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How to be your own best boss

- September 4, 2017 4 MIN READ

Being your own boss sounds great, but what if the boss you become is worse than any boss you’ve ever had in a ‘real’ job? Here are some tips to be your own boss.

One of the main reasons many of us became soloists was for the freedom.

Freedom from the commute, the office politics, and dealing with an arsehat boss.

No more boss man telling you what to do. No more grovelling at your annual review. No more laughing at the boss’ terrible jokes at the office Christmas party.

No more boss.

Except that’s not entirely true, is it? Because you’ve just replaced that boss with another one.


And if you’re anything like me, your new boss is much worse than your last one. In fact, they could win the award for the worst boss of all time.

Am I right?

So I’m going to share a few ways to be a better boss to yourself.

Make yourself employee of the month

Us soloists rarely get the recognition we deserve. A client may occasionally throw us a testimonial bone, but other than that, we have to pat our own backs. Which is hard if you have little T-Rex arms like me.

So every once in a while I declare myself Employee of the Month. I print a poster, pop it in a frame on my office wall, and feel the warm glow of recognition spread to my nether regions.

(And look. I made a poster you can use yourself.)

Take yourself on a team building day

Let’s be honest: it can be lonely working by yourself. So occasionally I send myself on a solo team building day.

It could be something creative (a trip to the cinema), something that tests my verbal communication skills (ordering a slap-up breakfast at my local café), or something really hands on (a massage).

But be warned: don’t try those solo trust exercises. I once did the whole ‘fall-back-to-see-if-I-catch-myself’ thing, and I’ve had a bruised coccyx ever since.

Give yourself a raise

If you’ve finished a particularly tough project, or just survived the week without punching the cat, then I think you deserve a raise.

Why not dip into petty cash and splash out on a nice bottle of wine?

You could raid the Christmas party fund for a nice takeaway.

Or you could drain the GST savings and buy yourself a four-week solo conference/holiday in the Bahamas.*

Whatever you do, you’ll be amazed how much it boosts your productivity.

* Don’t actually do this, or your accountant will slap you.

Fill out an anonymous employee satisfaction survey

Create a little survey to anonymously quiz yourself on your level of job happiness.  Here are some questions you can ask yourself:

  • How meaningful is your work?
  • In a typical week, how often do you feel stressed at work?
  • How much do your opinions about work matter to your co-workers?
  • How much does it annoy you when someone eats all the office biscuits?

Then leave it for a month (or until you’ve forgotten your answers) and read it through. Use the answers to dramatically change your company structure and mission statement.

Or not.

Send yourself on secondment

With real jobs, there’s often the possibility of exploring different careers by temporarily changing roles within the same company.

As soloists, we often play many roles already. But perhaps there’s a bit of your job you haven’t fully explored.

If the regular work is getting you down, why not take a few days to learn how to edit videos, do a quick writing course, or master a new app or piece of software?

Who knows? Perhaps going on secondment into a different part of your business will help you find whole new lease of life.

Cancel that meeting

Okay so there’s the meeting that ‘Last Week You’ scheduled for 6pm this Friday. What were you thinking?

Well ‘This Week You’ has the right to cancel it.

Working long hours makes you a sad employee, so remember that just as a good boss should respect their employees’ time, you should respect yours.

Call in sick

When we work at a ‘real’ job, we’re given ten days of paid sick leave. (I may have made this up.) And I can tell you that as an employee I took full advantage of this.

But as a self-employed person? Not so much.

Us soloists tend to just push on, and complain about our aches and chills on Facebook instead.

So occasionally I’ll call in sick. (Yes, I actually call my own number and leave a voicemail.) Then a few minutes later I listen to it, feel sorry for myself and give myself a day off. Win!

Tip: If you find yourself hard to convince, try calling while you’re lying on your back on a bed with your head hanging off the edge. You’ll sound really blocked up and totally convince yourself.

Change your job title

Remember when you had a real job, and your boss would give you a new role with more responsibility (but no more money) complete with snazzy new job title?

Well, you can do that too.

Right now you may be calling yourself ‘Founder’, or even just ‘Business owner’.

Why not try CEO, or something creative like ‘Chief Happiness Officer’? You could go with ‘Maximum Satisfaction Beast’ or even ‘BOSS OF MY JOB’ (which is what my son proudly tells his friends I am).

Order a hundred new business cards from your local printer, and put some of them into a smart new business card wallet.

Now swan around the house giving them out to your partner and your dog. It will work wonders for your self-esteem

I think it’s vital to think about how you’re treating yourself as an employee.

Are you pushing yourself too hard? Are setting unrealistic expectations about what your one-person team can achieve? Is your current boss way tougher than any real-life boss you’ve had?

Okay, so the somewhat silly suggestions in this post might not be right for you. But I hope they’ve inspired you to think about how you could be a better boss, and keep yourself motivated, happy and stress-free.