Trying to do a startup is hard, relative to regular work. Relative to regular work, I've noticed three poverties: poverty of validation, poverty of presence, and poverty of money.
The first is the poverty of validation. In regular employment, and also in school, there is a constant cycle of validation. After you complete an assignment (assignments which are scoped to be believably accomplishable by you), you get a new one, provided to you by someone (teacher, manager) who also validates you for completing the first task. It's a cycle of constant achievement, and it's actually great; the institutional structure of employment and education is very validating. However, as a founder, you’re no longer in an institution, so unless you create the same structure of validation for your day-to-day, you won’t get it. You have to replicate the cycle yourself. Here’s how I’ve been doing it:
- Scope tasks each day to be accomplishable and still ambitious.
- Make the completion of those tasks agnostic to a person's opinion except your own.
- Know what to do next.
This starts with small wins: waking up on time, eating a healthy breakfast, exercising. Each morning, these tasks chain each other, to propel validation. Then, do your hardest task of the day next. The rest of the day will already feel like a success.
The second poverty is the poverty of presence. Every moment that I feel I am not working, I feel as though I was wasting time. I feel like I should be working every moment. I feel constantly as though time is running out. When working for yourself, there’s something particularly existentially dreadful about it. And the dread deprives you of being present in the moments that should be joyous, like spending time with friends. And it deprives you of being present in the moments that used to just be monotonous, like driving to get groceries.
This dread is a form of anxiety, and should not be a reference for how you structure your labor. If you can’t be present with rest, then you won’t feel rested. You will burn yourself out if you only work, so while in the short term you may feel like you're getting more done, in the long term you will actually get less done. Founders pivot for years before finding an ounce of traction. Being a founder is a marathon, not a sprint, and it's a marathon you are running with yourself. That doesn't mean you're not trying to win the marathon, but you need to set pace. Pace yourself ambitiously, but realistically, and understand why pace is important: so you can keep going.
Another way to feel like you “deserve” rest or presence is if you believe that you worked hard while you were working. This is easier if you can point to goals that you set out for yourself and accomplished, which is also a solution to the first poverty. I’m also a fan of the 4000 Weeks approach to to-do lists: one list is for all the things you need to do (the “open” list), and one for all the things you can do today (the “closed” list). You don’t concern yourself with how many items are on the open list; there are only 24 hours in a day, and you need eight of them to sleep anyways. There’s no way you could do all of them today, so there’s no reason to stress about it. Accepting your own limitations is how you enable yourself to focus on the work you can do today, and that’s the work that’s on the closed list. The closed list is closed because you only add things to it when you’ve removed something else from it. 
The third poverty is the poverty of money (shocker). Today, a group of friends and I went to a brewery, and I felt anxious not being able to buy a beer and join them for dinner, and I just sat there empty-handed. Moments like this really make you feel poor, and after working a cushy tech job for three years, that is a feeling I am not used to. But I remind myself of two things: the first is that this pain may merely be a growing pain. I am going to be doing this for a while, and I am willing to bet that I will not feel this same anxiety in another month, that shortly down the road it will be easier for me to say no, and not feel fomo. The second thing is a reminder to myself, that this is all a choice. Each beer is actually an opportunity cost (in a small but real way). Each beer is less runway that I have in eleven months, which is less time to bet on myself. I am choosing to bet on myself, and I value that more than I value the beer. It is through constraint that we are reminded of our values by making real compromises, and it takes a constant re-centering of attention to those values to make the compromises we need to make, and still feel satisfied making them despite the unpleasant tradeoffs.
So of the three poverties I have noticed so far, none of them are unresolvable. The first is a question of personal structure, which is straightforward (though not necessarily easy) to institute for myself. The second is a matter of awareness of my human limits, and how I can work as best I can for as long as I can. The third merely requires me to take a step back, and remind myself why I’m doing this at all.
 This exercise was super helpful.
Originally published 1/21/2023.