Thoughts on Changing Careers at 34 — for the second time

Last week, in a job interview, the HR guy on the other end of our video call asked me: “You’ve done all this interesting stuff, and now you want to be a software developer? Are you crazy!?”

I’m not sure if the idea was to catch me off guard or not, but it did. I was prepared for the question of why I wanted to shift to a career in software development, after already shifting from a career in agriculture to education, but I wasn’t quite prepared for his exaggerated interrogation.

I admitted to him that, yes, I probably was crazy.

I don’t fault him for asking me that question. In fact, I’ve asked myself that question many times and it was surprisingly hard to answer. The truth is, I was doing other things that mattered to me at the time, none of which actually involved pursuing a career. I knew I had to make money, so I had jobs, but none of them seemed like careers I’d want to spend more than half a decade in.

How I got to this point is actually pretty simple. First of all, I doubt many people really know what they want to do for the rest of their lives when they’re 18. That was about the age I decided I wanted to study agriculture and help small-holder farmers around the world. But what I really wanted to do was just see the world, and using higher-education as the vehicle to do that seemed like the best way.

So I studied abroad, then I got accepted to an international Master’s program in Germany. My master’s program took me to Kenya for my thesis work. In the meantime, I took off on backpack trips to Berlin, Madrid, the Alps, the Arctic circle of Norway, Istanbul, and the Albanian coast. After finishing my program. I got offered a job and a PhD at the same time. Looking around me, I saw that all the people in PhD programs were miserable, so I took the job, but I hated it. I needed a way out.

Sunk-Cost

The “Sunk-Cost Fallacy” is an error in rational decision making where we refuse to cut our loses because of time, money, or energy invested. The sunk-cost, or bad “investment,” although usually financial, could just as easily be a bad relationship, a failing business, a horrible movie, or a poor career choice. The fallacy is that, most often, we keep pumping money into the business we worked hard to start even if it’s obviously failing, we sit through a bad movie even if we’d have a better time ditching it for an ice cream, and we stick it out through careers we don’t enjoy because of all we put in to get that Master’s Degree.

When looking towards the future, rationally speaking, past mistakes should be irrelevant, in the sense that any costs incurred prior to making the current decision have already been incurred. It is what it is, so cut your loses and move on. Julia Galef, author of “The Scout Mindset” points out, if you were halfway to the grocery store before you realised that the store was closed, you wouldn’t keep walking anyway because you’d already invested 15 minutes in getting there. No way. You’d turn around and go home. And that’s what I did after my first job in agricultural development.

The subsequent job search after that contract finished was horrible. My choices were looking grim. Within many of the job descriptions I saw the end of my autonomy and freedom, and the beginning of a hierarchical, bureaucratic mess. On the one hand, I could take positions in niche organisations in secluded German towns, or sign onto two-year development positions in remote villages in Eastern Africa. I wanted to see the world, definitely, but I also wanted to see my family and friends. So instead of continuing to walk further, I turned around.

The question I ask others is: why is it so common to submit to the sunk-cost fallacy with careers? But more importantly, the question I failed to ask myself was: why was I so ok with abandoning them?

Adventuring On

Looking back now, I can admit that I took the easy way out. Yes, I wanted to maintain my freedom and was terrified of answering to middle managers or thesis advisors, but the decisions I made afterwards were naive and arrogant. I decided to move to Spain to teach English in bilingual schools because getting the jobs were easy, and the thought of learning Spanish and living the mediterranean life was thrilling.

I was right. The mediterranean life was a great choice. The work, on the other hand, wasn’t. As a curious person, I confounded my love of learning with my interest in working as a teacher. The truth is, I have a lot of interests, and if I had multiple lives, I’d pursue or study a different topic in each one. But I quickly realized that most teachers in primary and secondary education don’t care much about what they do. They do it because it’s good job security (especially as a state worker in Spain) and they have summers off.

I was slowly getting disappointed and disillusioned by the work environment. The average co-worker put little effort into providing an interesting learning environment for the kids, and most of them resented their students. It’s hard not to blame them. Being forced to teach state-mandated curriculum to a class of 30 children with vastly varying interest and ability levels is hard work. Being a teacher is easy, but being a good teacher is very hard.

I was suffering from the difficulties of trying to be a good teacher too. I loved the kids, but it was draining. I didn’t have the resources I needed to teach the way I thought was right, and I didn’t like having to bend to the constraints of the mandated curriculum. I didn’t want to be forced to make kids in 3rd grade memorise the capitals of European countries, I wanted to teach a problem-solving based curriculum.

In the end, I was beginning to sense that I wasn’t being challenged, that I had departed from interesting work, and that I was capable of better things. I started to feel, for the first time, that I needed a career.

The Importance of Hard Work

Hard means worry: if you’re not worrying that something you’re making will come out badly, or that you won’t be able to understand something you’re studying, then it isn’t hard enough
— Paul Graham, “What you’ll wish you’d known”

Up until this point, I had always looked down on careerism, and I thought hard work was symptom of it. This was at odds with my desire to ideally be my own boss, a freelancer, a creator, or simply to pursue work on my own terms. I failed to realise that the people that accomplish these things, even the creatives and artists, work their asses off. I knew how to work hard, and had done it in spurts, but I generally only did enough to get by.

I should say that I wasn’t just drifting through life with no goals in mind at all. I had goals and established values. They were simple though: see the world, learn a new language, spend time with my friends and family, and create things. The only thing I was failing at was creating. And I wasn’t achieving what I believed I potentially could, because I wasn’t working at it with consistency, focus, and intention. But I didn’t quite realise this until the coronavirus pandemic.

What the pandemic took away, it replaced with ample time. I was lucky enough not to lose a job, because already by this time I was working from home teaching online, and planning to hopefully find a better job or perhaps make a return to academia. Around the same time, when everyone was making plans to get fit, learn how to paint, teach themselves to play guitar, or brush up on their French, I started to learn JavaScript on CodeCademy.com. This wasn’t my first foray into web development though. As a pre-teen I was making static websites for my favourite bands. I got started by viewing source code of other sites and effectively taught myself HTML and photoshop (I had a weekly image series and made “meme”-ish images of the band, or of myself skateboarding) via copy-paste trial-and-error.

This was, however, my first experience with a programming language, and I was loving it. I’d wrestle with the methods for hours, creating hypothetical problems to solve for no real reason other than just to figure out if I could. Learning new methods and getting code to produce even the smallest of desired results feels like a massive reward. I don’t know for sure, but I’d guess that a lot of programmers share a similar sentiment. Regardless, these small, incremental rewards kept me going. I was focused, working consistently on a topic, and I was learning at a fast pace. I was also amazed at what I had accomplished. It’s a powerful feeling being able to create apps that you love using yourself — even more so after just 9 months of learning a coding language.

Where It All Comes Together

It may seem quite obvious that consistency, focus, and patience yield great results, but I’m not ashamed that it took me a long time to truly realise this. And I think the reason it did was because I hadn’t found something that intrinsically motivated me like that in a very long time. It’s the kind of motivation that finds you straight back to work, first thing after waking up, in order to solve the problem you left unresolved the evening before.

You might have already heard about “Ikigai,” but if not, it’s a Japanese word that loosely translates to “reason for being,” and it is the intersection between doing what you love, what you’re good at, what the world needs, and what you can be paid for. You can probably see where I’m going with this, and, yes, I mean it honestly when I say that I think software development is my ikigai. Before, I was swimming too much in the unfulfilling waters of “what I was good at” and “what I could be paid for,” and not venturing towards that sweet spot.

I started this essay as a way to collect my thoughts and to ultimately be able to answer that HR guy’s question: are you crazy!? To outsiders, I admit, it may seem crazy, but it brought me to this point on my own volition, and I think there’s a lot of importance in that. Had I gotten here a different way, I probably wouldn’t have trusted it.

While most people get places by following a more linear path, sometimes I feel like I cast my life out like a net. They might take a few detours to see what’s around the corner, or correct-course if they get off route. I shot out in as many directions as I could, tasted as many flavours as possible, and tried on a bunch of different hats. I wanted to be open, not judgemental. I wanted flexibility, not wealth. But if you also desire to be good at things, you can’t spread yourself so thin. So I’ve started to reel in my lines and focus on catching fewer fish. I’m still out at sea, the captain of my own boat, but this time with a destination in mind, and with hopes of catching fewer, bigger fish.