiding difficulty… it's about evaluating the EARLY difficulty curve. Can you do something rewarding in the first 10 hours? The first 50? Can you actually see yourself improving, or does it feel like infinite plateau? Languages tend to be early-rewarding (you can have your first basic conversation in weeks). Instruments tend to be early-frustrating (you sound bad for a while before you sound okay). Neither is wrong. But you should know which type you're choosing and whether you can stomach the early phase.

A workable principle: pick projects where you can hit small, visible milestones in the first month. Completing a simple coding project. Holding a 5-minute conversation in your target language. Drawing something recognizable. These early wins feed the competence need and keep you going through the harder parts that follow.

This is the relatedness question, and it's the one most underrated by solo learners. Skills that have strong communities around them (chess, programming, language learning, music, board games, martial arts) have built-in motivation infrastructure. You can find a teacher, a study group, an online community, a local meetup. Each connection gives you another reason to keep showing up.

Skills that don't have communities, or where the communities are toxic or hard to access, fail more often. Not because the skill is worse, but because you're trying to maintain motivation entirely from your own internal resources. That's a much harder ask. Look at your potential learning projects and check: who else does this? Where do they hang out? Can I get to them? If the answer is "nobody, nowhere, no"… proceed with extra caution.

The deepest version of this framework. After all the practical questions, ask: why does this MATTER to me, beyond what it gets me? What part of who I am does this serve?

The answer doesn't have to be profound. "Because I find it genuinely fascinating." "Because I want to honor my grandmother who spoke this language." "Because I want to be the kind of person who can build things with their hands." "Because I love the puzzle of it." These deeper reasons are what carry you through the long flat middle of any serious learning project, when the novelty has worn off and the mastery is still far away.

If your only "why" is the outcome (the credential, the money, the impressive party-talk skill), you'll quit. Not because outcomes don't matter, but because they're too far away to fuel the daily work. You need something closer. Something about the doing itself, or about the kind of person doing it makes you.

If you're picking something for college specifically, the framework still applies, but with one addition: the cost of switching is high, so the cost of getting it wrong is also higher. I'd weight the daily-reality question even more heavily there. Spend real time WITH actual current students of any major you're considering. Sit in on their classes. Read their textbooks. Look at their homework. Don't pick based on what the careers brochure says the major leads to. Pick based on whether you can imagine doing four years of the actual work. Many people pick majors based on the imagined career and end up miserable in the major. Bad selection. Decade of regret. Don't.

For hobbies, the cost of getting it wrong is much lower, which means you can afford to experiment more. My current rule: I give myself 10 hours of trial time with any new potential hobby before committing to a longer arc with it. 10 hours is enough to know if the daily reality matches the fantasy. It's not enough to learn the thing, but it's enough to know if I'd want to. If after 10 hours I still want more, we proceed. If I'm relieved to put it down, I let it go without guilt. The blacksmithing kit, by this rule, would never have been purchased. Live and learn.

Here's what I want you to take from all this. Picking what to learn isn't a romantic question best answered by listening to your heart, and it isn't a strategic question best answered by spreadsheet. It's a motivational engineering problem. You're trying to set up conditions where your future self will keep showing up to do the work, weeks and months from now, when current-you's enthusiasm is long gone.

The frameworks people usually use for this (follow your passion, learn what pays, do what your parents did, do the opposite of what your parents did) all fail because they're missing the key variables. You need autonomy (genuine choice), competence (achievable progress), and relatedness (connection with others). You need the daily reality to match the fantasy. You need a "why" deeper than the prize.

When all those line up, the learning sustains itself. Hours stop feeling like effort and start feeling like the thing you do because it's who you are. That's the goal. Not passion in the moment of choosing… durable engagement in the moment of doing, every day, for years.

Choose carefully. Choose for the doing, not the having. Choose what your future self will thank you for. And maybe don't buy the blacksmithing kit on a Tuesday at midnight. That one's free advice.

Keep learning (and keep choosing wisely),

Ray