5 Reasons You Shouldn’t Quit Your Job to Freelance

This month marks my first full year as a solopreneur — twelve months since I left behind the benefits and security of a full-time job and became my own boss.

As you tend to do on anniversaries, I’ve spent the past few weeks reflecting on my experience thus far. It’s been a wild ride, y’all.

I could choose to focus on the highlight reel and share only the most positive aspects of my new career — like the fact that I can work from any location with a WiFi connection, start and end my workday whenever I choose and regularly wear yoga pants (or no pants).

I could tell you how much I love having the freedom to only take on the projects I’m interested in pursuing or how, in my first twelve months of full-time freelancing, I earned 40 percent more than my salary at my previous 9-to-5 role.

But I’m not a highlight-reel-only sort of person.

While all these things are true, painting the self-employment experience as casual and easy would be an incredible disservice to anyone seriously considering this path. Because the truth is, behind the perfectly filtered Instagram images of freelancers sipping lattes or posing with a laptop in some faraway tropical locale, there’s a hell of a lot of work.

The truth? The past twelve months have been some of the most satisfying of my professional life. But they were also full of late nights, carefully concealed bouts of imposter syndrome and tearful 2 a.m. proclamations that, “I can’t do this.”

I’ve worked harder than I’ve ever worked in my life, acting as my own salesperson, client manager, bookkeeper, one-woman marketing department and entire production team. I’ve navigated self-employment taxes (with the help of my brilliant CPA) and small business law (with the help of my brilliant attorney).

In that time, dozens of people have asked my advice about whether or not they should quit their jobs to follow a similar path. And while I am exceedingly passionate about people launching their own ventures, I always provide my encouragement with a caveat: the freelance life isn’t for everybody.

Here are five reasons you may not want to quit your day job to embark on a freelance career:

Everyone has days when they don’t feel like working — when even the smallest tasks seem a herculean struggle.

But it’s a lot easier to choose not to work when you don’t have a boss watching over your shoulder or team of coworkers expecting you to pull your weight.

There are days I stare out my office window at a cloudless, blue sky and want nothing more than to shirk my responsibilities and head to the closest pool. But choosing to procrastinate on my work often means missing sleep the following day or giving up part of my weekend — because failing to meet my clients’ expectations isn’t an option.

As with a 9-to-5, I have plenty of responsibilities and people relying on me to complete assignments on time — I just don’t have anyone supervising my time, monitoring when I stop and start my day or motivating me to keep going.

Yes, there are days when I decide to shut my laptop and spend a few hours in the sunshine (because balance is essential and that freedom is one of the many reasons I love my career), but I do so with the knowledge that I’ll be returning to my work later that day.

If you can’t trust yourself to hunker down and get shit done — even (and especially) when you’d rather do anything else — self-employment may not be the right path for you.

Even though nearly 58 million people in the U.S. work as freelancers (more than one-third of the national workforce), according to an annual report from UpWork Global Inc., this career path still carries a few annoying stigmas. And if you leave your job to pursue freelance work, some people in your life will make ludicrous assumptions about how you spend your time.

Since becoming self-employed, people have said things to me like, “It must be so nice to do whatever you want” or, “You’re so lucky you don’t have to work.”

Too many times, when people find out I’m a freelancer, they ask what my husband does. (Maybe they assume I’m living some charmed housewife lifestyle, lounging around the house in a silk robe, sipping champagne while my hard working partner funds my life of leisure.)

I’ve learned to shake it off because, quite frankly, I don’t have the energy to correct every misconception.

The truth is, sometimes I work 18-hour days. Sometimes I stay in my pajamas until dinner time — not because I want to, but because I’m on a tight deadline and can’t spare even a minute to change. I’ve landed jobs with massive, global brands through my own hard work and, believe it or not, my husband and I are in the same income bracket.

But these are things most people will never know. And no matter how far you get in your freelance career, there will always be people who, when you tell them what you do, respond with a solemn, sympathetic nod or advice for how you can find a “real job.”

(This is especially true if you’re a writer — a career people already file into the “starving artist” category. And the stigmas are even worse if you’re a self-employed woman rather than a self-employed man, but that’s a blog post for another time.)

If you’re deeply bothered by the thought of people assuming you do nothing while you’re toiling away behind-the-scenes, working as a freelancer will be a tough experience.

Before I tackle this one, let me share a couple of disclaimers:

  • Disclaimer 1: The number of hours you work will depend on your income expectation and your profession. But generally speaking, if you’re looking to replace a full-time income with a freelance career, you’re going to be working more.
  • Disclaimer 2: I’m a bit of a workaholic. I don’t “need” to work as much as I did this past year, but I wanted to scale my business quickly. I also defined a few lofty objectives for myself in my first few months as a full-time freelancer, and I tend to laser-focus on my goals. This sort of behavior can teeter on unhealthy, and I’ve recently dedicated myself to achieving a better balance.

That said, almost all the freelancers I know work a lot. Sure, we may sometimes work fewer hours in a given day or take longer or more frequent vacations than our traditionally employed counterparts, but getting a business off the ground requires a significant investment of time. And that includes unpaid hours, such as the time you spend designing your website, prospecting and pitching potential clients, sending invoices and managing your books, building your skill set and responding to emails.

In other words, while you’ll enjoy more flexibility, it’s doubtful you’ll be working less.

Let me level with you: There’s loads of bullshit out there, and plenty of people are spreading misinformation in an attempt to sell an e-course, membership to a mastermind group or some other product that may or may not provide real value. (No shade on coaches — some of them are brilliant and can legitimately change the course of your career. But some of them are shady AF.) If you’ve always wanted to try “that blogging thing” because you saw an ad on Facebook that said you could make six-figures a week, this is not the career for you.

That’s not to say you can’t make a fortune as a new freelancer. But it’s typically not as easy as these (in my opinion) irresponsible influencers would have you believe. Admittedly, I’m making the most money I’ve ever made — but I also have a decade of experience in my industry and a massive network. If you haven’t reached that level of your career, it will take some time to build your skill, contacts and credibility.

If you’re looking for an easy way to make a lot of money, freelancing isn’t it. But most of us don’t do it just for the money anyway — we do it mainly because we’re passionate about our work.

And that brings me to my next point.

I love writing with my whole heart and soul. You’d think after creating approximately one bazillion articles, e-books, email campaigns, video scripts, and various other pieces of content for my clients, I’d loathe the thought of writing, but I don’t. And that’s how I’m able to slog through the heaviest of workweeks without throwing in the towel.

I also thoroughly enjoy developing strategies and sitting down with clients to solve complex problems. It’s challenging and stimulating in all of the best kinds of ways.

But, you guys, if I weren’t head-over-heels about this stuff, I probably wouldn’t have lasted a month.

Some people turn to freelance writing because they heard it was a good way to earn a living, sitting at home in their pajamas. But as someone who has spent a significant chunk of my career sourcing and managing freelance writers, I can say with confidence: lazy writers are everywhere, but great writers are hard to find.

I can always tell who is passionate about the craft because it comes through in the quality of their work. (And those writers usually earn much more, too.) I’d wager this is true across all freelance professions.

In other words, if you want to quit your job to freelance, it’d better be something that fills you with joy. Because if you want to build your credibility and earn great money, you’ll be spending a lot of time doing it. And if you aren’t passionate about it, or don’t even particularly like doing it, you might suck.

Despite the late nights, the insane workload, the stigmas and the other challenges associated with this kind of career, I still believe it was the right choice for me. It’s been a year of ass-busting, but I’ve never felt more fulfilled by my work or proud of my accomplishments. I think the pros far outweigh any drawbacks I’ve experienced. Plus, there’s something magical about blazing your own trail, taking a massive leap, getting scrappy and making it work.

But when people ask me if they should quit their jobs to freelance, I don’t sugarcoat it or set unrealistic expectations. It might be the best career decision you’ll ever make, or you may hate every moment — but only you can determine if it’s the right move.

So ignore the Instagram highlight reel and the bogus claims of fast, easy money, and take time to reflect on why you want to become a freelancer. And before you take the plunge and hand in your notice, try freelancing as a side gig. It can be an exciting and rewarding career, but it’s important you approach it clear-eyed and ready to put in the work.

Still interested in making the jump from a 9-to-5 to the wild world of freelancing, but curious to know more? Feel free to drop me a line. I’m always happy to chat!

Originally published at http://carriedagenhard.com on April 24, 2019.

Freelance writer, content marketer, mental health advocate, and relentlessly curious human. “I know words. I have the best words.”

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