After the B&B fumble, I went back to my list and kept sending warm emails.

Another one of them landed, a local travel agency. We jumped on a call.

We talked for long about our city and a mix of other things. While speaking, I understood one pain point very clearly: she was frustrated with uneducated leads coming to her door. The ones which kind of expect she would do her work for free, because you get the same value online from their point of view. But at the same time, they want her work. Ah!

She was passionate in the way people get when they've been doing something for years and feel genuinely misunderstood. I liked her immediately. She knows the values she provides. People booking with her know too.

But everyone else? Very often, they just tend to undervalue her work.

So instead of jumping to rates and ad slots, I proposed something different. A series of editorial pieces. We'd tell the story of the agency: the philosophy behind it, what goes into planning a trip that actually works, and, honestly, when it makes sense to go it alone versus when you really should call someone who knows what they're doing. In short, an attempt to educate the reader on something they probably hadn't thought much about.

It clicked. She did not had a budget in mind, so I shot €200 for four or five editions as long as the content makes sense. She was fine with it, so we booked a follow-up meeting at her office to go through the details.

The in-person meeting was even better. We sat down with a rough draft of a series of articles, she started adding her own ideas, and the conversation was flowing well. We agreed she would write the first article draft and we would move from there.

Then...awkward silence. We watched each other. It was money time. Before entering the room, I said to myself I would not do any extra work for free. But still, I always have difficulty switching the conversation to money.

I know. It's a business transaction. It's completely normal. But there's something about asking for money in person that makes your brain briefly short-circuit when you're not used to it.

So instead of just saying "I'll send you the invoice, please send me your details," I said something more along the lines of... "so, about the payment, it's 200 as we talked about...if you're ok with it. If you can send me your details I can send over the invoice....maybe?"

She looked at me straight in the eyes.

"Don't be afraid to ask for money," she said. "You're doing a service. You're helping me reach my goal. This is a business transaction. You're not doing me a favor. Actually, you should kind of make me feel you're doing the favor to me by reserving the sponsorship space."

Then she said something that stuck. She told me she recognised herself in what I was doing. In italian there's a saying which translates to "bring water with your ears". It means overdoing, which is a bad combo when matched with being afraid of asking for money back.

She does everything for her clients. Goes above and beyond. Adds extras they didn't even ask for, which make it perceive from the client as it's not a cost for her ( while it is!). She told me I was making the same mistake. Overgiving, while make her perceive I was devaluing my own work because afraid of asking for money.

She was teaching me how to sell. In person. And I am grateful for it.

We're still working through the details, and the sponsorship isn't fully locked yet. But something shifted in that office that had nothing to do with the campaign. I walked in a newsletter operator trying to close a deal. I walked out with a clearer understanding of what I was doing wrong and why.

Selling to local businesses in person is completely different from anything I'd done before. There's no screen to hide behind. No time to reread your message before you hit send. You have to control your tone of voice, facial expression, phrasing and timing...everything.

Turns out I had a habit I didn't know I had. I was hedging every ask. Softening every number. Treating requests for payment in a very shy way. Essentially, like my work and time is not valuable.

That ends now. If the work is worth something, say so. Ask clearly. That does not mean you need to be a dick, but simply be clear where you stand and go from there. Who you have in front will appreciate and respect you.

Simple in theory. Apparently took me a very patient travel agent to actually learn it.

Keep shipping,
Michele