Someone asked me recently: “Is there a way to learn on your own? Are you self-taught, Sean?”
The short answer is yes and no. In some cases, I was taught. In other cases, I taught myself. But if you ask me which one I prefer, the answer is very clear. I would much rather be taught.
And here's a real-life example from a few years ago.
I'd started to take photography very seriously. However, the biggest problem with photos is that most of us take too many. On a camera, this situation gets even worse because the photos are shot in a format called RAW. Instead of tiny 2 MB images like the ones most people take on their phones, my files were about 90 MB each.
So the real question wasn't how to take photos.
It was: How was I supposed to download, sort, and categorise thousands of them?
Most photographers run into the same problem.
They download the images and tell themselves they'll edit them someday. But thousands more photos keep piling up. Eventually, the aspiring photographer gives up entirely. I knew there had to be a way to teach myself. Surely there was a course somewhere that explained how to manage all this.
Instead, I went straight to a wedding photographer and bought a few hours of his time. A wedding photographer routinely takes thousands of photos in a single event. What software did he use? What was his method for sorting through everything? What problems would I run into?
In a couple of hours of training, I learned everything I needed to know.
Today, just a few years later, I have more than 40,000 well-indexed photos, fully backed up. If you wanted me to retrieve a specific image, I could probably find it in under ten seconds. Best of all, I can sort through, eliminate, and process hundreds of photos in barely half an hour.
Isn't this a case against self-study?
Not really. For most of us, there are three levels of learning:
1- Self-study with a planned journey
2- A coach who gives you concepts, but may well be a poor teacher
3- A great coach who maps the entire journey and helps you every step of the way
Whenever possible, the third option is the best. But if you can't find that kind of teacher, you're left with the other two. And that's where most people run into trouble.
Unfortunately, the opposite experience is also very common.
I once paid about $400 to attend a four-week French class. The logistics of getting to the course itself were quite frustrating. It took almost three hours to get to class every day, and then I had to be in class for a couple of hours. You would imagine that such an investment of time and money would produce some kind of result. It didn't.
After weeks of effort, I learned almost nothing. This was due to the teacher's skill. She was able to teach the concepts, but was a very average trainer.
Undeterred, I invested another $1,300 with another trainer.
Once again, the result was close to zero. This is what I'd call the bad teacher syndrome. Most people turn to self-study not because self-study is superior, but because they have experienced bad teaching. After a few such experiences, they decide they are better off figuring things out themselves, and sometimes they are right.
However, despite their best intentions, many people don’t get very far with self-study.
There are several reasons why self-study can fail: you may make progress, get stuck, and not know how to get yourself out of the hole. Or you may start with excitement, only to find other priorities slowly crowding out your learning. But the biggest problem with self-study is something slightly less obvious. Like everyone else, I’ve had all three experiences: a great teacher, an average trainer, and times when I had to rely entirely on self-study.
So, to go back to the original question: how do I make self-study actually work for me?
The answer isn’t about discipline, talent, or resources. It’s about the journey. To understand why, let’s take a step back, all the way to the early Antarctic expeditions. When Ernest Shackleton prepared his 1914 Imperial Trans-Antarctic Expedition, the team didn’t know exactly what they would face.
The ice could trap their ship for months. Supplies could run out. The weather could turn deadly. Yet. Shackleton was taking almost no chances. To get his men ready, he trooped them all to the dentist. Every crew member had to have their teeth checked and treated before leaving. On an expedition that was already very costly, this added what would be equivalent to several thousand dollars today.
Which brings us back to the real issue in self-study: the journey itself.
Most people start off self-study almost like a New Year's resolution. They'll say something like: I'm going to learn a new language. They'll then proceed to write a few words and paste it on their fridge. Or worse, they'll switch to Duolingo (which, in my opinion, is a terrible choice).
In a few weeks, the entire process is derailed. On the other hand, someone who plans a Shackleton-type journey will understand that the journey is quite long. It's estimated that to learn a language like French, you'll need about 100,000 repetitions of sentences before you can have a really decent conversation. If you want to be quite fluent, you'll need between 200,000 and 300,000 sentences. Note that these are sentences, not words.
Suddenly Shackleton-like planning springs back to life, doesn't it?
If you don't prepare for the journey's length, how would you possibly get there? And it's not like we don't do this level of planning. Even to get to the airport for our flight, we have to factor in traffic, immigration, customs, etc.
We rarely step off at the destination thinking: Ah, well, I will figure something out. Instead, busy as we are, we plan the trip, work out at least some of the obstacles, and that's why so many holidays become memorable. Yet, when it comes to self-study, we rarely use the same rigour.
Planning the journey is what separates those who wander aimlessly in self-study from those who make real progress. It’s not enough to have enthusiasm or talent—you need a map, milestones, and provisions along the way.
Think of it like this:
With photography, I didn’t try to figure out 40,000 photos on my own. I planned a short coaching session, got the right tools, and organised my workflow. The journey was mapped before I even started.
With French, the lack of a plan and reliable guidance meant I stumbled for months, repeating mistakes without real progress. My journey was undefined, and it failed. In language learning, the scale of the journey—hundreds of thousands of sentences—requires patience, pacing, and deliberate structuring. Without acknowledging the length, you will burn out or give up.
The key insight is simple: you must treat self-study like an expedition.
Set the destination – What does success look like? Fluency, mastery, or just enough to get by?
Estimate the distance – How much time, effort, and repetition will it realistically take?
Provision carefully – What resources, tools, habits, or help do you need along the way?
Plan the route – Break the journey into manageable steps, with checkpoints to measure progress.
But what if you can't estimate the distance?
When you start learning something on your own, you often cannot estimate the distance. You don’t know if it will take 500 repetitions or 100,000. You don’t know where the biggest obstacles will appear. But you can still plan the journey.
- You can talk to someone who has travelled that path before.
- You can prepare tools and systems before you begin.
- You can remove obvious problems early, just as Shackleton removed the risk of dental emergencies.
In other words, you may not know the exact distance, but you can still prepare for the expedition.
Self-study fails because people often treat learning like a short stroll. It works a whole lot better when you treat it like a journey across Antarctica.
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