6 Things I Wish I Knew Before Full-Time Freelancing

When I pictured my first day as a full-time freelancer, I pictured freedom. Complete bliss. I’d hear the alarm, smile and stretch out like I was on a Folgers coffee commercial, and then glide out of bed with grace and determination. No more rushing out of the apartment or spending my days on small talk. I’d sip my coffee slowly and feel grateful for the day ahead. Finally, the control I wanted would be mine.

If you’ve been a freelancer for any amount of time, two days or two decades, you know this is a great big pile of she-has-no-idea-what’s-about-to-hit-her. I didn’t jump out of bed on my first day of “freedom.” Becoming a freelancer doesn't mean all of your problems go away.

Even if you think you’re prepared for full-time freelancing—you’ve read the books and taken the notes and you’ve impressed your clients—you’re still going to hit bumps and have bad days along the way. Hopefully, after reading about the things I wish I knew before I started, your road will be a little less bumpy than mine.

#1: You won’t magically become a morning person.

If you’re stuck in a job you hate right now, and cursing your alarm every morning, I hope it brings you a little relief or solidarity to know that most days I curse my alarm too. Coffee commercials and Instagram stories aside, becoming your own boss doesn’t mean you’re suddenly going to love waking up before the sun comes up. And I’m not saying you have to. (But mornings might be the best time to write and get ideas).

If you find your energy zapped at the end of the day and feel no motivation to work on your business, consider getting into a morning routine. I wish I started mine before I went full-time so I could have had more control over my days right from the beginning.

#2: You might still get the Sunday Scaries.

Life is still, well, life.

Any of the anxiety or stress you had before isn’t going to disappear. It’s just a different set of issues you’re facing now. Instead of stressing about your workload, you’re stressing about how you’re going to keep work coming in. Instead of stressing about your micromanaging boss, you’re juggling a handful of bosses who all have different management and communication styles that you have to navigate.

Of course, going into it, you know freelancing isn't a magic wand that'll erase your worries. You've heard the podcasts and read the blogs and know on some level this is going to be tough. But, before you quit your job and focus on your business, if you're honest with yourself, a part of you thought your insecurities would dissipate, and the tugging sensation that you're not doing enough would disappear if only you were the one in control of your days.

Having control over your days doesn't mean your life is any easier. I hate to admit it, but Sunday Scaries are still a thing. Maybe not every week, and maybe not as debilitating as they were before, but they're still there. Especially in the early days when you're still figuring out your process and your routine.

#3: You need some kind of daily routine.

Again, the opposite of the freedom idea I had in my head. I thought I’d follow the wind wherever it took me and that every day would be different. The latter is true to an extent, but I couldn’t just wander through my days and hope things worked out. I tried that for the first couple of weeks, and let me tell you, it was a waste of time and a whole lot of aimless research (a.k.a. comfort pretending to be research).

You can read articles about time management and time-blocking and the Pomodoro Method all day. But until you start applying the lessons you're learning, you're not moving your business forward.

As you experiment and try things out, you’ll start to determine what works best for you. You might think you want to do all of your client work at the beginning of the week and save focusing on your business later on, and then soon find out that Monday morning calls are your worst nightmare. The best advice I have for figuring out your routine is to start trying different schedule or time-blocking techniques each week. Notice what goes well and what doesn't. Then, shift things around as you see fit. You can plan all you want, but eventually you have to start.

#4: You’ll never feel ready the first time you do anything.

Or the first sixteen times.

I still don’t feel ready to write online, practice in public, or even share my two cents on a Twitter thread. I thought I was going to have a heart attack the first few networking events I attended.

But it’s just like those first few weeks of training to be a server at a restaurant. On the first night, you’re overwhelmed by all of the buttons in the POS system and panic when you can’t find the “Sub American Cheese” button. Then, after showing up for every shift and pushing through the panic, what was once overwhelming becomes second nature, and next thing you know, you’re helping the new hire figure everything out. The more you do something, the less painful and scary it will become.

You’re not going to feel ready for your first couple of sales calls, your first few cold pitches, or your first (any and all) number of networking events. Stop waiting until you’re ready. Because if you’ve never done it before, you’re never going to be ready to start.

#5: You can’t stay in the shadows.

In my traditional jobs before freelancing, I approached every day the same way: go above and beyond, make processes and communication smoother for customers and coworkers, and eventually someone will take notice. My unspoken mantra was to let my work speak for itself.

This approach doesn’t work as an entrepreneur. You can’t do great work for three clients and expect a line to form at your door—especially not as you’re starting out. Whether it’s building relationships on social media or sharing your blog content, you have to put yourself out there if you want this thing to take off.

Trying to build your network on Twitter? I love this quick guide that breaks down how to market yourself on Twitter as a freelancer.

#6: There’s no magic pill for success.

You know that. I know that. But do we really know that?

Sure, on some level, you know nothing is going to get handed to you. You’ve always fought your way through, and you’ll do it again.

But, when you first start out as a full-time freelancer, you don’t realize how hard it is to be stuck in your head all day. The second something gets too hard—a client decides she can’t afford you anymore, a proposal gets rejected—the negative thoughts start spinning. I’m not cut out for this, you tell yourself. And you spend the afternoon submitting resumes instead of cultivating relationships (because you just love chasing the high of rejection).

We love accepting defeat at the first obstacle that comes our way. When we stumble our way through one setback and make it to the next one, we think This is it; it’s over.

Here's the secret to getting through those moments of self-doubt:

Everything you're doing now will pay off in 3 months.

I wish I remember where I first heard this piece of advice, but it's a phrase I remind myself of constantly; a rule of thumb that keeps me going. "Whatever I do today will pay off three months from now." Ninety days of effort will lead to something bigger in the future. I just have to keep going.

It's easy to doubt yourself and assume your efforts are going to waste, your networking and content strategy aren't solid enough to keep opportunities rolling in.

But the connections you are making, the content you are creating, every conversation, project proposal, and swapped business card—all of your efforts will be worth it if you keep going.


Are you new to freelancing? What are some of the things you wish you knew before you started? I'd love to hear from you! Find me on Twitter or Instagram and let's get connected.