If you take nothing else from this essay, here’s what I hope you’ll hear:

  1. You can learn to be happy doing great things, even if you’re struggling with being happy or doing great things today.

  2. You should try to do great things: desire is good, and it doesn't need to be a contract with yourself to be unhappy until you get what you want.

  3. You can be happy in the belief that improvement is possible, well before you make any actual improvement.

What is skill-and-tool optimism?

Skill-and-tool optimism is the belief that people can acquire skills, build tools, and use those to make the world a better place. If you have a strong belief in that, then you can go after ambitious goals that are outside of your current ability, and use that as motivation to develop the skills and tools that bring it within your ability. Failure at any step becomes more like a QA test, failure is information you can use to build better skills or tools. Once you build them, you can try to pass the test again.

The power of this is in two things: First, it assumes failure is part of doing the work. Failure becomes a reflection of your current ability, not a reflection of you as a person. Second, it keeps everything within your locus of control. If you fail, you just have to figure out what skills and tools you need to build next.

That combination is powerful. It gives you strong intrinsic motivation because everything is within your control (the only thing out of your control is the time it will take you, which will be different for all people), and it allows you to be happy with your current state, even if you haven't accomplished your goal yet — after all, building skills and tools was part of the plan all along.

Take this as an example: imagine you wanted to chop down a tree alone in the middle of the desert without any tools. You know that it's possible, but it's highly unlikely that you could figure it out in a couple of hours. Even if you tried all sorts of bad ideas prior to deciding to build an axe, wouldn't you still feel pretty resourceful and smart when you figured out you needed to build an axe? Even if it took you a week to figure out how to make an axe from stones and branches around you, wouldn't you still feel pretty accomplished when you figured out how to seat the blade? You'd be reinventing some core parts of human knowledge from scratch — you'd expect some setbacks during that process and you'd take pride in having the gumption to stick with it. When something failed, you'd think about what skill or tool you were missing and how to build it.

Do you need to chase a big idea?

In their book Zero-to-One, Peter Thiel and Blake Masters argue that the world needs "Definite Optimism," where people set ambitious specific goals for how to improve the world (and then work to make them true), as opposed to "Indefinite Optimism," where people iterate in interesting spaces to discover improvements.

Their argument resonates with me. While you can do great things without a vision of what you want to accomplish, it's much harder to know whether you're making progress. When you have a clear vision you're working towards, encountering failure along the way is important information that you may be missing a skill or tool required to achieve your goal. Without a clear goal, it's easier to interpret failure as a dead end and move on to the next area. You may not improve your skills or tools, you just move on to another part of the idea space and hope for success there.

Skill-and-tool optimism can work whether you have a clear vision or not, but I would strongly bias you towards having one. If you have a big goal, believe that self-improvement is required to accomplish that, and (critically) focus mostly on the process of self-improvement that is required to achieve the outcome, then you don't have to worry that your vision may be slightly wrong (you can update it with new information) or that you haven't achieved your goal yet (you can figure out what skills and tools would let you keep working towards it). You can be content in the present moment while working for something you care about in the future.

How Skill & Tool Optimism works

Skill-and-tool optimism is a fantastic personal philosophy. You intentionally build beliefs that inspire both the actions and emotional state that you want. Then, the way those beliefs interact is self re-enforcing: when you believe that worthwhile change is both hard and possible, you are motivated to develop new skills and tools to try to accomplish it. When you see small breakthroughs because of your hard work, it gives you more faith that change is possible.

Developing a belief in skill-and-tool optimism is a simple practice. If you're reading this, you can do it. Here's what you have to do: find ways to develop and re-enforce the following beliefs:

  1. Optimism: a belief that huge positive changes are just hard, not impossible.

  2. Self-improvement: a belief that you can intentionally get better by developing skills and using tools, and that you can do so continuously.

  3. Internal focus: a belief that failure is just feedback that helps with self-improvement, not something that invalidates you or your efforts.

  4. Pro-social: a belief that people's success is proof of their effort and should re-enforce your optimism (and that yours is the same and will similarly inspire others).

  5. Desire: a belief that accomplishing something, even if it's hard, is satisfying and worthwhile.

Some of us are lucky enough to have experiences that lead us to develop those beliefs; most of us do not. But, if the experiences we have day-to-day are how we develop these beliefs, then we can choose experiences that start creating these beliefs. This is hard and can take some time, but it's not impossible. (There's my optimism showing through). If you hold these beliefs strongly, it makes you happier, more ambitious, more excited, and leads to you having better relationships with the world and people around you.

You may have some of these already. You may struggle with some more acutely. You may struggle with all of them. Everyone has a different starting point. As far as I can tell: even small improvements lead to small improvements in your life pretty immediately, these beliefs are reinforcing enough that you get more improvement for the same effort the longer you work at it, and there's no ceiling on how much better you can make your experience. Whether you're 8 or 80, why wouldn't you start now and get however far you can?

How to build the beliefs

You can build this muscle from almost any starting point, it just requires breaking a big goal into small-enough goals that your feedback loop is quick and positive enough to continue motivating you. This is a little bit like level-design in a video game: where you try to match the level's difficulty to the skill that the player has at that exact time: making it hard enough to be challenging, but not so hard that it's demotivating.

Finding the ideal balance on that is hard. It's possible to get a little lucky when starting out, either by [1] having a great coach/teacher/mentor or [2] having a natural ability to push through demotivating experiences. If you didn't get lucky in either way, it can be helpful to know that so that you have your expectations set properly and don't get demotivated early on. You don't need these.

Personally, I wasn't very lucky with coaches. Great teachers or coaches can help by using their experience to help us set achievable goals and connect them to a bigger outcome, but great teachers and coaches are rare. When I first started working on my interior life, my primary goal was to find ways to be happier and avoid depression/burnout. I've gotten lots of helpful ideas from people on that journey, especially therapists, but I wasn't lucky enough to find a good teacher or coach that could really guide me. Sometimes I progressed very slowly, sometimes I bit off more than I could chew, largely because I've had to be my own guide. (In retrospect, I see that this has been a very skill-and-tool optimistic way to come up with the idea of skill-and-tool optimism).

I was "lucky" in another area: I was born with a very obsessive personality. While my obsessive nature probably caused a lot of the challenges that led me to being unhappy in the first place, when I become obsessed with my interior life I got motivation and re-enforcement from learning about myself instead of achieving something that would be visible to others. That helped me do a lot of work without the fear of looking stupid (while I felt like a failure often in the early days, there was no external pass or fail test on how I reflected on my own thoughts).

Even with that one advantage, it took me about 20 years from the first time I experienced deep unhappiness to when I really started trying to solve this problem. In the 5-10 years since then, I've become more skilled, but I'm nowhere near done with the work. I doubt I'll ever feel done - I haven't hit diminishing returns on doing this work yet and I suspect there's relatively infinite compounding available in the lessons I can learn on this in the decades to come.

Where to start - Guided Rumination

Review those 5 beliefs that I think make up the core of S&T Optimism. Read these and honestly react to each one. Which of these feel natural? Which of these are you skeptical of? Which do you believe but struggle with? Which do you strongly disagree with?

  1. Optimism: a belief that huge positive changes are just hard, not impossible.

  2. Self-improvement: a belief that you can intentionally get better by developing skills and using tools, and that you can do so continuously.

  3. Internal focus: a belief that failure is just feedback that helps with self-improvement, not something that invalidates you or your efforts.

  4. Pro-social: a belief that people's success is proof of their effort and should re-enforce your optimism (and that yours is the same and will similarly inspire others).

  5. Desire: a belief that accomplishing something, even if it's hard, is satisfying and worthwhile.

PROMPT #1: Grab a journal and write out your thoughts. What emotional reaction do you have to each? In what situations recently have you acted like you believed that or not acted like you believed that? How did your parents encourage or discourage these beliefs when you were young? (Yes, I know this seems like a therapy trope, but there's a reason therapists ask about your childhood. Our beliefs are guided by our experiences, and we react to experiences in ways that are comfortable to us — experiences and beliefs reinforce each other and if a pattern gets set early, it creates a 'groove' that's easy for our thoughts to slip into and make into a strong habitual pattern over time).

Preferably, take a break at this point. Just reflect on those thoughts for a little while.

PROMPT #2: When you come back to this, try to put aside those reactions and think about a future you that believes these five things. How do you think you'd be different? Would being that person feel better? Does the idea of changing in these ways elicit any fear? Would you risk losing any part of yourself that you really love?

Take a break after this as well.

PROMPT #3: Describe a situation you had this week - whatever comes to mind as most important. What did you feel, experience, get frustrated by, worry about... whatever. Just free-write (you can also just voice this out loud using a transcription tool like Otter). Timebox this to only 30-60 minutes, but follow whatever threads seem like important context or seem interesting. After you're done - wait at least 15 minutes (I recommend taking a shower or going for a walk to clear your mind), come back and read what you wrote. While reading, do two things: [1] look for places where you or others exhibited one of the 5 key beliefs or failed to exhibit them and [2] look for when you wish you'd had a different way to do something (does that highlight a skill or tool you could develop?).

Split these reflections up, don't do them at the same time. I'd recommend giving yourself an hour to journal on each prompt. You can do these as regularly or irregularly as you want to. If you're just starting out, I'd recommend doing each prompt, in order, once a week, for 3 weeks. That should be enough time to understand if this is giving you a helpful way to understand and frame your experiences.

How to continue - focus on skills and tools.

The third prompt above is the core of the practice. You want to reflect on what you're experiencing and look for ways you're changing or could change. Like most practices that help you build self-awareness, this becomes a way to habitually separate action and reflection on action. You can do this in lots of ways, including by meditating, journaling, sitting quietly and thinking, or talking with a friend/coach/therapist/mentor regularly. The main goal is to give yourself explicit time to observe the things going on in your life as a witness, not a participant.