What To Do If You’re Self-Employed and Your Boss is a Dick

This morning I went to the gym, had breakfast with my family, cycled into Brighton along the seafront in the sunshine, and then spent a couple of hours drinking coffee, eating cake and reading interesting articles on the internet. If I were asked to describe my hypothetical perfect morning, it would probably look something like this.

So, why is it that when I came home I felt totally miserable?

When my wife asked me how the morning had been, I didn’t tell her about the quality of the winter air as I cycled along, or about what cake I ordered at the café, or about something cool I’d read that morning. When she asked me how my morning had been, I sighed and told her:


I’ve been in full-time self-employment for coming up to five years now. Five years of trying to create the kind of life-balance where work feels like leisure, where leisure can be work, and where – at the heart of the dream of self-employment – I get to ‘be my own boss’.

Who – stuck in a grinding 9 to 5, with a manager constantly pushing them to do more, faster, and with fewer resources – hasn’t dreamed of being their own boss? When you finally quit and step hopefully into the world of the self-employed you get a cool new boss – a boss who gets it, who doesn’t make unreasonable demands, and who just wants you to be happy – yes?

But what if your new boss is a dick?

What if your new boss turns out not really to care that much about what makes you happy, but is actually even more obsessed than the old one about the three P’s – professionalism, punctuality, and productivity? What then?

That’s the problem I’ve faced, on and off, all these years. It turns out that I’m not that great a boss. I’m incredibly hard on myself, I have to negotiate with myself furiously to get any time off, and – to my surprise – rather than the cool, friend-first-boss-second kind of boss I expected to be, it turns out that I am the worst kind of capitalist, productivity-obsessed, Dickensian-workhouse shitbag.

Just because I am not in a 9-5 job anymore, doesn’t mean that I’ve managed to shake off the 9-5 mentality. I may not have a time-sheet to fill out, but I find that there is a part of my brain still scrutinizing how I use every hour of my day and assessing it’s value in dismayingly capitalist terms: how productive was I?

This is annoying as hell, because when I listen to that part of my brain, I’m constantly coming up short and I feel miserable. Even stuff which should be bringing me joy ends up bringing me down.

But there is good news. It turns out I’ve actually got more than one boss now. The productivity-obsessed Dickensian Workhouse Shitbag certainly shows up a lot, and he definitely shouts loudest.

And there is another one too.

There is one who encourages me to judge myself by a different metric – not by how productive I was, but by the degree to which I was true to my values. One who is less inclined to assess the worth of each hour spent by how much further up the greasy and poorly-defined pole of ‘success’ I’ve shimmied, but more by how purposeful I was, and the degree to which I did stuff that is important to me.

It turns out that I just have to choose which one I engage with. I don’t anticipate that Mr Dickensian-Workhouse-Shitbag is going to disappear overnight, but I don’t have to struggle with him. If I want to I can choose to tune into Mr Do-What-Matters, and see what he has to say.

In Acceptance and Commitment Coaching we talk about the Thinking Self and the Observing Self. The Thinking Self is the part of us that is constantly assessing, analyzing, judging, strategizing – always thinking. And its voice is incredibly inconsistent, shifting and morphing all the time. The Observing Self is the part of us that simply notices the chattering of the Thinking Self, curiously and without judgement.

And it gets to choose – to choose which parts of the Thinking Self’s chit-chat it is going to pay attention to and be led by, and which parts it is going to just let slide for now.

The Observing Self is a tricky concept to get your head around theoretically, let alone practically. But mindfulness practice is one great way of starting to get acquainted with it – to experience the phenomenon of watching thoughts and feelings come and go, passing like clouds in the sky. The more you practice the easier it becomes – to observe those thoughts and feelings and to choose the ones that support you and help you move towards the stuff that you love in life.

So, when you go self-employed beware you don’t trade in one lame old boss for one cool one. You actually end up with a whole chorus of bosses – but now you get to decide which one is giving the orders.

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  • Dirk Swaegers
    Posted on 21st February 2018 at 9:04 pm

    Great post Jon, I love it and I sure recognize it.

    • jonhill
      Posted on 22nd February 2018 at 11:02 am

      Thanks Dirk! Good to know it’s not just me…which boss is in charge for you today?

      • Dirk Swaegers
        Posted on 22nd February 2018 at 11:28 am

        Today the boss that does not know very well what to do first : a boss that creates some confusion: we start with this, no this…., let’s do this first 🙂 Funny to be aware of this. In the end we are all human beings that do things that are typically human 🙂


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