I’mm 12 years old, on a football camp. I’mm sleeping in a tent, in a field, with three boys I’mve never met before. They’re better at me than football. They’re cooler than me. They’re friends with each other. How am I ever going to get through three whole days of this?

I’mm 15 years old, cycling across England with two friends from school. We get lost and end up on the summit of Great Gable (the 10th highest peak in England: that really is stupid lost!). I wipe away tears and carry my heavy bike down what feels like an eternity of scree slopes. It’s so hard, we’re so lost, I’mm so much slower than the others. I don’t think I can do it.

I’mm 18 years old, driving into a place the like of which I’mve never seen in all my life. A shanty town of shacks, bullet holes on the walls, people staring at me. It’s my first day in Africa. I cannot imagine how I can live here for an entire year. I’mm terrified.

I’mm surrounded by porters, clamouring at me in Urdu. The night is hot and the air is heavy with sweat and curry and the crazy noise and music of Asia. It’s my first day in Pakistan. My first overseas bike journey. I need to get to a hotel, hide for the night, sort myself, take refuge from all this. A porter promises to help me get my bike and kit into a taxi. He carries it 20 yards to the car. I ask him how much I owe. £20, he tells me. I’mm too scared to argue. I’mm overwhelmed by the sheer foreign-ness of this place. I no longer want to cycle to China. I want to go home.

I’mm standing in front of a class of teenagers. One of them tells his mate to f*** off, loudly. I choose to pretend I didn’t hear it, to begin the lesson instead. Beyond the bored and rolling eyes of the bolshy teenagers are the impassive eyes of the assessor. He’s here to judge me today, to see if I can make it as a teacher in this tough school. Can I? Right now I don’t think so.

I’mm outside my Mum and Dad’s house. It’s a beautiful summer’s day. I’mve just said goodbye. I climb on my bike. I’mve told everyone I’mm going to cycle round the world. Can I really do this? Absolutely no chance.

I’mm at the front of a small room.  There are three rows of chairs, perhaps 30 people in all. They are looking at me. They’ve come to hear me give a talk. Me?! A talk about myself and my travels so far. I’mve been so nervous today that I haven’t eaten. I feel sweat trickling from my armpits. Not only have I got to remember what to say, I now need to remember to keep my arms clamped to my side! Speaking in public is terrifying. I vow never to do it again.

I’mm in an interview room. The window blinds are closed. I’mve sat exams for months and months to get this far. My final interview. The hardest intellectual challenge I’mve ever attempted. A panel of five introduce themselves. “Take off your jacket,” one man says. “It’s a hot day.”
“I’md rather not thank you – I only ironed the front of my shirt.”
They laugh, fortunately. It’s the only moment of laughter. I know these questions are going to be harder than any I’mve ever faced before, the stakes higher still.

I’mm in my boss’s office. I’mm about to quit my job. Jack in the salary and the pension and the sensible working hours. I’mm going to be self employed. “You’re going to do what?” says my boss.
“I’mm going to be an adventurer.”
No, I’mm not. Unless I can earn some money, I’mm going to be unemployed.

I’mm in a rowing boat with three men I barely know. I’mve been vomiting for days. The storm batters the boat. We’re locked in a tiny cabin, sweating against one another. We are at the mercy of the ocean. Ahead of us lie several thousand more miles of this. I’mm plumbing new depths of misery and helplessness.

I’mm in a cinema. Beer and popcorn. Lights off, film about to start. Comfy chairs. I’mm anonymous and surrounded by people. Strangers who are about to watch my first ever film. What if nobody laughs? What if they laugh in the wrong bits? Worse – what if they just fidget, a bit bored? I ought to be happy that my first expedition film has even made it this far. But instead, as always, I’mm afraid and out of my depth. At least this time there is beer and popcorn. So perhaps I am making a bit of progress, after all…

*

The point of all this? That continually pushing against my comfort zone means I have cajoled myself to do stuff beyond what I thought possible. At each stage in this narrative I would never have imagined that I would attempt what came next, let alone believe that I could accomplish it.

Looking back like this helps me appreciate how much I have grown. And I guess that gives me a bit more confidence that I’mll be able to work my way through whatever the next big, daunting hurdle is that appears before me.

I’mm not writing this as a showing-off story: I think everyone who tries to live by pushing against their limits will have a similar pattern. The limits you push may be physical, mental, business-related, artistic or musical. That doesn’t make any difference.  Each incremental challenge you overcome helps raise you towards where you want to be in life, even if you don’t really quite know where that is just yet. Think Small. Start Small. But do Start.

Thank you, Derek Sivers, for the title and original version of this post.