No FearThe real reason why you’re all “hi ho, the freelancing life” (with apologies to Stephen Sondheim) isn’t “lifestyle design.” It’s earning money from things you really give a shit about, on your own terms.

Yet despite the cons of your day job, creating a side hustle is scary in its own right. On one hand, you have no idea whether you can pull your pie-in-the-sky secret dream off, let alone whether there’s even a market for it.

On the other hand, you get this horrid feeling when you contemplate something a little more mainstream — that you’re setting yourself up for something you care about as much as your day job. And if that’s so, why are you trying to escape the 9-to-5 in the first place?

But are you being too hard on yourself? There could be some gold yet to be unearthed from your day job that could serve you well as a side business. (Click here to tweet this thought.)

Here are three things to remember when contemplating the kind of work you could do for your side hustle:


Accept That There Are Good Bits in Your Day Job

Mind the temptation to reject everything about your old job out of hand. Are you sure you’re not throwing the baby — or even babies — out with the bathwater?

Sit yourself down, grab a pen and paper and make a list of the things you do at your job. If that feels a little overwhelming, just go over the last work week and list as many of the things you did in that time as you can. Then cross off the things you wish you didn’t have to deal with and look at what’s left.

This shows you there are things that don’t relate to The Dream but that you can still safely make into a side hustle.


You Enjoy Lots of Things, and The Dream Is Only One of Them

One trap us folks who want to change our lives for the better fall into is the notion that each of us has One Calling. If we pursue anything other than it, we’re doing ourselves and the world a disservice.

The problems with this mindset are:

  1. A calling can be hard to find, especially when we in the Western World have so many damned options these days. (Was everyone who came before us screwed? What if you had the right stuff to be an app developer but were born in the Twelfth Century?)
  2. Choosing to wait until you find “it” before you start a side business could mean passing up a whole bunch of opportunities to do engaging, involving work for people willing to pay you for it.

If The Dream (upper-cased) seems out of reach, try taking one of your dreams (lower-cased) on as a business.

And even if the dream you pick doesn’t work as a sideline…


You Can Wind Your Current Side Hustle Down and Move On

This is probably your greatest fear as a freelancer in the making: That you create a side hustle you care about as much as your day job — and get stuck with it as you make commitments to clients

Yet it’s also the most groundless.

I’ve spoken with freelancers who’ve grown dissatisfied with their hustle, including one who went back to employee-dom (and was just as happy as she was being a freelancer, if not more so). They used the routines they’d built for their current side hustle to give themselves the time and space to develop the next one.

Once they were ready to move on, they let all their clients know they were winding their current business down and negotiated the completion of any remaining work as needed.

You have the added benefit of your 9-to-5 as a fiscal backstop; if you discover your current sideline isn’t for you, let yourself try something new.

Treat your clients with respect and give them enough notice for the both of you to wrap up your work together. They may well have a need for your new product as well.


Learn to Stop Worrying and Love the Work

Trust me, I’m not trying to advocate remaining in a situation that may well be toxic. Quite the opposite. Worrying about what you’re trying to create may well cause you to stay in your current situation when you’re more than ready to tackle a side business in your spare time.

It’s okay to base your side hustle on what you know you can do, especially if you’re still a touch nervous about making The Dream into your reality. You may find not only that that it’s good practice for taking The Dream on, but you may well enjoy it more than you think you will.

When it comes to a side hustle, what’s your biggest fear? Share in the comments!

Image: Flickr