Latest / The Comeback Career Podcast with Fexingo: Returning After a Gap, Stay-at-Home Re-Entry / How a Career Gap Can Help You Build a Side Business
Transcript
- Lucas: So you take a year or two away from the corporate ladder — maybe to raise kids, care for a parent, or just recover from burnout — and at some point you think, I could start something on the side. Not a full business, but something that brings in a little money and keeps my skills sharp. Luna: That's exactly what Maria did. She was a marketing manager at a midsize tech company, took a two-year gap after her second child, and by month four she had a freelance copywriting practice bringing in two thousand dollars a month. Lucas: Two thousand a month — not life-changing money, but real. And when she went back to full-time work, that side business became her single biggest negotiation chip. She could walk into interviews and say, 'I have been generating revenue independently for the past eighteen months. I am not desperate.' Luna: That confidence alone probably got her a better offer. But I want to break down how she actually did it, because the 'start a side business' advice is everywhere, but the execution is tricky. Lucas: Totally. And hey, before we go deep — if today's conversation helps you think through a career move or gives you one concrete idea to act on, honestly, that's the link. Buy me a coffee dot com slash fexingo. It's the smallest way to keep this show ad-free and focused on real stories like Maria's. Luna: Yeah, and we really appreciate those who do. It makes a difference. Lucas: Okay, so Maria's first step was validation. She didn't quit her gap and immediately build a website. She asked three former colleagues if they'd pay her to write a blog post or an email sequence. Two said yes. That's all she needed. Luna: She essentially did a smoke test with zero investment. And those first two clients gave her testimonials she could use on Upwork. Lucas: Exactly. Upwork was her primary platform for the first six months. She started at thirty dollars per hour, which felt low compared to her old corporate salary of eighty-five an hour, but it got her reviews. After twenty-five jobs and a five-star rating, she raised her rate to fifty dollars. Luna: And the reviews were the key. Because on a platform like Upwork, new freelancers without reviews get buried. She strategically took lower-paying projects just to build that track record. Lucas: Right. The principle is simple: you need social proof before you can command market rates. Maria said the hardest part was the first three months — she made only eight hundred dollars total. But month four, one recurring client gave her steady work, and that's when things clicked. Luna: So the side business wasn't just about income. It gave her structure. She had deadlines, she had to manage her time between parenting and client work, and she had tangible results to discuss in interviews. Lucas: And that's a huge point. When recruiters see a two-year gap, they often wonder, 'Did this person lose their edge?' Maria could point to a portfolio of published work, client feedback, and revenue growth. That's concrete proof of competence. Luna: But let's talk about the negotiation angle specifically. How did she use it? Lucas: She told me that in her final round interview for a senior marketing manager role, the hiring manager said, 'We're concerned about your two-year break.' Maria responded, 'I have been running a freelance copywriting business for eighteen months. I've worked with six clients, generated forty-two thousand dollars in revenue, and managed my own pipeline. That's not a break — that's a different kind of work.' Luna: Wow. That reframes the gap entirely. It's not a blank space — it's a startup. Lucas: Exactly. And she negotiated a starting salary that was ten percent higher than her previous role. The hiring manager told her later that the side business was the deciding factor. It showed initiative and resilience. Luna: So if someone is currently in a career gap and thinking about a side business, what's the first thing they should do? Lucas: I would say: pick one skill you already have — writing, design, consulting, bookkeeping — and find one person who will pay you for it. Don't worry about scale. Don't worry about branding. Just get that first transaction. Luna: And don't fall into the trap of over-preparing. Maria spent zero dollars on a website. She used a free LinkedIn profile and a simple portfolio on Google Drive. Lucas: That's a great point. The minimum viable product approach works for side businesses too. She didn't incorporate. She didn't open a separate bank account until she hit five thousand dollars in revenue. She kept it simple. Luna: But there are pitfalls. What are the most common mistakes you see? Lucas: The biggest one is confusing activity with revenue. People spend hours on social media, networking, and building a 'brand' before they ever make a sale. Maria focused on one thing: getting paid. That's it. Luna: Another mistake is underpricing too long. It's okay to start low to get reviews, but you have to have a plan to raise rates. Some freelancers stay at twenty dollars an hour for years. Lucas: Right. Maria had a clear rate schedule: thirty dollars for the first ten jobs, forty for the next fifteen, then fifty. She communicated it to clients upfront. 'My rate will increase after we complete ten projects together.' That transparency worked. Luna: And what about the transition back to full-time? She kept the side business going? Lucas: She did, but she scaled it back. She kept her two favorite clients and reduced to about five hours a week. That extra income — about eight hundred a month — gave her financial breathing room and a safety net. She said it made her less anxious about the corporate job. Luna: That's a smart move. Many people think they have to choose between the side business and the full-time job. But keeping a small version running can actually reduce stress. Lucas: Yeah, and it also keeps the door open. If the corporate job doesn't work out, she has a fallback. Plus, she can always scale the side business back up. It's like an insurance policy. Luna: So the key takeaway: a career gap doesn't have to be a blank space. You can use it to build something that not only generates income but also strengthens your negotiation position when you re-enter. Lucas: And you don't need a grand vision. Just one skill, one client, one transaction. Start there. The rest follows. Luna: I love that. One small step leads to momentum. Thanks, Lucas. Lucas: Thanks, Luna. And to everyone listening — if this episode gave you a practical idea, share it with a friend who's on a career gap. That's the best way to grow the show.