The Founder's Series, Part 3: Michael Jones, Founder, The Cool Humans Club

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The Intro


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.


The Highlights


  • On why we’re all creative: “Our imaginations are infinite. We’re always generating ideas. No one — myself included — has a monopoly on creativity.”

  • On our responsibility as creators: “We’re not here to be bystanders or observers. We’re here to start where we are with what we have to leave the world better than we found it.”

  • On the limitations of technology: “Technology is awesome for making my ideas happen. But when it comes to generating ideas and shaping them into something meaningful, all of that usually happens when I’m out in the world.”

  • On overcoming creative blocks: “When I’m in a rut, I’ll either create my way out of it, do something like a crossword puzzle or get around people to make their life better.”

  • On his creative process: “What works about my process is that it’s gives me enough structure so as I’m out in the world and paying attention to what I react to, [I’ve already removed] a lot of guesswork and anxiety because when I sit down to work, I’ve already brainstormed and planned everything out.


The Conversation

Michael Jones interviewed by Christine Cauthen on December 11, 2018. This conversation is the third installment of The Founder’s Series, a four-part deep-dive into the life and work of the founder of The Cool Humans Club. This interview has been edited and condensed.


I’ve always admired your creativity. From an outsider's perspective, you make it look so easy to brainstorm and pump out incredible ideas, for businesses, editorials, etc. Do you find it easy to tap into your creative side?

First of all, thank you! Here’s how I’ll answer your question: Our imaginations are infinite. We’re always generating ideas. Whether you have a job that pays you for your creative output or you’re daydreaming to distract you from the job you wished paid you for your creative output. So I always bristle when people tell me they’re not creative. No one — myself included — has a monopoly on creativity.

I remember when I was doing customer research during the early stages of The Cool Humans Club. What I found is that most of the professionals I interviewed had more than enough ideas to last a lifetime.

I think what distinguishes me and the people who have ownership over their work and life from those that don’t is that I produce my creativity. And then I share and sell that production in public. That’s all good when people are noticing and paying for what you’ve poured God knows how much time, effort and money into to create a product, service or experience. But on the flipside, I also flop in public a lot too.

And that’s the part that makes creativity scary. Because not every idea’s going to be a home run. In fact, most ideas won’t be. People are gonna judge. Technology will go bonkers at the worst times. You’ll probably underestimate how much budget you need and overestimate how much revenue you’ll earn.

So all things considered, Christine, I can understand why people would rather hold their ideas hostage in their imaginations instead of making them happen in reality. It keeps you insulated from market scrutiny. There’s little risk involved. It’s safe.

But I’ve always enjoyed the challenge of being the answer to issues that matter to me and the people who connect with my work and world view. So in a sense, I consider my creativity and the ideas that come from it the catalyst to help me be the best answer to the most critical issues.

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Has that always been the case?

Oh, absolutely. [Laughs] My mind is always at work. I’m always curious about and fascinated by why things are the way they are and why they have to stay that way if we don’t want them to.

So anytime I couldn’t get access to or afford a seat at the table, I created my own and invited people to it. I learned early on that creativity could get me places that I’d normally be excluded from as a black gay man from the south. I always wanted a big, amazing, beautiful life. I learned early on creativity could get me places that I’d normally be excluded from.

I also think what’s helped me along the way is that I’ve always had a pretty clear and consistent point of view. So my creativity isn’t as all over the place as people sometimes think. It’s grounded in a few expressions that have obviously evolved over the years but remained really consistent for the most part.

I’m not creative for the sake of causing a ruckus — God bless the people who are, by the way — I’m creative because I actually believe in the people I’m looking to empower through my work.

What’s your ideal environment for tapping into your fountain of creativity?

As far away from my computer or phone as possible. [Laughs] Technology is awesome for making my ideas happen. But when it comes to generating ideas and shaping them into something meaningful, all of that usually happens when I’m out in the world.

This question actually reminds me of when I worked in magazines. Most fashion publications have what are called “market editors.” And those editors are responsible for a specific “market” or category like denim or jewelry or the French ready-to-wear market or American contemporary designer market.

The best market editors spend as much time in their market learning about the people, themes, trends and economics that are driving the fashion within that category. Then they come back to the office and conceptualize their discoveries into stories and features that their readers can shop and consume.

That’s kind of how I approach my work today. Nowadays, the world is my market. So I spend as much time out in the world. Then I settle in behind the desk to create products and services and experiences that reflect my point of view and empower my people to work and live on their own terms.

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How do you approach moments where you might feel a creative block?

There’s a saying in basketball that “shooters shoot.” When someone like Steph Curry or LeBron [James] is going through a slump, they don’t stop shooting. They do one of three things: 1) They shoot themselves out of the slump. 2) They make an easy play to give them the confidence to take more challenging shots. 3) They look to make life for their teammates better by getting them involved in the action.

I approach my work like an athlete. But instead of using my body to make my first $1 million, I’m using my mind.

So when I’m in a rut, I’ll either create my way out of it, do something like a crossword puzzle or get around people to make their life better.

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What inspires you?

I’m so inspired by the human experience. I mentioned how resilient humans are in Part 2 of this series. And it’s so inspiring how we have the capacity to create the change we want to see on the planet. It’s inspiring how humans can reinvent themselves.

I’m inspired by our capacity to source love, grace, patience and transformation if we’re willing to bet on ourselves and bet on the hearts of people — even those we don’t agree with. Even those who are unwilling to acknowledge our humanity.

I’m inspired by everything that’s not working in the world. Because it’s proof that we were created for such a time as this. We’re not here to be bystanders or observers. We’re here to start where we are with what we have to leave the world better than we found it. I’m inspired by the people willing to accept that call to action.

Nature inspires me too. I’m often humbled when I think about the fact that we were born into a world already stocked with the natural resources we would need to become the best version of ourselves. Man oh man.

Who do you look up to as creators or entrepreneurs?

Hmmmm. [Extended silence] They’re not entrepreneurs (yet?), but I look up to my niece Jordan and my nephew Micah. They’re as creative and dynamic as they come. I want to be like them when I grow up.

What advice do you have for creators who are struggling to make time for themselves and their ideas in the midst of working in a corporate environment?

If possible, share your creative ambitions with decision makers and people who have the resources, access and influence to help you dedicate more time to whatever you’re working on. Sometimes these people will be your managers, other times they’ll be leaders in other areas of your organization who are willing to create a win-win for everyone involved.

I shared a story in Part 1 about a boss who knew I wanted to be a fashion journalist. So when I told her about [my blog] The Stylish Standout, she let me come in a few hours early or stay a few hours late so I could get some writing and editing done during the day.

And remember Leigh, my editor at Lucky, who let me write cover lines and assigned me my own column because she knew I wanted more time to write? I had tons of other responsibilities, but she really worked with me so I could get it all done.

If that’s not possible yet, then look at how you’re spending the time you do have ownership of. You may have to make some trade offs but remember that they’re in service to your vision. Also, if you want to make your creative project how you get paid, then consider developing a three-, six- or 12-month exit strategy for how you’ll leave your corporate job and transition into self-employment.

Also establish, optimize and document the strategies, systems, processes you use in your creative project. If you can’t carve out more time to produce your creativity, then your next best bet is to figure out how to be more efficient with the time you do have.

Ultimately, what I’d offer to creators who have a side hustle is to be exceptional at your main gig. Performance is usually what drives decision-makers to give their employees more autonomy to work on secondary projects.

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What’s your creative process?

Everything starts with a deadline. [Laughs] My procrastination and perfectionism rear their ugly heads if my work isn’t guided by a due date.

I have a master calendar that has all the release dates for the deliverables I’m writing, developing and designing. It’s a living document that gets tweaked occasionally but it’s nice to kind of have a roadmap to manage my productivity.

I break up those deliverables from the master calendar into a monthly work plan. The work plan lists all the tasks that are required to make the deliverable happen. A lot of people use a tool like Asana to manage their work, but I use a simple Google Doc. [Laughs] Anyway, so each morning, I prioritize my work by what’s due then just start completing as many tasks as possible. I rinse and repeat this process until the deliverable is ready for the world.

My work plans also include links to templates I created in Google Docs for every task within each deliverable. And I also link to the tech and software I use to produce the deliverables. So everything I need to get my work done is always in the work plan. I like to have everything I need in front of me when I start working so I can focus on working as hard as I can for as long as I can.

Before all that occurs though, I schedule time on or around the 15th of each month to plan my work. I like to work three months ahead so January’s planning session will be for April’s deliverables. I pull up a blank work plan and start filling in dates, deadlines and details for the deliverables. That way I know the people I’m interviewing for Cool Convos, the topics and themes I’m covering in the content for The Club and all that good stuff long before I start working on it.

What works about my process is that it’s gives me enough structure so as I’m out in the world and paying attention to what I react to, I can immediately say, “Oooh, this would be good for Cool Convos!” Or “I should cover this topic in next month’s pop-up workshop!” Or “I can recommend this book in an upcoming Scavenger Hunt!” It removes a lot of guesswork and anxiety because when I sit down to work, I’ve already brainstormed and planned everything out.

How do your habits support your creative process?

Every day I schedule a block of “Focus Time” where I complete tasks for whatever deliverable I’m working on. I schedule the rest of my day — meetings, calls, appointments — around my Focus Time. I enjoy the peace of mind that comes with knowing that whatever else may be going on in my life or business, I’ve already dedicated time to focus on meaningful work that matters to me.

Just like I schedule my Focus Time, I also carve out a few blocks for “Field Trips” each week.

Sometimes it’s to a section of the bookstore that has nothing to do with my expertise. Other times, I’ll walk into an art gallery to take in a new installation. And more often than not, I simply get on the train only to hop off at a random stop and allow myself to be lost in my new-ish surroundings.

I also schedule “Study Bursts,” 30- to 90-minute frames where I can research what’s going on in business, education, technology and human behavior. I believe in the concept of “garbage in, garbage out” — the quality of the output is determined by the quality of the input — so I’m intentional about consuming information that can fuel my creative output. A lot of the insights I get from Study Bursts are incorporated into the learning content I develop for The Cool Humans Club.

Lastly, what may be the most important habit is to shutdown. I’m getting much better at not working when I’m not working.


The Recommendations


Michael’s picks for documenting and organizing your ideas:

1) Moleskine notebooks: Never leave home without a notebook, friends.

2) Muji gel pens: My former boss Eva got me hooked on these pens. I buy ‘em by the damn-near dozen whenever I’m in SoHo. They write so smoothly.

3) iPhone Voice Memo app: If I’m unable to write down or type out an idea, I’ll record a quick voice memo so I can refer to it later.

4) Evernote: I use this tool as a digital version of my Moleskine. You’ll love it because it seamlessly syncs to all your devices.

5) Instapaper: I get most of my news from newsletters. So as I’m browsing a newsletter, I’ll save articles love to save articles to this bookmarking tool.