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We talk about bootstrapping in the context of a real human life.

We talk about bootstrapping in the context of a real human life. Mortgage, kids, spouse, and dwindling personal bank accounts!

How do you deal with the stress and the pressure that's created by trying to build something out of nothing? How do you make good decisions?

on December 18, 2018
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    Hey Justin, so great, thoughtful and deeply personal episod with JC btw. I have a very simple framework to apply. Before making any decision I'm usually asking myself "would I regreat about it at the end of my life/career at the company/year or decade"? Would I try that (making app, starting family, quiting a job) no matter what's the result just for the fact I did actually try that in my life? So the question is actually "would you regret if you stop building/growing Transistor now"? "Would you regret if you'll take funding before product market fit?" "Would you regret by slacking down on your courses busines in favour of consulting"? Those all are very hard questions to ask and answer.

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    That's a hard-hitting question. I've been through (or participated in!) some insane, ridiculous, Jerry Springer-worthy situations, and stayed in some burning houses for far too long insisting everything was fine. I've worked on projects that were magnificent innovations, but had to do it in times of great personal strife and ongoing battles, immense pressure. Funny thing is, I seem to be OK under pressure, and can perform. But when it gets intense and you don't pay attention, you just don't have the freedom, room for input, or time to make good decisions. This has led me many times to make some terrible, awful, no-good decisions. When those fires are solidly burning, I usually go through a long, BAD, burnout process which leaves me indecisive, low in confidence, and unproductive, which can last for months at a time. A year or so ago I decided I was probably old enough to not be making so many bed decisions and repeating the same mistakes. So I tried to start paying attention to what I was doing wrong. Still got a ways to go, but getting there.

    After all, I LIKE making decisions, it's empowering, and life is a series of big and small decisions!

    To help me make good decisions, or at least avoid bad decisions, I do these things when I can catch myself in time. Some might seem crazy, but...

    • Try to not make directional decisions when I'm upset or tired. My risk appetite and impulse control seems to go way way up when I'm mad, sad, or exhausted
    • I sleep on buying things, especially recurring expenses or anything costing > $25. (I've queued up domain names and bought bulk domain packages, to later wonder what the heck I was thinking). Ideally, I sleep on it twice
    • I validate ideas which other people are going to have to experience in more than a passing way, or pay for. Spent too many years working on projects in the dark, spent months making awesome games/apps no one but me liked!
    • I take voice notes/memos, and transcribe them. When an idea spark/stream comes on me, I need to capture it and handle it. I would maybe remember 1/10 of those random thoughts. I have gotten into the habit of using the Notes app on my phone while driving (speech recognition), and the Notes app or Google Docs on my laptop when at home/working. This lets me have the luxury to explore things for a bit mentally, get the notes down without trying to make sense of it all. Soon the idea spark is quiet (but captured!), and I have something to look at later. This is the important part, because I no longer feel like I let things fall through the cracks as much, and this helps me make better decisions because I don't fear missing out like I used to and can avoid acting on impulse. It also helps me remember important things I don't want to forget to do. Huge for me. I even made a mobile app once to help me do this
    • I get input. I like to vary my activity to get input from the outside world. My brain needs to see things, hear things, smell things, eavesdrop on conversations, see people doing things in the real life. There are parallels and patterns mirrored everywhere. You never know what your brain is going to see and pick up on to help you make a good decision. So I get out and get stimulated. For me, that means varying driving routes, walking in new places, and smiling a lot when I talk to strangers and store clerks
    • I don't wallow in my past, but I try to remember it. I try to remember to think "what happened last time I did something like this", to see if there was a better way to do it now, or if some variable needs to change for a better outcome. I guess this is like continuous process improvement by introducing random variables, and to some it might seem like I'm very random and inconsistent. However, it leads me to some patterns that work and whipping out a working pattern frees me up to move forward. This looks like moving fast to some people, but it's confidence in the patterns that causes the illusion. A bonus is that trying new things (or at least changing out the variables) is pretty freeing and fun.
    • I slow down a bit. I took a course in Anger Management last year after a long period of living in frustration, and making lots of poor decisions from a bad place. I had no idea what I didn't know. In particular, the stages of anger (annoyed, frustrated, angry, very angry, enraged), how to recognize them and avoid acceleration, are precious life lessons. Knowing yourself and knowing when to slow down leads you on the path you WANT to be on, and de-escalates stages of anger to get you where you need to be. Unless you're fighting for your life. If you're fighting for your life or defending the weak, get to enraged and stay there as long as needed :) I wish I had learned some of those techniques 20 years ago, and they might have saved me from making some pretty bad decisions.

    So while I still make plenty of bad decisions, I'm in a much better place to make good ones these days, and have a couple hard-earned skills in the Batman Belt to help.

    To your other questions, to deal with stress, I take me time to go for a walk, do some mundane chores, go for a swim when it's warm, or drive (which fold nicely into "get input" above). It can be the most important thing I do all day. Dwindling personal bank accounts are a part of my life. Except for a couple really awesome periods of life where things just went up, up, up, and that gives me something to look forward to. In the meantime, peaks and valleys.. peaks and valleys.