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From corporate to startups

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 attending banks’ recruitment fair. That is when investment banks set up on campus to tell students about the lives of financiers and other spreadsheet handlers.

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

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 plan1:

First Part of Life: Do what you have to do

Second Part of Life: Do what you want to do

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 an exit” out while sitting at that desk.

I had to quit first; thoughts and inspiration would come second. I had to get exit my day-to-day life as a financier to start thinking otherwise.

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. I had to leave first to figure out what I could be doing next.

It took me three months, a few inspirational meetings with entrepreneurs, artists and other non-finance people to break out from the finance mindset. In other words, it took me three months to get rid of my finance working identity.

[W]ho 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.”2

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 became a month, then two months. I finally ended up volunteering as a sailing instructor for the whole summer at Glénans Sailing School, a non-for profit.

I was away from the corporate world, spreadsheets, suits, squeezed lunch break and endless conference calls. Still, 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 felt present.

Realize deeply that the present moment is all you have. Make the now the primary focus of your life.”3– Eckhart Tolle

I kept sailing and went on for nine months. Besides sailing, I also spent time exploring in Jordan and China.

I’d rather fail than regret

While sailing, I always thought I’d rather give it a try than regret not doing it. I would rather give it if I felt like doing it - with no expectation.

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 sailing to the Caribbean.

I kept sailing because I did not want to regret not doing it.

I kept sailing 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 yacht to another taking sailing jobs as they came. There was lots of excitation and satisfaction in finding my own gigs.

I 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 finance role.

My lifestyle had become my work and my work had become my lifestyle. I felt I was coming closer to a lifestyle that suits me.

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.”


  1. The Four-Hour Work Week, Tim Ferris

  2. How to Stay Stuck in the Wrong Career, Harvad Business Review, Herminia Ibarra

  3. The Power of Now, Eckhart Tolle

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