He whispers, “I'd like to be an artist”

Coming to terms with my story and who I’d like to become

Hi there. Today is my birthday (please don’t steal my identity, hackers!), and so I’ve written something pretty personal about who I am and who I’m becoming. Hope you enjoy.

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I drew this the other day because I love a Venn diagram, and if you’re wondering, yes, I see it. It looks like two ovum being circled by dying sperm, but I guess that adds to the cringe. So I’m keeping it.

I drew this Venn Diaphragm Diagram after rewatching a video I had made last year:

I am, all at once, SO PROUD of these Harry Potter-themed barbs, and also SO EMBARRASSED that I filmed it like this, in my kitchen. This is cringe. But also, it’s amazing.

Maybe it would help if you knew that I made this video as a response to my (then) 10-year-old who was living DEEP in the Wizarding World (finishing the 7th book), and had just sent me (unprompted) a video of her doing a Dumbledore rap.

I’d share that video, but I’ve made a commitment to keep my kids off the internet, until they are old enough to choose their own online presence. Dad of the Year award? Why yes, thank you, I’ll have one.

Is this art?

Why do I make things like this?

Some people seem happy to live a quiet life, running in their own lane, but I seem to want more. What a diva I am!

There’s an entire corner of the internet dedicated to “dad jokes.” Bad puns that fathers say to embarrass their kids (or worse, they don’t realize how much the people around them pity their wordplay, and worst of all, they don’t care).

But not me. I have chosen to share these dad jokes and stories on stage at open mics. OPEN MICS, people! And here, with you.

Why? Is it some insecurity or brokenness that wants this?

What’s happening with me?

It was a Major Decision

I looked down the list of possible majors.

A few were obviously not for me. Science, Political Science (yuck), and Sports Med.

I was 18 years old. An incoming freshman at Pepperdine University.

I had to choose SOMETHING.

An overachiever could NEVER tick “undecided.” No way.

At the top of the alphabetical list was “Business Administration,” which seemed good enough. Useful enough.

I was good at math and liked the idea of having money, and I could always change it later, so I checked it.

But I never did change it.

And after four years of classes in Macro- and Microeconomics, Accounting, Strategy, Business Law and the like, I held a Business degree in my hands.

I don't regret getting that degree. But I'm not sure it was the right call.

Because what that 18-year-old kid REALLY loved doing was making funny videos (using a VHS camcorder!), rewriting song lyrics like Weird Al Yankovic, imitating Dana Carvey's impressions from SNL, and listening to Jeff Foxworthy's "You might be a redneck" comedy CD.

The problem was… there wasn't really a major for those things.

I could have checked Creative Writing, or Theater or maybe Telecommunications (what a terrible 90s name for video production!). Maybe I was fearful that those didn't feel solid enough. Not enough earning potential.

I found creative outlets in my own way, teaching myself website design and working in digital marketing. Creative-adjacent, respectable career choices.

I worked “two jobs” in my 20s — a web designer by day, aspiring actor and writer by night. I even studied Shakespeare at the Royal Academy of Dramatic Art in London. (brag)

My creative work turned into a successful run as an advertising agency founder — and ten years ago, that business was acquired, a tentpole life moment.

Somewhere along the way, I internalized the idea that I am a businessman.

As we were acquired, I exchanged my creative leadership role for an operational one. From CCO to COO, literally.

At the time, I told myself that I did this out of necessity. It’s what the company needed.

But honestly, I did it out of fear that my creative voice was unwelcomed, unnecessary, and that, in the acquiring company, there seemed to be value in operational sophistication.

I changed my professional identity to fit in. Wore the clothes. Talked the talk.

Here’s the thing, though. Being a “well-rounded executive” means smoothing away your most interesting parts.

Somewhere along the way, I forgot that I like art and creative ideas and jokes and speeches.

But little glimmers poked through.

Like when I (nearly) improvised this “bedtime story” about our company at the end-of-year presentation in 2016.

Is this art?

It felt like it.

I remember loving that experience — I got a standing ovation btw, nbd — but I also remember thinking that performing like that made me less valuable. Less professional. Less executive.

And I hid that little voice away.

I leaned into the idea that I was a successful entrepreneur.

After my company was acquired, I had a little extra money to my name, so I did what (I've since learned) most people do in my situation: they become investors.

"I'm good at my own business, therefore I must be a genius at advising others in business!"

In the past decade, I've made 124 small investments in 99 startup companies as an angel investor.

I am a businessman.

“I am diversifying my capital,” I thought, “and this is a great way of expressing my businessman genius.”

I started a new company with my former co-founder and friend.

Because my identity was “businessman,” I waffled between an operations-centric role and trying to be a creative leader. It didn't work. I spun out. Couldn't find my place. Even in my own company. I felt stuck. Even amongst friends and colleagues who desperately wanted me to succeed.

I left that company, with the support of that whole team (shout out to Alan and Bailey, especially) and I started doing three things:

1. I started a new company. A small brand consultancy called Spotlight & Co, named for my lifelong attraction for being centerstage (and occasionally cowering from the bright lights). We help organizations with creative work, writing, and strategy. I have a small, supportive team. We're good at this. Honestly, it's not a “good” business... meaning, it's not software or a product. There's no scale in professional services. But I don't care. We like solving problems and I like the fact that I get to show up, as my full self, to the work.

2. I started writing and sharing publicly. While I'm disappointed by the lack of METEORIC VIRAL GROWTH here on Substack, the process has been good. I'm not sure what this is, or even who it's for. Sometimes it's stories. Sometimes it's complaining(?). Sometimes it's jokes. It feels too loose to be worthwhile for anyone. Is this comedy? Satire? Self-help? What is this building toward?

3. I started getting on stage. Again, I don't know what this is. I've been doing storytelling and stand-up comedy, in rooms where most people are where I was 20 years ago. At their start. Most days, I worry that I've started too late. That I don't have the drive to get “10,000 hours” under my belt to be really good. That I don’t have what it takes to muster 3,000 performances. That success (by any defintion), is not available for me because I quit this path in my 20s.

Me and Jay-Z

“I'm not a businessman, I'm a business, man.” (Jay-Z, 2005)

“I’m not a businessman, and I'm not sure I care.” (me, 2025)

Today, I’m shedding the identity of businessman.

I’m admitting to friends and family, “I’m not sure I love this part of me.”

It was an idea I made for myself and served me well. Maybe it’s something I thought others wanted me to be.

The coat looked good on the mannequin, but never quite fit right.

I’m choosing that I can be IN business, but don’t have to BE business.

He gently whispers into his hand, so no one else can hear, except for God,

“I’d like to be an artist.”

But what does it mean?

It means letting go of what others expected you to be, or even the identity you thought would complete you. Being a “well-rounded businessman” meant shaving off your edges.

Being an artist is picking those pointy bits back up and gluing them back on, and mustering up the bravery to try again.

I’m looking at who I’m becoming, and again, I ask you…

Is this art?

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Thanks for reading along and for your support along the journey.

If you’d like to give me a birthday present, you can do any of the below:

1. Leave a comment or just reply to this email. I’d love to hear from you.
   

2. Sign up for the Westside Story Club email list. I’m producing and hosting the first stage show March 23rd (in Los Angeles), and I’d love you to come. Tickets info soon.

3. Brand conversations. Maybe you want to talk marketing, organizational values, or creative campaigns for your company? You can reach out to me and the Spotlight team.

4. Invite me to speak. I have a lot of stories about business, creative work, life as a dad, and more. If you have a venue or a conference or an opportunity in 2025, I’d love to hear from you.

Whew, this was a long one.

Looking forward to hearing from you.

Here we gooooooooooo—

Alec