What I learnt from quitting too early

I've quit my job to become self-employed, twice. 

The first time, wasn't quite rage quitting - but just about. I had always seen myself as self-employed. At some point, I decided to leave my job and launch a website.

It was the beginning of a global financial crisis (not this one, the other one) and I lacked the confidence to trust my instincts to follow through along with a financial runway that enabled me to tough it out until I had real income coming in.  

At the time I felt that "getting a job again" was a failure, but I made a plan to round off the skills I felt I was lacking at the time and set myself a list of criteria for my next ideal role - that would get me closer to realising my goal of launching my own business:

My new role needed to be: 

  1. Working within a start-up environment
  2. Mostly online (at the time, most businesses were still struggling to get a website up and running)

These became my non-negotiables, things that I knew would get me closer to my goal. 

This set me up on a path, where I've spent the last 15 years working in start-up environments, each one has given me valuable insights into how to set up and run a business, plus plenty of examples of what to avoid! 

The second time I quit, I made sure I had my financials in order - with enough of a runway to help me stay on the path. That was 7 years ago.


If you've always had an inkling to become self-employed, check if now is the right time:

  1. Financially - how long can you survive without an income? 
  2. Motivations - are your reasons more about wanting to exit an uncomfortable situation?
  3. Make an adjustment - is there something you could do that would take you closer to where you want to be in the short term?


By asking yourself the questions above, you're taking the first steps to approaching self-employment sensibly, getting you close to answering the question - is self-employment right for you, right now.

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