If you know me, you know when I find something I like, I tend to buy the same boots over and over. Keen, the ones that last forever and let me stand at an event all day and never once think about my feet.

I am a fan. Keen knows it, so they email to remind me they make boots I love.

I already own the boots. I am wearing them right now. And still the emails come, and I don't mind a single one.

Another favorite, REI, sends emails reminding me that I like being outside and should get out more, and that they can help.

Verizon emails me to remind me my phone is somehow already obsolete. Emails emails emails…but to tell you the truth I am not upset to hear from all of them, because I like these companies, their products and services.

But when it comes to ME sending out an email to clients? Then I start to worry…I sat down last week to email a client I drew for last year. Just a short note. A note to say “my fall calendar is filling up, I'd love to get your dates on it” kind of thing.

Suddenly I felt like a pest. Like I was “bothering” them. But if I take the same approach of thinking they (hopefully) like my services and products, am I really pestering?

Better With Markers than Emails

Some part of me still believes the work should speak for itself. That if the drawing is good enough, I should never have to send the email at all.

I can see the cost of that belief now when I look back. All the emails I did NOT send because of that worry.

I’m pretty confident to say that my drawing today is miles past where it was back in 2021. But the way I “sell” has barely moved. I have spent years getting better at the art and almost no time getting better at the part that puts the art in front of people.

The truth is I would rather just draw. That is the part I love, the part that feels like breathing. The selling is the part I would happily hand to someone else.

I said it out loud on a call this week. Can I just draw your sales funnel? Do I have to make my own?

Welcome to being an artist. You want to do the one thing. You would give almost anything to never think about the other thing.

The only difference

I’ve come to realize (with time and some gentle nudging from my business coach and a few colleagues) that if you are proud of your work, there is almost no difference between you and a company like Keen.

Keen makes great shoes and are proud of them. So they remind the people who already love them to put another pair on.

You make something people keep, the kind of thing that outlasts the AI meeting summary nobody ever reopens. Same pride, same thing worth telling people about.

The one difference is that Keen, or rather the people who work at Keen, do not lie awake wondering if the email is a bother. They just send it. You agonize over it.

But a reminder to someone who was glad to have you last year is not chasing. A friend of mine says the secret to marketing is to be known before you are needed. Sending that note means staying known, so when they need someone, you are already the first name on their mind.

You send it because you are proud of what you made for them.

And the note takes ten minutes. What costs you is the five hours you spend dreading it first.

So I am going to take my own advice. I am going to keep wearing the Keens, and I am going to send the email.

It’s kind to remind.

Grateful you are here,

Wade

PS - One more reminder: I'm building a course on how I turn live conversations into drawings at events. If you're interested, get on the list here and I'll let you know when it's ready.