How to Be Authentic in Everything You Do

01: Creativity

There’s something in the air. Maybe it’s summer giving way to fall. Maybe it’s school supply season. Or maybe it’s some creativity-inducing virus or bug. Whatever it is, everyone seems to be writing again. And everyone seems to want to be authentic.

In the past two weeks alone, I’ve had two friends restart their newsletters.

“I’ve been wanting to and wanting to [write]… putting pressure on myself as to what to write and finally decided yesterday—just to do it and see what happens.”Jason Flamm (Sketchpad Comedy)

“I want you to know that I’d prefer to have introduced myself earlier. I’ve been hiding behind bland, emotionless emails that I’ve sent out because I thought I needed to send something, anything. I’ve wanted to write you but I haven’t been able to find my voice. I find that I only write genuinely when wide awake late at night.”Steven Harowitz (Campfire)

Now, they’re back. But their newsletters are…different. They used to have singular foci—Steven on promoting his storytelling series, Jason on helping people write and produce sketch comedy. And while those nuclei are still there, still the motivation behind joining the newsletters in the first place, they’re increasingly subordinate to meeting the person behind the page.

More and more, I’m seeing newsletters reborn with a more personal touch. Newsletters that could have only been written by that author—with humanity front and center. It’s a welcome change from the days I used to spend on Medium reading dispassionate articles about the same six hacks to increase your productivity. The same articles over and over that could have been written by anyone (even a robot).

It’s possible that I self-select out of that kind of writing these days (because there’s obviously plenty of it), but I’m sensing something new in the air, a change in the weather—one that’s forcing us to be storytellers, to be authentic, to be more human. Writing that doesn’t say “do X then Y,” but instead creates the ghost of an image, letting the reader discover the lesson for themselves.

It may be more work for the writer and the reader, but it promises a more rewarding and memorable experience for everyone involved.

02: Improv

Although I’m writing this newsletter on Thursday, by the time you read it Monday, my first improv teaching session will be at an end.

It’s bittersweet.

On the bright side, I’m scheduled to teach another class that kicks off in two weeks—a Level 2 section—and I’ll get to continue teaching some of those students from Level 1. But, on a more disappointing note, I know some of those Level 1 students won’t return. They’ll each have their own reason as to why not—they didn’t end up liking longform, they only ever planned on taking one class, financial concerns, summer ending, my teaching—who knows. The scary thing, though, is that if I don’t get a few more signups, the class won’t run.

  • Personally (selfishly), it’d be upsetting. I wouldn’t have anything improv related to do. Since my Harold team was cut a couple months ago, I haven’t found or joined a new team. That was a conscious decision, but one I made with the assumption that I’d be teaching. And the prospect of no improv whatsoever isn’t something I’ve seriously contemplated since I started five years ago.
  • For the theater, new students are the lifeblood of the community. Yes, there’s a financial angle, but even more than that, new talent keeps things fresh—inspiring new teams and new shows, pushing everyone to improve.
  • Beyond my own or the theater’s self-interest—and most importantly—I think taking improv classes is just a good thing for folks to do. I’m not being hyperbolic when I say that improv changed my life, and I know it could do the same for many of my students if they stick with it.

What’s unique about my theater (or, what I think is unique) is that they don’t do a lot of advertising. Its growth is based primarily on experience and word of mouth. That’s a lot of pressure, because it means the community needs to consistently be welcoming, supportive, and non-cliquey. But it’s also empowering. I’ve spent eight weeks getting to know these guys, which means I have the responsibility, but also the awesome power, to reach out. To ask them, human-to-human, to continue classes—not for my own benefit, but with a personal story, with authenticity, and deeply-held conviction that it can change their lives.

03: Inspiration

At work last week, I got some disappointing news—a TV campaign I’ve been working on for six months was put on an indefinite hold. It wasn’t because of the work itself (there were some unrelated business considerations at play) but that doesn’t make it any less of a shame. The commercials featured real people, sharing real stories—they were personal and human, which I think makes for the best kind of advertising. Because true stories stand out.

Serendipitously, Faye, a reader of this newsletter, emailed me a few weeks ago with a similar insight. She told me about a direct mail campaign from the 90s that she still remembers today.

“What made those ads memorable was the “personal letter” written by the founder of the company. This “personal letter” obviously included information about the products being sold, but it felt personal because it included irrelevant details, like his son Duke buying a load of some kind of fabric the company had no use for. The sale helped out Duke’s college roommate buddy but something had to be done to use this material (it was taking up too much storage space in their warehouse) and this is the result. The product was almost irrelevant; what was important was the story that showed why they ended up with this material in the first place. Duke was always doing something impulsive and his father figured a way to use those impulses in a practical way. These “family stories” made the ad enjoyable.”

I did some digging and actually found one of those old letters in a book, appropriately titled The Greatest Sales Letters of All Time. Here’s an excerpt (but you can read the whole letter here).

“But y’know what? I can’t back up a car, as proven by the well-rolled lawn on both sides of my driveway. And again, y’all know what? I don’t give a hoot! I have my own speciality in doing things backwards. I reverse fashion trends! It works two ways. In the first place I don’t expose my customers to every freak fashion that comes down the pike. Secondly, I reject the idea that fashion starts at the top price lines and then has to trickle down to the rest of us when all the glamour is gone…”

The letter is long—four pages in this book—but there’s something compelling about it. It clearly wasn’t written by committee. It wasn’t focused-tested to death. It wasn’t triple-checked by lawyers.

It’s personal. It’s funny. It’s real. And Faye remembered it twenty years later because of its humanity. It’s another reminder to be authentic. That no matter what you’re selling—clothing, improv classes, even yourself—it’s not really about the product, it’s about the human connection.

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.