Why I'll Always Find Joy in Gig Work (Even When It Stings)

How to turn rejection into data, build your own support system, and find stability in uncertainty

Greetings.

Last year, I got turned down for a project I really wanted. The kind that would have been perfect for my schedule, paid well, and involved people I genuinely liked working with. The email was polite, professional, and yet it felt like a punch in the gut.

If you've been following along, you know I've been writing about life as a gig worker. Juggling 5+ jobs has become a way of life for me—and for millions of others. According to recent data, 76% of gig workers say they are very satisfied with their choice, but that doesn't mean rejection doesn't hurt.

Here's what I've learned about finding joy in gig work, even when the "No, thanks" emails pile up.

The Numbers Game (And Why That's Actually Good News)

Let's talk real life for a minute. The majority of gig workers, earn $10 to $14.99/hour, which sounds discouraging until you consider this: 65% of gig workers report earning more as freelancers than they did with their traditional jobs.

The math tells the story. In traditional employment, you put all your eggs in one basket—one boss, one company, one paycheck. In gig work, you're playing a numbers game where every "no" gets you closer to the right "yes."

I keep track of my rejection rate because I've become a data person. (Occupational hazard of being a finance writer.) Early on in my career, my success rate meant that for every four projects I pitched, I got one. That means a 75% rejection rate. Sounds terrible, right?

Wrong. Some of the projects I won were huge. And, it taught me to be more selective about what I wanted to do. Over the years, I got better at pitching projects, but more importantly, my clients started coming back to me. We developed long-term relationships which mean more regularity to project wins, and more money.

Still, rejection is rejection. It stings. That’s why you have to….

Reframe the Rejection Conversation

When that email landed in my inbox last year, my first thought was the usual: "What did I do wrong?" Then I caught myself. I've been doing this long enough to know better.

Instead, I asked: "What can I learn here?"

Sometimes the answer is nothing. Sometimes the client had no budget, or their brother-in-law decided he wanted to try freelance writing, or they changed direction entirely. Sometimes—and this is important—you dodged a bullet - which you might find out later and under different circumstances.

That project I mentioned? Three weeks later, I heard through the grapevine that it wasn’t going well and had become a bit of a nightmare. Unclear expectations, scope creep, and payment delays. My rejection had been a blessing.

Build Your Own Advisory Board

Here's something I wish someone had told me when I started: you need people who get it. And, who get you!

Working any of these jobs would be difficult to do well. It's even harder to keep it straight when you're doing 5+ jobs at the same time. You can't do this alone.

I have a cadre of supporters, advisors, and pros who can help me through the tough times, including my husband, Sam (a real estate attorney who has his own practice and gets the self-employment struggle).

These aren't people to complain to—they're my reality check. My brain trust. We work through problems together. If I’m down over a rejection, they remind me of the projects I've landed, the relationships I've built, and the skills I've developed. And, they help me refocus on what’s important.

The Portfolio Approach

As I’ve mentioned, I do a lot of different jobs. Writing, editing, consulting, inventing new ways for companies to communicate directly with the clients, customers, and employees, and directing big content projects are all skills I’ve built over the decades. But I'm also a Pay Dirt Columnist for Slate (you can see some past columns here), and I'm a contributor, past show host and sometimes fill-in host for WGN radio. Some of you know me just from Substack.

Each of these roles informs the others. Writing for Slate taught me to tackle sensitive financial questions with empathy. Radio (WGN-AM and WSB-AM, plus being an on-air reporter/producer for WGN-TV long ago) improved my ability to explain complex concepts quickly. This newsletter lets me test ideas and get direct feedback from readers.

These days, when one gig ends or doesn't work out, I'm not starting from zero. I'm building on a foundation of diverse experiences that make me more valuable for the next opportunity. I’ve embraced change and look forward to it (something I’ll address in a future post). You can do it, too.

Create Your Own Stability Anchors

The uncertainty of gig work can be energizing or paralyzing—and sometimes both in the same week. The key is creating your own constants.

For me, it's my syndicated column (here’s week #1,699 and and I’m about to release week #1,700, so watch your inbox), my weekly Pay Dirt column, and now, this newsletter. Every week, rain or shine, good news or rejection, I'm here talking with you about money, real estate, and MyGig life. It's something I control completely. And, it’s fun.

Maybe for you it's a weekly coffee with another freelancer, a consistent morning routine, or a recurring client that provides baseline income. The goal isn't to eliminate uncertainty—it's to build enough structure that uncertainty becomes manageable.

Your Rejection Recovery Toolkit

Here's my go-to routine when disappointment hits:

First, I take a walk or go for a bike ride. Physical movement resets my energy and gets me out of my head. It’s also why I do a bootcamp class 4-5 days a week.)

Then I update something—my LinkedIn profile, my portfolio, my website. Forward motion, even small steps, counteracts the feeling of being stuck.

Finally, I reach out to someone in my network. Not to complain about the rejection, but to check in, share something interesting I've read, or ask how their latest project is going.

The faster I can move from "that sucked" to "what's next," the more resilient I become.

The Long Game Perspective

Resilience is something you build up over time. When you begin to realize that you’re not just working on individual projects anymore. You’re building a career that can adapt to economic changes, technological shifts, and life circumstances.

That client who turned me down last year? They might remember me six months from now when they have a different project. The editor who said "not this time" could become a regular contact. A different project that fell through led to a connection that landed my biggest contract to date.

Resilience compounds over time. So, play the long game.

The Real Joy of Gig Work

At the end of the day, you decide what you're going to do. You're your own boss. For better or worse, richer or poorer.

Yes, rejection stings. But it's also freedom from office politics, permission to experiment, and the ability to build something that's uniquely yours.

Every rejection teaches you to handle the next one with more grace. Every difficult client helps you spot red flags earlier. Every feast-and-famine cycle builds confidence that you can weather uncertainty.

The joy isn't despite the challenges—it's because of how those challenges shape you into someone more resilient, more creative, and more authentically yourself.

Now stop reading newsletters about gig work and go create something worth getting hired for.

What About You?

What's been your most valuable rejection? The "no" that led to something better? I'd love to hear your stories. Drop them in the comments below.

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