Best Career Decision?

A very cool thread that has some neat answers from folks who shared about some of their best career decisions. There are some good answers:

Emotionally detaching. I was a workaholic from age 16 until 33 and this was my primary identity. I used to always be proud of the work I did, no matter how lame the company or how many times I was screwed over. Then one day my father died, and I was fired from a company who I truly believed in and for whom I had sacrificed.

This sounds cynical, but it’s really peaceful. With the emotional energy and sheer time saved I am able to cultivate strong relationships, passionate devote myself to music, be a better father/husband/son, discover new interests that have nothing to do with the internet.

I frequently espouse the virtues of a “Fuck you, pay me” work attitude, and I recommend everybody examine their relationship with their careers and ask themselves if on their deathbed they will wish they had worked more.


Taking a chance and joining a very large corporation.
Previously I was all about startups or small companies and was very much against the mega-corp environment.

Over several months a colleague “recruited” me to join their team and I don’t regret it.

I’ve been able to climb pretty high within this corp and it has been a wild ride. Never in a million years would I have thought I’d have any sort of influence over technology strategy that one of the largest US corporations would follow for the next decade.

So, I’ve learned to keep an open mind and not let preconceived notions on how others do business until I see it for myself. If I had not done this I’d still be hopping from start-up to start-up.


I was a mid-level developer at a large software company making a very competitive salary and quit to join the U.S. Marine Corps and train to become a Naval Aviator.
I’m now a ‘mid-level’ AH-1Z pilot.


Circa-2000 I was in my final year of university and working as a Windows service desk monkey in the SysAdmin team of a Sydney-based company that developed a platform for hosting (legitimate, regulated) gambling websites.
Sun Microsystems happened to be across the road from us. My mind was blown the first time I saw the value of the invoices for servers and Solaris licenses that we bought both for ourselves and on behalf of our customers. That’s where a lot of those dotcom-era “investment” dollars ended up – at Sun.

One day we needed a router + firewall for some internal service. One of the Unix sysadmins in the team grabbed a spare i386 desktop PC, stuck a 2nd NIC in it, installed Slackware Linux and configured ipchains. Job done: no budget, no managerial approval, no licenses, nothing. I couldn’t believe it.

I asked him about Linux and after learning more came to the conclusion that it could basically do most things that Solaris could do but was 1) free and 2) ran on cheap, commodity hardware.

That was the writing on the wall for me. I taught myself Linux and pretty soon had my first bona-fide Linux Sysadmin job. Linux went on to become the OS that runs the world and I’ve never struggled to find relatively interesting, well-paid work since then.


I can’t pinpoint a single one, but a few in a sequence:

1. Before I built my reputation and experience, I said Yes to a lot of things. Not all of them I could do, but once I said yes and jumped in the deep end, I found out I can do them and do them very well. Necessity was a big driver.

2. Life style trumps “exit”. I worked with various start ups for 20 years. I founded and co founded 4 of them. At some point I decided that if a company succeeds or fails, I want it to be because of me, not despite me. So in 2 of those startups I had no investors and full control. I work at and dictate my own pace.

3. Best decision: My time and family come first. Nothing urgent has never been really that urgent. Nothing requires me to work 20 hour days. Nothing justifies my family being hurt because I’m somewhere working more than I should be.


Long story short – I was brave and stood up for myself, demanding the righteous thing.
I was 15 years old back then. I had just learned how to code and my hunger for programming was insatiable. I didn’t think much, browsed through relevant classifieds and sent out a couple of honest e-mails stating that I really want to have a job, but I have no real life experience.

A company replied within a few days and they were interested. It was a very small company, consisting of a CTO and CEO. We agreed on 200$ for a portal type of website(it was a thing back then), with user sign-ups, public and private posts, comments and a few more things.

This company was hired by a rather large media company, to develop a dedicated website for them. I knew who was behind it and I was hoping that I would get recognized by the media company.

I dreamed about writing lines of code in my sleep, daydreamed through school and spent all time I could on coding the whole thing.

I think I was done in three months or so, and then came the day I asked to be paid. I had put daily changes on their FTP server, as we agreed, so I had literally no leverage. And they stopped responding. I tried reaching out to them in numerous ways, such as using my mom’s cell to call the CEO, but he hung up immediately after realizing it was me who called.

As I realized that I had been scammed, since we did not have any form of written contract and had agreed that I would be paid in cash when the whole thing was done. Therefore I went on the media group’s website, found the contact section and somehow managed to stumble upon the personal cellphone of the CEO of the media company. And I called him. I was an emotional teenager, but I spoke the truth. I did not have any demands other than to be heard. After a 10 minute long discussion where I explained that I was ripped off and worked for free for months, the CEO invited me over. I still remember the awe everyone was in, when they realized that a kid had just called them and walked through their front door in a few hours.

That phone call has been the best career decision I have ever made. The media company terminated their contract with the agency that had ripped me off because of terms violation – they were prohibited from outsourcing any development to any third parties, without a written permission given by the customer a.k.a media company.

And so I landed my first job! The people working for this media company were so genuine, mature and supportive, that I did not lose my love for what I did and had been in web development ever since.

It pays off to be brave and righteous in the end.

Wow… and…

Teaching myself to program. Nothing caused such a hockey stick in opportuinities. I was able to make way more money in a very short time period and work in much more interesting companies.
I never took anything so seriously in my life as when I decided to become a programmer. I bought dozens of used textbooks, read and meticulously underlined them, relentlessly wrote code and read all the programming interview books, made guides for myself to study, said yes to every contract and bug I could help with regardless of the tech stack. I refused to be anal about picking one programming language over another.

I have a marketing degree from a not good school. If I could do it again I would (a) drop out and move to a major tech metro and (b) identify a high growth tech stack and study it intensively. Never should have wasted time getting a useless degree.

The best thing learning to program taught me was how to read books properly – Write in the margins, take extensive notes, phrase and rephrase the lessons, write my own articles and guides to solidify the learnings.

This year I mad $350,000 and got promoted to manage five people. I couldn’t have gotten here without learning to code.


Don’t make money your first priority. Take it into account, yes, and fight for raises if you deserve them; but prioritize other things that have a greater impact on quality of life, such as location, commute time or absence of overtime.

The best paid job I ever had was also the worst by any other measure.


At age 42 (11 years ago), going back to school and completing a Masters degree in Enterprise Architecture. I had been in the same job for 5 years when I made the decision. Work had a self-education program that paid for my tuition. The decision was literally made in the space of a couple of days before the mid-year intake. If I’d had to wait another 6 months, I probably would have talked myself out of it. It was hard work (had a young family at the time), but paid off handsomely when my stupid employer not only refused to utilise me in my chosen field (having graduated top of the class at their cost), but literally pushed me out of the company. One of my industry lecturers got me my first contracting gig and I haven’t looked back since.
I guess I learned a few things:

1) don’t overthink decisions (which is not to say “don’t think”);

2) to back myself and my abilities with the requisite effort. I’m typically smarter than I think but I need to put in a matching level of effort. When I got my Bachelor degree 20 years earlier, I literally skidded out the door in a haze of alcohol and with a shit grade. That cost me a few years;

3) don’t be afraid of a challenge; don’t be afraid of the unknown;

4) be sensitive to where you are in your life – can you afford to take a hit if things go pear shaped? Time-box your attempt to shake things up in your life;

5) If you work as a contractor – networking and self-brand management rules. I rely heavily on LinkedIn and the network of contacts I have cultivated, and keep my brand alive with posts and articles relevant to the kinds of work I want to be doing – not necessarily flavour of the month.

There’s probably more but that’s pretty much it. My income now is almost 3 times what it was in 2007, and while I’m not suggesting that’s the only measure of success (far from it), it affords me a professional freedom to be more picky in the work I take on, and to live with far less fear than before.

EDITED TO ADD: The reason I chose Enterprise Architecture was because it suited my temperament. I discovered I was a “systems” thinker pretty early on, and as I moved through a typical IT career trajectory, the “systems” I was thinking about became bigger and bigger. EA probably sounds pretty passe compared to all the “it” technologies people are playing with, but it’s kinda like politics – reality is gritty, the problems are hard, endless and fascinating (if you’re so inclined).


Tactically: public speaking. Strategically: forget about titles and career path and comp and just figure out how to provide value to the people around you. The other stuff takes care of itself.


I decided to be honest with myself about what I do and do not like, to work my ass off at the things I do like, and to be vigilant about checking my feelings and following my gut. It’s paid enormous dividends. I taught myself to program and have gotten good jobs because of it, and I’ve also avoided going down a lot of blind alleys. I quit academia after completing a Master’s rather than chase a PhD I didn’t really want and saved myself enormous heartache there. Several times I’ve started developing skills only to realize, “I hate doing this.” So I just stopped. I left numerous jobs where I was unhappy for various reasons and have stayed at one where so far I’ve been happy. And overall this attitude has kept me growing and pretty happy in my career and life generally.

EDIT: As a part of this: I was honest with myself that I cared about money (to a point). For a while I stayed in a job I liked that didn’t pay me well, trying to convince myself that “quality of life” was more important than money. The reality for me is that money is part of the quality of life equation, and I’m glad I admitted that to myself. It was also sort of a canary that I wasn’t being challenged and could do tougher work that paid better.

So good.

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