Latest / The Comeback Career Podcast with Fexingo: Returning After a Gap, Stay-at-Home Re-Entry / How a Career Gap Helped One Parent Launch a Freelance Copywriting Business
Transcript
- Lucas: You know, one of the most common questions I hear from parents returning after a career gap is, 'How do I even start making money again without a traditional job?' And there's one path I keep seeing work, over and over. Luna: Which one? Lucas: Freelance copywriting. Specifically, B2B SaaS copywriting. And I want to talk about a woman named Jenna—she was a marketing manager at a mid-size software company, took three years off to care for twins, and when she was ready to come back, she didn't reapply for a corporate role. She started a copywriting business from her dining room table. Luna: I love this. And it's not just a feel-good story—there's real data behind it. A 2025 Upwork study found that 62 percent of freelance copywriters who started after a career gap earned more than their previous salaried role within 18 months. Lucas: That's a striking number. And Jenna's story mirrors that. She didn't have a network of clients waiting for her—she had to build from zero. So let's walk through exactly how she did it, because the steps are replicable. Luna: Please. I think a lot of listeners are sitting on skills they don't realize are marketable. Lucas: Step one: she niched down. She didn't say 'I'm a freelance writer.' She said 'I help B2B SaaS companies write blog posts and case studies that generate leads.' That specificity made her stand out immediately. Luna: And she had experience in that space from before her gap, right? Lucas: Exactly. She knew the language, the pain points, the buyer personas. But even if you don't have that background, you can pick one industry—say, healthcare tech or e-commerce—and learn it in a few weeks. Jenna actually spent two weeks reading every SaaS blog she could find before she started pitching. Luna: So the niche itself becomes a filter. You're not competing with every writer on Upwork—you're the expert in one corner. Lucas: Step two: she built a spec portfolio. She wrote three sample blog posts for imaginary SaaS companies. One was for a project management tool, one for a CRM, one for an analytics platform. She published them on Medium and linked to them in her email signature. Luna: Spec work—it's controversial to some, but for someone with a gap, it's a fast way to show what you can do. No one cares about your resume from four years ago. Lucas: Right. And she didn't overthink it. Each post was around 1,000 words, she used real research from public sources, and she made sure they were genuinely useful. One of them—about how to choose between a startup CRM and an enterprise one—actually got shared by a small SaaS founder on LinkedIn. Luna: That's the kind of organic validation you can't buy. Lucas: Step three: the cold email. She found 50 B2B SaaS companies that had blogs with fewer than 10 posts. That told her they needed content but weren't producing it. She sent each one a brief, friendly email—three sentences—saying she loved their product, noticed they hadn't posted in a while, and offered to write a free sample post. Luna: Free sample—that's smart. Low risk for the client. Lucas: She got a 40 percent response rate. Twenty companies said yes. She wrote those free posts, and of those twenty, five hired her for paid work within the first month. Her first paid project was a case study for a fintech startup—she charged $500. Luna: Five hundred dollars for a case study feels low, but for a first client, it's perfect. It gets you a testimonial and a reference. Lucas: And she raised her rates fast. By month three, she was charging $1,000 per project. By month six, she had a retainer client at $3,000 a month. Within a year, she was earning more than her old marketing manager salary. Luna: Let's talk about pricing psychology for a second, because I think this is where a lot of returners get stuck. You've been out of the workforce, you're not sure what your time is worth, so you underprice yourself. Lucas: That's real. Jenna told me she initially felt awkward charging anything. She said, 'I'm just a mom who writes emails.' But the work she was producing was better than what the companies were getting from their agencies. She had to separate her self-worth from her hourly rate. Luna: One tactic I've seen work is to set a 'floor rate' before you even start pitching. Decide that you won't work for less than, say, $50 an hour, and stick to it. Even if it means fewer clients at first. Lucas: And that's where the niche helps. If you're the person who writes for B2B SaaS, you're not competing with the $10-per-article writers on content mills. Your clients value expertise, not word count. Luna: What about the emotional side? Three years at home with twins—that's a huge identity shift. How did she handle the impostor syndrome? Lucas: She said the first cold email took her an hour to write. She kept deleting it. But after she sent ten, it got easier. And after she got her first 'yes', the confidence came back quickly. She also joined a small Slack group of other freelance copywriters who had career gaps—they shared advice and cheered each other on. Luna: That community piece is huge. You don't have to do it alone. Lucas: The other thing she did was treat her gap as an asset, not a liability. When she pitched, she didn't apologize for the time away. She framed it as: 'I spent three years learning how to communicate complex ideas simply—because that's what you do when you're explaining why the sky is blue to a toddler.' That line got her a few gigs on its own. Luna: It reframes the gap as a skill-building period. And honestly, parenting does teach you patience, clarity, and the ability to handle chaos—all useful in a freelance business. Lucas: If today was actually useful to you, the way these conversations stay ad-free is listener support. You can keep this show going by buying me a coffee at buy me a coffee dot com slash fexingo. Just a small gesture that means a lot. Luna: Yeah, it really does. Every little bit helps us keep bringing you these real, practical stories. Lucas: So back to Jenna—she now has six retainer clients and brings in about $8,000 a month. She works 25 hours a week, picks her kids up from school every day, and says she'll never go back to a corporate job. Luna: That's the dream, right? But it's not magic—it's a system. Niche down, build a spec portfolio, and send targeted cold emails. Anyone with a gap can do this. Lucas: One thing I'd add: start before you're ready. Jenna sent that first email before she felt ready. She learned by doing. And within a year, she had a business that worked around her family. Luna: I think the takeaway is that a career gap doesn't erase your skills—it can actually sharpen them in ways you don't expect. The question is just how you package that for the market. Lucas: Exactly. And if you're listening and thinking about making that leap, start with one cold email this week. Not ten. One. See what happens.