When Is It A Good Idea to Leave Your Job?

Matt has talked about the mental battle that goes on when figuring out whether quitting your job will be a massive mistake. Rob has talked about picking the right business idea. We have been running our Startup MBA program for a year now, helping Escape the City members test the viability of their business ideas before walking away from a steady pay cheque.

It was during the first intake that I first met Ollie Codrington (@olliecod). He remains the most reluctant prospective Startup MBA student I have met: he called me a few days before the course repeating his hesitation at coming along. After a lot of cajoling, I promised him that I would give him a full refund if he wasn’t thoroughly (a) getting value out of the course and (b) enjoying himself, after the first day.

So Ollie came along. He loved it. I wanted to give him the chance to share his story here. Ollie started his career in law. Now, he’s founding brojure.com and acting as a mentor for two great charities, Bathtub2Boardroom, giving entrepreneurs office space and business support, and Mosaic, giving secondary school children regular access to coaching for confidence building and long-term employability. Here, Ollie talks about his journey so far.


How and Why I Left the City

In a former life I was Head of Compliance and Licensing for the British Horseracing Authority. I really enjoyed my job and loved the team that I had worked hard to build and yet, during a holiday in South Africa in 2010, I made the rather spontaneous decision to leave.

For me, ‘the law’ is a set of skills rather than the particular application of a bank of knowledge. I had variety in my role and I was given responsibility early in my career but yet the role did not allow sufficient commercial scope, nor did it satisfy my entrepreneurial itch! I found myself fighting against antiquated processes and ‘decision by committee’ attitudes. It was clear they were not particularly tolerant of someone always suggesting a new way of doing things. I was operating as an agile entrepreneur in a quasi-governmental organization – something had to give.

My experience was that lawyers are only ever called on to deliver bad news and our job is to spot the problem, rather than necessarily to solve it.

I financed the transition by selling my flat and later, my car. My lifestyle took a massive hit, there is no doubt, but I don’t regret it for a moment and I fully intend to look back with considerable pride.

Owning Decisions

I spoke to various friends and advisers about my decision to leave, but very few agreed with it. The general attitude of friends and family was nervousness. “But, what will you do?” was the common question.

With hindsight, perhaps I should have taken more steps to prepare before leaving, but I also tend to feel that you owe it to your current employer not to be spending your time plotting your escape when you should be working. I’m a big believer in jumping and relying on skill and intuition to guide you down. There’ll always be a reason to wait until next month otherwise.

My advice is don’t go looking for validation, it’s your life and if it feels right, go for it.

Since leaving full time employment (3.5 years ago now) it is really only in the last year that I feel my eyes are fully open to the world of opportunities that lie right in front of us.

Sometimes I do miss litigation. There’s something immeasurably satisfying about preparing and presenting a coherent argument as to why you’re right and someone else is wrong (my cross-examination skills aren’t so appreciated at home!).

However, my legal experience is called on almost every day. The main skill of a lawyer, in my view, is having the confidence to ask the right questions at the right time (and of the right people). Couple that with communication skills and superior intellect 😉 and there isn’t a company in the world that won’t derive value from you. Or at least that’s what I tell the mirror every morning ☺.

You Only Live Once

The Startup MBA came at an important moment for me; I was just embarking on a Return To The City all but ready to consider my entrepreneurial journey a sabbatical. Before the course, I was in a bad place, my tail hanging low, I had folded my own company having lost time and money to some poor decisions. I was all out of ideas and, crucially, inspiration.

I desperately wanted to align myself with a startup where I could put my skills to good use but also be responsible for building something from the ground up. I wanted to be able to look back, with my head held high and say “I did that”. I certainly didn’t want to ever look back and say “I wish I’d done that”!

The SMBA taught me that there are others who are similarly lost, similarly unsure but deep down, similarly driven. I made some great friends and I reminded myself that life is a journey where the winners are the ones who beat their own path, meeting and hopefully influencing others along the way.

Thankfully I left the course full of motivation, with a head full of inspiration and an email list of new friends and potential business partners.

I actually met my co-founder on the course so for that and many other good reasons, I am its strongest supporter. Ironically, I very nearly didn’t turn up to the course. I had this eleventh hour panic that without the ‘big idea’ of my own I would be wasting my time and exposing myself to criticism for having left a lucrative career without a ‘plan’ (or at least a good one!).

Forging a New Path

The best advice that I’ve received: “You only live once and it’s always better to regret doing, than not having had the courage to do.”

The advice I’d give to someone who is thinking about leaving the law (or any other job) is this: can you see yourself doing your boss’ job in 10 years time? If the answer is “No” then leave and let someone else have your space in the queue.

Opportunities are everywhere but I really don’t think you’ll see them on your lunch break.

Have confidence in your own ability but find partners who complement your skill set and can put up with you ☺

Please do get in touch, we’re all in this together…

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