I don’t think anyone would ever ask me if I regretted making the move to self-employment, because I’ve spent so long going on about how much I love it and how the excuses I’d made and downsides I’d envisaged just haven’t materialised (although I would like more time please. That’d be really nice).

However, one question people have asked me is: “Do you wish you’d done it sooner?”

And surprisingly, for someone who spends hours regretting eating one too many chocolate chip cookies, the answer to that is no.

I’m not a big fan of the whole “[X catastrophic event] made me the person I am today. It’s all part of my JOURNEY and I wouldn’t change a THING!!” school of thought. If I hadn’t had any bad stuff happen, I’d be some kind of beautiful rich unicorn robot right now (or at least a size 8 champion skier whose biggest problem is what shoes to wear, like 99% of the people on my university course).

Looking back now, I think I could have ended up going down the “move back home with parents, try some freelancing stuff out” type route. But I’m not sure it would have worked for me. Or if it did, I’d probably be in the same place now because you can’t fast track experience, no matter where it comes from or what the journey is. Perhaps I would be more comfortable with failing at things. Perhaps this blog would still be as popular as it was once upon a time.

But in terms of regrets of self-employment sooner, I don’t think it would have helped. I learned so much stuff that I needed to know about how to do things and how not to do things, that I don’t think we’d be giving our customers as good an experience without me having in-house knowledge. In many ways I owe a hell of a lot to the three company owners I worked for in my last two jobs. Some things I do just like them, and some things I do completely unlike them, but both those things are a conscious choice. And I think that’s really important.

Sometimes I read business books or articles with breakdowns of doing things and why they should be done like that, and mentally I do A-Z without thinking about the letters in between. So when I see that B, C, D, E and so on exist in people’s processes, my mind is totally blown. Those are my subconscious letters, the ones that other people do plans and processes and breakdowns and discussions and meetings and masterminds and deadlines and sign offs and retros and a million other things for.

I like doing things. I don’t like doing things that are tangentially related to things, or pre-thing things, or things “because everyone else is doing them things”. I don’t start my day with meditation and manifestation, I start it with my phone in my hand and my cats yelling at me because it’s DAYLIGHT and there’s NO FOOD. (There is food, but that’s beside the point).

Another reason I don’t regret starting sooner is, paradoxically enough, time. I don’t think Lyrical Host would be as good as it is if we’d had years to develop every tiny branding detail. We’d probably still be trying to decide on a name, for one thing. (The name was the hardest part, but actually we had someone sign up just because of our name – she’s really musical – so I think we did fine with that). We set up the business and launched quickly, and so there wasn’t much time for second guessing. I think this worked massively in our favour, because it stopped analysis paralysis in its tracks and made us focus on what was important.

Time and experience together meant we were already familiar with most of the tools and services we needed. We knew prices, margins, and loss-leaders, even though we only had minimal product management knowledge.

Personally, I think it was also a good time for us. We had (and still have) no debt outside of our mortgage and student loans. We live in an area with an extremely low cost of living, but with amazing free business support and grassroots events. We know a ton of amazing, talented people from every tech-related walk of life. I was at a point where I needed to change something and hitting thirty made me realise I needed to discover my purpose. I spent a huge chunk of 2014 being very ill, and although I might not have been ill at all had I been self-employed, I would also have missed out on a lot of opportunities, including meeting some fantastic people and learning tons of stuff. I have so many work highlights in general, including speaking at Google and going to lots of great, very expensive events I would otherwise never have gone to, and lots of skills and tools I would never have gained or used, that I can’t regret any of that stuff. Some of my best days ever were spent at work, and that’s something I’m very grateful for.

So I think in terms of having regrets, and being a ‘wish I’d done that differently’ kind of person anyway, I don’t really have any. Ask me again in a year ;)

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