When we talk about our lives we're encouraged to share the highlights. The greatest hits. And when we talk about success, we largely only hear the brave tales from the survivors. Those stories are usually tainted by hindsight bias. We hear about the inevitability of success, but not the pain of failure and the trepidation of uncertainty.

All of us are at various stages in our Hero's Journey. Regardless of our path and years of experience, it seems there is always some chasm to cross. Sometimes we want the comfort of knowing rough tides will pass. Other times we just need to know it's okay to be scared out of our minds.

A conversation with students on my course moved me to draft notes in my journal one morning, and 7 pages of notes turned into a +3000 word essay. There's no way I'm dropping that into your inbox all at once. I respect your time. So I've split it into a few chunks. Here's the first. An honest account from the other side of the void. It's extremely personal, but it's a slice of reality. I hope it helps!

History is written in retrospect. The stories of most of your favourite heroes would likely look a lot different if they were crafted live, in the moment, from the protagonist’s diary.

Every moment of uncertainty, doubt and dread would be laid bare. You’d feel the fear when they’re trapped with their back against the wall, and no real idea how they’ll escape the next crisis. You would see through every bluff and bald-faced lie. Every feint and sleight of hand. The elation of succeeding against the odds and the numbing depression in the wake of each setback.

When you’re in the thick of it, even when you have an irrational self-belief that everything is going to be okay, the tiny gap between faith and certainty can be wide enough to swallow you whole. If you were watching events unfold on the big screen, you may still be cognisant that you’re only halfway through this particular episode. And this episode isn’t even the season finale. So things can’t end here. This can’t be it. The hero must live.

Real life doesn’t make great cinema. There’s no punchy dialog, glamorous backdrops, time jumps or plot armour. You toil in darkness, perpetually at risk. You can only hope you survive long enough to craft your own happy ending.

I’m not always a fan of compliments. Compliments usually follow achievements or success, but success isn’t finite. The acknowledgement of reaching a milestone often masks the difficulty of the journey and the slim odds of completion. In video games, you receive kudos for clearing a level. Nobody asks how many times you died facing the final boss. We don’t want to know how many times you almost gave up, throwing your controller at the wall in frustration. We only want the highlights. The hero's journey.

So today, I thought I’d be honest. Peel back the ameliorative gloss. Tell you about all the times optimism escaped me. The times I wasn’t sure I was going to make it. Moments I couldn’t tell the difference between a cliffhanger and a tragic ending.

This may just be a list of all the times I cried like a loser - I have no idea - I’m writing this live.

[Author’s note: I often think my writing would be a lot cooler if I swore. I recognise the crisp emphasis they can bring to written text. At first, I didn’t swear for religious reasons. Now I don’t out of habit, and because I think it’s lazy.

It takes some fortitude to use real words. Swearing is a form of emotional shorthand. Habitual cursing, in my mind, indicates a lack of restraint, control, or imagination. Refusing to default to it is a useful constraint that promotes thoughtfulness.

It’s a little drop of discipline. And my unnecessarily competitive nature means that because I can still count on one hand the number of times I’ve slipped up, I’m destined to maintain the practice forever. The rest of this essay will be quite emotionally charged, so if you’re that way inclined, I’ll tell you where to add the exclamatory f-bombs.]

Sown into every great leap of faith is an insane amount of fear. Feel free to impute a giant f-bomb right before fear.

The danger of taking an unconventional path is there is no psychological safety net. People often come to me for advice on whether they should drop out of college (like I did) and pursue their own path. It's a hard question to answer. Largely because the options you have before you are only half the equation. The rest is a mental game.

The earlier you fall out of the traditional/ideal funnel the harder it becomes to forge forward. Once you're off the beaten track you have to keep going until you emerge on the other side. You don't get to recline listlessly under the canvas of some degree or certification. There are no breaks. I have nothing to fall back on except my record of outcomes.

There’s no heuristic by which you could impute my competence. I have to prove it every single time. I don’t get to go do a Master’s degree when I’m feeling stuck. I can’t do an MBA to catapult to the next level.

All you can do is go to war. Keep your boots on and your rifle by your bed. This is not a drill.

When you take the road less travelled by, your entire life is a Covid passport. At every checkpoint people want proof. They need evidence. You can’t fly without it.

Every hoop I jump through feels like hand-to-hand combat. But the truth is I’ve been fighting my whole life.

It’s been over 20 years since I was first held at gunpoint. I was young. In Nigeria. My parents were away. I was at home with a babysitter, a young girl from church, in a tiny one-bedroom flat.

The night's soundtrack emanated from an old TV set. I remember every song it played that night. I believe I can fly. Michael Jackson’s Thriller. It was my first time seeing that legendary music video.

I never really talked about that night. At home or anywhere else. My parents thought I must have forgotten - maybe I was too young to remember. I don’t think you can ever be too young. You can’t forget a night in a room with four Ak-47s. The unmistakable electricity of a gun muzzle at the back of your skull. If you were too young to remember anything else, this would become your first memory. You’ll never be more alive than when death is right behind you.

Let’s fast forward - I don’t want to bore you. Skip past childhood illnesses - most of my earliest memories were of car rides to and from the hospital - and ignore the three separate occasions I was stuck in a car that caught on fire. Skip another two car crashes and the first time I saw someone get stabbed. Life is scary, we get it.

But there’s more to fear than that.

Not going to make it

How do you really know that everything is going to be okay?

Cultivating the will to survive takes an irrational sense of self-determination.

You’re going to make it. Say that to yourself. You’re going to make it.

Even when everyone around you stops believing, you have to stay resolute. Present unflinching conviction, or at least the appearance of it. That’s the hard part. Swallowing fear. Forging on. Like Dumbledore at the lake of inferi.

I remember sitting on a park bench in central London while a mentor and personal hero of mine - a war veteran still learning to walk after being paralysed from the waist down by a car bomb - told me that my dream of becoming a lawyer was almost impossible.

I had just told him that I wanted to apply to my dream firm. They were about to start a new scheme that would allow me to start at the firm full time while studying on evenings and weekends.  If I got in I’d be one of the first, if not the only, fee-earner at any City firm allowed to start without first completing a degree.

He pointed over my shoulder, from his wheelchair, at the small cafe which had just served us coffee. “Look, they’re hiring. You should apply”. I stared blankly. “This?” He said, holding up the piece of paper I had just handed him, “don’t waste your time. I love you, but seriously, what are the odds?” He asked me how many first-year trainees the firm hired each year. I mumbled my response under my breath. Just ten. From thousands of applicants. And they would only be willing to take on one person like me, on a pilot basis.

The odds that year were 1500:1. That’s what the managing partner told me three months later as he welcomed us to the firm. Little old me, a small boy from Lagos, at one of the biggest corporate law firms on the planet.

I remember crying after my second final interview. I had two final interviews because it was that close. My first 'final' interview went great, but apparently they still couldn’t decide. So I had to come back.

My second set of interviewers were senior partners. They asked how I had managed to get my first graduate job without actually graduating. So I told them. In many ways, it was quite simple. When you’re taking big swings be ready to knock the ball out of the park. When you’re going against the grain, nothing short of a home run will do.

I was initially headhunted for that role. The recruiter saw I’d spent some time at Google, and I was just returning from Shanghai having spent some time at a pan-Asian law firm during what should have been my final year at university.

I clarified over the phone that I hadn’t actually completed my degree but convinced them to let me through to the next stage of interviews anyway.

After a second interview and a packed assessment day, my last task was a presentation to the directors. I was shown to a spare desk and given 45 minutes to cobble together a 10-minute presentation answering the question: ‘How did bankers create the credit crunch?’

I didn’t bother switching on the computer I was given. Being a perfectionist by nature, I could easily have spent 5 hours crafting the perfect PowerPoint. There wasn't enough time. Instead, I took a notepad from my bag and wrote down everything I knew about the financial crisis. With five minutes to go, I wrote my headings in large font horizontally across spare notebook pages.

When I was called upon to present, I tore the pages out and held them up one at a time as I talked through a presentation about how the financial crisis in 2008 was caused by the fall of the Berlin wall almost 20 years prior.

Without a global antagonist to balance against, capitalism had proliferated unchecked. I talked about how collateralised debt obligations emerged during the same period and how their use became continually abstracted from the underlying debt as financial instruments became more sophisticated. You get the idea. I sounded pretty smart. The less glamorous truth was that I happened to live across the road from a library. It’s where I hid when I had nothing to do, and I happened to have read several books on finance by chance. All I needed was an original angle.

I presented to five directors. Four said yes. The one that said no ended up being my boss.

I took a similar approach to my interview with the law firm. The thesis I’d developed by this point was that the more audacious it was for me to be in the interview room in the first place, the more outrageous I would need to be in order to pull it off.

So when the senior partner asked me to propose a solution to speculation that Greece might leave the Eurozone and revert to the Drachma (an event fondly referred to as Grexit), I told him the real solution was for Germany to leave the EU instead, and revert to the Deutsche Mark.

I remember leaving that interview having no idea how it went. I had thought on my feet and defended my ideas well, but the stone faces on the other side of the table gave me no clues.

I sat in the courtyard in the shadow of the building and let myself shed a tear or six.

Almost every morning for the next five years I had the good fortune to walk past that spot where I cried, as an occasional reminder that the ‘impossible’ in ‘impossible dream’ is a figment of your imagination.

You are going to make it.

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If you have any thoughts on fear and success I’d love to hear from you! Reply via email, leave a comment, or send me a tweet!

I’d also love any thoughts on what I should write about next.

Read on for this week’s recommendations >>

Photo: by David Elikwu, in Skopje

Reading list

Books I’ve read/seen/will impulsively buy and add to my “to read” shelf on Goodreads. Recommendations from newsletter readers are always welcome:

  1. The Unfair Advantage by Ash Ali and Hasan Kubba - seen. This book came highly recommended, and was a really good read. Great insights from the background of the authors, as well as a raft of connected anecdotes.
  2. The Spy Who Came in from the Cold by John le Carré - impulsively bought. Finally got around to reading this old classic. The writing is as good as the story.
  3. Scythe by Neal Shusterman - read. I should have rated this higher than I did, but the ending ruined an otherwise great book. The premise, characters and worldbuilding are all good. I just wanted a little more chaos.

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