I was one year and two weeks into teaching high school when I realized it was–without a doubt–not a good fit. I didn’t know what to do with myself. I’d won awards in the position I had left the previous year but, while I was certainly happier in sales than in teaching, that profession didn’t speak to me either. With a measly three years of post-college life under my belt, I’d experienced success without satisfaction in my first “real” job and then neither success nor satisfaction in my second. (Today is a good day to thank a teacher, people!).
I had harbored the “someday” dream of having my own business the moment I realized it was a thing. But picturing a future of business suits, uncomfortable shoes, and having a schedule set for me felt like going backwards. Oh and by the way: nobody was responding to my resume anyway. The timing didn’t seem right and I didn’t have the experience, but I was feeling backed into a corner. So with a little nudge from my circumstances, I went for it. Here’s what I would tell myself after a decade plus charting my own course.
The true risk isn’t the first one that comes to mind. In comparison with a 9-5 job, freelancing is risky. You absolutely could lose everything…or at least be very, very hungry at times. I mean it. You could have clients who pay late or don’t pay at all. You will have slow months that land you in the red and times you’re trying to figure out how to create a meal from whatever you can find in the freezer (“use by” date be damned) and the last quarter cup of rice in your pantry. Risk aversion is real, but if it keeps you in your swivel chair at a 9-5 you hate, then you’re afraid of the wrong kind of risk. Because there’s nothing more risky than staying in a job where you feeling like you’re wasting your life.
The biggest companies take the longest to pay. I won’t name names, but I can say that our biggest clients often take the longest to pay. I followed up with a Fortune 500 company for two years before they finally paid an overdue invoice. It wasn’t malicious. I just had to navigate their system and got passed around from person to person. Cash flow is a big deal when you’re a small business. When we’re paying our mortgage based on that invoice, I’d rather work with the mom and pop shops that pay right away than get a recognizable logo on our client list.
The freedom is fantastic, but it comes at a price. Yes, the dreams of working from the beach and choosing the jobs that excite you are real. To overworked, under-appreciated 9-5ers, freelancing may seem like the holy grail. But going out on your own isn’t just a world of free-flowing creative juices, coffee breaks, and wads of money. Freelancing can make you feel just as burnt out and unstimulated as whatever made you take a hike from your previous gig in the first place.
Your “boss” may be liberal about time off, but you still have to answer to your bank account. You’re your own boss. That means you can take Friday off because it’s a great powder day (that’s the Colorado girl in me speaking). Still, if you want to build a solid business, you have to put in the work. And if you want leave of any kind–vacation, maternity/paternity, sick days, etc.– you have to create it yourself. Ideally, that means building yourself a solid savings account with 3 months+ living expenses. The hope is that, because you’re building your own dream (and not someone else’s/one you don’t believe in) that you’ll at least enjoy it more. While it can be enormously satisfying and liberating to build your own business from the ground up, that doesn’t mean it’s easy. Some days, you’ll get to take a Friday off because you want to. Others, you’ll grind away on a Saturday because you have to. Any workday can be a weekend and any weekend can be a workday.
You don’t have to starve. The “starving artist” is a familiar refrain for a reason, but it doesn’t have to be your reality. Start by producing work you can be proud of. From there, you’ll get some experience and can feel good about charging fair prices for it. Getting to a point where you can walk away from that don’t exactly stimulate you is so satisfying. My husband fondly recounts one of his early video editing jobs for a veterinarian client. He got feedback to show a dog’s anus at 50% opacity (i.e. tone down the butt shots). Keep the long-term goal in mind and you can keep the less than stellar projects in perspective. You’re building something. You’re building your thing. Once you have a steady flow of clients, you can be more selective and you can charge more as your experience grows. Remember that being able to walk away puts you in the best position to negotiate more freely.
It’s easier than ever to burn out. I know how easy it is to have your life and energy sucked away by a “regular” job. The counterintuitive truth for many freelancers is that it’s even harder when it’s your business. You can pay your mortgage and your car loan and your grocery bill because you pounded the pavement to find the client and then pounded it again to produce a product they valued. When you’re in business for yourself, it’s easier than ever to just do, do, do all the time. The trap is the lie that you have to. But you give yourself out completely and guess what? There’s nothing left. There’s nothing left for your bedtime routine with your kids, or those glorious miles on the trail with your sneakers and your earbuds. Here’s the real, counterintuitive kick in the pants: If you don’t have time for the stuff the fuels you, you don’t have a business. As a freelancer, your business is you. It’s’ your creativity, your talent, your brains, and your guts. That’s something you simply cannot phone in. You have to be fueled, which means you can’t give everything to your business. You have to give something to yourself, which in turn, gives everything to your business.
The Bottom Line
Once you go out on your own, you live and die by your own work. The allure of working from home in your pjs and not having a boss breathing down your neck is real. But the struggle of life without a full time, “safe” job is real, too. It’s awesome. It’s terrifying. It’s not easy. Whether you’re on your own or working a “safe” job, you will kill yourself if you don’t find balance. But here’s the truth about freelancing, if you can handle it. And you can handle it, by the way, because you are scrappy enough to think about launching out on your own in the first place. It’s hard, gut-wrenching, kick you in the seat of your pants, pride-swallowing work. And it’s all yours, which is absolutely fantastic.
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