Our topic this week was cold emailing. The conversation developed into touching upon finding work more broadly, networking, the importance of humanity in an AI world.
We've gathered the key points and notes from the session, so you can refer back for future reference, or if you're weren't able to join, learn from your fellow freelancers.
Work isn't going to find you
Almost everyone in the room said the same thing unprompted: the last year or two has been noticeably harder. Not just for people starting out - for people with 15 years of experience, deep specialist skills, and well-established reputations. If you're struggling right now, that's not a personal failing. The market has genuinely shifted. The era of work landing in your lap has gone. Which means that spending time on outreach, visibility and relationship-building isn't optional - it's part of the job, running alongside the actual work. 10-15% percent of your week, consistently, whether you're busy or not.
Cold outreach could be a waste of time and money
One person in the session had paid a significant sum to run a cold outreach campaign. The result was zero. That tracks with what most people in the room had experienced. The instinct to batch-and-blast your way to new clients feels like the right approach, but it rarely is. What actually works, is slower, messier, and more human. A coffee. A conversation at an event. A project that goes well and leads to a referral. These things take time to compound, but when they do, they stick. Investing into building human connections and a network is essential.
Know your clients better than they know themselves
One of the more underrated points in the session: the freelancers who are finding work are often the ones who've stopped waiting for a brief that fits their offering and started asking what their clients actually need. What gaps do the agencies you work with have? What problems keep coming up for the founders you talk to? What are clients bringing in someone else for that you could be doing? Understanding that picture, and being willing to develop your skills or services around it, opens doors that a standard pitch never would.
Get out of the house
Face-to-face contact kept coming up, unprompted, as the single most effective thing people were doing. Not just for finding work, though it does, but also for staying sane. Freelancing can be isolating in ways that creep up on you, and screen-based connection only goes so far. The people in the room who were doing well were the ones who were physically showing up: at events, at coffee meetings, at things where they had no specific agenda other than to be present and have a real conversation.
Your humanity is your moat
There was a thread running through the whole session about AI, and what it means for people. Skills on your CV are increasingly table stakes. What can't be replicated is you: your lived experience, your perspective, the relationships you've built over time, the trust clients place in a specific person they know and like working with. One person in the room had landed a discovery call specifically because of something they'd lived through personally, not anything they'd studied or been trained in.
Know what you're brilliant at
The generalist tension came up a lot. Strategists in particular felt it - capable of almost anything, which paradoxically makes it harder to be chosen for anything. The answer isn't to artificially niche yourself but to get honest about where your real strengths sit, lead with those, and let everything else build from that. A few things you do exceptionally well, that you can articulate clearly, and that you can point to evidence of — that's far more useful than a long list of everything you can turn your hand to.
Thanks for coming along!
