Lessons From 1 Year of Freelancing Full-Time

Happy Quittiversary to Me!

How the time flies when you’re working 60-hour works and neglecting to shower or eat properly…

Yes, kids, this coming Saturday, May 17th, will be my one-year anniversary of quitting my day job to freelance full-time.

It has not been the best of times, as I’ve recently divulged, but it’s certainly been a lesson-packed time, and I so wish I’d known half the things I’m about to share when I embarked on this journey a year ago.

So if you’re thinking of quitting, have recently quit, or (like me) are deep in the quagmire of what happens after quitting, here are the biggest things I’ve learned from one full year of freelancing full-time:


Lesson #1: There’s No Point in a Lifestyle Biz If You Don’t Have a Life

This has by far been the biggest struggle for me. When you’re trying to establish a business—especially a business that sustains your entire household single-handedly—it can be hard to justify that whole “life” part of work/life balance.

Every client you take on is one more bit of security.

Every project you accept is one more bullet point on your portfolio.

Every nap you take or coffee you have with friends, on the other hand, is one more missed opportunity to keep growing that all-consuming monster that has become your business.

But here’s the rub: You business exists to serve you, not the other way around. (Tweet!)

Most of us who go off on our own do so because we can’t stand pigeonholing our lives into the 9-5, work-for-someone-else structure. We want the freedom to visit the doctor whenever we’re sick and enjoy the weather when it’s nice and go grocery shopping when 95% of the population isn’t also grocery shopping. We want the ability to live our lives on our own terms. And if you spend your newfound freedom on a constant hamster wheel of work, you’ve defeated the entire purpose. You may as well go back to the 9-5, because at least then you had “off” time.

It can be hella hard to justify “me” time when you’re in full-on entrepreneurial mode. And, to some extent, you do need that period of all-out work to get yourself to a point where your biz can serve you (see below). But at some point, you’ve gotta take your foot off the pedal and let what you’ve built up so well carry you along instead of the other way around.

Work is a means of making your life possible. Tattoo that inside your eyelids if necessary, because it’s the most important lesson you’ll ever learn as a lifestyle designer. (Disclaimer: I am not actually advocating eyelid tattoos, inner or outer, as that shit would hurt like nobody’s business and most likely is a serious health hazard.)


Lesson #2: Hustle Isn’t a Virtue; It’s a Tool

When you start your own business, especially if you’ve been side hustling for a few years to build it up, you can fall into the mentality that hustling is a virtue in and of itself. The corollary to that, then, is that if you’re not hustling, you’re somehow not giving enough.

12-hour workdays become a virtue. Letting the weekend just be the weekend becomes selfish or slackerly.

But (see above) hustle isn’t the end goal. It’s just one of several tools in your tool belt. And that means that while it needs to come out from time to time to get the job done, there are plenty of other times when you need to place it securely back in its holster and let some other tool do its job.

There is a time and a place for hustle. When you’re launching something, when a big deadline is looming, when you’re working ahead so you can enjoy a day off down the road—these are all times when hustle should be employed. As a day-to-day modus operandi, however, hustle is worth shit. You can’t maintain it indefinitely; it will burn you out and ruin everything. So use wisely.

(Note the difference here between “hustle” and “hard work.” You can give your all to your projects without letting them consume your life. You can produce great things without depleting every last stock of energy and enthusiasm. You can work smart and play hard and create infinitely better results than keeping yourself at a constant simmer of exhaustion all the time.)


Lesson #3: You’re the Boss. Start Acting Like It.

“Freelance” means you make your own rules. You choose the clients you take on. You choose the projects that occupy your days. You decide what you want your business to look like, and you and only you have the power and the responsibility to make that happen.

The thing that distinguishes the amateurs from the pros is knowing how to say “no” to work that is perfectly fine, but not the right fit for you.

This has been a huge evolution for me.

As someone who’s gone through the side hustle phase, when anything that will get you closer to freedom is worth chasing, it’s taken a while to realize that just having work on my plate is no longer the goal—it’s having work on my plate that I look forward to doing.

Also, as someone whose husband hasn’t worked for a year—and will never work regularly again—it’s been extremely uncomfortable not jumping at any and every offer that comes my way. It’s felt counterintuitive really stupid turning down work that pays well that I know I can accomplish.

But (see lesson #1), I did not decide to freelance so that I could make tons of money. I decided to freelance because I wanted a life that makes me happy. It’s time I start acting accordingly.

You set your rates—and enforce your rates.

You set your working conditions—and enforce your working conditions.

You don’t “have to” do anything unless you decide you have to do it.

Once you realize that—really, truly realize it—the whole game changes.


Lesson #4: Stop Trying to Be a Superhero

The hardest part about the past year has been the feeling that I am constantly, inescapably behind.

That every day ended with a slew of to-dos there was no way in hell I’d be able to check off.

That every day began with a chest-tighteningly long list of new to-dos I just knew, from the start, there was no way in hell I’d be able to check off.

I am a doer. I am an (over)achiever. From kindergarten on, I have thrived on taking on big challenges and kicking their ass. This past year, I found myself devolving into someone who was forever asking for extensions, burning the midnight oil and still coming up short.

But here’s the mindfuck that gets too many entrepreneurs in trouble: Just because you can do anything you set your mind to, that doesn’t mean you can do the impossible just by setting your mind to it.

The corollary to that being: If you can’t do something you’ve set your mind to, that may be a sign you’ve set your mind too high.

When you’re out on your own, with no office hours to reign you in and no “off” time to tell you it’s time to stop, it can be easy to fall into the fallacy that you can take on anything and everything and somehow find time to make it work. You’re a hustler. You’ve freed yourself. You can do anything!

But you can’t. That way lies madness. Learn to accept your limits and be OK with saying “I can’t.” It doesn’t make you any less capable or awesome. It just makes you sane. (And sane is a nice thing to be. I’m fairly new to it, but I’m liking it.)


Lesson #5: Stop Looking at What Everyone Else Is Doing

What surprised me the most about publishing my “I was wrong; this sucks” post was the reaction it got from other freelancers. Freelancers I look up to, whose shit seemed to be infinitely more together than mine. Whose launches and announcements and perfectly crafted email marketing campaigns always made me feel like the reason things were so hard for me was simply because I was doing them wrong (see above).

Turns out they were going through the exact same struggle I was.

I’m also in two masterminds with some seriously impressive, tail-kicking ladies, and it never ceases to amaze me that they suffer from uncertainty and burnout and comparison syndrome, too.

No one has their shit fully together. Not me, not you, not A-listers like Ash Ambirge. So stop wondering why things are so tangly and worrisome for you, because they’re like that for everyone. We’re all just learning as we go along.

Furthermore, no one’s business is your business. That’s not a warning against OPP, but a reminder that just because everyone else is launching, or webinaring, or coaching, or email marketing, that doesn’t mean you have to or need to.

Your business is on its own trajectory, and if you start trying to mimic what every other freelancer is doing out of fear you’re missing out on something, you’re defeating the entire purpose of going off on your own.

Make your own road map. Call your own shots. By all means, take note of the cool things other people are doing that you might want to consider implementing yourself, but don’t play the keeping up with the Joneses game. The Joneses are on their own track, and you are on yours.

So rock it howsoever you feel inspired to rock it.

All you freelancers in the hizzy: What lessons have you learned so far that you wish you would have known starting out?


Image: slworking2 on Flickr

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