The Secret Entrepreneur: Living with insecurities

Growing a business raises big questions: How do you manage? Will people believe you know what you’re doing? And is it still fun?

When I started my first business, it was exhausting, but exhilarating. I was determined, rightly or wrongly, to be the master of my own destiny and so rather than taking on funding I bootstrapped, doing almost everything myself for as long as I could, until I could afford to employ someone else.

Things changed a bit when I took on my first employee. I had to make sure they were gainfully employed and doing the right things at the right time. I failed massively there, but they moved on, I learnt from it, and hired someone else. That worked out better.

Adding the next person to the team added a bit more work, as did the next, but all the time I had a small team things were pretty easy. Everyone knew what was going on without me having to put much effort in and I could spend more time doing things and less time managing.

As we continued to grow, that changed. On reflection I think the magic number was 12 people. Less than that and you don’t need to formalise communications. More than that and it suddenly becomes a massive issue keeping people up to speed with what’s happening. This can be particularly troublesome if, as I was, you’re still working out how to restrain your entrepreneur’s urge to try out new stuff and change everything, all the time.

At that point came the next stage – employing proper managers and letting them run their own teams. That seemed like an easy solution, I could make solving the communications issue their problem.

It wasn’t an easy solution. It just changed the magnitude of the issue. All of a sudden I had to work even harder to make sure all of the managers were up to speed with what was going on, because any confusion just gets magnified as it gets communicated down. A small miscommunication between two teams and suddenly £10k’s worth of work is wasted. I’d failed to realise that, ironically, managers needed to be managed.

This was a difficult leap for me. Suddenly I had to lead a company and manage a group of extremely capable people, and make it look like I knew what I was doing.

And yet, I had no idea what I was doing. None at all. I’m still not sure I really do, but I’ve grown to accept it. The people bit of management is messy and it always will be, but communication is the key to it. It’s impossible to over-communicate but all too easy to get distracted by the next shiny thing and forget to tell someone something important.

I’ve put structures in place to make sure I don’t do this now. We have weekly management meetings, weekly all-hands meetings and I have scheduled individual check-ins with my managers, on top of all the ad-hoc communications I have with them all. I’ve accepted that a large chunk of my time has to be spent repeating myself (and making sure I’m consistent when I do…)

I’m pretty sure that’s why most entrepreneurs eventually move on and start something new. While it’s rewarding to lead a growing company and get everyone pulling in the same direction, as you continue to grow the ‘proper CEO’ role becomes very, very different from the hands-on days where you could spend most of your time doing and not just talking. I’m still trying to decide if I like it. Read previous Secret Entrepreneur columns here on


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