How to Be Your Own Boss (Without Acting Like One)

You don’t have to answer to a boss.

You can work the hours you want.

You can work from where you want.

You can choose your own clients and ventures.

You can do things your way.

With those things in mind, it’s no wonder that being self-employed is often seen as something worth envying.

When I tell people what I do for a living, it’s surprising how often I get the response: “Wow — how can I do that?”

Most of those who’re envious of my workstyle earn quite a bit more than me — so it’s obviously not about the money!

In truth, I think it all comes down to one thing: the assumption that being self-employed must equal a stress-free lifestyle.

I think the root of this idea is that the toughest aspect of work is answering to others. Once you remove that from the equation, it seems logical that stress would leave with it.

This is not quite true. There are a million ways to earn a living through self-employment, but you will always have to answer to at least one person: you.

How would you grade your inner-boss?

It’s time for some digital water-cooler catharsis.

My inner-boss definitely has some room for improvement. She’ll load me up with an inhuman amount of work and expect me to get it done at any cost.

When I don’t get it done, my inner-boss assures me that it wasn’t the amount of work that was the problem — it was my own inability to be more effective.

In other words, my own inner-boss isn’t so different to the kind of hairy, fleshy boss you find in hi-rise buildings and on factory floors.

Judging by the sense of guilt permeating productivity blogs — particularly among the self-employed — I don’t think I’m the only person who left a real, unreasonable boss to create another one for myself.

How to retrain your inner-boss

Understand that it’s not always your fault.

Remember the last time a real boss expected you to finish ten complicated tasks in half as many hours?

This scenario happens because your boss has no idea what goes into getting the work done — and can’t be bothered to find out. Don’t let your inner-boss start to show the same behavior.

If you don’t have a realistic idea of how long certain tasks take, your workload becomes a matter of luck.

Sometimes you’ll give yourself too little (and your inner boss will say that, really, you were just particularly effective), and sometimes — probably more often — you will give yourself too much (and your inner boss will say that, really, you were lazy).

While it’s not necessary to keep obsessive track of time, thinking about it and keeping rough tabs on it is worth doing.

Once you’ve recorded some rough values, average them out. If you spend 7 hours a week checking email, you can deduce that it takes about an hour on average, so you’ll know to set aside an hour for that, instead of estimating that it takes 15 minutes.

An “it takes however long it takes” attitude — something I personally struggle with — will make it hard to keep your work day under control.

Stop feeling guilty about life outside work.

This is where your inner-boss gets sneaky. It won’t yell at you for doing something other than work, and you might not think about him/her at all while you’re taking an hour or so to watch television, have a nap, do some craft, or play a video game.

When it’s time to go back to work, though, your inner-boss is very good at using guilt to its advantage. It’s hard not to start thinking about what you could have accomplished if you had worked for an extra hour instead of going out for pizza, or doing any other thing that makes you happy.

As self-employed people, our flexibility can be a problem. We can (technically) work as much as we want, and the amount of time we spend working can directly affect our income.

An office-worker paid to work 40 hours a week isn’t going to be paid twice as much if she or he works 80 hours. This is not necessarily true for us.

One truth should be enough to mute your inner-boss when it attempts to make you feel guilty:

Work is something you do so you can enjoy life more.

If work (or your approach to it) is making it harder to enjoy life, then something needs to change.

Learn something from the 9 to 5ers.

Working whenever you want is an incredible perk, but that’s no excuse to avoid making a conscious decision about how much you want to work.

My dad is a complete technophobe and, as a result, is fascinated by what I do because he doesn’t quite understand it.

For a while, his favorite thing to do when calling me up to talk would be to ask: “How many hours did you work this week?” He knew my answer would be: “I don’t know!” — which amused him no end.

As someone who earns an income either passively or per task, counting hours seemed unnecessary to me for a long time.

My dad’s question, although meant as nothing more than a joke, did help me realize that being unable to estimate the amount of hours I’d worked even to the nearest ten made work/life balance impossible.

On a business-sense level, not setting limits around work-hours will increase procrastination tenfold and productivity none.

After all — you can always do it later. Once you set limits, you can’t use that excuse any more. Personal deadlines start to mean something.

While you certainly don’t have to work 9 to 5, it’s important to make a conscious decision about the amount of hours you want in your work-week — whether it’s 4 or 40.

Once you decide on a figure, multiply it by two. That’s your target work-total for two weeks. A longer time-frame gives you more flexibility.

From there, you might work out a steady work routine that you’ll stick to without deviation, customized to allow time for the things that matter most.

Alternately, you might shift around your hours fluidly from week to week, depending on what your schedule is like. Setting limits doesn’t require that you sacrifice your flexibility.

While your inner-boss will tempt you to work overtime, you can blunt this by enforcing a simple policy: for each hour of overtime you work, add an hour of free time.

You can use up your earned hours in bursts, or save up eight hours to take a day off.

About Skellie

Massive nerd who just happens to enjoy anything related to blogging, creativity, and online marketing.

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