The “Boss” Illusion

Trapped in a job I hate. I need to get out! Only problem: I’m the boss.


Starting a business usually means having to report to a lot more stake-holders than any employee does. Your customers, clients, users, staff, shareholders, the industry, anyone who believes they have a right to judge or comment because it’s “business”…


It was a Sunday afternoon and already I was feeling uncomfortable about the day and week ahead. A situation not reserved simply for mistreated employees. Why as owner and sole Director was I feeling this way? I was in a job I hated at a company I loved.

Not long before, we had released a new version of our product Donor Strategy, a release I had failed to manage well, and there was a lot of smoothing over to be done. But it wasn’t just this. I would sit at a desk, wearing a suit worrying about how I met payroll that month. Each day was becoming a chore as the uninspiring work slowly sipped from my cup of life.

Anyone who knows me, knows that finance is something I find overwhelmingly boring. It’s in number one spot with anything legal in second. Queuing comes close third. So, to spend every day worrying and carrying this load for a team of thirty, was like visiting the dentist every day.  It was like having a recurring appointment with the school bully, or walking a long journey on razor blades and glass.

How do you end up in a job you hate, when you’re in control of what you do?

This question is not reserved for a business owner. This is a question for everyone.

When we moved into our first office I remember being with my wife before we had kids. We stayed up all night painting it. Becky slept on the floor, while I finished off and sloshed paint around, replaced carpet tiles and made a home for the growing company.

Donor Strategy grew from being just me to a team. Debbie, Paul, Dmitri, one by one people added. My wonderful friend Ian and so many others helped as we dynamically created and worked through problems to make a culture that I was proud to be a part of.

This was my first taste of being an employer and it was a complicated taste – a bit like trying alcohol for the first time. Deciding on pay, job titles, conditions, desks and more was all made easier by a team that had low expectations and enjoyed the work: with charities.

As I recruited, I was reluctant to ever ask anyone to do anything I hadn’t already done or was able to do. Imagine how limiting this was!

Lesson: Employ people to do the jobs your hate, not those you love!

For some reason, I kept employing people to do the jobs I love. I did the jobs I didn’t think anyone else would do. Maybe there was a mix of believing I had to fulfil this “Managing Director” role, when infact, I’ve always known I’m not a good managing director.

I also have no idea why I wore a suit. I think it was about being taken seriously, or fitting in with other suppliers. There was no need for it. I never once felt comfortable in a suit.

Lesson: Wear what’s most effective for getting the job done well

I wonder if wearing a suit did make anyone take me seriously. I doubt it. I remember seeing a client in a supermarket or some public place and hiding from them! I was just wearing jeans and I felt exposed and small. Maybe the suit was actually covering up my insecurity?

It’s easy to think that being your own boss is the key to freedom, when in fact for many, it can be the opposite. To own your own company means you get to do what you want. It simply isn’t true. Even without shareholders or any staff, if it’s got any kind of stakeholder at all – then you are held to account. You have obligations whether employee or employer.

In each case, being in control – whether running a business or working for someone, is about being clear what your purpose is. Why are you working in this company/this role? Then holding what’s important in focus as much as possible, constantly aligning to ensure it remains central.

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