What are the best decisions you’ve made?

1. Quitting a very stable tech job to start a company. I was 40, had a one year old and stay at home wife

2. Trying everything possible to make the company a success. Learning a lot in the process.

3. Realizing 2 years later, the business wasn't going to work. Shutting it down while I had some money left in the bank and finding a full time job. Ironically, the new company valued the combination of professional and founder experience highly, and I ended up with a 40% bump from my pre-founder income

4. Then prioritizing paying off nearly $70k in credit card debt (business related) over the next couple of years. Again, learning a lot in the process.

5. Consciously communicating and making decisions with the wife throughout the journey. Now it seems like if we could survive that experience financially, we can survive anything.

I learnt more about risk, negotiation, personal finances, communication and above all my own biases & limitations in these 4 years than in my 15 years of career prior to that. Wouldn't trade for anything.

Hard to say which was best, so I will list several good decisions:

1) quitting a job to ride a bicycle up the east coast 2) spending 6 months in New Zealand and Australia 3) buying my first house 4) buying my second house across the street from a park oh I have it, Falling in love with programming, my career.

Getting back into exercising and dropping off booze and cigs.

I realized it's hard to take care of others when we cant even take care of ourselves. The mental clarity and the stamina wasnt just there.

Hard to know best because I don’t know the opportunity cost.

1. Moving from Aus to US to be in the hub of where software is made.

2. Marrying my wife (again hard to know opp cost since I’ve only been married once. But life is deffo better than being single)

3. Switching jobs every couple of years to work on something interesting and impactful.

4. Healthy habits such as healthy eating, exercise, read books, call friends, save and invest, travel international once an year.

I guess the biggest decision is to invest in habit building (habits compound over time)

Therapy.

I realized at some point that my life wasn’t going in a direction where I felt fulfilled, and couldn’t seem to make the changes I needed to get it there. Therapy allowed me to see how I held myself back and the things I didn’t know I was carrying with me from my youth. I’m happier, more focused, have a better understanding of myself and where I’m going, and I think I’m kinder to others as well. I cannot recommend therapy highly enough.

Quitting a job after 9 years once I realized I wasn't happy there anymore. I'm not the type who likes change, but this was the best decision I made in my life. I now work at a company with a much better culture, with a significant salary bump (over 4 years here and still happy with it).

This taught me to not be afraid to make significant changes, even when the outcome is not so certain.

The two best decisions I ever made were living and working overseas for several years when I was in my early 20s, and then moving to a small town in Vermont in my early 30s. I had a lot of adventures early, learned new skills, and then settled down somewhere with a great home - work balance.

Going back to university in my thirties to pursue a CS degree. Although sometimes odd being the oldest, i kinda feel this is the best decision i’ve ever made.

Booting negative people out of my life

Not committing suicide. and also, Meditation.

- Moving from Europe to the US, Bay Area specifically, right after college. No other place would have given me such amount of wealth in a relatively short amount of time (10 years now). Growing up poor, I appreciate it tremendously and it enables a lot of freedom for my future self.

- Live a very frugal and minimalistic lifestyle. I live on about 4% of my gross income (crazy! See previous point) and I love it. I eat healthy, exercise a lot, have a wonderful partner, plenty of discretionary time because we don’t have to care for material belongings.

I am also firmly in the camp of not wanting kids, and firmly believe it is the right decision for me: I’ll let you know in a few decades if it was a good call or not :-)

Moving to London when I was in my 20s. Moving to Berlin and changing jobs at the same time in my 30s (was doing security consulting before, but switched to development). Starting a company when approaching 40s. Leaving a company I was involved with and that wasn’t going anywhere. Pushing my own company to go fully remote 5 years ago or so.

Recently helping my own company switch to 4-day workweeks[0] although the jury is still out on this one.

[0] https://blog.gingerlime.com/2020/how-we-switched-to-4-day-we...

That doing good is a deliberate act: I have 'decided' to be a better son, a better bother, a better friend, a better lover, a better human than I were the day before.

This made it that even though my lifestyle is so much different than my family's and that of most of society, we still get along on a deeper level.

Deciding to have the hard conversations. Some ten minute conversations have had the highest 'return on investment'.

Deciding to always aim at the meta-thing right after I have the thing. One specific example is asking a question on the #python IRC channel years ago about a library and receiving an answer from someone who's never used it, immediately thanking them and asking how they did to find the answer. That process was much more valuable to me, because I could use it on other things [they did a git grep on the repo].

Deciding to use money as an instrument for myself and others. I mostly buy time and experiences. I did it when I was in highschool and continue to do so now.

Ars longa, vita brevis.

Quitting my corporate (high paying) job and getting into my own business. I now have a 24-7 thing (for now) but I love it.

That's a really tough question. I guess I'm not happy enough with my life to have an answer for this.

I refer to my daughters as "the 2 best questionable decisions I ever made".

But seriously learning software development was my best decision. I spent most of my working life in food service (read: broke) and then 6 years as a massage therapist at a high end practice. I taught myself Ruby and JavaScript in between clients and on breaks.

It was already a good decision pre-pandemic, but if I was still a waiter or an MT, we would have been just so horribly fucked. I would have basically had months of no work or income, which would force me to go back to work during the pandemic. I'm so grateful that I don't do that kind of work anymore. I literally don't know how we would have gotten by.

No longer working for bad clients.

There are so many bad clients out there which will actively hurt you to press the most benefit out of you until you drop. dead.

you can only hurt me once. the second strike is only possible because i did not quit the first time. So it is my fault.

Quitting my job at Amazon, only second to going on the record and explaining to my boss that the reason I quit was "oranges" - I did this because I knew my boss would be reprimanded and asked by HR / mgmt "why did your employee quit because of this reason here?" and have to explain why I quit because of "oranges". I should add, that almost all of the other lead engineers moved to other teams or also left.

It's taken me more than a year to un-learn and cleanse my head of all the stupid games I had to play at that bullshit company.

Finally, quitting drinking. I never really drank that much, but at this point I don't really crave alcohol at all.

Can't know what would have happened the other way in each case, but I'd say it's changing jobs. The first handful of times it was really hard as workmates were also good friends. I learn so much more in a new position that I would staying 3/4+ years at the technical top of a current one. Working a different sizes of companies has also been good exposure (though this wasn't entirely a choice). Not keeping in active contact with friends is likely my worst nondecision/inaction.

1) quitting smoking

2) Leaving engineering to become a firefighter paramedic at age 36

3) Getting a master's degree in computer science

4) working a crap ton of over time and 2nd job to pay down mortgage

5) leaving firefighter paramedic after 14 years to work as a software developer fulltime.

Becoming a software engineer when I was almost 30. Changed my life.

1. Cutting ties with my parents 2. Pushing through the hard computer science classes 3. Getting into bouldering 4. Making and maintaining good friendships

Not caring anymore what others think about me

Dropping alcohol

Working really, really hard when I was younger. I still work, but only on what I want to work on.

1) software career

2) getting outside help with dating

3) quitting Twitter (50 hours a month back)

Going to college, seeing a psychiatrist