I’m going to list out things that I’m afraid of. I’m going to try and avoid virtue-signalling and be useful to myself.

I’m afraid of making mistakes. Why? Because I’m afraid people will think I’m stupid, or incompetent.

Reality: It’s okay to make mistakes, the worst mistake is to be paralyzed with inaction. I don’t need to make big public mistakes. Instead, I can share my work with people I trust and get corrections and recommendations before I share it with the world at large.

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I’m afraid of making decisions. Why? Because I’m afraid that I’d get things wrong.

Reality: It’s better to get some things wrong than to do nothing at all. If you want to have a good life, you’ll want to make as many good decisions as you can. And it’s a good idea to just practice making as many decisions as possible. Live an intentional life, don’t defer to the default setting. When you were a kid, you didn’t trust yourself to make good decisions and you were willing to drift along. But you’ve learned now that you can get better at making decisions, and that drifters don’t drift anywhere great. Nobody drifts to the Olympics, or to the top of a mountain, or to anything worth doing. As Chris Hadfield said, don’t let life kick you around into becoming a person you don’t want to be.

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I’m afraid I’ll never accomplish anything great.

Reality: That’s a good fear. But that doesn’t mean you avoid trying. Great things are achieved with baby steps. What are the baby steps that you need to take in order to achieve the great things that you want to achieve?

I’m afraid I’ll never be able to become a productive person, that I’m cursed to constantly be playing catch up with my life.

Reality: Other people have had this fear too, and overcome it. It’s all about learning a new skill. Didn’t you once believe you’d never be able to squat your bodyweight, or that you’d never be able to play music? You can become a productive person. You just need to be clear about how and why.

You already know that obligation debt is a painful, miserable thing. You have a very good reason for becoming a productive person. You’ll be able to contribute more. You’ll be able to be a force for good for everyone in your life. You can challenge and inspire your friends to become better. You can repay debts to everyone that you feel obligated to. You can come out on top and have a net surplus. So that’s that for the why’s.

Now, the more important things – the How. Listen, I know you look at your history and you see a series of mistakes. Like every minor success is just a stepping stone to the next failure. But here’s the thing, that’s entirely a function of your perspective. (Your perspective in turn is colored by things like your physical state, so make sure you’re getting enough sleep, exercise, healthy food, human contact and so on– because if those things are on the fritz then your perspective is going to shit).

Decide that you’re going to level yourself up. That you’re going to learn how to do things that you weren’t able to do before. You are capable of learning and growing. You’ve learned to cook, haven’t you? You’ve learned to navigate an unfamiliar environment (the kitchen), to use unfamiliar tools (pots and pans), to work with unfamiliar material (pasta, meat, oil, spices), to put them through an unfamiliar process (cooking), and you’ve created something amazing – food that’s so delicious that you actually look forward to eating it again. You did the same thing when you bought a squat rack to teach yourself how to squat.

You can do the same thing with your time. Remember how scared you used to be of food prep, of going into a kitchen, feeling like an idiot about it? Now, remember how scared you used to be of schedules? Of deadlines, and so on? It’s the same thing as the kitchen. You’re going to navigate an unfamiliar environment (clocktime), use unfamiliar tools (calendars, task plans, sub-steps), put them through an unfamiliar process (careful monotasking interspersed with reflection) and create something amazing – an output that exceeds your commitments. And you’ll feel great about it. You vaguely know this to be true from moments of accidental or incidental effectiveness. Let’s make it your new default state, as if you were going to be cooking every day. As with cooking, don’t start out with massive expectations of getting everything done. Just think of it as dipping your feet in unfamiliar waters. You just want to get used to what it feels like, and then you can start experimenting.

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I’m afraid I don’t have enough time, and I’m afraid to face that so I have this habit of ignoring the problem and hoping it goes away. Of course, it never goes away, but eventually I get too tired or exhausted to be able to do anything about it, and then nobody can fault me for it because I sat there and ran out the clock. Nobody will ever have the patience to spend their entire life policing me; they have their own life to live too. So as long as I’m sitting here running out the clock, I have some sort of autonomy or control over my life. It’s a very shitty, limited autonomy, like a tiny-ass blanket that doesn’t cover anything, but it’s all I knew at some point.

Reality: You already know the answer to this. Yes, you don’t have enough time, but that doesn’t mean you give up and avoid your problems. That just makes things worse. If you don’t have much time, you’re going to have to be smart about it. You’re going to have to renegotiate. Simplify things. Do some bare minimum for each thing. Make some progress. Let go of this sad life of misery and guilt. Throw away the safety blanket – set it on fire and watch it burn.