You can’t change the past and I don’t believe it does any good to dwell on what ifs, or wishing you could go back and do things differently. That doesn’t stop me from occasionally thinking about where my life might be if I had made different choices at certain points in time, and then throwing these rambling thoughts down in a blog post.
In all honesty there is not much I would change if I had the chance. I’m very happy with where my life is right now. One thing I’ve been considering though is that, with the benefit of hindsight, I could have ended up at this same place except sooner.
There all kinds of mistakes and things I did when I was younger that put bumps in my road, or caused me to take wrong turns. The one that picks at me the most is the decision to go back to school to take Computer Science.
It’s not because I don’t see the value in the program or that I didn’t learn anything. In fact I really enjoyed my time at Acadia, the people I met, and I learned so much. The reason I regret it mainly is because where I ended up, and for how much of my degree I actually use, I didn’t need to go deep into debt in student loans to learn the skills and knowledge I now use in my career.
My time and money would have been much better spent buying and reading books specifically about web development. That is what I was really interested in and where I wanted to spend my career. Instead of writing command line Java programs I could have been building and experimenting with side projects or client work on my own.
At the time though all the local jobs with employers I thought would be good to work for wanted someone with a degree. Truly I didn’t even think about the possibility of working remotely at the time. Even though I was already doing it to an extent making websites for people I never met in person. It also didn’t occur that I would find a company where I really could make a career providing customer support. With those assumptions and narrow focus the logical route seemed to be to spend four years going to University.
After graduating I was able to sustain life being self employed doing web development for people. However I didn’t make it to a point where I was earning enough to repay my loans. For a number of years I deferred payments. This means there are still a lot of years I’ll be paying them back. Getting close to 40 years old and seeing the final date to having them paid so far away is a bit deflating.
This isn’t a complaint against student loans, I’m fully aware how fortunate I am that I was able to get loans, go to school, and then defer their payments afterwards. I’m just day dreaming about how I could have done it differently now that I have the benefit of looking back.
Even before I went back to school I was already on a path which could have led me to Automattic. My passion was in the web, I loved building things to help people, and helping people get a presence online. The whole while I was teaching myself how to do these things in my spare time. While building websites I came to a point where static html files weren’t the best way to do things and started looking at content management systems. Playing with things like WordPress and Joomla or Mambo at the time. In 2009 I signed up for a WordPress.com account, though I didn’t end up doing much with it for some time.
Later in 2010 I ended up hearing a Big Web Show podcast on 5by5 where Matt Mullenweg was interviewed. In it he talked about Automattic and in particular Happiness Engineers is what caught my attention. That was my first time starting to think that it could be a cool job, but put it out of my mind before looking into it because I was making money on my own. In that interview Matt also talked about a theory that the time was right for a product like WordPress to evolve and that if it wasn’t WordPress something else would have come along which met the needs of the web. My thought is that my career at Automattic is sort of like. A career like this, with a company like this, was needed in my life and we ended up connecting together.
If I hadn’t gone to University I could have learned a lot by myself in that same time frame and maybe when I heard that podcast I would have been more open to looking into working at Automattic. Then I could have been four years ahead in my career and without all the student loan debt.
Despite the regret I’m still just so thankful for having the life I do. With my family and career I really have nothing to complain about. Just in case my path wouldn’t have led me here without my going through University, than I’m even more grateful for my experiences I gained there and will try my best not to be so down on paying back the loans.
Sandy McFadden 
Really interesting post, Sandy. I’ve done the same thing many times, with many different decisions and life paths I’ve chosen.
For me personally, I came to the realization that the reason I’m able to look back on them the way I do is based on what I know now. If I’d known it then, I would have made different decisions then. And the only way I was able to learn what I know now was to follow the path I took.
So for me, it’s all good. And really glad that we both found our way to Automattic. 😉
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So much love for this post Sandy, I have VERY similar feelings about my career path.
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Great post, Sandy. I totally get what you mean about the benefit of hindsight here.
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Oof, yeah, I often have the same regrets, especially in comparing myself to younger folks at a8c. I often think of how much farther along I’d be if I had gone right into something lucrative in school and spent my 20s in a traditionally productive way instead of farting around in the arts. But then I realize I gained all the personal skills I have now through the path that I took — I simply wasn’t ready to lead the kind of life I have now in my early 20s and if I went back, I still wouldn’t be. And I got a lot of great things out of those years! They just weren’t the same things others would value, but they were what I wanted and was ready for at the time.
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