Growing up I found myself instilled with the strong impression that things were supposed to be difficult, and that when I was older I would need to keep doing really difficult things to be successful in life.
In school, you’re not really taught to learn in an incremental way, and the feedback loop between learning and succeeding is needlessly protracted. Back in the UK — and I’m sure elsewhere too — schools and university programs involved endless cycles of:
- Spending a year or two studying a ton of different subjects, all in parallel. Some are mandatory, some you get to choose.
- Taking a huge set of exams on absolutely everything you’ve learned, all in the space of a week or two.
- Celebrating the wins, commiserating over the losses.
- Repeating the cycle over again
I’m not a genius, but I did managed to get through those cycles relatively unscathed with decent enough grades to show for it. That said, this waterfall-esque approach to learning was difficult.
It wasn’t difficult in the sense of it being a lot of work. I can deal with a lot of work. It was difficult in that I felt like the system was geared to fight against me, adding more and more exams with higher and higher passing grades, in an unending attempt to separate out the wheat from the chaff. Like a video-game with no end that gets progressively more difficult, until you eventually fail and get a high score, and that score ends up defining your worth.
That left me with a pretty warped perception of the world.
But it turns out in the real world — providing you have good health and the right opportunities — you really can make things work just by putting one foot in front of the other, and by gathering small incremental successes. And as it turns out, there are always people out there who actively want to help you along the way.
A quick aside — yes, I am a white male, and yes, I grew up in a middle-class family, and yes, I did have plenty of opportunities and not much to hold me back.
This isn’t an article where I’m trying to claim everyone has the same privilege or opportunity. They clearly do not.
This is an indictment of how we’re taught to learn and progress in an ‘all or nothing’ fashion, when regardless of privilege, the world simply doesn’t work that way.
I learned this lesson time and time again after leaving the school and university system. Here are some examples:
If I had taken the ‘all or nothing’ approach to learning to code, I would have enrolled in a three year course, learned a bunch of useful (and less useful) concepts and principles, and then crammed at the end to get a good score in an exam. Instead, I just started hacking away on things that interested me. At the time, my interest was in building Counter Strike server mods, using a small shell language that was popular at the time. Every new line of code I wrote was a victory. I’ll be forever grateful to my mentor at the time, a guy called Mattie with the patience of a saint who taught me that literally anyone can learn to program.
If I had taken the ‘all or nothing’ approach to finding a job, I would have spent months hand-crafting my resume, worked to get as many relevant certifications as possible, taken the right courses in school and university, then practiced interviewing non-stop. Instead, I took whatever arbitrary freelance roles I could find on craigslist or reddit/r/forhire, sometimes getting in over my head, but mostly scraping by. Every new reply I received to an email was a win; every new site or app I deployed was a victory. Once again someone took big a chance on me, this time my former boss Alex. He interviewed and hired me as young engineer with very little formal or big-company experience, into a major Silicon Valley company.
If I had taken the ‘all or nothing’ approach to advancing myself in the valley, I would have done bi-weekly 1:1s with my manager, come up with a career progression plan, and tried to check all of the boxes to move me closer to the top of the pack. Instead, I just tried to do whatever felt like the right thing at any given time, and I put everything I had into that. Often learning to identify ‘the right thing’ was the real challenge, and of course I got in over my head a few more times. I told my boss Brian, who I reported to for the largest chunk of the last decade and who taught me what it means to be a leader: “let’s not do 1:1s too frequently — just give me a little nudge if I’m heading down the wrong path”. He did, and it worked out pretty well.
In the last decade, I came to realize that while I’m certainly privileged, I’m not actually that smart. I’m just reasonably good at recognizing the fact that things are not actually that difficult if you chip away at them incrementally. If I can find a way to get started out on a new thing in a super minor way, and motivate myself to not stop until I’ve actually achieved something noteworthy, I’ll usually end up in an ok place.
So if you want to learn a new programming language or framework or library, don’t read a whole book about it, read the first few code samples on GitHub and try to do the simplest thing possible. If you want to try writing, just start writing, anything at all. If you want to get new leads or investment for your startup, start writing emails and making calls. Allow yourself to learn as you go, rather than studying for some fictitious final exam.
Turns out, if you do that, it isn’t that difficult after all.
My next challenge is building a startup called OneText, with my friend and co-founder Jonathan. I have no fucking clue how to do a startup. But we just got a check from our first investor, and we’re keeping ourselves super busy with new leads. We’re doing one small thing at a time. And it seems to be working. :)