Five Hard Truths Of Being Your Own Boss

Being your own boss is undoubtedly in vogue right now. No longer exclusively the domain of the highly educated, devoutly driven entrepreneur, it’s almost a rite of passage for young people to give self employment a crack – especially in this brave new world where millennials are convinced they will grow up to follow in Evan Spiegel’s model-marryin’ millionaire footsteps. There are indeed many glorious advantages to answering to no one, but there are also a lot of harsh realities to be stumbled upon while you’re ‘living the dream’.

After six years of running a small business, it’s my pleasure to drop some truth bombs upon ya. Here’s a ‘heads up’ on a couple of things to consider before you quit your day job.

You’ve got to actually do this stuff.

There are many, brilliant, creative, inspired people out there with fantastic business ideas. The thing is, you can have all the genius business propositions in the world but they are worth precisely nada if you don’t have the capacity to go out and make them happen. In fact, a lot of the time the ability to come up with an idea and the ability to translate said idea into an executable business are two mutually exclusive attributes.

You’ve got to talk big game

In order to inwardly encourage yourself when times are tough and outwardly convince others to back your proverbial horse, you need a bit of confidence. You don’t need Zuckerberg’s vaguely irritating sense of world-conquering self assuredness or an egomaniac’s inclination to blatantly lie about his own achievements, but you do need the capacity to stick to your guns and sell your business at key moments. And it’s hard.

Because many of your ideas will inevitably be flawed, undercooked and prone to being bowled over by your nearest competitor. But those pivotal figures won’t back you if you don’t back yourself.

You’ve got to put your business first.

Being your own boss means you must show restraint in many aspects of your day-to-day life, including your finances. Many self-employed bosses running small businesses will attest to the white-knuckled discipline required to funnel all available funds to your business, when it would be really nice to just spend that money on a beer.

Even harder still is continuing to keep your hands off your funds when things start going well. Sinking the money you make back into improving and growing your business is not only highly recommended by many financial experts, it’s also deliciously tax deductible. But you know what it isn’t, really? Fun.


You’ve got to fire people.

Ew. Ew, ew, ew. Being your own boss is all well and good when you’re dictating your own generous and incredibly flexible work hours. It’s even more fun when you can work while travelling interstate, overseas or with your tiny kiddo sleeping in the next room. But it’s thoroughly unenjoyable when your staff (whether there’s a hundred of them or just a couple) aren’t serving your business well and need to be politely cut loose.

They might be punctual and super enthusiastic but if they’re not bettering your business, they need to be let go.

You might get on like a Poelher/Fey combo on awards night and they’ve even been to your house for dinner but if they’re not bettering your business, they need to be let go.

They might cook brownies for the office on the reg and be a super duper person, but if they’re not bettering your business….you know how this ends.

Having employees is one of those things that in theory sounds rather satisfying. In practise it can be stressful at best, utterly heartbreaking at worst.

You’ve got to pat your own back, because no one else is going to.

One of the most underrated parts of being employed as part of a bigger organisation is that often you’ll find yourself with a superior, colleague or shareholder who will provide a little support and encouragement. As part of a bigger team, you might even find your efforts being formally acknowledged or even rewarded. This is hard to come by when you’re your own boss. As a result it can be pretty common to feel frustrated and undervalued.  Thankfully though, it teaches you to resist relying on others for positive reinforcement, which is one hell of a killer skill that’s gonna serve you beautifully in life and labour.