Latest / Freelance Careers with Fexingo: Independent Work, Consulting, and Self-Employment / How One Freelancer Built a Recurring Revenue Model
Transcript
- Lucas: So we get a lot of questions from freelancers who say the hardest part isn't the work — it's the unpredictability of when the next paycheck lands. Luna: Feast or famine. I've been there myself. One month you're swimming, the next you're wondering if you need to pick up a part-time gig. Lucas: Exactly. And there's a specific model that a lot of freelancers overlook that directly solves that problem: the retainer. Not just a one-off project fee, but a recurring monthly arrangement where a client pays you a fixed amount for an ongoing scope of work. Luna: It sounds ideal, but in practice, most freelancers I know struggle to land retainers. They feel like clients only want to hire them for discrete projects. Lucas: That's the perception. But I want to walk through a real case: a freelancer named Jenna Torres. She started out as a marketing manager at a mid-sized software company, went independent in 2022, and for the first eighteen months she was doing pure project work — website copy, email sequences, the occasional brand guide. She was good, but she was also exhausted by the constant sales cycle. Luna: What did she change? Lucas: She decided to target a specific type of client: early-stage startups that had just raised a seed round. They had product-market fit but no real marketing infrastructure. She pitched them on a monthly advisory retainer — four hours per week of strategic marketing advice, plus a monthly content audit. Her initial ask was $1,500 per month. Luna: Four hours a week, so roughly sixteen hours a month. At $1,500, that's about $94 an hour. That's decent, but not out-of-this-world for a specialist. Luna: So she went from feast or famine to a base of nearly a hundred thousand dollars a year just from retainers. And that's before any additional project work. Lucas: That's the multiplier. She still took on the occasional high-value project — a full brand refresh for $10,000 or a website overhaul — but those became bonuses on top of the stable base. The psychological shift is enormous. She told me, 'I stopped waking up at 3 AM wondering if I'd have work next month.' Luna: I think a lot of listeners are going to wonder: does this only work for marketing? Can a graphic designer or a web developer or a writer do the same thing? Lucas: Great question. Jenna's model works best for roles that involve some strategic component — it's harder to put a retainer around pure execution like data entry. But I've seen web developers do it by offering a monthly maintenance retainer: security updates, performance monitoring, a certain number of content updates per month. A graphic designer can offer a monthly brand retainer: social media templates, one larger design asset, quarterly brand audit. The key is that the client perceives ongoing value, not just a one-time deliverable. Luna: What about the negotiation itself? How do you bring up a retainer without scaring off a client who's used to project-based pricing? Lucas: Jenna's approach was to start with a project. Do the first engagement as a fixed-fee project — a one-month marketing sprint or a brand audit. Deliver excellent work. Then, at the end, have a conversation: 'You've seen what I can do in a focused month. Would it be valuable to have a lighter version of this every month? Here's what that would look like.' She found that about forty percent of project clients converted to a retainer when she framed it as a continuation rather than a whole new thing. Luna: So the project is basically a trial. That makes sense. And it lowers the risk for the client. Lucas: Exactly. There's no pressure to sign a year-long contract upfront. Most of her retainers started month to month after the initial project. The trust was already built. Luna: What about scope creep? I've heard horror stories where a retainer starts at four hours a week and then the client starts expecting eight hours of work. How do you hold the line? Lucas: Jenna had a simple rule: any request that would take more than thirty minutes goes into a queue, and if the monthly hours are used up, it rolls to next month or becomes a separate project. She also sent a weekly summary of what she accomplished within the retainer hours. That transparency actually reduced requests, because clients saw exactly where the time went. Luna: So the documentation itself is a tool for managing expectations. I like that. Lucas: I also want to mention a strategy Jenna calls the 'spider web.' Once she had a retainer client, she'd ask them quarterly: 'Who else in your network is facing a similar challenge?' She didn't ask for referrals in that typical awkward way. She framed it as: 'I'm trying to understand the landscape better. Who else is scaling marketing right now?' That led to introductions to other founders. Three of her four retainers came from one initial client's network. Luna: That's a spider web — one connection leads to multiple others. It's a lot more efficient than cold outreach. Lucas: And it's warmer. The introduction comes with an implicit endorsement. Jenna said she never pitched a retainer on a cold call. Every retainer started with someone who already knew her work. Luna: I think there's a broader lesson here about positioning. You're not just selling a service; you're selling a relationship and a predictable outcome. That commands a higher price. Lucas: And it changes how you think about your own business. Instead of looking for the next one-off transaction, you're building a small portfolio of long-term relationships. That's more stable and honestly more fulfilling. Luna: Before we go further, I want to mention something that makes this conversation possible. We don't run ads on Fexingo Business — that's a deliberate choice. If you find episodes like this useful and you want to keep the show free and independent, you can support us through buy me a coffee dot com slash fexingo. That's it — low-key, no pressure, just a way for listeners who value the content to chip in. Lucas: Yeah, it genuinely makes a difference. Even a couple of dollars helps cover hosting and research time. Alright, back to Jenna's story. Lucas: One more thing she did that I found smart: she created what she called a 'retainer ladder.' New retainers started at $1,500 per month for a baseline scope. After six months, she'd offer an upgrade to $2,000 per month that included a monthly strategy call and a competitive analysis. About half of her clients took that upgrade. She didn't raise prices on existing clients without adding value — she expanded the scope. Luna: That's a classic land and expand strategy. Get in the door with a low-risk offer, then grow the relationship over time. Lucas: And it works because the client already trusts you. They've seen six months of results. Adding another $500 per month feels like a no-brainer if the value is clear. Luna: What about freelancers who are just starting out and don't have a track record yet? Can they still use a retainer model? Lucas: It's tougher, but not impossible. I'd suggest starting with a low-risk project like Jenna did — maybe even a free or discounted initial consultation to build a case study. Then propose a retainer. The other approach is to work with a smaller business or a nonprofit that values predictability. You might start at $500 per month for something very narrow, like social media scheduling and one monthly report. Once you have a few case studies, you can raise rates. Luna: It's almost like you're building a product around your service. The retainer becomes a productized offering with a clear scope and price. Lucas: Exactly. And the clearer you are about what's included and what's not, the easier it is to sell. Jenna had a one-page PDF that listed exactly what a retainer covered: weekly check-in, monthly content audit, quarterly strategy review. No ambiguity. Luna: I also want to circle back to the psychology. When you have retainer income, it changes how you approach new opportunities. You can be more selective. You can say no to bad projects. Lucas: That's the hidden benefit. Jenna told me that before retainers, she said yes to everything because she was scared of the next dry spell. After she had $8,000 a month locked in, she started turning down projects that weren't a good fit. And ironically, that made her more attractive to better clients. Luna: It's the confidence of knowing you have a base. Clients can sense desperation, and they also sense when someone is in demand. Lucas: Right. So the takeaway for today isn't 'go get a retainer tomorrow.' It's: think about how you can reframe your service as an ongoing relationship rather than a one-time transaction. Start small. Use a project as a trial. Deliver so much value that the client wants to keep paying you every month. Luna: And if you're listening and you've already tried retainers but they didn't stick, what's the most common mistake you see? Lucas: Underpricing. Freelancers often set a retainer fee that's too low because they're afraid to ask for more. But a $500 retainer that barely covers two hours of work doesn't give you stability — it just gives you a low-paying obligation. Jenna was very deliberate about pricing her retainer at a level that made it worth her time and that the client perceived as valuable. $1,500 felt like a real commitment on both sides. Luna: So the retainer has to be meaningful enough that it's worth maintaining. Too low and it's not worth the administrative overhead. Lucas: Exactly. And one final thought: Jenna's story isn't unique. I've interviewed a dozen freelancers who've built similar models. The specifics differ — a web developer might charge $1,000 per month for maintenance, a copywriter might charge $2,000 for monthly blog posts and newsletter content — but the structure is the same. Find a recurring need, package it, build trust, and grow from there. Luna: That's a great note to end on. If you want to share your own retainer story or ask questions, we're always listening. Thanks for hanging out. Lucas: And if today's episode was useful to you and you want to keep it ad-free, buy me a coffee dot com slash fexingo helps. We'll be back next time with another deep dive.