Meet Sam Barone

We recently connected with Sam Barone and have shared our conversation below.

Sam, first a big thank you for taking the time to share your thoughts and insights with us today. I’m sure many of our readers will benefit from your wisdom, and one of the areas where we think your insight might be most helpful is related to imposter syndrome. Imposter syndrome is holding so many people back from reaching their true and highest potential and so we’d love to hear about your journey and how you overcame imposter syndrome.

Imposter syndrome is going to be felt no matter what. I just typed out answers to 6 of these other questions and deleted each one before coming back to this one. Why? I felt like I had no business talking like I’ve “figured things out.” Who am I to dole out intellectual anecdotes when in reality I have no clue how I overcome writers block (other than procrastination, and stress eating). I can’t trust myself to tell others how I do things because I don’t consider myself successful… which is a lot deeper than feeling like an “imposter” (and something I have to work on). I think behind every time someone feels “imposter syndrome” there’s a hard truth about themselves they’re not coming face to face to. But imposter makes it sound like we’re frauds. We’re not. We’re just people trying to be better. I’ll accept my truth and work on it. I can make a little list at the end of the week of my successes, or make a new (achievable) goal for each month, so I can remind myself to be proud of what I do.

Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?

I’ve been a standup comedian for over a decade. Around 2019 I started to feel that standup wasn’t a true expression of my comedy. I ended up quitting my job and moving back to Milwaukee to get a fresh start and idea on who I was. Being back in this city made me realize the friends I had left behind moved on to some amazing ventures. Small businesses, music projects, and artistic endeavors all made them who they were. I wanted to be the person to celebrate that while also showcasing who I could be. Milwaukey to the City was a born concept.

I took the format of a Late Night Show and made it work for me. There are 3 guests; A comedian, a local business owner, and a musical act–all from Milwaukee. Each guests performs, interviews, and plays made up games with me. For each local business on the show, we’ll go and film on location. I’ll “work there for a day,” or take a tour and we document how the business the operates. We premier the video live during the show! There’s lots of Milwaukee celebration.

The show lets me be myself completely. I make all the props and prizes, write all the interviews, host and book the entire year. It’s been an amazing learning experience. While the show is done for 2024, there’s a lot of exciting news we’ll be announcing for 2025. I can’t say anything yet though!

If you had to pick three qualities that are most important to develop, which three would you say matter most?

1) Write everything down. Writing things down makes them one step closer to becoming materialized. At any given point there’s a thousand ideas in my head, and only 10 of them will ever be made (whether it’s now, next week, or next decade), and you’ll never know which ones those are. The other 990 are good, but take up space. Even though I know i won’t make all of them, It’s important to write them all down. Otherwise your brain makes it a bad habit of always “remembering” them and it tends to create more stress than not. You try to come up with new ideas, but that one is always at the front. Write it down and forget about it so your brain can too.

2) Just make the thing. Whatever it is just make it. Stop thinking about what it’s going to be (good, bad, ugly, beautiful, amateur, bumpy) and just start. Took me too long to realize that good ideas done poorly are a lot better than good ideas not done at all. You can not, and will not, get better at something if you don’t do it all the time. The coolest part about ideas is that you can always redo them. Are you a better sculptor now than you were 3 years ago? Try something from the past, again.

3) Break things down. Admittedly I’m very bad at this. If there’s something I’m confident will only take 6 hours, I’ll wait until 7 hours before it’s due to even start. Don’t do that. It’s dumb. While I do get some amazing ideas under pressure, I’m also probably taking away 4 days from my life due to the stress put on my heart. Make a schedule and break up those project hours. 3 hours here, 1 hour there, will save yourself a lot of pileup. DON’T trick yourself into thinking that procrastination is helping you become creative. I do this all the time, but I’m an idiot. I’ve done plenty of long term projects that have been incredible because I chipped away at them instead of doing it all at once. If you’re procrastinating, dive deep into the stress you’re feeling and work on it. Chances are there’s something else you’re worried about instead of the “deadline” and your brain just doesn’t want to deal with it.

Awesome, really appreciate you opening up with us today and before we close maybe you can share a book recommendation with us. Has there been a book that’s been impactful in your growth and development?

Calvin and Hobbes is always within reach to me. Calvin’s daydreaming, yet substantially solid view of the world always strikes me. It’s silly, but I’ll always admire Calvin, and hope to be him some day. I can’t really elaborate. He’s just got it figured out.

Hobbes is just as unique. Is he a tiger, or a stuffed animal? It’s never said and both are always implied. Depending on who you ask you’ll get either answer. It’s said that’s why C&H never made it past the pages. Bill Watterson never wanted to merchandize because you’d lose the wonder in who Hobbes is. Depending on where you are in your life, Hobbes changes, and I think that’s really wonderful.

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Diego Avila

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