Timm Chiusano: Challenges are an opportunity to do things differently
An interview with corporate America's nicest content creator
Welcome to Human Pursuits, the column that features need-to-know names and stories in media and other creative spaces. Today, a conversation with creator, and advisor for all things corporate America, Timm Chiusano
Some mornings, everything snaps into place.
I move seamlessly from my bed to the kitchen to the outside world, making friends and cherished memories along the way.
Other mornings, not so much.
I had one of those other mornings recently — where the alarm was too loud, and the coffee was too bitter, and the people on the bus were too rude, too smelly, too overwhelming.
It was enough that I briefly considered throwing in the towel. Turning around and going home.
But then I thought about Timm Chiusano, and what he might do.
As a creative executive at a Fortune 100 company, Timm built an audience of 1.1M followers by posting TikToks documenting the trials and tribulations of everyday corporate existence. In an era where every LinkedIn acquaintance is eager to share what the latest episode of Severance taught them about B2B sales, Timm’s vlogs stand apart in their sincerity. There’s no hard sell, or hustle culture solipsism. Just a guy trying to make work-life better for himself and his team.
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Ironically, his videos became so popular that, last summer, he “responsibly fired” himself from the job he spent five years documenting. He now creates content full-time. His team of more than 200 people dropped to one.
But while he no longer has to take the subway to midtown Manhattan, Timm still has his work cut out for him. If he has any instinct to turn back — to go home and hide under the covers — he hides it well.
By giving his best effort. By celebrating the wins where he can get them. By learning from his failures. It’s some real Human Pursuits stuff.
And so we had much to discuss.
Our edited and condensed conversation touched on spring cleaning, grace, meeting Ken Burns, creator content teams, his recipe for fish tacos, and more.
ES: How’s your morning going? It seems like you’re running at full speed.
TC: Yes, as always, but such is the good life. I’m trying to do some spring cleaning. I just had somebody come by to help me go through a whole bunch of crap that I’ve accumulated over the years.
ES: I watched some of your recent videos while prepping for this call, so I’m guessing today’s cleaning has to do with your massive sneaker collection.
TC: It’s more to do with all my clothes. I bought all of this stuff but I was working in an office and never got to wear it because I wore suits all the time. Now I work from home and can wear whatever I want, but I have too much shit! I can’t decide what to wear. This is an attempt to cleanse my soul, so to speak.
ES: You’re famously routine-oriented. Has it been hard moving away from that traditional 9-to-5 corporate structure?
TC: It’s fine. My biggest conundrum is determining what the hell my content strategy should be. The day-to-day posting. I feel like I should know what I’m doing tomorrow, and that should be halfway done already, rather than making it up on the fly. That lack of clarity eats up a lot of time.
ES: Did that on-the-fly strategy make more sense when you still had your office job? I’m interested to hear how exactly it has changed for you.
TC: The thing that changed is I’ve gone from being a conductor to being the whole orchestra. I’m the conductor, but I’m also the string section and the drums. I’m everything.
Before I could be like, “Cool, I have a $30M P&L and 240 people reporting to me.” Content was not my job, so the feeling was more “Whatever happens, happens.” I never really had to think about it too much. I spent so much time responsibly firing myself from that job, that I put no time or thought into what my day-to-day would be like on the other side. I’m still figuring that part out… I’m trying to give myself grace and fumble through it as best I can.
ES: This came up in last week’s interview with Isabel Pless, but it’s weird when your passion becomes your job. You were creating content because it presumably made you happy, but now you have to figure out how to protect that feeling, while also treating it like a serious operation.
TC: The amount of stuff that I learned while performing in a corporate environment is encyclopedia-worthy. Not because I was super smart, but because I was exposed to so many different facets of the business. The question now is: how do I extract that the right way? What audience am I trying to reach, and what tone or approach should I take? I want to get to a place where I can say “Next Tuesday I’m dropping part five or such-and-such a series…” The whole thing is one fascinating Rubik's cube.
ES: It’s worth remembering, though, that a lot of the bigger content creators that we all know often have teams helping them behind the scenes. I think of someone like Ryan Holiday, who I know you’re friendly with…
There’s not a single human being on the planet that [I think] I'm better than.
TC: Dude, thank you for saying that. One of the biggest things I’ve had to remind myself is that many people have strategists and writers whereas I’m doing almost everything myself. I have an editor helping me with long-form stuff, but that’s about it. It's tough when I see Lewis Howes or Jay Shetty racking up hundreds of thousands of likes and they’re copy-pasting other people’s tweets. It feels unfair to a certain extent. But I have to remind myself to make good shit and not care about the rest.
ES: They’re like little media companies unto themselves. You’re a solo operator.
TC: But also one of the reasons I’m a happy-go-lucky dude is that I genuinely understand there’s not a single human being on the planet that I'm better than. This is a bit of an aside but stick with me. The core argument within that idea is that I don’t know what anybody else has been through in their life, or what led up to the moment where I potentially cross paths with them… All to say, Ryan Holiday did the work to get there. He made different decisions along the way, but he did the work. It’s easy for me to sit here and say “Goddammit, I could hire someone too if I didn’t have to spend money on my kid’s tuition this year” but I’d rather be able to send her to a great school than have someone helping me edit TikToks.
ES: One thing I appreciate about your content is that you’re transparent about what could be seen as the overwhelming nature of being an independent operator. Sometimes it seems like you bite off more than you can chew, but you share that journey, and it feels relatable.
TC: Thank you. Some days you get beat up in the comments. “Oh this guy is pretentious” “He’s got an eating disorder.” But if I can sit here and confidently say that I’m still my mother’s son, then it must be okay, right?
In terms of biting off more than you can chew, I spent 20 years in corporate America. I’ve published all of my performance reviews from 2013 up until last year. That’s a bit of an anomaly within the career-oriented self-help space if we’re calling it that. Some high-level people have five direct reports. That’s not a small job, but I spent 10 years going through that, times a thousand. Maybe it seems like I’m taking on too much, but my resume shows I’ve got the goods to figure it out.
ES: Imagine how powerful you’d be if you didn’t read the comments.
TC: It’s funny, I haven’t opened TikTok other than to post since last Easter. I know that’s not smart for a multitude of reasons, and I’m sure it’s hurt me substantially performance-wise. But I’m trying to cut down on how much time I spend going to each platform. Right now I’m researching if there are tools that aggregate everything into a single inbox.
Some people see potential challenges as a hindrance. I want to see challenges as opportunities to do things differently.
ES: I was lucky enough to get married over the summer. Your wife Kelly appears in a lot of your content, and I wonder what the conversation was like when you told her you were “responsibly firing” yourself.
TC: She pushed me to do it way longer than I’d even contemplated.
ES: Really!
TC: Yeah. That’s how lucky I am. She said, “It’s not a question as to whether you can do it, it’s just a matter of how soon…” And also, she wanted me to hurry up to a certain extent, because she loves having me around.
For us, the weirder conversations started once I started having an audience and making connections. For example, three years ago, another TikTok creator named Old Time Hawkey flew to New York and went to a hockey game with us. We had never met him in person before. She was like, “Where is he going to stay?” It was more about random things than big life decisions.
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ES: That’s wild. One thing I’m always trying to be mindful of is how much I incorporate Leah or other friends into the newsletter because it is so personal. How do you navigate that?
TC: I look at it this way: if I’m smart about where her headspace is, and where the energy is in the house, then I’m picking my spots appropriately. There are definitely times when she’s like “Put your phone away, I don’t want to do this today”, but lately, it’s more about considering my daughter. She’s gonna be 13 this year, and so I’m trying to dial back how much she’s in it without her suggesting that she’s in it.
When I was at the office I could just do whatever the fuck I wanted, point the camera myself all day long. I’ve had to adjust because Monday is the only day where I have the house completely to myself all day. Some people see potential challenges as a hindrance. I want to see challenges as opportunities to do things differently.
ES: You met Ken Burns recently. How was that?
TC: Surreal. He’s an amazing, wonderful human being. He was kind and generous with his time and he was smart and as engaging as I would have ever expected him to be. It was the moment of a lifetime to meet somebody who is truly a storytelling hero of mine. I remember watching Baseball in my parents’ basement and it opened my eyes. I haven’t seen all of his work, but it was wild.
ES: Is Baseball your favourite Burns?
TC: I would recommend that to any sports fan. If you’re not a sports fan, watch Brooklyn Bridge.
ES: We’re almost out of time, but I wanted to talk about food. Your videos often include family dinners, specifically fish tacos. How do I make it Timm’s way?
TC: It’s gotta be a light white fish. As much as people hate on tilapia, it’s perfect here. It’s gotta be baked, not fried. Strawberry cabbage slaw is essential.
ES: Anything on the side?
TC: Guacamole always, but that's it.
ES: Homemade?
TC: We used to make homemade guacamole all the time, but it’s hard to get it good. We have a local place that makes fresh guacamole, so we’ll get a small tub of that. My daughter usually gets half an avocado because she’s not huge on guacamole yet.
ES: And for to drink?
TC: One shot of tequila, preferably still strength. I’ll take a sip of it when we start and a sip of it when we’re through, which leaves about half an ounce that I finish off at the end of the night.
Timm Chiusano is a content creator and advisor for all things corporate America. He lives in New York City.