Better than a master of one

I’m currently going through a third career crisis of my adult life.

My first crisis was in 2012, after I graduated from my undergraduate degree in Experimental Psychology. I chose to study Psychology because I enjoyed the subject while I was at school and thought I could end up in research. But, after I graduated, I felt I wasn’t ready to join the “real world” yet, and decided to make my mum happy by following in her footsteps and doing a degree in Law.

While I was studying my MA in Law, I discovered the world of Computer Science through a friend. Even though I had always been interested in computers and did some programming as a hobby, I never actually knew it was something I could study due to poor/nonexistent career counselling. So, when I graduated in 2014, I had my second career crisis. Would I continue down the path of Law or take a chance on Web Development without any formal education/training? After much deliberation (and against the advice of many), I decided to go with the latter. Luckily for me, it worked out.

I’ve now been working in the technology industry for a decade. But at the beginning of that journey, I was already struggling with feeling boxed into my role as a frontend web developer. In Feb 2015, I published part one of this article, “A Master of None?”, in which I wrote:

I have a problem with not knowing things. But even more, I seem to have a problem with not being able to do everything. Essentially, I am a serial ‘jack-of-all-trades’. .. I guess there is a part of me that is always dissatisfied with my current knowledge and ability. This trait does have its good sides. It means that I am always up for learning something new, which is essential in the technology industry. But it also means that I may unfortunately always be a master of none.

It’s honestly so interesting to read back what I wrote then, and to still be struggling with the same things almost a decade later 😅.

I’m currently in the third wave of my career crisis as I no longer know if being a web developer is what I’ll continue to do (as my main job anyway, I’ll likely always write code as a hobby). Co-founding a startup forced me to expand my abilities beyond just technology, and I discovered that I also enjoyed the business/operations/finance side. The amount of impact you’re able to make when you move beyond being solely a technical contributor can be incredibly fulfilling.

So, last year, I decided I would do an MBA. I spent most of the latter half of 2023 studying then taking the GMAT and doing school applications, which was basically a full-time job in itself. I applied to 3 schools, which I got admissions to, and ultimately decided to accept a position at INSEAD starting in August this year.

My main goal for doing the MBA is to take some time to explore my options for what I’d like to do next. At the moment, I’m very interested in finance, but haven’t decided what form that would take or if it’s even the best fit for me. Over the first half of this year, I decided to really immerse myself in finance and took Level 1 of the CFA programme. As an aside, this was definitely the most challenging educational endeavour I’ve ever taken and I’m incredibly proud of myself for having passed (and above the 90th percentile) 🥳! This was a really valuable course to do as it not only vastly expanded my knowledge of finance but also proved that I am interested enough to pursue a career in the industry.

But herein lies the career crisis.

1. Can I really start again?

Firstly, I’m definitely hesitant at the idea of potentially throwing away the tech career I’ve built for myself over the past decade. It’s scary to consider essentially starting again, potentially in a field where the skills I’ve built are not directly transferrable. It is possible I’ll end up in a form of finance that does leverage my tech skills, but that may not be the case.

I have thought about this a lot and, to some extent, I’ve made my peace with the idea. However, it’s definitely still a scary leap to make. I comfort myself with the knowledge that, if becoming a finance bro doesn’t work out, I could still return to tech.

2. A master of none?

The second, deeper, issue I’m facing is feeling like I’m trying to do too many things and never really specialising enough in one thing. I think this is more of an issue for potential future employers, as most traditional roles value people who do just one thing. They want to see a CV of consistent experience in one field. Right now, my CV looks like I just do anything and everything. Psychology, Law, Engineering, Business, Finance.

While I have enjoyed every aspect of my journey, I do realise that most traditional institutions don’t really see the value in this. I was recently rejected for a scholarship and the feedback they gave was that I needed to have a more clear/singular career goal and align my experiences towards that 🙁 .

But I guess the important thing is that I see the value in the range of my experiences. Maybe it does make it more difficult to enter any one field. But maybe that means, ultimately, I’ll end up working for myself.

In my original article, I took inspiration from the famous quote by William Shakespeare for the title:

A jack of all trades is a master of none

However, that quote is often mis-quoted as ending there, which I didn’t know at the time. The full quote is actually:

A jack of all trades is a master of none, but oftentimes better than a master of one.

I’m learning that I have a pretty unique ability to learn things very well, and I shouldn’t shy away from that just because a lot of the world seemingly values specialists over generalists.

A few years ago I read the book “Range: How Generalists Triumph in a Specialized World”, and one part really stuck with me. It was about a study of highly fulfilled and successful people and how they arrived at their roles:

It turned out virtually every person had followed what seemed like an unusual path. “What was even more incredible is that they all thought they were the anomaly,” … Forty-five of the first fifty subjects detailed professional paths so sinuous that they expressed embarrassment over jumping from thing to thing over their careers. … “They had been told that getting off their initial path was so risky. But actually we should all understand, this is not weird, it’s the norm.”

Leaning into the unknown is definitely scary, but I’m excited to take the leap!