Latest / The Comeback Career Podcast with Fexingo: Returning After a Gap, Stay-at-Home Re-Entry / How to Use a Career Gap to Start a Side Hustle
Transcript
- Lucas: So you've been out of the workforce for three, five, maybe eight years, and you're thinking about going back. But here's a question I don't hear people ask nearly enough: what if you used that gap to build something that actually becomes a selling point on your resume, not just a blank space you have to explain? Luna: You're talking about starting a side hustle during your career gap rather than just waiting to be hired again. Lucas: Exactly. And I want to anchor this with a real story. Maria — former marketing manager at a mid-sized CPG company — stepped away in 2019 when her second child was born. Planned to go back after a year. Then COVID hit, schools shut down, and her return kept getting pushed. By 2023, she'd been out six years. She told me she felt 'invisible' at networking events. But she'd also been building something on the side the whole time: a line of custom planners and productivity journals on Etsy. Luna: I love that. She turned the organizational skills she was using at home into a product. Lucas: Right. In her first full year, she did $50,000 in revenue. Not life-changing money, but proof of concept. And when she started interviewing for marketing roles again last year, that Etsy shop became the centerpiece of her portfolio. She didn't have to apologize for the gap — she led with 'I built a business that taught me e-commerce, customer acquisition, and inventory management.' Luna: That's a compelling narrative. So how does someone listening right now — maybe still in the middle of their gap — start down that path? Lucas: Three steps. First, identify a skill you actually used during your gap that has market value. Maybe you managed the family budget — that's bookkeeping. Maybe you coordinated a school fundraiser — that's event planning and donor relations. Maybe you helped a relative with their small business website — that's web design. Most people don't realize how much transferable work they've been doing. Luna: And step two? Lucas: Validate before you invest. Maria started with a single planner design. She printed five copies, photographed them on her kitchen table, and listed them. Within a week, three sold. That's your proof of demand. Don't build a whole inventory, don't buy a domain, don't incorporate an LLC until someone pays you for something. Luna: That's smart. Low-cost experiments. I read a ZipRecruiter survey from last year — 2025 — that found 42 percent of people returning to work after a gap had started some kind of side business during that time. And 68 percent of them said that experience directly helped them land their next job. Lucas: Those numbers are higher than I would have guessed, but they make sense. Employers in 2026 are hungry for evidence of initiative and adaptability. A gap with a side hustle tells a story. A gap with no explanation tells a mystery. Luna: But what about the practical challenges? Time, energy, maybe lack of confidence. If you're home with small kids or caring for an aging parent, where do you find the bandwidth? Lucas: That's the hardest part, and I don't want to gloss over it. Maria was putting in maybe five hours a week — late evenings after the kids went to bed. She wasn't trying to build a unicorn. She was trying to keep one foot in the professional world. And honestly, the constraint forced her to be focused. She didn't waste time on logo design or packaging aesthetics. She just made a product people wanted and listed it. Luna: So the key is to start small, really small, and let the side hustle grow at the pace your life allows. Lucas: Exactly. And there's a nice side effect. A lot of returners tell me the side hustle rebuilt their professional confidence long before they got a job offer. When you get a positive review from a stranger, or you make your first hundred dollars, it reminds you that you're capable. That's hard to replicate in a traditional job search where you're mostly getting rejections. Luna: I want to talk about the resume piece too. How do you frame a side hustle without it looking like a hobby? Lucas: Don't call it a side hustle on the resume. Call it what it is: 'Founder, ' or 'Independent Contractor.' List your responsibilities and results just like any other job. Maria put her Etsy shop under 'Professional Experience' with bullet points like 'Managed product lifecycle from concept to fulfillment across 12 SKUs' and 'Acquired 500+ customers through organic social media.' Luna: That's powerful. It turns a potential red flag into a career highlight. And I imagine it also helps with the age bias that some returners face. Showing you've been actively building skills — digital marketing, e-commerce, customer service — signals you're current, not rusty. Lucas: That's a great point. And it's worth noting that some side hustles can even lead directly to full-time offers. I know a woman in Chicago who started a dog-walking business during her gap. She ended up being hired by a pet insurance company as a marketing manager because they valued her direct experience in the pet owner community. Luna: That's a perfect example of how a side hustle can function as a career pivot tool, not just a gap filler. Lucas: Before we go further — and I don't want to break the flow here — I want to mention something quickly. We keep this podcast ad-free, and that's intentional. The only reason we can do that is because a small group of listeners supports us monthly through buy me a coffee dot com slash fexingo. If you've found our episodes helpful — whether it's the one on framing your resume or this one on side hustles — that's what keeps the lights on. Luna: Yeah, it's a pretty simple model. No sponsors, no ads, just listeners who value the show chipping in. It's been great to see that community grow. Lucas: Alright — back to the practical side. Let's talk about taxes, because this catches a lot of people off guard. If you earn more than $400 from a side business in a year, you need to report it and pay self-employment tax. That's roughly 15.3 percent on net earnings. So set aside a chunk of every payment you receive. Luna: And you can deduct expenses, right? Like supplies, a portion of your internet bill, maybe even a home office deduction if you have a dedicated space. Lucas: Exactly. Keep receipts. Open a separate bank account for the side hustle. And if you're not comfortable doing it yourself, the IRS has a free tax clinic program in many cities. Maria used the first year's deduction to offset most of her tax liability, which made the $50,000 revenue more like $42,000 net. Still a solid return on a few hours a week. Luna: One thing that comes up a lot in our listener questions is how to choose what kind of side hustle to pursue. There are so many options — freelancing, selling products, consulting, content creation. Any rules of thumb? Lucas: I'd say two things. One, pick something that leverages a skill you already have — don't try to learn a whole new field from scratch while you're also managing a gap. Two, pick something that produces a tangible output you can show an employer. A blog post is okay. A product you designed and sold is better. A consulting project with a real client is best. Luna: So the output should be something you can point to and say, 'I did this, here's the result.' Lucas: Right. And if you can get a testimonial or a review from a customer, even better. Maria had over a hundred five-star reviews on Etsy. She printed a few and brought them to interviews. That's social proof that speaks louder than any cover letter. Luna: I also want to mention that some platforms are designed specifically for career returners. There's a site called 'Mom Project' that connects women re-entering the workforce with companies that value their experience. And 'Path Forward' offers returnships — temp to hire programs — where a side hustle can be a strong differentiator. Lucas: Great additions. And let's not forget that the side hustle itself can become a full-time business if it takes off. Not everyone needs to go back to a traditional job. Some people use their gap to discover they'd rather be their own boss. Maria actually got an offer for a marketing director role last year but turned it down because her Etsy shop was growing 30 percent year-over-year and she preferred the flexibility. Luna: So the side hustle isn't just a bridge back to employment — it can be a destination in itself. Lucas: Exactly. And that's the thing about career gaps. They're usually framed as a problem to solve. But if you approach them with intention, they can be the most entrepreneurial period of your life. You have time to experiment, to fail small, to learn what you actually want. Luna: I think the key takeaway for our listeners is: don't just wait out your gap. Use it to build something, even if it's tiny. That tiny thing can open doors you didn't know existed. Lucas: And if you're already in a gap and thinking 'I have no idea where to start,' pick one skill you used this week — cooking, budgeting, organizing a playdate — and ask yourself how that could be a service or product someone would pay for. The answer might surprise you. Luna: Great advice. Thanks, Lucas. And thanks to everyone listening. We'll be back next week with another episode. Lucas: Take care, everyone.