Notes from the Trail · No. 5

Where to find clients when every inbox is full

Use digital for the research and planning. For the actual outreach, get out of cyberspace and into the room.

Issue No. 5 · October 17, 2026

Hey there -

A lot of people picture their freelance business running entirely from behind a laptop. Automate the prospecting, let the software send the emails, keep every conversation in text, and never actually have to talk to anyone. I get the appeal. It's efficient, it scales, and it skips the part most of us would rather avoid, which is walking up to a stranger and starting a conversation about their business.

But here's the thing - everybody else had the same idea, and now they've all got AI doing it for them. Every decision-maker at every company you'd want to work with is sitting on an inbox full of "personalized" outreach that was generated in bulk, a LinkedIn inbox full of the same, and whatever's leaking in through the contact form. They've stopped reading it. They glance at the sender, file it under spam in their head, and get on with their day. We’re all doing the same thing, right? How many emails did YOU get this week that you filed away as spam without even reading them? So when your perfectly good email arrives, it's one more item in a pile that was judged before it even got read.

To me, the mistake is treating digital as the whole business rather than one half of it. Digital is amazing for the research and planning side - picking the industry to serve, finding the companies in it that are growing, working out who the actual decision-maker is, reading what the trade press says their problems are this quarter etc. And AI has made that part faster than it's ever been. But the moment you move from learning about the prospect to talking to the prospect, my advice is to get out of cyberspace and into the room.

The room is the regional industry association meeting, the trade show your niche attends every year, the local chapter breakfast, the conference where your prospects are the ones speaking on the panels etc. And the reason it works is simple - nobody in a room is screening you. A person standing in front of them with a name badge and a sensible question about their business is someone they'll gladly talk to, even though that same person's email would have been deleted unread that morning. It doesn't need to be a pitch, either. Something like "I keep hearing that the new labeling rules are a headache for everybody in packaging right now - how is it hitting you?" opens a twenty-minute conversation about their industry, and twenty minutes of honest conversation does more than any 12-step email sequence ever will. A relationship has started, and as I always say, service business is relationship business.

My view is that this is also where you get ahead of your competitors. The freelancers leaning on AI for everything have picked the most crowded channel on earth, and the AI makes it more crowded every month. Meanwhile, back in meat space, the room has gotten less crowded because so many people decided showing up in person was old-fashioned. The competition moved into the inbox and left the trade show floor to whoever still bothers to turn up.

Use the laptop to find out who to talk to. Then close it and go talk to them.

I used digital outreach just like everyone else. But in the last 5+ years I’ve been reaching out to prospects via phone and in person much more often, and to much better results. But even going back decades, much of my work has come from people I met, people they introduced me to, and the repeat business and referrals that followed, which is a very short list of channels and none of them is an inbox. The relationships that carried me through two decades of industry shifts were started in person, by somebody deciding I was worth a conversation. That doesn't happen over email, and it barely happens over DMs.

So the question to carry into your week: where does your niche physically gather? Pick ONE event in the next 90 days and go. Bring a good question about their business rather than a pitch, and then do what all good salespeople do - listen to the answer.