Michael Jones is a New York City-based instructor, editor and recovering perfectionist. He’s also the founder of The Cool Humans Club, a members-only online education resource for modern professionals. Michael was formerly digital style editor and “Ask Michael” columnist at Condé Nast’s now-defunct Lucky magazine.
On relocating to New York City: “I booked a one-way ticket to New York City then drove to my parents’ house to tell them the news. Six days later, I was a New Yorker.”
On finally getting his dream job: “I got to do everything I’d ever wanted to do: Cover the shows, interview my favorite designers and influencers, attend press events, write, write, write — and write some more. It was my dream job.”
On the difference between print and digital media: “Digital was awesome because you really own your story from pitch to publication. With print, each department owned a specific part of a story, but when you’re a digital editor, you’re responsible for it all.”
On why he left media: “I missed learning and development. And I still wanted to have a hand in editorial. There aren’t many jobs out there that would allow me to flex both of those muscles.”
On the early days of entrepreneurship: “I wasn’t courageous to trust my own instincts, I listened to what other people thought I should be doing, which led me to give time to projects that cost me time, money and energy.”
In your own words, what do you do for a living? What’s your title, and how would you describe yourself beyond the restraints of a title?
Officially, I’m the founder of The Cool Humans Club, where I design, develop and deliver education and tools to a growing community of members who want to get noticed and get paid for the brilliance they bring to the world.
I’m also the editorial director of this site, which means I manage and execute the editorial process — researching and booking Cool Humans for conversations like these, editing and scheduling features for the site and planning upcoming special projects including roundtable discussions and live events.
In everyday terms, I’m a instructor, editor and recovering perfectionist who’s dedicated to winning in our new economy and helping others do the same.
When did you move to New York and what made you take the leap when you did?
I relocated to New York City from Dallas in 2014 to fulfill my dream of working in magazines. I got my first taste of the Big Apple in 2008 by little-white-lying my way into a freelance reporting gig covering New York Fashion Week for a regional newspaper in Los Angeles (I told the editor I was based in NYC when in fact I was in Texas). I fell in love with the city and was so sad when I had to leave. But I was still in school. And it really meant a lot to my parents for my sister and me to get educated.
After experiencing NYFW, I quickly recognized that the fashion world wasn’t designed to be accessible to people who looked and lived like I did, so I’d need to create my own platforms to get the experience I needed in case I ever caught a break. So when I got back to campus, I started a low-budget — well, in reality, it was a no-budget — independent digital magazine called JAYE that really helped me refine my editorial point of view.
I recruited an all-star staff of journalists to work on the project — including Evette Dionne, who’s now the editor-in-chief of Bitch Media and author [of the upcoming Fat Girls Deserve Fairytales Too], Chloe Metzger, who’s killing it as digital beauty editor at Marie Claire and Melissa Kimble, the founder of #blkcreatives and former social media manager at EBONY — and learned just as much about managing different personalities as I did about editing a magazine.
Anyway, it was a really hard time when I finally entered the “real world” after college. It was during the worst part of The Great Recession. Most of my friends and I deferred our dreams in an attempt to kind of just find our way through the economic wilderness — and figure out how the hell we were gonna climb out of our enormous student loan debt.
That had to be tough to try to tackle your dreams in that economy.
The pre-NYC days were a struggle. I worked retail and lived with my parents. I was resentful toward them because growing up they told me and my sister that if we got educated, worked hard and were decent people, we’d be set. So I was pissed when that didn’t happen immediately. Plus, from the outside looking in they had what seemed like stable jobs, health insurance, luxury cars, they could afford to go out to eat a couple of nights a week. Meanwhile, I couldn’t afford toothpaste. [Laughs]
To make matters worse, I felt like my parents didn’t really understand my creative ambitions. I started to believe that my dreams were less valid because they didn’t immediately translate to dollars and cents. And at the time, it seemed like that was all my parents cared about with regard to my sister and me. It produced a lot of family tension.
I also experienced a devastating heartbreak that spiraled me into a depression that was no-doubt exacerbated by my unwillingness to process my emotions in a healthy way — or get help from someone who could support me in doing that work.
My nephew Micah was really the bright spot of that period of my life. We were inseparable during those few years. He’ll probably be the bright spot of any period of my life, if I’m keeping it real.
When did things start to turn around?
Around 2012, I stopped worrying about becoming a magazine editor and just focused on getting the hell out of my parents’ house.
I got a job working at this startup financial services firm processing loan modifications for Bank of America customers affected by the housing crisis. It was an easy gig and enabled me to get my own apartment in a really nice part of Dallas. It felt nice to have a stable job, health insurance, and a luxury car. I could even afford to go out to eat a couple of nights a week. (Cyclone Anaya’s Mexican Kitchen used to be our after-work spot every Friday!) And I could finally afford toothpaste. [Laughs]
Eventually, we ran out of loans to process so they shut my department down.
Yeah, but by then I had my own team and they were really high performers so I’d made a name for myself within the company. They gave me a heads-up that they’d be getting more contracts in other departments and they would make sure I landed somewhere else.
I didn’t know it at the time, but my boss recommended me for an open position in the human resources department on the training team. I had the raw skills to be an effective trainer, but not the experience. So they threw me into the deep end and had me facilitate a few trainings and develop some curriculum on a trial basis.
I would go home and research stuff like “ADDIE instructional design method” and read books on how to facilitate workshops and techniques to hold the room. I knew if I got the position, I’d be making more money than I’d ever made. Plus, it was a cross-functional role with a ton of influence and would have me in front of executive decision makers and clients. I really wanted it. [Laughs]
Like I said, I’d given up on my magazine dreams and was resigned to be an exceptional corporate trainer and instructional designer.
Anyway, I got the gig and served as the lead trainer for some of the company’s biggest accounts. And I had an amazing boss who gave me a lot of autonomy to design and deliver curriculum in a way that felt authentic to my training and communication style.
Didn’t you and I connect around that time too?
Yes! I needed a creative outlet. So I started a fashion site called The Stylish Standout. It was like JAYE 2.0 but in blog format. So I would deliver trainings all day and write and edit posts for TSS all night. Those were some crazy times back then. We were such scrappy editors. [Laughs]
In early 2014, we found out Bank of America would be taking the work they hired us to do back in house. And the economy had started to bounce back so our company had a hard time attracting new clients.
Because my job fell under HR, all the trainers knew we would be one of the last teams to be laid off. So for months, we’d come to work and get paid to do nothing.
Sounds like a sweet deal to me!
It was! I would work on The Stylish Standout all day long. I loved it. Then on my birthday that year, my boss called me to her desk and asked me, “Why are you still here? You come in and work on your site all day and you’re so good at it. And it makes you so happy. Why don’t you just go to New York and do what you really want to do?”
I’m so grateful for that conversation because it made me reconsider New York City as an actual reality for me.
So I went home the day I got laid off and started crunching numbers. I knew based on how much severance I’d get that I could give NYC a shot. The next day, I asked my boss, who had a daughter the same age as me, what questions she’d have as a parent if her daughter told her she was moving to New York.
I wrote the questions down and answered them so I’d be prepared if my parents asked when I told them I was moving.
I booked a one-way ticket to New York City then drove to my parents’ house to tell them the news. Six days later, I was a New Yorker.
That was quick! What happened when you finally got to New York?
Listen, it was a rough few months. I’d worked so hard to get myself to a quality standard of living. And now here I was unemployed in one of the most expensive cities in the country. I applied for media jobs first thing each morning, then worked on The Stylish Standout. And most afternoons, I’d catch the 2-Train to Times Square to walk by the old Condé Nast Building because that’s where the offices for Lucky, the magazine I wanted to work at, were headquartered. I'd stand outside the doors and declare, "I'm going to work here one day." Then I’d go to the Barnes & Noble on Fifth Avenue and read all the magazines I couldn’t afford to buy. That was my routine.
Then about four months after my relocation, I was on LinkedIn. I saw a post from a friend who used to write for me at The Stylish Standout. She was an assistant at Lucky and she said they were looking for someone to start in the fashion closet ASAP. I sent her my résumé and had an interview scheduled 10 minutes later.
After a few rounds of interviews, I got the offer. And while I was excited to finally catch my break, I was insecure about the fact that I was 28 at the time and would be working with girls who were 21 or 22 or 23 and just out of college. Not to mention, the job only paid minimum wage. But I talked to my parents about it and they knew how much it meant to me — they said to go for it and we’d figure it out.
What was it like finally working at your dream magazine?
It was definitely a lot of grunt work. You had to pay your dues. But I loved the process of making magazines and producing fashion stories. Plus, I was obsessed with Eva Chen and the team she put together to execute her vision for Lucky. And now I was a part of that team? It was so wild to me when I thought about it.
Once I got over the mystique of working at Condé Nast, I realized I had a unique opportunity as an assistant to see how some of the sharpest editors in the entire world went about their business.
I took a notebook with me everywhere and asked questions about everything. I would go to "the wall" in the art department at 3:00 every afternoon to see which photos were selected for features — then ask the art directors why that photo was picked over this photo. I would ask market editors how they requested items from publicists or what they looked for when they were at market appointments. I would ask our features editors how they pitched story ideas for their sections to Eva and Leigh [Belz Ray, Lucky’s former executive editor]. And I would ask our beauty editors if I could take some cosmetics home to all my girlfriends, because, I mean, why not? [Laughs]
Eventually, I transitioned into another fashion assistant role. I still had administrative responsibilities — filing expenses, scheduling run-throughs, prepping for shoots — but I also got to edit the home and tech markets, which was really cool. I would call in samples for shoots and serve as the on-set art director for all our still-life photography in the magazine to make sure the stylists and photographers translated our editors’ vision into beautiful imagery.
What was so awesome about working at Lucky is how empowering the editors were. For example, Leigh knew I eventually wanted to edit and that I loved to write so she invited me to write cover lines for an issue — even though I had never done it before. Even though I was an assistant, they never made me feel like one.
Things were cool until Women’s Wear Daily reported Eva was resigning as editor-in-chief before she made it public. After that, nothing was the same.
What happened next?
They killed the print magazine and I got laid off. [Laughs] This layoff was different though because it was written about in the media on Fashionista, Refinery29, Women’s Wear, all the major fashion sites. So yeah, it really sucked to see your reality treated as tabloid fodder.
A friend knew I was looking for work and gave me a heads-up that Harper’s BAZAAR was looking for an e-commerce writer to write product copy for their shopping website ShopBAZAAR.
I wrote lots of product descriptions for The Stylish Standout and Lucky was a shopping magazine so I was familiar with captions and stuff, so I aced the edit test and got the gig.
It was cool to experience another magazine’s culture. Lucky was really fun and laid back. BAZAAR was really serious and fashion-with-a-capital-F, but not in a bad way. Lucky was all about high-low shopping, mix-and-match styling. BAZAAR was all about luxury. It was cool to write about clothes and accessories that cost more than my rent. That experience definitely gave me a boost of industry cred.
While I was freelancing at BAZAAR, Amanda [Keiser, Lucky’s former digital style director] hit me up. They needed someone to come in and return all the samples to the publicists who wanted their stuff back from the print stories they were borrowed for.
When I finished that project, she asked if I’d be interested in writing a few freelance articles for the website (Lucky was digital-only at this point). I said hell yeah, and she sent me an edit test. I knew Lucky like the back of my hand so I beasted that edit test too. So much so, Amanda and Verena von Pfetten [Lucky’s former executive digital director] created a staff position for me — digital style editor — which obviously I immediately accepted.
Your dream finally came true.
It was more than I could have imagined. Amanda ended up leaving to go to Club Monaco right after I got back to Lucky, but I learned so much from her. Miss Thing could write the shit out of a headline and she had such a grasp of what trends our readers would connect with. She was a really sharp editor too — I learned how to get the most out of copy from her.
Anyway, since Amanda left, they didn’t fill her position. So I reported to Leigh, who was now our digital editorial director. Leigh is by far the best editor I know. She really showed me how to top-edit a story and connect the dots for the reader. And she gave me so much rope to really make the section reflect my point of view. It was even her idea for me to write my weekly “Ask Michael” style column, which was such a cool opportunity.
Digital was awesome because you really own your story from pitch to publication. With print, each department owned a specific part of a story — fashion called in the clothes, photo booked the creative team and shoot location, features wrote the text for the editorial, art designed the layouts, production made sure we closed on time. But when you’re a digital editor, you’re responsible for it all.
I got to do everything I’d ever wanted to do: Cover the shows, interview my favorite designers and influencers, attend press events, write, write, write — and write some more. It was my dream job.
What were the hours like?
We worked a lot. At that point, the team was really small. Leigh would go pick her daughter up from school in Brooklyn and me and the other editors would go to press events after work. Then we would text or Slack in the evening over the lineup for the next day. I would stay up late working on my first feature for next day the day, then wake up early to help cover news before going to a press breakfast or market appointment. Then I’d finally go to the office and write two or three more stories.
To date, I’ve never been around more hard-working people than my Lucky crew. They made coming to work worth it every day.
But all good things must come to an end, huh?
Exactly. In hindsight, I think I was such an ambitious editor because in the back of my head, I knew our days were numbered. I wanted to get clips so I could have them to help me get another job in media. And when Condé Nast couldn’t find a company to buy the magazine, they closed up shop for good. I was one of eight employees there until the very bittersweet end.
Why did you ultimately decide to leave media?
At that point, I thought I’d be used to getting laid off — it was my fourth in almost as many years — but each one hurt more than the last.
After I got laid off, I applied and interviewed for lots of editorial jobs at magazines and for brands. But my heart really wasn’t in it. I knew I’d never have a job like Lucky because there’ll never be another magazine like Lucky. So I took a step back to think about what I wanted to do.
How did you make the leap into entrepreneurship from more traditional career paths?
It was more of a stumble into entrepreneurship. [Laughs] I call myself an “accidental entrepreneur” because I never imagined I’d be doing what I’m doing now. I thought I’d work in magazines forever.
But I missed learning and development. And I still wanted to have a hand in editorial. There aren’t many jobs out there that would allow me to flex both of those muscles. So my original intention in starting a business was to create the space for me to do both on my own terms.
I sorely underestimated what it took to be an entrepreneur. I didn’t understand the business of running a business. It was a steep, painful learning curve.
And because I wasn’t courageous to trust my own instincts, I listened to what other people thought I should be doing, which led me to give time to projects that cost me time, money and energy.
And when I wasn’t listening to other people, I was looking for shortcuts to make quick cash instead of focusing on building a sustainable business that could adapt to the evolution of our new economy.
Once I hit rock bottom in 2017, I went home to Dallas for about a month to reset. And I decided to come back to New York and give this business thing one more go. And it’s finally starting to be what I thought it could be. My new online education resource The Cool Humans Club enables me to practice my learning and development expertise, and this site reflects my editorial point of view in such a honest, thoughtful and inspiring way.
Pretty cool, huh?
Michael’s go-to spots in New York City:
The Union Square Greenmarket: “I started a ritual when I got to NYC where I’d go to Union Square every Saturday and buy flowers from the farmer’s market before popping into the Barnes & Noble across the street to grab a new book. I usually give the flowers away on my way home as a way to bring some joy to a fellow New Yorker.”
Spacious: “Spacious turns unused space into workspaces for mobile professionals like me. Even though I can work from any location in the Spacious network, I usually stick to Saxon + Parole in the Bowery or Café Medi on the Lower East Side.”
Muji Soho: “I’m that guy that still relies on pen and paper to keep track of everything. I’m obsessed with the gel pens and notebooks from this Japanese retail company.”
La Chula Harlem: “My friend Keomi took me here the other week and I can’t wait to get back. She swears by the fish and shrimp tacos. I’m about that chicken quesadilla life.”
First Corinthian Baptist Church: “So my mom would be on board with me moving to NYC, I made her three promises: I won’t become a drug dealer/addict, I won’t sell my body and I’ll find a church home. Joining FCBC is one of the best decisions I’ve made. Pastor Mike’s dynamic teaching and preaching has changed my life.”
???: “I love to hop on a train, get off at random stop and explore a new neighborhood through the eyes of a tourist. I always come away with inspiration for my business and a new appreciation of the city.”