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Want to Work for Yourself? 7 Things You Need to Know

by Hanna Brooks Olsen
featured, freelancing, money & life

Think you’d be happier being your own boss? Statistically speaking, it’s probably true; according to a Gallup poll, 80% of small business owners say they’d do it all over again if given the chance. However, turning your hobby into your job can also come with plenty of challenges.

When you’re ultra-passionate about your side project, your hobby, or whatever it is you do on nights, weekends, and the occasional long lunch, it’s really easy to start fantasizing about how you can turn it into your full-time work. Unfortunately, not every labor of love can become a labor of income — and not everyone is cut out to (or maybe just ready to) be their own boss. So how do you know? When should your hobby be your job?

Here are a few things to consider before selling the proverbial bike shop and going all-in on your passion:

Who am I supporting?

This is probably the biggest question regarding a decision that could really shake up your finances. It can take years for small businesses to turn a profit, meaning that if you’re the sole earner for a family, you might find yourself in a place of real hardship without a steady pay-check. But if you’re just starting out, and it’s just you (and you’re comfortable with the idea of eating ramen out of an upturned Frisbee for a few years), a financial pinch might be worth the freedom of being your own boss.

What’s my savings situation?

If you’ve always collected regular income from a regular job, you may not realize how quickly money slips through your fingers. A few big jobs may seem like they’ll be enough to stretch through the months, but odds are, you’ll be dipping into your savings on the regular when you first start out…and then even after that. If you’re not super-solid on savings right now, it might be a good idea to work steadily for a few more years, then revisit the question of “should you hobby be your job” once you’ve got a little more in the bank.

Do I have a supportive network?

Freelance work and small business ownership is a very different way of life than office culture — and it can be lonesome. Look into area freelancing circles, or check out some of the national organizations, like the Freelancers Union. It also might be a good idea to reach out to those friends who may have work for you in exchange for services they can offer, like legal assistance, bookkeeping, and personal finance. Now’s a great time to call up your college roommate who went on to become a CPA and see what she’s up to…and if she needs any photo/video/writing/design/whatever done in exchange for a business plan.

How much work do I have lined up?

Building a steady body of work (and a full contact list of connections) before you jump the 9-to-5 ship can make the transition a lot easier, and can help you get an idea of what kind of work you can be looking forward to. Start hitting the pavement while you’re still fully employed — not only will that help you build the aforementioned savings, it’ll also allow you to hit the ground running (rather than hit the couch in sweatpants) on that blissful first day of self-employment.

Do I have the tools I need?

Tools for freelancing or self-employment run the gamut from physical (cameras, software, professional attire) to mental (understanding of your local tax code, a good grasp of social media marketing), but you need all of them. Or at least, you need someone close to you who has some of them and is willing to lend them to you, probably for a fee. The hardest part about being your own boss is that you are your own company, which means you’re also your own HR department, your own accounts payable, your own marketing team, etc…so not only do you have to have all of the stuff you need to do the thing you love, but also all of the stuff that each of those departments requires to run.

Am I comfortable self-promoting?

Remember that thing about marketing? Marketing is so crucial — and a lot of times, that means checking your ego and asking the people around you to like you on Facebook, recommend you on LinkedIn, and follow you on Twitter. Self-promotion feels weird to a lot of creative people, but it’s a non-negotiable. If you’re too uncomfortable with the idea of asking around for support and being your own advertising team, you may want to consider teaming up with a business partner, or finding a small company that allows you to have creative control, without actually being the boss.

How’s my time-management?

Every freelancer has heard someone sigh in exasperation, “I want to do what you do, but I’m just not that disciplined.” If there’s a doubt in your mind if you’re that disciplined, freelancing or small business ownership might not be for you. Being able to manage your time (which includes such necessities as getting up on time, getting to meetings on time, and getting necessary papers and assignments turned in on time) is a huge part of your success as a freelancer or small business owner — and unlike a lot of the other things you’ll need, it’s a really, really hard one to teach.

Want more tools for your small business or freelance career? Check out our Money & Life channel, which has classes on everything from software education to healthy living. 

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Hanna Brooks Olsen

Hanna Brooks Olsen is a writer and editor for CreativeLive, longtime reporter, and the co-founder of Seattlish. Follow her on Twitter at @mshannabrooks or go to her website for more stuff.