From Corporate to Startups

6 min read

I studied at a British university, where most of us had been lured with City boys’ tales and the prospect of an overblown career in finance like Jordan Berlfort aka The Wolf of Wall Street. The reality of a pre-finance life at university was of students engulfing fancy sandwiches and downing fresh squeezed orange juice at recruitment days.” That is when investment banks set up on campus to tell students about the glamorous lives of spreadsheet handlers.

These banker’s tales had built momentum and had shaped, as well as restricted, our early-career goals.

We were heading straight to the City.

Finance had become the only career start most of my peers were considering. The inertia, the lack of other options, is what pushed most students into banking careers. An often-repeated line at banking information sessions was: Get through two years of investment banking, and you can do anything you want afterward.”

Getting into banking thinking a couple of years there will help you get where you want to be is the new deferred career plan — an allusion to Tim Ferriss’s 4-hour work week strategy.

Getting rid of your 9-to-5 working identity

The story

A few years down the line I was sitting at an equity desk working as a research associate, my role was satisfying but some personal reason I quit. Back on the job market, I embarked on a series of binge networking events to connect with finance folks. For the first three months I was still acting under the stimulation of a potential work-hard / play-hard finance career but after a while my attention and interests started to broaden and drift.

I thought of other undertakings.

The Revelation

Taking a step back, I realise I could not have imagine doing something different than finance when I was sitting at my equity desk.

There was no way to plan what was going to happen.

There was no way to plan an exit out while sitting at that desk.

I had to act first; thoughts and inspiration would come second.

The theory

As Herminia Ibarra puts it in her Harvard Business Review article How to Stay Stuck in the Wrong Career:

We like to think that the key to a successful career change is knowing what we want to do next, then using that knowledge to guide our actions. But studying people in the throes of the career change process […] led [her] to a startling conclusion: Change actually happens the other way around. Doing comes first, knowing second.”

Finance was my working identity.

It took me three months, a few inspirational meetings with entrepreneurs, artists and non-finance professionals to defocus from the finance game and stop binge networking. In other words, it took me three months to get rid of my working identity.

who we are and what we do are tightly connected, the result of years of action; to change that connection, we must also resort to action — exactly what the conventional wisdom cautions us against.” — Herminia Ibarra, How to Stay Stuck in the Wrong Career

One encounter can change it all. It did.

Do what you feel is right

The first thing I did once I had stopped binge networking was to go sailing for a couple of weeks. Two weeks drifted into a month, then two months. I finally ended up volunteering as a cruising instructor for the summer at Glénans Sailing School.

I was away from the corporate world, spreadsheets, suits, squeezed lunch break and endless conference calls but I was working hard, sailing days and nights, seven days a week. I learnt so much. At that time, I felt I was doing the right thing, I had no doubt about whether I should be sailing or not.

I kept sailing and went on for nine months. Besides sailing, I also spent time in Los Angeles, then flew to Jordan and China for a month to explore and network.

I’d rather fail than regret

While sailing, I always thought I’d rather give it a try than regret not doing it.

That was a challenge and a risk, but I went by this motto: I’d rather fail than regret — that took me all the way to the Caribbean. I passed my cruising instructor exam in France, got certified as a Yachtmaster with the Royal Yachting Association in the United Kingdom and sailed across the Atlantic. At each stage of these undertakings, I thought of going back to look for a regular job, I was constantly asking myself: am I making the right choice by staying at sea?

I stayed because I did not want to regret not doing it.

I sailed because this is what I wanted to do at the time.

I accepted all the sailing jobs until I felt satiated. I wanted to go all the way so I can move forward with no regrets hindering my next steps.

The idea of thinking outside the box as a career

During my time as a sailor I embarked on ventures in the Mediterranean, around the UK, off the African coasts, across the Atlantic all the way to America. I was going from one sailing vessel to another taking sailing jobs as they came. I was comfortable having no set routine; no set career path.

Actually, there was lots of excitation and satisfaction in finding my own gigs.

I also realised the outcome of uncertainty associated with not having a set routine was mostly positive and had brought me a lot more happiness, thrill and pride than my previous role.

My lifestyle had become my work and my work had become my lifestyle. I don’t mean that sailing had become my lifestyle and that I was meant to be a sailor. I mean I felt I was coming closer to a lifestyle that suits me:

Connecting with people to built things from scratch in a environment that rewards results outside - my comfort zone.

I realized that is my vision of doing things. That feeling is beautifully reflected in a quote from French writer François-René de Chateaubriand written over a century ago:

A master in the art of living draws no sharp distinction between his work and his play; his labor and his leisure; his mind and his body; his education and his recreation. He hardly knows which is which. He simply pursues his vision of excellence through whatever he is doing, and leaves others to determine whether he is working or playing. To himself, he always appears to be doing both.”

Back on land, I was ready to start my own venture, I had nurtured a few ideas while sailing and more importantly had had the time and experiences to evolve a risk-taking mindset.

It has not been a restful, financially safe and emotionally smooth path to reach where I am at today — and there is still a long way to go — but it is worth it.

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