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Why I left a six figure salary at GitHub to go solo

Discover John's story, he decided to quit his job as a Director at GitHub to pursue his dream of launching his own startup and decided to trust Le Wagon to start his new entrepreneurial journey.
Last week I left GitHub. 

I stepped away from job security (whatever that means nowadays), exceptional colleagues, and the thrill of working for an admired brand within the developer community –  all for an uncertain future of working for myself, building startups.

I was earning a six figure salary plus stock and bonuses, and had received multiple promotions in the last two years. 

I levelled up rapidly within the Support organization at GitHub –  moving from an individual contributor (Support Engineer) in 2016 to a Manager role in 2018, and finally a Director position at the start of 2020.

Why leave?

I didn’t leave GitHub because I disliked the work or the company. 

In fact, it’s an inspiring place to work and if you ever get the chance to work there, I’d highly recommend you take the opportunity.

I worked with the most intelligent, kind and empathetic people, at a company that is helping to build the future. I don’t regret it at all. 

So why leave all of that? 


My role at GitHub involved leading, directing, motivating and managing towards company objectives – ever heard of OKRs

Managing people is great, and I like to think that I’m a half decent manager and leader. I thrived doing this work, and I loved helping fellow Hubbers grow and level up in their careers. 

But in the back of my mind, I had an itch. An itch I just couldn’t quite scratch. 

I want to build. To innovate and dream and pursue crazy ideas – to harness those millions of random electrical impulses in my brain – and turn them into something real. Something I can see, touch and feel.

There is nothing quite like the constant learning and growth that you go through when facing the challenges of startup life. Don’t get me wrong, I understand all too well the stress, anxiety, late nights and early mornings associated with this path (I’ve done it before but that’s a story for another time).

Ultimately though, the desire to create something outweighs these challenges.

At this point you might be thinking…why not start a side project or build something in your spare time, while continuing to receive a steady paycheck? Well, I’m glad you asked. I agree, that would be a better approach, and in fact, that’s the one I recommend most people take. 

However, there is a big gotcha with that approach. A caveat that I just couldn’t circumvent.

It assumes you have the available resource of time and the focus to go along with it.

Focus in particular was a challenge for me. In order to do my job at GitHub well, I had to devote a significant mental capacity and energy – not to mention hours of each day. Finding time over the weekends or after a long day just didn’t work.

I decided the opportunity to have complete FOCUS on my next project was worth the risk. 

Funding the journey

I’m fortunate to have gathered together enough resources (money and investments) to be able to have at least a year’s worth of runway that will allow me to explore ideas and work on my own projects without the stress of having to worry about paying the bills.

That’s great and all, but most people can’t simply leave their jobs to work for themselves, and I understand that. In fact, I strongly advise that you don’t quit your job. 

Rather, at least attempt the recommended approach of building something small on the side (if that’s something your current employment contract allows) which generates revenue. There is an entire community that you can leverage to make this happen – over at Indie Hackers.

Grow that project until the revenue matches your salary, and then go all in. Infinite runway will allow you so much more freedom to pursue your dreams.

Either way, it’s important to note that you should be adequately prepared before leaving your full time job.
Learn to code

What’s next?

I’ve been writing code since I learned Delphi 5, when I was 16.

I have hacked together a couple projects over the years, but I haven’t written much code (read zero) in the last 6 years. I know. I know. It’s ironic when you consider I worked for GitHub for the last four years.

All that said, my immediate next step is to take a crash course in the tools I need to be able to achieve my goals without having to rely on much outside help.

For the next two months I’m attending a bootcamp at Le Wagon (already in progress). 
Le Wagon Web Development Bootcamp
I hope to sharpen my skills and learn a ton of new ones that will allow me the freedom to create without relying on anyone else. 

Then, next up it’s time to build.

My (still in progress) strategy is to launch a number of products over the next 12 months – following in the footsteps of others who I have watched and admired as they built their businesses in public and shared their journey along the way.  

I’ll be taking inspiration from 12 startups in 12 months and Hardcore Year among others.

And from there, who knows what might happen.

I am documenting and sharing my journey and insights every step of the way on Twitter too, so follow me over there for more.
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