What I Learned from My First Two Years Freelancing

I feel like I started freelancing yesterday. But according to the calendar, two years have already gone by.  

These past two years have been some of the most professionally fulfilling years of my life. While I won’t lie and say that everything’s been smooth sailing, it has been a journey well worth going on.

What I’ve learned over the past two years, and how I’ve grown as a writer and a business owner, could probably fill a short book. But here’s a brief summary.

Half of Success Really Is Just Showing Up

As a freelancer working from home, I obviously don’t literally show up anywhere. But virtually showing up means just as much.

By “virtually showing up,” I mean being proactive about keeping communication open: replying to emails in a timely manner, following up about the status of projects, delivering work on or ahead of deadline, and communicating about potential delays ahead of time.

To me, these types of tasks feel as obvious as showing up to a traditional job would be. But obvious or not, clients really appreciate these small actions.

It’s Okay to Work at Any Time of Day

One of the primary reasons people freelance is for the flexibility to work whenever they want to. But even so, I found it surprisingly difficult to break free from the 9-5 mindset.

Without any reason to work odd hours, I initially thought I’d stick to the 9-5 schedule I was used to from working a traditional job. But the truth is, I’m incredibly unproductive at 9am. My mind doesn’t seem to come online until late in the morning.

No matter how hard I tried to start writing early, I ended up spending half my mornings staring blankly at my computer. I would then mentally berate myself about my inability to focus — a habit that only made focusing harder.

All this angst over a few hours of lag time was incredibly silly. My clients were getting their deliverables on time, regardless of what time of day I started working. If it didn’t impact my output, why did it matter?

Once I realized this and embraced my natural rhythm, I became more satisfied and more productive.

I know people who do their best writing after midnight, and others who feel most productive getting up at dawn. Everyone has their own natural rhythm.

When you’re not forced into someone else’s schedule, you usually end up settling into the one that works best with your rhythm. You generally get more done when you follow those instincts instead of fighting them.

You’ll Get Ghosted When You Least Expect It (But You’ll Hear from People When You Least Expect It, Too)

Ghosting — when someone stops replying to your messages — is unfortunately a common part of freelancing.

I’ve been dropped by prospective clients countless times, and more upsetting, I’ve been ignored by people I had been just about to start working with. It’s incredibly frustrating, and it’s hard not to take personally. But it’s not personal, and I’ve learned that it’s just one of the punches you have to roll with in this business.

Working independently, without access to any updates (or gossip) from the companies I’m doing business with, means circumstances often change without my knowledge. Work will unexpectedly dry up, points of contact will leave a company, and people will have family emergencies that make freelancer management a low priority.

There’s so much more than I’ll ever know going on behind the scenes with my clients, and sometimes that means people or projects will disappear.

The upside is, it also means that people and projects will sometimes appear at the most unexpected times. I’ve been hired by former colleagues I hadn’t spoken to in five years, been referred to new opportunities by old clients who I thought had forgotten me, and been contacted by prospectives I thought were dead ends after months of silence.

I believe the takeaway is to just be forgiving and accepting. Ghosting hurts, but if you remain open to connection, new opportunities will come when you least expect it.

The Best Gigs Aren’t Found Through Ads

The majority of opportunities I’ve found on freelancer job boards have been low-paying and uninteresting. For work that pays fairly and matches my skills, I’ve mostly had to rely on networking.

The thing about job boards is that they attract a lot of beginners who don’t have much experience. This lowers the average rate available on these boards. When you’re finding work through your network, though, you have more power to explain what makes your services unique and why you’re worth what you’re asking.

I hated hearing this when I was starting out. I’m extremely introverted, and the word “networking” made me a little nauseous. But it’s actually not as hard as I thought it would be. It doesn’t involve jumping in the DMs of everyone I know and aggressively asking for work. It just involves staying alert to how I can support people I already know.

Building a network isn’t quite as difficult as I thought it would be, either. If you’ve worked any kind of job before, and you were kind and diligent while you were in that position, every colleague from that role is now part of your network.

So is every classmate you’ve had, friend you’ve made, and person you’ve met in your neighborhood. Nurturing those relationships is a much better use of your time than sending a dozen applications a day to a low-paying job board.

You Have to Be Proactive About Making Connections

New clients don’t magically appear without you doing anything. Sounds obvious, doesn’t it?

But when I started out two years ago, it kind of felt like business was magically coming to me. After just a couple LinkedIn posts, old acquaintances were pouring out of the woodwork to ask for my services. I had a period when every prospective client I connected with turned into a real client. It was wonderful. And it lulled me into a false sense of security.

I realize in retrospect that these good times were partially due to economic forces. In early 2021, people were optimistic about the economy roaring back and eager to spend money on new projects. 2022 tempered that their optimism. Just as quickly as clients had arrived, they began to disappear.

Even in difficult economic times, though, there’s a compelling business case for working with freelancers. Freelancers can help organizations save on personnel costs while still turning out high-quality marketing and other projects.

But a lot of hiring managers don’t know to turn to freelancers for support. We have to be proactive about making connections and finding appropriate opportunities to propose our services.

I tended to be fairly passive in the past. But I’ve learned that passivity doesn’t help anyone — not me, and not the clients whose lives I could make easier.

It’s Worth It

Freelancing isn’t perfect. I’ve dealt with sudden ghosting, delayed payments, and the loneliness of working for myself, and my earnings haven’t yet surpassed what I was making in a 9-5.

And I wouldn’t give it up for a second.

The freedom, flexibility, and fun of being in business for myself is worth every struggle. I’ve learned so much from so many different clients, and I’ve had opportunities to tackle exciting, challenging projects. And I’ve never had more pride in what I do.

Could your business benefit from some writing or editing expertise? Contact me to learn how we can work together.