Latest / The Career Mentor Podcast with Fexingo: Finding Mentors, Sponsors, and Career Advisors / How to Find a Mentor When You Are Self-Employed
Transcript
- Lucas: So Luna, you know that feeling when you're self-employed and you hit a wall — maybe a client's about to churn, or you're pricing yourself into a corner — and you think, 'Who do I call? There's no boss, no HR, no team lead to bounce this off.' You're the entire company, and the company has a problem. Luna: Yeah, and that's exactly the moment where a mentor would be gold. But when you're self-employed, the traditional path to mentorship just doesn't exist. There's no org chart, no 'mentor program' sign-up sheet. Lucas: Right. And that's the gap we're digging into today — how do freelancers, gig workers, and solo business owners actually find mentors when there's no corporate structure to hand them one? This is episode 159, and we're calling it 'Finding a Mentor When You Are Self-Employed.' Luna: And I love this angle because it's a huge and growing population. The latest Bureau of Labor Statistics numbers from last month showed about 36 percent of the U.S. workforce is now freelancing in some capacity. That's over fifty-five million people, and most of them are flying solo. Lucas: So let's start with the why. A 2026 study from the Freelancers Union and a couple of university researchers — I think it was Upwork's data team that helped — found that self-employed professionals who met with a mentor at least quarterly were thirty-eight percent more likely to report revenue growth year-over-year. That's not a tiny edge. Luna: Thirty-eight percent is huge. But the study also noted something interesting: only about one in five self-employed workers actually has a mentor. So the people who have one are getting a real advantage, but most are just… not doing it. Lucas: And that's the paradox. You'd think the people who most need guidance — the ones without a safety net — would be the most eager to find it. But when you're self-employed, you're also juggling client work, admin, marketing. Mentorship feels like a luxury you can't afford, both in time and money. Luna: So what's the realistic play? I mean, you can't just walk into your boss's office and ask for a mentor. Who do you even approach? Lucas: Let's break it into three concrete lanes. First: specialized online platforms. There's MentorCruise and GrowthMentor — those are two that are built specifically for freelancers and solo founders. You pay a monthly fee, get access to a vetted pool of mentors, mostly people with serious operating experience. Luna: I've heard of those. And the pricing is actually pretty accessible — some mentors on MentorCruise charge as little as thirty or forty dollars a month for a weekly check-in. That's less than a dinner out. Lucas: Exactly. And the beauty is the vetting process — they check backgrounds, they check reviews. You're not rolling the dice on a random LinkedIn connection. But here's the thing: you still have to be smart about who you pick. Don't just pick the first person with a shiny title. Look for someone who's actually built something in your niche, or even adjacent to it. Luna: What's lane number two? Lucas: Lane two is the mastermind group. This isn't one-on-one mentorship, but it's a close cousin. A mastermind is typically four to eight self-employed people who meet weekly or biweekly to hold each other accountable and share war stories. You're effectively getting mentorship from a small group, and you're also giving it. Luna: And there are structured versions of this — like Dynamite Circle for location-independent entrepreneurs, or the 10x Freelance Mastermind. But you can also start your own. I've seen people just put the word out in local co-working spaces or online communities and form a group that works really well. Lucas: That's a solid point. And actually, the research on peer mentorship in self-employment is pretty compelling. A 2025 study in the Journal of Business Venturing found that solo founders who participated in structured peer groups showed higher resilience and better decision-making under uncertainty. It's not just about getting answers — it's about not feeling like you're the only one facing the problem. Luna: And lane three? You mentioned three lanes. Lucas: Lane three is the one most people skip: approaching former competitors or people who have done what you're doing, but in a different market or a slightly different niche. Say you're a freelance graphic designer in Austin. There's a designer in Portland who's been doing it for fifteen years and has built a studio. They're not your direct competitor anymore — you're in different cities. But they've already solved the exact problems you're facing: how to raise rates, how to fire a bad client, how to hire subcontractors. Luna: That's a clever angle. And the ask isn't 'will you be my mentor?' — which feels heavy. It's more like, 'I admire what you've built. Could I buy you a coffee and pick your brain for thirty minutes?' Lucas: Right. And most people say yes. I've seen a lot of successful freelancers say that some of their best mentors came from a cold email that was specific, respectful, and low-pressure. But you have to be ready to reciprocate in some way — maybe you offer to help with something you're good at, or you just send a thank-you note and a small gift card. Luna: That reciprocity piece is key. Mentorship is a two-way street even when it's informal. So what about the financial side? Is it worth paying for a mentor when you're self-employed and cash flow can be tight? Lucas: That's a great question, and the answer is nuanced. If you're early and you're just trying to figure out the basics, free or low-cost options — like a mastermind or a former competitor — can get you a long way. But there's a real value in paying for a mentor because they're not doing you a favor. They're going to be more direct, more honest, because they're not worried about hurting your feelings or maintaining a friendship. Luna: And that honesty is exactly what you need when you're making decisions alone. A paid mentor can be the one person who tells you 'your pricing is too low' or 'that client is a time-suck' without sugar-coating it. Lucas: But here's a trap: the 'yes-person' mentor. If you're paying someone and they just validate everything you do, you're wasting your money. A good mentor should challenge you. They should ask hard questions. If you're paying and they're not doing that, it's time to find someone else. Luna: How do you vet that before you commit? I mean, on a platform you can read reviews, but with a former competitor you're just going on a hunch. Lucas: Good point. Before you commit to a long-term paid arrangement, do a trial run. Most platforms let you book a single session. And for the informal route, have a discovery call and come with three specific questions. Pay attention to how they answer — do they give you a clear, actionable answer, or do they hedge? Do they ask you follow-up questions? That's a signal they're actually thinking about your situation. Luna: And I'd add: check their track record. Have they actually built what you want to build? If you're a solo consultant trying to scale to a small agency, a mentor who's done exactly that is worth more than a retired corporate exec who's never run their own business. Lucas: That's a crucial distinction. And it leads to a point about industry fit. A mentor from a completely different industry can be incredibly valuable because they see your blind spots without being steeped in your industry's assumptions. But they need to understand the fundamentals of self-employment — the cash flow swings, the client acquisition struggle, the isolation. Luna: You know, that isolation piece — I think that's something people don't talk about enough. It's not just about advice. A mentor can be a lifeline for your mental health. There's research that links self-employment with higher rates of loneliness and stress, and having a regular touchpoint with someone who gets it can make a real difference. Lucas: Absolutely. And that's where the cadence comes in. It's not enough to have a mentor you talk to once a year. The study we mentioned earlier found the benefit kicks in when you meet at least quarterly. Some of the best arrangements are a thirty-minute call every two weeks, and that structure alone can help you feel anchored. Luna: So let's talk about the practical 'how.' Say I'm a freelance writer who's been going for two years. I want a mentor. What's my first step this week? Lucas: Step one: identify the gap. Write down the three biggest problems you're facing right now. Is it finding clients? Raising rates? Managing scope creep? Then match a mentor to that gap — don't just look for a generic 'successful writer.' If your problem is pricing, find someone who's written about pricing or who's built a profitable freelance business. Luna: And step two? Lucas: Step two: make a list of ten potential mentors. Ten. Mix it up — two from platforms you can pay, four from your network or second-degree connections, and four from the 'former competitor in a different city' bucket. Then reach out to all ten with a specific, personalized message. Mention something you admire about their work, state your problem clearly, and ask for a thirty-minute call. Expect maybe half to respond. That gives you five conversations to work with. Luna: That's a concrete plan. And I'd add one more thing: don't forget about the 'unofficial' mentors who are already in your life. That could be a former boss who now runs their own shop, or a colleague who left corporate to freelance six months before you did. They're not formal mentors, but they can be incredibly useful. Lucas: That's a great point. And it ties back to something broader — mentorship when you're self-employed looks different. It's not a formal program with a start and end date. It's a mesh of relationships: a paid mentor for specific skills, a peer group for accountability, a former competitor for war stories. You're building a personal board of advisors, but with a solo-operator twist. Luna: And that reminds me — we've talked a lot about finding mentors, but we should also mention the other side: being a good mentee when you're self-employed. The rules are a bit different than in a corporate setting. You're not being assigned a mentor, so you have to be even more respectful of their time. Lucas: Right. Come prepared to every meeting. Send an agenda beforehand. Follow up with a thank-you note and a summary of what you're going to do differently. Show them their advice had an impact. That's what keeps a mentor engaged. And when you can, reciprocate — maybe you offer to help with their website, or you send them a referral, or you just pay it forward by mentoring someone else when you're further along. Luna: Yeah, that's how the whole ecosystem stays healthy. And honestly, I think that's one of the best parts of being self-employed — you get to build your own mentorship constellation, on your own terms. It's not handed to you, which makes it feel more earned. Lucas: Well said. And that's the spirit we want to leave you with. If you're self-employed, you don't have to go it alone. There are platforms, there are peer groups, there are people who've been where you are. The key is to be intentional, be specific, and be willing to give as much as you get. Luna: And that's exactly what we do here on the show, too. We're listener-supported, which means we don't have a giant corporation backing us — it's just a handful of people who chip in a few dollars a month through buy me a coffee dot com slash fexingo. That's literally what keeps these episodes coming out, ad-free. Lucas: Yeah, it's a small group right now, but it makes a real difference. If you've gotten something useful from our conversations, and you've got five bucks to spare, that's the kind of thing that keeps us going. No pressure, but it does feel good to know people value what we're doing. Luna: Totally. And on that note — we'll leave you with a challenge. Before the week is out, send one message to someone you admire in your field, and ask for thirty minutes. Worst case, they say no. Best case, you've just found a mentor who could help you grow your business and your confidence. Lucas: That's the move. Thanks for listening, and here's to finding the mentors that help you build something you're proud of.