A career in ‘learning’

Image CC BY-NC-SA brianjmatis

If there is a requirement or trope within career advice articles, it is seemingly to start with a statement like “it’s alright to not know what you want to do, or even what you are currently doing” and write out from there. This is so universal, seemingly so effortless, and makes perfect sense to all. Almost everyone you’ll talk to will say the same thing.

But it’s not that easy, right?

I have had a weird career and one which I wish was I was more able to present as a ‘how-to’ guide. I started as a graduate of a classical music degree (which essentially qualifies one to die in poverty). Then, with perhaps as shameful and ignoble as a motivation it is, and at lack of a better idea, I pursued a teacher-training qualification and became a teacher, lecturer, department-manager and institutional manager in as many years. I moved via Dubai to San Francisco as a software engineer for one of the best education technology companies in the world and then came back home for one that wants to be. I’ve done alright from “I don’t know what I want to do” — I still don’t, and I’m happy with that because I’m learning it. I’m still trying to wrap my head around “I don’t know what I’m currently doing”. I guess the unifying thing with both is that I feel universally better when I can suffix either of them with ‘..but I’m learning’ and also have the freedom to do just that.

Though I worked in different jobs, I’ve never quite escaped ‘learning’. Being a teacher was at the same time the most rewarding and most draining job I think it is possible to have. I worked hard, but teaching is perhaps uniquely a job where you are never truly “done”: feedback can always be better; lessons can always be tweaked; students can always be supported more. Through all that however, I can’t help but believe I got so much more than I gave. I learnt so much: from the trivial (to know precisely how long something would take people to do; how to present convincingly without any preparation; how to essentially sell something in knowledge that people don’t want to buy), to the — for me at least — revolutionary (how to learn and teach from mistakes; how to give people a clean slate every day; how to make people believe things they can’t yet comprehend themselves).

I also strove to learn as much as I could about my craft. I completed a full-time Masters while working and am currently struggling through a part-time PhD. But I also strove to learn something else everyday in a non-formal setting: I read voraciously, learnt to teach new subjects, learnt to code and did the things we all could do if we wanted and had the time. I’ll admit I enjoy the academic process and look back at my studies with pride — but they certainly don’t define me or anyone else. Some of the most interesting and engaging people I know come from different educational backgrounds to me. It is the drive to have and enjoy the freedom to learn — to be the autodidact — to improve and grow that defines us.


If there is a second trope in this genre, it is to misuse and abuse a literary quote:

If you set yourself to it, you can live the same life, rich or poor. You can keep on with your books and your ideas. You just got to say to yourself, “I’m a free man in here” — he tapped his forehead — “and you’re all right.”
George Orwell, Down and Out in Paris & London

Freedom in the context of your work is not “not having to do it”, but doing something because you want to do it. David Foster Wallace offered that the alternative to this freedom is ‘unconsciousness, the default setting, the “rat race” — the constant gnawing sense of having had and lost some infinite thing.’

In my experience at least, working is an iterative process and it is certainly something you don’t always get right the first time. I’ve always — and luckily — been acutely aware of what I don’t like about my jobs (in order: unhealthy work-life balance, uninspiring colleagues, not “home”, lack of focus), and this has helped me make tiny moves to end up closer to where I think I want to be. I think we should all be chasing some infinite thing, perhaps instead of some immediate one.


My final piece of advice is one that I’m still struggling to work out myself: learn to understand the difference between challenge and difficulty. For me, this remains the ultimate tension between between learning and freedom.

I was once asked by a CEO of a company I’d eventually go on to work for what my ideal job would be. That sounds amazing right? Freedom.

I panicked.

Then, in an almost surreal moment of clarity I replied “one where everyday someone sent me an email beginning with “betcha’ can’t…”. He would go on to send me daily messages with interesting challenges until I took the job, and then continued while I worked there. I’m temperamentally someone who enjoys a challenge and quickly tires of an insufficient level of difficulty — I love learning and I suspect many other people are the same. But just as too much learning or freedom is perhaps harmful, these things come in different proportions in work and you have to find the right balance for you. Being able to do this is perhaps freedom in its truest sense.

Doing more things of a greater difficulty in the same time is challenging, halving the time you have to do them is difficult. Taking on and growing with extra responsibility is challenging; having to do more work alongside what you already do is just plain difficult.

The freedom to strive for is the freedom to chase interesting problems and then challenge yourself to solve them. I’m nearly at a point where this is my job, but even when it wasn’t or when it isn’t, it is that wish to learn that keeps me going and keeps me doing the right thing — for me at least.


Learning and Freedom are big ideas; both worthy of capital letters. They are quixotic in employment and are ultimately powerful tools to start, progress and move careers. Wanting the freedom to learn something or learning so you have the freedom to do something is what has got me through the maze of decisions I’ve made.

They are also ultimately both in your hands. Not in your job. That’s freedom. Learn.

One clap, two clap, three clap, forty?

By clapping more or less, you can signal to us which stories really stand out.