Latest / The Side Hustle Career Podcast with Fexingo: Second Income, Freelancing While Employed / How a Former Teacher Built a Six-Figure Consulting Side Hustle
Transcript
- Lucas: So I want to start today with a story that I think will feel familiar to a lot of you — especially if you've ever looked at your day job and thought, 'I could do this on my own.' Luna: That's a dangerous thought — in a good way. Lucas: Exactly. So this is about a woman named Jenna — former middle school teacher, taught history for about seven years. Loved the classroom, but she hit a ceiling on income and impact. So she started a side hustle doing curriculum design for educational publishers. Luna: That's a pretty natural pivot — she knows the content and the audience better than most. Lucas: Right. But here's where it gets interesting. She didn't go on Upwork or Fiverr. She went straight to LinkedIn. Started posting about lesson planning frameworks, engagement strategies, things she genuinely knew. And within a few months, a director at a learning management system company reached out. Luna: So she built authority before she had a portfolio of freelance work. Lucas: Exactly. Her portfolio was her teaching experience. The director asked if she could design a series of onboarding modules for new teachers using their platform. She said yes, quoted two thousand five hundred dollars for a six-week project — which was huge for her at the time — and delivered early. Luna: Two thousand five hundred — that's more than a month of take-home pay for most teachers. Lucas: It was. And she later told me that was the moment she realized she'd been drastically undervaluing her skills. That first client then turned into an eight-thousand-dollar monthly retainer for ongoing content updates. Within eighteen months, she was earning more from the side hustle than her teaching salary. Luna: So she didn't quit immediately? Lucas: No. She kept teaching for another year. She wanted the stability. But she used that time to build systems — a Notion database to track leads, a simple contract template, a pricing model that moved from hourly to value-based. Luna: Let's talk about that pricing shift. Because I think a lot of freelancers get stuck on hourly billing. Lucas: Totally. Jenna started out charging fifty dollars an hour. But she quickly realized that a project that took her twenty hours was worth far more to the client than just a thousand bucks. So she started quoting flat project fees based on the outcome. Luna: And how did clients react? Lucas: Surprisingly well. Because she framed it around value, not time. She'd say, 'This curriculum pack will save your teachers forty hours of prep each semester. I'm charging three thousand dollars.' That's an easy yes. Luna: It reframes the conversation from cost to investment. Lucas: Exactly. And she also learned to handle scope creep. Early on, a client asked for 'just a few more modules' after the project was signed. She did it for free. The second time, she had a clause in her contract that any changes beyond the original scope trigger a new quote. Luna: That's a hard lesson — especially when you're new and eager to please. Lucas: It is. But once she had that in place, her average project value actually went up, because clients started taking her more seriously. She went from two thousand dollar projects to five and six thousand. Luna: So what's the key takeaway for someone listening who wants to do something similar? Maybe they're not a teacher, but they have deep expertise in something. Lucas: I think the core lesson is: identify your transferable skills, then position them as solutions to business problems. Jenna didn't sell 'curriculum design.' She sold 'reduced teacher onboarding time' and 'higher standardized test scores.' Luna: It's about packaging what you know in the language of the buyer. Lucas: Right. And start where your audience already is. For Jenna, it was LinkedIn. She didn't need a website or a portfolio — she just needed to show she knew her stuff. One post about 'How to design a unit that meets state standards' got her first client. Luna: That's a great example. I want to ask about the Notion system she built. What did that look like? Lucas: She had a simple database with columns: company name, contact name, date of first outreach, status — warm lead, cold, proposal sent, closed. She'd log every conversation. That way she could see which channels worked best. Turns out, inbound from LinkedIn had the highest close rate, so she doubled down on that. Luna: So she used data to decide where to spend her limited side-hustle time. Lucas: Exactly. Because when you're working full-time and building a business at night, every hour counts. She was ruthless about tracking what worked. Luna: Let's talk about a mistake she made. You mentioned undercharging early on. What else? Lucas: Her biggest regret was not raising prices sooner. She kept the same rates for the first six months because she was afraid of losing clients. But when she finally doubled her prices — for new clients — she lost exactly zero. And the ones who stayed became bigger accounts. Luna: That's a powerful data point. Fear of price increases is almost always worse than reality. Lucas: It is. She also wished she'd niched down earlier. For the first year, she took any education-adjacent project. But once she focused specifically on teacher training for ed-tech companies, her reputation got sharper and referrals came in faster. Luna: So narrowing your focus actually widens your pipeline. Lucas: Counterintuitive, but true. People remember the specialist. They refer the specialist. Luna: Okay, so for someone listening right now — maybe they're a nurse, a mechanic, a librarian — what's the first step they should take this week? Lucas: I'd say pick one skill that you know better than ninety percent of the population, and write three LinkedIn posts explaining a specific problem that skill solves. Use real examples from your work. Don't pitch anything. Just demonstrate competence. Luna: And if no one bites after a month? Lucas: Then refine the messaging. Or try a different platform. But don't stop. Jenna's first ten posts got almost no engagement. The eleventh one — a breakdown of how she designs a unit backwards from the final assessment — got shared by a principal, and that led to her first lead. Luna: Consistency plus iteration. Lucas: Exactly. And I think that's a good place to mention something about the show itself. Luna: Yeah? Lucas: If these episodes have helped you think through a career move or a side hustle decision, we want you to know why they exist. We keep this podcast completely ad-free — no sponsors, no mid-rolls, none of that. And that's possible because a small group of listeners chip in monthly through Buy Me a Coffee dot com slash fexingo. Luna: It's a simple way to support the work we put into researching and scripting these episodes. And it genuinely makes a difference. Lucas: Yeah. So if you've gotten value from any of these stories, that's where you can help keep them coming. No pressure, ever. Just wanted you to know how it works. Luna: Alright. Back to Jenna — what's she doing now? Lucas: She left teaching last year. Her side hustle is now her full-time consulting practice. She's got three retainers and a waitlist. And she told me the weirdest part is that she earns more now working thirty hours a week than she did teaching fifty. Luna: That's the dream, right? More money, more time. Lucas: It is. But it didn't happen overnight. It took deliberate positioning, a willingness to raise prices, and a system to track what worked. Luna: So for anyone listening who's thinking about starting a side hustle, the blueprint is there. It's not magic. Lucas: It's not. It's just a series of intentional steps. Start with one post. See what happens.