I’ve heard a bunch of people talking about going all in, burning bridges and other macho BS chest-thumping about the process of starting your own business.

I want to put a different side to the story.

It’s the slow-burn version of how I ditched my day job, that played out over a decade.

Step 1 was probably in the early part of the dotcom boom.

I wanted to know how this digital stuff worked, so I could see opportunities inside existing businesses.

I worked for a big data acquisition business at the time and we knew we could speed up data collection and acting on it with digital forms.

The business was mired in people with old-school thinking and I realised I needed to get out and into some fresh thinking.

So, with enough knowledge to be dangerous I jumped ship to an agency in the BBDO group.

I won a couple of non-wanky awards (ones you needed to show results for) but ultimately butted heads with the agency heads who had brought me in for direct response skills, then stuck me on brand accounts.

I was account director for ActionMan.com. FFS, that still remains the most ridiculous job title I’ve ever held, and I was incapable of taking it seriously.

I’d started to form an identity around the kind of work I wanted to do with my life.

I wanted things that I could look and say “I did that”, and that had real, bottom line results. I wanted to make things that people acted on, not just things to give them a warm feeling but were quickly forgotten.

Eventually I quit and went to work for the email SaaS we’d used at the agency. I could see the potential in their technology, but their team were tech salesmen, while their budget holders were in marketing.

I bridged that gap and we cleaned up the UK print media market, running emails for all the major B2C and B2B magazine titles.

This was about the point that I was getting serious with my own side-hustles. I was building lists, and affiliate marketing had started to crop up. I had “fuck you” money growing in an account I never touched.

In amongst this are some signs that you have something valuable:

  1. There’s industries that are getting screwed with your new skill. Make sure you’re on the outside, punching in. Unless you’re the one milking the cash cow, it’s not a place you’ll learn much
  2. Your skill makes money. At whatever scale, you need someone to part with cash to validate “valuable”. Your skill isn’t what it took to acquire it, it’s what it pays back. Ask any fire-eater.
  3. You do it for fun, after hours. This is the sign you’re on to something. Your obsession will drive you ahead of the pack as long as you keep producing, shipping, and making connections around your skill.

The long game in the story is that I launched an agency, using my affiliate sites as my first portfolio pieces.

These were good pieces of work because they didn’t have some broke-ass client screwing them up after I’d worked at knock-down rates for them.

I knew the type of clients who would value our work and I knew how to deliver them.

The steps after that were just doing everything faster, better and bigger.