On Cake

01: Creativity

Email is impersonal. It’s cheap. It’s ubiquitous. It’s unavoidable. Unlike a letter, made personable by handwriting, fancy cardstock, and one-of-a-kind-ness, email is black type on white. It’s basically effortless. Mindless. And can be sent to thousands without a second thought.

No one likes getting email for those reasons and more. Which is too bad. Because most of the time, there’s a living, breathing human on the other side of the screen who knows as little about you as you know about them. Someone who’s sitting there, wondering what you’re thinking…if you’re thinking about them at all.

I promise this is not autobiographical whining. Or, it’s not intended to be. It’s actually something even I forget sometimes.

A few months ago, I started following an entrepreneur, Jay, who publishes daily emails. I was catching up on a bunch of them the other day and came across one with the spectacular subject line “Do you guys listen to good hip hop that doesn’t talk about guns and pussy?” As Jay describes in the email, that line was the opener to a pitch, by a random guy on the street, for an upcoming hip hop show. Although those are the interactions we typically walk away from, Jay stopped and heard the guy out. And, in the end, they exchanged phone numbers with plans for a future show together.

It was just a short email, but there was something authentic and touching about the story. That’s when I remembered Jay was a guy, just like me. So I responded. Nothing big or fancy—just a little thank you for his thoughts.

Jay immediately wrote back with a thank you. But that wasn’t all. He asked if there was any way he could help me (which was obviously above and beyond since the guy sends me an email every day).

But he asked, so I answered.

I said I was impressed by the amount he was writing, and I could tell he was really passionate about his work. I confessed that I had been feeling uninspired. That I was struggling to send out a single email every other week. Serendipitously, he had just record a podcast episode with his friend David on that exact topic.

The episode was great, but there was one thing David had said that I wished he’d spent more time on. I told Jay as much. And what did he do? He cc’d David and set up a call between the two of us so I could personally follow up with my question.

As it turns out, David is one of the founders of Death to the Stock Photo. If that doesn’t mean anything to you, then what you should know is that David’s kind of a big deal. He runs a profitable, successful newsletter where he shares stellar photography—his own and other artists—for use in blogs, websites, and more (for free). I was a bit starstruck. Here was a guy with 500,000 followers who was going to give me a half-hour of his time to talk about my dumb creative blocks. And all because I fired off a random, complimentary email.

02: Improv

While all of this was happening online, IRL I was dealing with some improv highs and lows. After the team I’d been coaching for a year was disbanded, the team I’d been performing with for two and a half years was cut. Two big improv projects gone.

Thankfully, the month before all that went down, I’d expressed interest in teaching at my theater’s training center, and the director generously gave me his Level One class. I was elated. So when the two teams were cut, it wasn’t like I had nothing, but I did feel the need to fill the space. I didn’t want to walk into my first day of Level One without a team to show for myself.

I turned around and auditioned for a new show, but (thankfully) wasn’t cast. It wasn’t a good fit—I wasn’t passionate about the idea. I just wanted to be able to say I was on a team, which is a bad reason to do anything. And once I realized that, I felt freer.

I didn’t need a team. There’s nothing wrong with taking a few months off while I figure out the kind of improv I want to perform. Now I have more time to enjoy and learn from this new teaching gig.

And for the record, none of my students have asked why I’m not on a team…

03: Inspiration

So what does all this have to do with a new email format?

When I talked to David, he made a few great points. Nothing that I didn’t already know in the back of my head. But having him explicitly say what I’d been thinking was powerful.

The day after our conversation, he followed up via text:

david's cake text

I do not know if he initially meant cake one way or the other or both, but it felt serendipitous and meaningful.

A big reason why writing this blog has been hard in the last couple months is that I’ve felt compelled to stick to what I’ve always been doing. That got me here, so why stop now? I worry that if I experiment, if I do something different, I might lose folks. But that’s the opposite of what I should be doing. It’s unnecessary and harmful stress.

Blogging is like improv in that way—trying to do “good” improv or “correct” improv is the easiest way to fail.

I started this project as a way to experiment. To write differently than I do at work. To explore topics that interest me. So I shouldn’t stop doing that. I should be eating cake.

That’s where the new email format comes in. It’s an experiment. And since we’re in the inspiration section, I will happily admit that I borrowed this idea from Manjula Martin’s Three Cents newsletter. For now, I’m hoping to focus on three things with this new format (which is no longer called the Monday Memo but Three Things, obviously)—creativity, improv, and inspiration (again, obviously). So, let’s see where this goes. I hope you’ll join me…because I can’t eat all this cake alone.

Each week, I write a new article helping busy people find meaning and fulfillment through sustainable creative habits. If you enjoyed this week’s letter, you can sign up to get them delivered to your inbox each week by digital carrier pigeon.