#48: Free Agency

This is gonna be a long one, strap in.

This week, I found out that I’m being laid off from my job at the end of January.

Because of this life update, today’s newsletter is going to be a little different. I got an idea last night while working on updating my resume: I’m going to share my real resume with every job I’ve had the last 11 years with a key lesson I learned at every stop of my professional journey thus far. Consider this like an annotated resume on steroids. Before we begin, you should listen to this song for context into my mind right now so you fully understand the energy I’m bringing to my job search (and life in general):

ERNEST C. WILKINS III <—— That’s me.

I’m @ernestwilkins everywhere on social/Here’s my LinkedIn!


Mess Marketing: February 2019 - January 2020

Director of Content

Co-creator/Producer of podcasts: “Overserved” (food/drink), “Rockin’ With The Bigs” (sports) and “Office Hours with Ernest Wilkins” (business/culture).

Despite not knowing how to make a podcast at the beginning of the year. I made 67 podcasts from start to finish in 2019. (“From start to finish” to me means BRED: Booked it. Recorded it. Edited it. Distributed it.)

This year, I was lucky enough to help bring Overserved to life alongside Ari and Maggie. We were named one of Chicago’s best food podcasts and I know more about food and drink now that I’d ever dream possible (Don’t worry, there will be a season two!).

(A fun thing: if you podcast and use Transistor.FM as your distribution platform, that’s me on the homepage)

Key Takeaway: One Thing A Week

Whether it be a podcast, a newsletter, an event activation or just a playlist, I have created one new thing every week this year. It is a pain in the ass to make One Thing A Week. However, it only gets better the more you do it, like smoking meat or having sex. The key is to build a habit of creation.

One Thing A Week.  

Hold yourself to that one standard in your creative pursuits. You can do it, I promise!!!

Reverb.com: December 2017 - October 2018 

Marketing Manager, Reverb LP

Reverb is a music equipment community and reseller that was recently acquired by Etsy.  In my role, I helped to create the brand identity, brand voice and content strategy for Reverb LP, the recorded music category for Reverb.com. As a bonus, I got an on-the-job MBA in product marketing and got to work with Reverb’s supremely-underrated content marketing and social operations to build out LP-focused content like this: 

We got John Oates to rank Hall and Oates albums!

Key Takeaway: Learning On The Job Is The Job

There’s this thing that happens once folks get past age 30 where it feels like there’s nothing else to learn, especially if your role is heavy project management or process-based. If that’s how you feel, adjust that thinking pattern. You don’t know as much as you think you do and even if you’re the rare exception that’s at the top of your game, you still can learn from adapting other perspectives. Even in the most soul-killing jobs where you don’t learn a new skill, learning life things like office politics or learning how to finesse a system will put you ahead of everyone else. Wherever I land next, I can promise that I won’t come in guns blazing, acting like I know everything because Learning On The Job Is The Job.

Red Bull: February 2015 - December 2017

Activation Manager, Culture

  • Lead Storyteller for art/music/dance projects across the Red Bull portfolio in my region.

  • Lead content strategy and content production, Red Bull Music Festival - Chicago (2017)

  • Helped to build full digital communications and marketing plans for Red Bull House of Art (now Red Bull Arts: Detroit)

Key Takeaway: Culture Is Important! 

Red Bull’s reputation in the action sports world is well-earned but I believe they’re on a very short list of brands that can say they ran culture marketing in the 2010s. I’ve seen up close the structural and financial investments into local scenes, the impact of spending those time and resources on demographics early has had on the bottom line — psst, marketing folks: you shouldn’t have had to make a specific strategy to target Hispanic audiences, you should have been talking to them from jump!!! — and because of those investments into culture, I’ve been lucky enough to be in the presence of greatness way before they broke big:

(Jamila Woods, Lizzo and a fan, 2016)

Culture is Important. Your office culture, the culture around your brand, the local culture your business exists in. It’s all important. I’m always skeptical of people who either dismiss the importance of culture for a brand — these are the people who are usually the main ones who never want to spend on marketing their projects, also they’re usually real snoozes at parties — or those companies that over-communicate how perfect and happy their brand culture is. Cult Vibes are out in the 2020’s. 


2009 - 2015

Staff Writer

I wrote columns across music, sports, culture, men’s interest and nightlife during a pivotal time in Chicago’s cultural legacy.

Exhibit A:

Exhibit B:

I also got to dip a toe into personality/hosting:

Key Takeaway: Put Yourself Out There

Redeye helped develop my voice as a writer. I wrote about my dad dying and why the WNBA deserves your respect (Here’s a video of me getting my ass kicked on the court by future 2-time WNBA MVP Elena Delle Donne). The gig and my entire career wouldn’t be as successful if there wasn’t an full investment into putting myself out there. As a creative, you’re making something unique to you and your view on the world, right? Put yourself out there so people can fall in love with your perspective.

Freelance Content Strategist                         

2009 - present

  • Consulted on the digital marketing campaign for Season 4 of “The Boondocks” for Cartoon Network’s Adult Swim.

Freelance writer

2009 - present

I’ve been lucky enough to write for publications including GQ, Complex, Pigeons and Planes (I still believe I got the best Smino interview to-date), Rolling Stone, Pitchfork, Jordan Brand, Chicago Magazine and the late great Deadspin (I’m not linking to the current site because I don’t want to give them clicks because fuck them)

Key Takeaway: Do One Thing For You.

I’ll write about this in a later issue, but I have one major spring/summer and fall/winter project a year. For example, Office Hours is my spring/summer 2019 project. My fall/winter 2020 project is already underway. I love having multiple things going on! This format isn’t a foreign concept if you’re a homeowner, there’s always a project to do, right? That’s how I process my creative output. Do one thing for you. In my ideal next job, I’d be able to execute high-level projects while still being able to pursue my side hustles. Regardless, Do One Thing For You. If you’re in a spot where you don’t have time to do a huge thing, do a little one. Be kind to yourself while you’re doing it, too!

So that’s that. 11 years of experience summed up in one newsletter. The hope is that something you read here today will help you in your own explorations as a creative businessperson or push you to finally jump into that side hustle you’ve been eyeing. The world is going to shit anyway, might as well do something that makes you happy, right? 

In the meantime, if you have a lead on a full-time gig you think I’d be perfect for or want to collaborate on a project or just want to give me tickets to the 2020 NBA All-Star Dunk Contest, e-mail me!!!

If you enjoyed today’s Office Hours, I hope you’ll consider a paid subscription. Paid subscriptions allow for a better newsletter from me which means more value for you. In addition, paid subscribers will receive exclusive newsletters and early access to the live Office Hours tapings.



Every quarter for the last 7 years, I make a playlist and throw in songs. At the end of year, whatever was in each playlist gets put into one playlist. Here’s 2019’s! 

Office Hours is written by Ernest Wilkins. Seriously, he can use a job.