5 downsides of quitting the 9 to 5 & why you should totally do it

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Being your own boss is pretty damn sweet. You choose when you want to work, what you want to work on, who you want to work with, and all that jazz.

But it would be remiss of me not to point out the downsides that come with it. It’s a bumpy ride, to say the least. But while challenging, it forces you to grow in ways you’d never imagine you could.

Here are 5 downsides of quitting the 9 to 5, and why you should totally do it.

1. failure is inevitable

It sucks when an idea fails to take off the way you expect it to, but failing quickly is the best way forwardthough it might not feel that way. The sooner you wrap your head around this, the better you’ll be able to navigate your path.

When I quit the 9 to 5 two years ago, I wrote to Derek Sivers for advice on my transition. He was kind enough to share this valuable piece of advice with me:

“Much of success is luck. What the public loves will usually be a surprise. So do many things, giving each one 100%, but if the public just isn’t excited about it, walk away and do something completely different. Knowing this in advance, your first step should be to just do anything useful to others, realising it’s just the first of your many endeavours and shouldn’t be taken too seriously.”

Over the last two years, I’ve come to appreciate the significance of Derek’s words. In 2014, I had to make the difficult decision of leaving a startup I had spent a whole year building. The truth was, it failed to catch on the way we had expected it to, and after much deliberation, I felt it was time to let go and move on to something else.

Failure is just how we learn and get better. So don’t beat yourself up (too much) if an idea fails. Learn from it and move on.

2. nagging self-doubt

You’ll doubt whether you can make it on your own. You might feel like a fraud (I certainly did for the longest time). I didn’t think anyone would pay me to write. I didn’t think I was good enough.

BUT if you don’t try, you won’t know. The best way to kill self-doubt is to put your work out there and see what happens. I didn’t think I was good enough, but I’ve landed writing gigs for clients both local and international. And this goes without sayingthe more time and effort you put into honing your craft, the better you will get at it.

Moderate self-doubt is healthy, but too much of it kills creativity. So the next time you feel a wave of self-doubt surging within, silence it with decisive action.

3. paralysing fear

“You cannot discover new oceans unless you have the courage to lose sight of the shore.” — Andre Gide

Fear can paralyse you into inaction if you allow it tobut it’s also one hell of a motivator. It spurs you on to try things you never imagined you would (or could). It forces you to step out of your comfort zone. And that’s how you grow.

I like Chris Guillebeau’s take on it: “Asking yourself, ‘What’s the absolute worst thing that could happen?’ if something goes wrong can be very empowering. It helps you put things in their proper perspective.” (The Art of Non-Conformity)

If you’re afraid something doesn’t pan out, just ask yourself "what’s the worst that could happen?". It probably won’t be the end of the world. And that’s how you give fear the middle finger.

4. struggling to make rent

There might be days when you struggle to make rent. I’ve been there. It’s no fun, but that’s when your priorities become crystal clear. If your instincts tell you this is the right path for you, your priorities will define how you tackle the obstacles you face.

It’s amazing how far you can stretch your financial resources when you really have to, and are determined to. It’s certainly taught me to embrace simplicity and appreciate the simple pleasures in life.

It’s easy to take money for granted when you know you’re guaranteed a monthly paycheck. But when you’re on your own, you develop a newfound appreciation for money and what it signifies.

And you’ll discover just how resourceful you can be, when you need to be.

5. an emotional roller coaster of a ride

You will feel a crazy range of emotions, from ecstatic highs to rock-bottom lows. There will be days when you wonder for the thousandth time whether you’ve gone totally bonkers. You’ll have restless nights worrying about generating a steady cash flow.

But you’ll also feel on top of the world when you get emails from random strangers expressing interest in your services, thanks to Google.

The thrill of it (for me) is not quite knowing what to expect. Potential clients who seem the most enthusiastic might drag their feet for months before confirming a project, while some just get on with it without any fuss. And then there are those who start a project all raring to go, but just can’t seem to decide what they really want. Though they be challenging, I learn something from each of them.

So brace yourself for the ride. It’s going to be scary, nerve-racking even, but it will be one of the most liberating experiences you ever have.

“The biggest adventure you can take is to live the life of your dreams.” — Oprah Winfrey

There are definite downsides of quitting the 9 to 5but overcoming them will empower you to achieve more than you ever dreamt possible. It’s not easy, but it’s simple, and very possible.

Are you ready to get liberated?