Latest / The Comeback Career Podcast with Fexingo: Returning After a Gap, Stay-at-Home Re-Entry / How a Career Gap Helped One Parent Return as a Freelance Writer on Upwork
Transcript
- Lucas: Luna, I want to talk about a specific path back to work that I think gets overlooked because it's not a traditional job — freelancing on platforms like Upwork. Luna: Yeah, I've seen a lot of parents take that route. It's flexible, but it's also super competitive. How does someone with a career gap even get that first client? Lucas: Great question. So today I'm looking at the story of a woman named Priya — former marketing manager at a mid-sized consumer goods company. She took five years off to raise twins. When she wanted to go back, she didn't want the full-time commute. She decided to try freelance writing. Luna: Did she have any writing background, or was she starting from scratch? Lucas: She had some — she wrote quarterly reports and internal newsletters in her marketing role. But she'd never been a 'writer' per se. So she set up an Upwork profile. And the first three months? Nothing. Zero invites. Luna: Ouch. That's the part people don't talk about. What did she change? Lucas: She realised her profile was too generic. 'Marketing professional available for writing projects.' That could be anyone. So she narrowed it to a niche: writing blog posts and case studies for B2B software companies. And she started bidding on tiny jobs — $15 for a 500-word article. Luna: Fifteen dollars. That's below minimum wage in most states. Lucas: Exactly. But the goal wasn't to make money at that point. It was to get five-star reviews and build a track record. She did ten of those low-paying gigs in two weeks. Then she raised her rate to $25 per article. Then $40. Within six months, she was charging $75 for a 1000-word piece. Luna: So she treated it like a ladder. The first rung is almost unpaid, but it gets your foot in the door. Lucas: Right. And the key thing is she was transparent about her career gap. She put 'returning professional with five years raising a family' in her bio. Clients actually liked it — it showed she was organised and committed. Luna: That's smart. Instead of hiding it, she made it part of her story. Did she ever hit a ceiling on Upwork? Lucas: She did. After about a year, she was making $40,000 annually from regular clients. But she wanted to break $100,000. The problem was that Upwork takes a 20 percent cut from new clients, and eventually she realised she needed to go direct. Luna: So how did she transition off the platform? Lucas: She started telling her best clients, 'If you want to work with me directly, I can offer a lower rate because there's no platform fee.' A few said yes. She also built a simple website and started pitching guest posts on marketing blogs. That got her inbound leads. Luna: And now? Today, June 2026 — where is she? Lucas: She's been freelancing full-time for three years. She charges $150 an hour for content strategy consulting. Last year she grossed $120,000. And she works from home while her kids are in school. Luna: That's a great outcome. But I wonder — for every Priya, how many people try Upwork and give up after those first silent months? Lucas: Probably a lot. And that's what I want to dig into. The psychology of the gap and the platform economy. Because the skills are often there — it's the confidence that's missing. Luna: Yeah. And also the willingness to start small. A lot of people think, 'I was a marketing manager, I'm not writing for $15.' But the alternative is zero dollars and zero momentum. Lucas: Exactly. And here's another thing Priya did that I think is replicable. She didn't just wait for jobs. She wrote a sample article about a common problem in B2B marketing — 'How to Write White Papers That Actually Get Read' — and published it on LinkedIn. That one piece got her two inbound client inquiries. Luna: So she used content marketing to market herself as a content marketer. Meta. Lucas: Exactly. And that sample also served as proof when clients asked for writing samples. She didn't have to say, 'Well, here's a report from five years ago.' She had fresh, relevant work. Luna: Right. So the takeaway is: even if you're coming back after a gap, you can create new evidence of your skills today. You don't have to rely on old work. Lucas: Yes. And the freelancing path has another advantage: it's a trial run. You can test whether you even enjoy the work before committing to a full-time job. Priya realised she loved writing strategy but hated the administrative side of marketing. That helped her choose her next steps. Luna: So she could shape her career around her preferences, not just take whatever job was available. Lucas: Exactly. And that's the upside of a freelance re-entry. You're not just returning to the same role you left. You can pivot into something that fits your life now. Luna: I think a lot of parents worry that a gap makes them look outdated. But Priya's story shows you can rebuild credibility from scratch in a few months. Lucas: Yeah. And honestly, the fact that we can profile stories like this every week is because of listeners who support the show. Quick honest thing — a handful of listeners chip in monthly through buy me a coffee dot com slash fexingo, and that's literally what funds making this many of these episodes. No ads, just listener support. Luna: Yeah, it's a small group but it makes a huge difference. Keeps us independent and lets us cover niche topics like freelancing from a gap. Lucas: Exactly. So back to Priya — the other thing she did was network. She joined a few Slack communities for freelance writers. She wasn't just a lone operator. Luna: That's huge. Freelancing can be isolating. Having a community for advice, referrals, and moral support. Lucas: Right. And she got her first referral from a fellow freelancer who had too much work. That's often how it happens — someone passes a client along. Luna: So if you're a parent thinking about this path, what's the first concrete step? Should they create a sample, or set up the profile first? Lucas: I'd say do both simultaneously. Spend one day writing a strong sample article in your niche. Post it on LinkedIn, Medium, or your own blog. Then create an Upwork profile that highlights that sample and your gap transparently. Then start bidding on tiny jobs. Luna: And how many tiny jobs before you can raise rates? Lucas: Priya did ten. But I think even five good reviews can be enough. Once you have a track record, you can double your rates. The key is to never stop raising them. Every three months, reassess. Luna: So it's a systematic climb. Not just hoping for better clients, but actively pricing yourself upward. Lucas: Exactly. And one more thing — Priya recommends that if you're targeting a specific industry, use their jargon. In her B2B software niche, terms like 'ROI', 'lead generation', and 'pipeline' showed she knew the space. Luna: Right. So you're not just a writer — you're a writer who speaks the client's language. Lucas: Exactly. And that's the edge over someone who's never worked in that industry, even if they have a degree in English. Luna: One last question — what about the tax side? Freelancing means self-employment tax, quarterly estimated payments. That can be intimidating. Lucas: It's a hurdle for sure. Priya used a CPA her first year, and then she used accounting software. She set aside 30 percent of every payment. The key is to not ignore it. Luna: So the admin is doable. It just takes discipline. Lucas: Yeah. And look, the freelancing path isn't for everyone. But for a parent returning after a gap, it offers something a lot of jobs don't: control over your schedule, your rates, and your career direction. Priya's story is proof it can work. Luna: And she started with $15 articles. That's a low barrier to entry. Lucas: Exactly. So if you're listening and you're a stay-at-home parent thinking about going back, maybe try one $15 article. See how it feels. You might be surprised. Luna: Yeah. And if you've done it, we'd love to hear your story. Reach out to us. Lucas: Alright, that's it for this episode. Next time, we're looking at how a career gap helped one parent become a certified project manager.