Here’s What Every Freelancer Needs To Know

What I Wish I'd Known 14 Years Ago When I Started Freelancing

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What if getting the boss coffee meant pouring one for yourself? What if your daily commute was a stroll down the hall… from your kitchen?

For 55 million Americans, that’s a regular workday. According to freelancing platform Upwork, freelancers comprised 35% of the U.S. workforce in 2016. It’s an impressive number that continues to grow, yet its true significance lies beneath the surface.

Unlike in the past, when professionals took on freelance projects between full-time jobs, more of us are choosing to freelance. A significant number of us are opting out of W-2s and into 1099s. We’re stepping away from employer-funded health insurance and 401-K matching, and into a career and life that we’re responsible for building one project at a time.

It’s a fairly intense choice, and one that my husband and I know well. Freelancing is, after all, what we chose days after signing our first mortgage, and weeks before getting married. Fourteen-plus years later, we’re busier than ever, parents to a great kid, living in a community we love and a house we had built from the ground up.

I could tell you it’s been seamless—that all we had to do is break a sweat in the early years and the success that followed felt like Christmas morning for five-year olds.

Sounds nice, doesn’t it?

The truth is, we’ve achieved many dreams, big and small, doing work we love. Like most, we wake up some Mondays with that Ugh, it’s Monday feeling. More often than not, though, we look around and smile. Nearly a decade and a half after quitting our full-time jobs, we still get to create the varied, creative, frustrating, interesting, and forever challenging life that freelancing has allowed us to live.

Moment of truth? We’ve been knocked down more times than we could handle, and it has hurt. We’ve lost projects we desperately needed, taken on debt to pay unexpected bills, met deadlines and then waited months (and more months) to be paid. We’ve juggled so much work for so long that we burnt out… and still had to meet deadlines. We’ve worked through destination vacations, cancelled others, had to skip reunions and buckle down on holidays that everyone we knew celebrated with friends and family.

To be honest the overall journey has been a lot bumpier than we ever imagined. No one’s more shocked than we are that with each new challenge we’ve somehow managed to grow stronger.

Looking back, one thing is clear. We really could have used some guidance. We really could have profited professionally and personally from someone or something to support us through the sharp turns and mental/physical/emotional/financial power outages that followed. After all these years, we thought we’d share some of the core lessons we wish we’d known when we were starting out:

1. Your business is your life, and your life is your business.

When you’re freelancing, the lines between life and work become especially blurry. Life is crazy, and there are endless excuses to blow off healthy lifestyle habits, but the bottom line is this:

The healthier you are, the healthier your business can become.

Everything from regular exercise, meditation and nourishing food to setting healthy boundaries in relationships, getting sufficient sleep, and more will prove to be the difference between being able to freelance full-time doing work you love… or not.

2. Ever seen those success graphs that show a mostly smooth upward trajectory? One thing you should know…

Freelance success more often feels a rollercoaster ride. It’s rarely “nothing but up from here.” Flying high today, this week, month, or year? Great! Cultivate it. Just know, it probably won’t last.

That sounds negative, I know. It will feel foreboding, even cruel, to be reminded of that when things are humming along beautifully.

However, down the road, when a slump does hit, you’ll practically be kissing the ground because you followed the guidance that successful individuals and companies live by…

No matter how fulfilling the future seems now, always, always protect the downside.

Plan for the worst case scenario—a tax bill larger than you ever imagined, an out-of-the-blue health insurance rate hike, or, say, getting seriously ill before a critical deadline or accidentally drenching your laptop in coffee.

Go ahead, hate us now. It’s cool. You can thank us later.

3. Freelancing can be the ride of your life… just keep this in mind:

One more thing about those upward-gliding success graphs… You know how they usually include a bumpy patch or two—those jagged little bits that go down, then back up?

In graph form those down times look so innocent, like a blip. Why sweat the small stuff, right? No biggie.

I assure you, that is NOT how you’ll experience those times, especially during the early years. One disappointing outcome, one cancelled project or unhappy client, and your primitive brain, which is wired to magnify fear, will FREAK OUT. Trust us, those little blips will feel huge and foreboding. Here’s the thing, though:

You can get up.

That sounds silly and simplistic when you’re in the thick of it, but it’s also what will save you.

Everyday do at least one thing—market your business online, reach out to a former client, network, publish and promote new content, restart your meditation practice, etc.—to get yourself moving forward.

Even when a J-O-B seems like your only savior (and it’s okay if that’s necessary at times), keep taking little steps every single day to refine, define, and promote your work.

That’s how you get up; you take positive action. Even when things feel hopeless and pointless, get up and do something.

4. Remembering this also won’t hurt…

Cliché as it may sound, you’re not alone. In addition to the millions of others, we can personally assure you that we’re out there somewhere, gnawing on our nails, working on Labor Day (and Memorial Day, and probably New Years Day, too), attending conference calls at dinnertime, and loving our sometimes stressful and frustrating but basically awesome life. So cheers to you, our fellow freelancers, we’re here and rooting for you through every topsy-turvy step of the way.

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