The Third Year of Freelancing? Not Exactly Charming

"Handle your business, mommy," said my almost-five-year-old from across the dinner table. I almost choked on my pizza in surprise, then snort-laughed.

"Where did you hear that, TJ?" I asked.

"Ms. Jordan said it." (Not the first time he picked up a hilarious older-than-his-years phrase from one of his favorite preschool teachers.)

"Handle your business" has become something of an inside joke for us ever since. But as I started reflecting on my third anniversary as a freelancer over the past week, I realized "handle your business" was an apt theme for the past 12 months. I encountered a bunch of awkward, challenging, and downright painful professional situations. I took them personally. I went through the stages of grief with them. I second-, third-, and fourth-guessed my decisions about them. Ultimately, I handled my business with each of them—and I learned some important things in the process.

I handled being "fired" for the first time.

A client that I'd worked with for more than a year suddenly decided they didn't want to do so anymore. The news shocked me—not because I think my sh*t doesn't stink, but rather the project I was working on built upon many months of previous work that they (allegedly) liked a lot. Apparently the feeling wasn't mutual, and there was no room to argue: I was asked to produce an invoice for work completed to date, then to roll off immediately.

Nearly a year later, I still feel the sting of that email.

I'm not for everyone, and that's OK. What I can control is doing the best work I can, protecting myself contractually, and conducting myself as professionally as possible (even when it's unpleasant).

I fell into a funk for weeks, scouring past emails and draft comments from the client, trying to pinpoint where things went wrong. I questioned whether I was really cut out for freelance work, in both skill and psychological disposition. That cloud of self-doubt began affecting my ability to complete assignments for other clients.

And it was those clients who helped pull me out of my funk. I still had them, and they all believed in me and my work. If I wallowed in self-pity for much longer, though, that would change. I had to stop my spiral—so I did.

What I Learned: I'm not for everyone, and that's OK. What I can control is doing the best work I can, protecting myself contractually, and conducting myself as professionally as possible (even when it's unpleasant).

I handled a repeatedly late-paying client.

Speaking of unpleasant: I had a client fail to pay me on time not once but twice. I wasn't sure whether to let it slide or to cut ties. As I considered my options, I remembered something I once heard in a seminar: You can't negotiate well unless you know clearly what you want out of a situation. In this instance, I didn't want to lose the client, but I also didn't want to be taken advantage of.

Difficult conversations make me nervous—I'm much better in writing than off-the-cuff. But a nuanced conversation like this one had to be voice-to-voice, if not face-to-face. I scheduled a call with my contact and put together a plan for what I wanted to cover:

• Hearing their side: Why was the payment late?
• Sharing my side: How does a late payment affect me and my family?
• Reiterating my policy: Payments beyond net-30 are charged a $100 late fee.
• Continuing our work: I care about their mission and want to keep supporting them.
• Finding middle ground: How can we move forward amicably?

What I Learned: When you freelance, you've got no choice but to stand up for yourself. Focusing on your goal and determining what lines you're willing to cross (and not) in a negotiation ensures that, whatever the conversation's outcome, you've done your best for you.

Year Three of my freelance career prepared me for turbulence. It forced me to learn lessons I'll lean on to fight back the scarcity mindset that our current freelance market can trigger.

I handled a B I G mistake.

I became a subcontractor for a new client who assigned me to a project that got complicated in a hurry. I struggled to keep up with the end-client's shifting parameters and adjust to my client's processes and procedures. And in one big meeting, I made a big mistake.

We were discussing a part of the project I hadn't been fully briefed on when the end-client asked an unexpected question to each member of our consulting team. When they came to me, I replied with candor—but candor was not what my client wanted from me at the time.

Before my last sentence left my lips, I knew I'd screwed up. The moment the meeting ended, I drafted an apology email, but my client beat me to the punch. In their email, they expressed their disappointment in my conduct and underscored the importance of alignment within our team.

In reply, I owned up to the gaffe. It wasn't intentional, but my mistake could have damaged the relationship between my client and the end-client—and that's never acceptable. I apologized without excuses, and I committed to doing better in the future.

I wouldn't have protested if they fired me on the spot, but they kept me on. And since then, I've lived up to my promise to learn from that mistake.

What I Learned: Don't waste time explaining away mistakes. Offering a genuine apology and demonstrating how you've learned from the experience are the two best things you can do to preserve your client relationship. (And it's the best way to stop beating yourself up over the mistake, too.)

Year Three Prepared Me for Year Four

Like much of the job market, the independent contractor market right now is ... not great. A quick scan of freelancer accounts on Twitter, Threads, and LinkedIn shows I'm not the only one feeling this. Longtime clients aren't asking for work at their usual clip. Previously steady streams of recommendations are drying to trickles. Outreach strategies are yielding fewer responses. And fewer potential clients are becoming real clients.

This environment forces you to question yourself, asking "Am I good enough for this?" or "Can I survive this?" It has you considering projects you know you can do but also know you won't like. It has you thinking about accepting clients who pay below your rate because the voice in your head says, "You'd better take what you can—there's not much out there."

Difficult as it was, Year Three of my freelance career prepared me for turbulence. It forced me to learn lessons I'll lean on to fight back the scarcity mindset that our current freelance market can trigger—to focus on the factors that I can control, to stand up for myself even when it's scary, and to be confident I can recover from setbacks.

You know, how to handle my business.