Freelance Debrief 22nd Nov: The unsexy side of freelancing

In this episode, I’m pulling back the curtain on something I haven’t done in years: I launched a brand new service. Aaaaand... It kind of happened by accident. After 12 years in business, adding something new feels very different to when you’re just starting out. There’s more reputation, more pressure, more imposter syndrome. I found myself thinking, Who am I to offer this? What if I mess it up? But what unfolded was a completely organic pivot inside an existing client relationship. In this episode, I walk you through: How this new service evolved from a single blog post The exact 3-pillar structure I created to turn an idea into a real offer How I handled pricing something I’d never sold before Why I offered a transparent “trial month” (and what happened after) The mindset shift that helped me move through imposter syndrome Why you don’t have to do a dramatic reinvention to evolve your business

In this episode, I’m digging into one of the most frustrating questions freelancers face: is it you, or is it the market? And the honest answer is… it’s usually a mix of both, just not in the way most people talk about. I break down the real (often invisible) reasons some freelancers stay fully booked while others struggle, even when they’re talented, experienced, and doing “all the right things.” We’ll talk about positioning, reputation, relationships, visibility, mindset, and the role privilege and timing play. I also share practical shifts you can make if you’re feeling stuck right now: how to clarify what you offer, build trust before clients are ready to buy, stay visible without burning out, and move from passive “post and pray” marketing to something that actually works.

In this episode, I’m easing back into the podcast with a very honest January debrief. I’m sharing how I actually felt wrapping up 2025, why last year felt so turbulent for freelancers across the board, and how things are starting to shift as I head into 2026. We’ll talk about: Why 2025 felt so uncertain for freelancers (and why it wasn’t just you) Taking proper time off, and why delaying client work can sometimes be the best move What’s been happening in my business since coming back in January Existing clients increasing their workloads again (and what that signals) How I approach January planning without locking myself into rigid, year-long goals I’m also sharing how I use January as a kind of “testing ground” for the year ahead. I pay attention to what’s coming in, how I’m feeling, and let that guide my next moves instead of over-planning too far in advance.

In this episode, I’m breaking down the ridiculously simple nurturing system that helped me stop chasing hundreds of leads and start building real relationships that actually turn into clients. I used to believe I needed this huge outreach machine that involved endless DMs, massive spreadsheets, and a “pipeline” I could never keep up with.  Now, I focus on intentionally nurturing just 5–10 people a month, even when I’m not actively looking for work. I’ll walk you through exactly how I do it, why it works, and why most freelancers don’t need more leads, they just need the right people to feel familiar with them. 

In this Freelance Debrief, I’m pulling back the curtain on the messy, unsexy backend of my business, from switching accountants to finally reviewing my expenses, and why every freelancer needs to do a regular business audit. I’m also talking honestly about one of the toughest parts of freelancing: clients going silent. At the start of November, four clients promised briefs… and only two delivered, which completely threw off my schedule and revenue planning. I share how I’m navigating that, why the usual “just get paid upfront” advice doesn’t always fix the problem, and what freelancers can do instead. Plus: diversifying my offers, why freelancers are craving personalised 1:1 help more than ever, mentoring sessions selling out fast, and the surprising new client enquiries that came in, including one from a huge international brand. 

In this episode, I’m breaking down the one framework that completely transformed the way I generate freelance leads... the idea that every opportunity arrives on one of two timelines. For years, I lived in panic mode, refreshing my inbox and wondering why my lead flow felt so unpredictable. It wasn’t until I understood the difference between my short-term pipeline (the quick wins) and my long-term pipeline (the assets that compound over time) that everything finally clicked into place. In this episode, I share: ✨ The real reason some freelancers stay consistently booked ✨ The controversial truth about what’s actually holding most people back ✨ How to balance short-term momentum with long-term authority ✨ The simple rhythm I use to keep both pipelines working without burning out ✨ Practical examples you can start using today, even if your pipeline feels empty If you’ve ever felt like you’re either hustling too hard or waiting too long for leads to appear, this episode will give you a grounded, philosophical, and honestly refreshing way to think about your business.

In this Freelancer Debrief episode, I’m breaking down exactly what’s been happening behind the scenes in my business over the past couple of weeks. I walk you through the brands I’m currently working with, the types of content I’m creating, and what’s changing in my client lineup. I also dig into the two client “buckets” I’ve identified in my business. Plus, I share a peek into the warm-pitching system I teach inside Pitch & Prosper and how I’m currently using it myself to expand my network. I talk through my LinkedIn connection strategy, the little experiment I’m running around sending messages with connection requests, and some early wins from students putting the system into action.

In this episode, I break down exactly what I’d do if I were a freelancer struggling with inconsistent income and craving more stability. This topic has come up again and again in my mentoring sessions lately, especially among freelancers who are wildly talented but stuck in a cycle of one-off projects, feast-or-famine income, and constantly starting from scratch. I walk through the real process I’m using right now with one of my mentees, from mapping the last 12–24 months of client work to uncover hidden patterns, to building simple “client buckets” that help you identify where the ongoing work really is. I also share how I would generate a warm list of 50–100 potential prospects, reactivate former clients, and start outreach in a way that feels natural, human, and low-pressure (no awkward sliding into DMs or cold pitching strangers).

In this fortnight’s debrief, I chat about my freelancing retreat in Morocco, how it helped me shake off a creative rut, and why I’m leaning back into the kind of work that actually lights me up. I also share a little behind-the-scenes story about a client and AI (and why I’m still firmly team “human craft”), plus some good news about client renewals and the mentoring sessions I’ve been running. If you’ve been feeling a bit flat with work or questioning what you want your next chapter to look like, this one’s a cosy catch-up with lots of reflection and gentle momentum.

In this episode, I’m breaking down the two phases every freelancer cycles through: seeking work and maintenance mode. I’ll walk you through the lean system I use when I need clients fast, plus what to do once you’re fully booked to keep your network warm. This is the exact rhythm that’s helped me stay consistently booked without constant pitching or panic.