Latest / The Comeback Career Podcast with Fexingo: Returning After a Gap, Stay-at-Home Re-Entry / How to Return as a Freelance Writer After a Career Gap
Transcript
- Lucas: So you take a five-year break from paid work to raise kids, and suddenly your resume has this big blank space where your marketing coordinator title used to be. The conventional advice is to volunteer, take a course, network. But today I want to talk about a different path — one that a listener named Jenna actually took to re-enter as a freelance writer. Luna: Jenna — she's the one who wrote in after episode 97, right? The one who said she felt like her writing skills had 'rusted'? Lucas: Exactly. Jenna was a marketing coordinator for a mid-size retailer before she had twins. She left in 2019, and by early 2025, she wanted back in. But she didn't want to go back to a 9-to-5 because her kids' school schedule was still a patchwork. So she decided to try freelance writing. Luna: And the big fear there is usually — 'I haven't written anything professional in five years. Who's going to pay me?' Lucas: Right. So Jenna didn't start by pitching The Atlantic. She started with a very specific three-step strategy. Step one: she wrote two guest posts for a parenting blog called Motherly — no pay, just bylines. Step two: she took those posts and built a portfolio on Contently, which is a free platform where writers showcase clips. Step three: she started pitching paid gigs to small businesses in the parenting and lifestyle space. Luna: So the unpaid work was basically her portfolio investment. How long did that take her? Lucas: About six weeks from the first guest post to her first paid assignment — a $150 blog post for a baby gear company. Within four months, she was averaging $2,000 a month from five regular clients. And the key insight here is that she used her parenting experience as a credential, not a liability. Luna: That's a smart reframe. Instead of saying 'I have a five-year gap,' she's saying 'I have five years of hands-on experience in the exact niche I'm writing for.' Lucas: Exactly. And this isn't just for parents. I talked to a former middle school teacher named Marcus who had a three-year gap after burnout. He wanted to write about education technology. Same playbook — guest post on EdSurge, portfolio on Contently, then pitch ed-tech startups. His first paid piece was $200 for a company called Nearpod. Within six months, he was earning $3,500 a month from four clients. Luna: I think a lot of people underestimate how much the freelance writing market has grown. According to a 2025 report from Upwork, the number of businesses hiring freelance content writers was up 34 percent from 2020. Lucas: Yeah, and the barrier to entry is lower than people think. You don't need a journalism degree. You need two or three solid clips, a professional email address, and the ability to deliver on deadline. Jenna's first client told her she got the gig because her pitch was clear, not because her resume was perfect. Luna: So let's talk about the pitch itself. What did Jenna's email look like? Lucas: She kept it simple. Subject line: 'Blog post ideas for — from a mom who uses your products.' Then two or three specific topic ideas with a sentence each. She linked to her Contently portfolio and offered to write a sample piece on spec. That's it. No long bio, no apology for the gap. Luna: And the response rate? Lucas: She said she pitched 30 companies and heard back from 10. That's a 33 percent response rate, which is actually high. Average cold pitch response rates are around 10 to 15 percent. But her niche was narrow — parenting and lifestyle — and she was pitching companies that already had blogs. They needed content, and she made it easy for them. Luna: What about rates? I know a lot of people are worried about undervaluing themselves. Lucas: Great question. Jenna started at $0.10 per word, which for a 1,500-word post is $150. Within a year, she was charging $0.25 per word — $375 per post. And she had repeat clients, so she wasn't constantly pitching. The freelance writers' union, the Editorial Freelancers Association, publishes rate guides. For an intermediate writer, the median rate is about $0.30 per word. So Jenna's trajectory is pretty typical. Luna: And I imagine the confidence builds with each paycheck. The first one is the hardest. Lucas: Absolutely. In fact, Jenna said her biggest hurdle was not the gap — it was imposter syndrome. She told me, 'I kept thinking, why would anyone pay me to write? Then I realized, because they need content and I can produce it faster than they can.' That's the mindset shift. Luna: I love that. One thing I want to flag — freelance writing isn't passive income. It takes discipline. You have to manage your own time, handle taxes, deal with slow-paying clients. But for someone coming back from a gap, the flexibility is a huge plus. Lucas: Right. And you can scale up or down. Jenna works about 20 hours a week now. She's never going to be a millionaire from it, but she's earning more than she did as a marketing coordinator, and she controls her schedule. That's the trade-off. Luna: And speaking of trade-offs — Lucas, you mentioned that a small number of listeners help keep this show going without ads. I think it's worth pausing to say that if Jenna's story or any of our episodes have helped you think about your own comeback, that's exactly why we do this. We keep the podcast ad-free, and a handful of listeners chip in on buy me a coffee dot com slash fexingo to cover the hosting and research costs. Lucas: Yeah, it's a small group, but it makes a real difference. No pressure ever — just if it's useful to you, that's the whole point. And if you ever want to toss a few bucks in the virtual tip jar, it helps us keep making these episodes for everyone. Luna: Exactly. Okay, back to the writing path. Let's talk about the common pitfalls. Lucas: Sure. The biggest one is burnout from over-pitching. Jenna's advice is to send no more than five pitches a week, and spend the rest of the time writing for existing clients. Another pitfall is accepting rates that are too low. If a client offers $25 for a 1,000-word post, that's $0.025 per word — below minimum wage. Say no. Luna: And what about the fear of rejection? That can be paralyzing. Lucas: Jenna's rule: expect a 70 percent rejection rate, and don't take it personally. Every 'no' is just a mismatch. She keeps a spreadsheet of pitches, responses, and follow-ups. That way, rejection becomes data, not a verdict on her worth. Luna: That's a good practice. I also think it helps to have a niche. Generalist writers have a harder time standing out. Lucas: Absolutely. Jenna's niche is 'parenting from a working mom's perspective, with a focus on baby gear and sleep.' Marcus's niche is 'ed-tech tools for middle school classrooms.' The more specific you are, the easier it is to find clients who need exactly what you offer. Luna: So if someone is listening and thinking, 'I have a gap, but I don't have a clear niche yet,' what should they do? Lucas: Write about what you did during the gap. If you volunteered, that's a niche — nonprofit communications. If you managed a household budget, that's personal finance. If you planned a family move, that's relocation and logistics. Your gap isn't empty; it's full of experience you just haven't framed as expertise. Luna: I like that reframe. And for listeners who want to start today, what's the single most actionable step? Lucas: Write one guest post for a blog in your niche. It doesn't have to be perfect. Just get it published. Then link to it in your email signature, your LinkedIn profile, and your portfolio. That one clip is your proof of concept. Everything else builds from there. Luna: And if you're nervous about the quality, remember that most small business owners are not professional writers. They're just glad someone else can produce the content. Lucas: Exactly. Jenna's first client told her, 'Your first draft was better than anything I could have written in a week.' That's the bar — not perfection, but reliability. So if you're sitting on the fence with a career gap, consider freelance writing. It's a low-cost, high-flexibility way to rebuild your professional identity. Luna: And if you try it and it's not for you, that's fine too. But the data says the demand is there, and the path is clearer than most people think. Lucas: Yeah. So to sum up: start with one guest post, build a free portfolio, and send 10 pitches a week. Track everything, ignore the rejections, and raise your rates every six months. That's the playbook. Luna: And we'd love to hear from you if you try it. You can always reach out through the show's page on Fexingo. Lucas: Absolutely. Until next time, keep writing.