Burning the boats or how to quit your dream job

March 16, 2015

Starting a new job is always unnerving. At the start of 2011, I started a new job with much excitement but also with some trepidation. I was joining a very large company that was much bigger than the agency I worked at previously. It was going to be a huge challenge since I was the first business development employee in the province. Coming in, I had a set of assumptions. I expected rules, processes, and red tape. I found none of that. In its place, there was a set of guidelines and tap on the back. It felt like a startup, albeit a very well funded one.

Fast forward four amazing years, I felt like I was on top of the world: an amazing job, opportunities to travel around world and most importantly, free lunch.

There was still something wrong though, there was something eating inside of me. An entrepreneurial bug bit me. The startup world was calling and would not let me go. Investing and working alongside a few really smart startups made me feel that this dream was possible. A new challenge was around the corner and the time to move on had come.

Burning the boats

How does one give up working at one the best companies in the world? It was not an easy decision. When the final decision was made, I sent this video to my partners. It is the story of a Spanish conquistador who came to vanquish a yet undefeated Aztec empire. Upon landing on the shores of South America, he ordered his soldiers to burn the boats. The only way they were going to go back to Spain was with the ships of the conquered land. The only way for his army to win was for them to believe that there was no going back.

In the same spirit, I burned my boats. It was all or nothing. Here are some tips if you are considering leaving the cushy corporate environment for the uncertainty and risk of a startup. It will certainly be low wages, bitter long nights, doubtful safe return but honour and recognition if successful. That’s why you need to be prepared.

‘The minute you have a back up plan, you’ve admitted you’re not going to succeed’ Elizabeth Holmes

  1. Start working before you quit

There’s no reason you should resign immediately. Start working on your project on the side until you build up enough clients / revenue that requires you to go full time. Get to the point where you’re confident of product market fit if you can. In my startup, my partners and I tested our business model on several clients and won a few contracts before quitting.

  1. Financial support

You think you’ve saved up enough money to last at least a year? Take the number you think needed and multiply it by three. You will need to conserve your capital especially at the beginning in order to avoid the stress that comes with little or no salary.

  1. Rest and recharge

Take some time off. Go to Europe or Asia or le Massif. Just get some rest because you will need it. It’s a marathon not a sprint. Use the time off in between to recharge mentally and physically. Personally, I went backpacking in Europe which helped me disconnect.

  1. Find the right partners

Choosing your partners particularly at the start up phase is critically important. I’m lucky to work side by side with partners that are all in and get it. Even when we disagree, there is a huge benefit to having the same long-term vision.

  1. Prepare yourself psychologically

Startups are the best / startups are the worst. Managing your psychology is probably the most important factor in success or failure. There will be many highs and many many lows. The challenges are real & inevitable. It is the way that you react to them that is key. Confidence to overcome these challenges is critical, one must not be overcome by the daily grind of running a startup. Ten minutes of meditation every day makes a big difference for me.

  1. Strategic planning

I’m sure most people will use the business model canvas, product/market fit models to help them plan. One that gets overlooked is good old fashioned strategic planning. It really helped us put the 2015 plan together and stay focused on our most important goals.

  1. Stay agile

Conversely to the previous point, you can’t stick with something that isn’t working either. Pivot when you need to. The team at Spoil (freshly accepted into YCombinator) used a rapid persist or pivot methodology to develop their business model.

  1. Enjoy every minute

When you start, there’s no going back. Don’t forget to be grateful and enjoy the ride. And remember one thing; there’s no turning back. Success is your only option, failure’s not.