3 Lessons from Jumping Into Jeremy Cowart's Creative Process

If you got to step inside the creative process of one of the most talented creatives alive today would you?

If even for a minute?

• Play a round with John Mayer?

• Do a cold read with Kate Winslet?

• Hop in front of Jeremy Cowart’s lens?

That’s what I did this week.

Jeremy Cowart, prolific artist and photographer who has photographed everyone from Gwyneth Paltrow to Spike Lee, opened up his studio to normies like me for 90-second sessions.

After admiring his work for over a decade and interviewing him on the Hustle & Grace podcast, I knew if I had the chance to be photographed by him I would do it.

So in a whirlwind of an afternoon I swooped into his studio, stepped in front of his camera, and was done within minutes. 

Takeaways:

1. There are very few moments in life where it pays off to focus on your insecurities. I had one minute to relax and be a good subject for Jeremy. Thinking too much about myself wasn’t helpful.
    

2. Do things out of your comfort zone from time to time. I did this shoot with Jeremy to kick off a creative business retreat. Doing something radically different from my typical Friday afternoon was a great way to shake my brain awake and look at things from a fresh perspective.
    

3. Art, business, and new experiences are all better with friends. This photo shoot and 48-hour adventure were enriched because I did them along with my oldest friend Bonnie. Life is richer in community. Period.

Want creative and career encouragement like this in your inbox once or twice a month? Sign up for my email newsletter here and I’ll send you my mini ebook (featuring Jeremy, among others!) 12 Little Hacks for the Mindful Creative.

My Top 10 Books of the 2010s

I’m still not quite done looking back on the last decade…

…(after all, who among us noticed the decade was coming to a close until approximately December 27?) So today I want to share the books that made the biggest impact on me from 2010-2019.

These aren’t necessarily books that were published between 2010-2019, but they were books that I read during the period from my mid-twenties to my mid-thirties (a pretty pivotal period of life.)

All the books that meant the most to me settle into two categories: “Creativity and Work” and “Personal Development.” I picked five for each. And yep, they’re all nonfiction. (I know, I know…) Goal for the next decade: diversify.

My Top 10 Books of the 2010s

Creativity and Work

The Artist’s Way by Julia Cameron
I loved the 12-week study on rediscovering creativity. This should be standard fare for anyone in a creative field or who enjoys creative hobbies. I read this in a reading group with several other people. I highly recommend doing it that way. 

Creativity, Inc. by Ed Catmull 
This is a fascinating look into the brilliance of how Pixar Animation is run. I stole the “personal board of directors” concept from this book and still use it today.

4-Hour Work Week by Tim Ferris 
This book has made the biggest impact on how I approach my career of any book I’ve read. Batching tasks, outsourcing, and minimum effective dose are all concepts that I learned in this book that I use every single week. 

Big Magic by Elizabeth Gilbert 
This book taught me not to take talent, success, recognition, and creativity so seriously. If you love something, do it for the joy of it. Don’t put expectations on it. I loved this book so much I even wrote a blog post about it and made a pretty printable discussion question guide.

The Creative Habit by Twyla Tharp
The connections Tharp draws between routine and creativity transformed my perspective on what it means to be creative. Don’t expect inspiration to simply strike. Habits and discipline lead to creativity.  

Personal Development

Atomic Habits by James Clear
This book transformed my perspective on goals and habits. Tiny changes can have a mammoth impact. This is a book I will re-read. 

Essentialism by Greg McKeown 
This is one of the most challenging books I’ve ever read because I tend to be a person who likes a smorgasbord of options. But this book encourages its reader to ruthlessly pare down so you can accomplish what’s truly most important.

Digital Minimalism by Cal Newport 
I read this one along with its predecessor, Deep Work, just last year. Newport gives some incredible food for thought on what’s wrong with our culture’s passive relationship with technology. 

The Wisdom of the Enneagram by Riso & Hudson
This deep resource on the Enneagram had a profound impact on me. I wrote about what I learned about the Enneagram, anxiety, and gratitude here. 

168 Hours by Laura Vanderkam 
“You have more time than you think.” This book re-shaped my way of looking at my calendar, scheduling, and time. If it weren’t for this book I wouldn’t be able to do what I do and be as present for Eloise as I am. (Thank you Laura.) 

These are the ten books I read in the last decade that impacted my approach to career and life the most. I also read a lot of memoirs and these two were my favorites: Booked: Literature in the Soul of Me by Dr. Karen Swallow Prior and Born Standing Up by Steve Martin. 

What books did you read in the last decade that were transformative? I’d love to hear. 

Catching Up on Hustle & Grace Episodes 7-13

I kind of can’t believe it but we’re already up to 13 episodes on Hustle & Grace!

(You can find quick recaps of 1-6 here). 

Have I mentioned what joy this podcast is giving me?

Now, honestly, as awesome as that is, it's not really the point of the podcast. It’s about bringing you value, takeaways, and inspiration, but an awesome bonus has been how totally delightful it is to dream up each episode, talk with fascinating people, learn a TON, and then share it with the world. Thank you, thank you, thank you for listening!

If you've taken a little summer vacay from your podcast listening routine, here's the dish on what you'll want to catch up on ASAP: 

Episode 7: Caitlin Pyle began her work-at-home journey after getting brutally fired from her $16-per-hour corporate job in 2011. She quickly replaced her lost income by freelancing as a proofreader. Then she transitioned to helping others build their own work-at-home incomes through her blog, ProofreadAnywhere.com and later through WorkAtHomeSchool.com. Through plenty of hustle and grace, Caitlin's freelance business evolved into the multimillion-dollar media company it is today.

In this episode, Caitlin shares tips she swears by in running her own business and creating the life of her dreams. We discuss the exciting project that brought us together: WorkAtHomeSchool.com.

More About Caitlin: https://caitlinpyle.co/

Caitlin’s podcast: Work-At-Home Heroes 

Episode 8: Lisa Rowan is a senior writer and on-air analyst at The Penny Hoarder, one of the largest personal finance websites in America. She also cohosts Pop Fashion, a top-rated weekly podcast about the business of fashion and culture. A former full-time freelance writer and vintage shop owner, she is well versed in the gig economy and the small-business landscape. Her financial advice has been featured in Women’s Health, Family Circle, Refinery29, Real Simple, The New York Times, and NBC News.

In this episode Hilary brings Lisa, millennial finance expert, all her burning questions about budgeting on multiple income streams, what millennials need to know about saving, and the finance trends everyone under 40 should be paying attention to.  

Recommendations from Lisa:
ThePennyHoarder.com
Get Money by Kristin Wong
Broke Millennial by Erin Lowry
Planet Money

Connect with Lisa on Twitter and Instagram @LisaTella.

Episode 9: Susan Shain is a freelance writer and digital nomad who's been traveling around the world since 2008. She's written about personal finance, travel, and food for outlets like The New York Times and CNN, and does content marketing writing for businesses of all sizes. She's also the founder of WhereToPitch.com, a website for freelance writers, and author of a pay-what-you-want eBook called "The Ultimate Guide to Seasonal Jobs: How to Have Fun, Make Money, and Travel the World."

In this episode, Susan shares how she has made a living living working in locations all over the world. She shares her tips for breaking into seasonal work and freelance writing and why community is a critical component of self-care for digital nomads and seasonal workers alike. 

Recommendations from Susan:
Duolingo
Trello
The Art of Nonconformity by Chris Guillebeau
CoolWorks.com
Pimsleur

Connect with Susan at SusanShain.com and on Twitter at Susan_Shain.

Episode 10: Austin Graff leads talent marketing, brand, and social media for The Washington Post and is a contributor to On Parenting, news, advice, and essays for parents from The Washington Post. Prior to joining The Washington Post, Austin led digital, social, and influencer marketing for Coca-Cola’s Honest Tea brand, America’s #1 organic iced tea company. He started out his career leading social media and celebrity relationships for International Justice Mission, the largest human rights organization in the world. After growing up in Russia and Kazakhstan and attending boarding school in Germany, Austin came to the USA for university. He now proudly lives in Washington, D.C. with his wife, baby daughter, and two roommates.

In this episode, Austin talks about his career at The Washington Post, Honest Tea, and International Justice Mission. He also unpacks his unique philosophy of living with roommates while parenting, his time management hacks, and how he cultivates boundaries and balance in his life. 

Connect with Austin on Instagram and Twitter.

Episode 11: The Truth About Freelancing: In this episode, I unpack the state of freelancing in the U.S., the drawbacks of freelancing, the benefits, and 10 characteristics of people who thrive as freelancers. If you want to know more about my story and experience as a freelancer, go here. 

Connect with me on Twitter, Instagram, and Facebook.

Episode 12: Ashley Gorley has written 37 #1 singles and has had more than 300 songs recorded by artists such as Luke Bryan, Carrie Underwood, Florida Georgia Line, Blake Shelton, Brad Paisley, Jason Aldean and Darius Rucker.  He was named the ASCAP Country Songwriter of the Year in 2009, 2014, 2015, 2016, and 2017, Billboard Country Songwriter of the Year in 2013, 2016, and 2017, and the NSAI Songwriter of the Year in 2013, 2016 and 2017.  Gorley has been nominated for multiple Grammy and CMA and ACM Awards, and has received the CMA’s Triple Play Award eleven times in his career, which recognizes songwriters with three or more #1 songs in one year. In 2016, he became the first songwriter to be honored with three CMA Triple Play Awards in a single year, for earning nine chart-topping songs in a 12-month period. In 2011, Gorley formed Tape Room Music, a publishing company with a focus on artist development. Writers for Tape Room Music have already celebrated twelve #1 songs and eight top ten singles by artists such as Florida Georgia Line, Sam Hunt, Keith Urban, and Dustin Lynch.

At just 41, Nashville songwriter Ashley Gorley has written a mind-boggling 37 #1 hits. He has writing credits on over 300 recorded songs. Hilary got to sit down with the prolific songwriter, publisher, and producer to learn more about the hitmaker, what his day-to-day life is like, and why he prefers for Carrie Underwood to not do the singing in a writing session. 

Learn more about Ashley's publishing company, Tape Room Music.
Listen to the Spotify playlist of Ashley's #1 songs.

Episode 13: Melissa Guller, is the Head of Special Projects at Teachable - an online tool that allows anyone to create and sell their own online courses - and ever since she launched her first side hustle in 2015, Melissa has been hooked on online entrepreneurship and empowering people to go for their big, awesome dreams. A bit of a side hustle queen herself, Melissa has been a top-rated instructor at General Assembly NYC for 2+ years, and she has 1300+ students currently enrolled in her Skillshare course, “What Great Managers Do Differently.” Most recently, Melissa founded The Kindling, a community for millennial women building online businesses, blogs, and podcasts they love. 

Melissa Guller has made a career out of helping people monetize their expertise online. In this episode, Melissa and Hilary discuss tools to create online courses, Melissa's side hustle ventures, and why she swears by a "relaxed" list to avoid burnout.

Connect with Melissa on Instagram.

There is so much more to come in upcoming episodes I'm thrilled to share with you! Make sure you don't miss an episode by subscribing:  Apple Podcasts | Android | Google Play | Stitcher | RSS

Conversation with a Creative: Meet Creativity Expert & Facebook Product Designer Tanner Christensen

I'm a writer, yes, but I'm coming up short on words to communicate how utterly stoked I am to speak with today's Conversation with a Creative guest. Tanner Christensen is a product designer at Facebook, author of the Creative Challenge, founder of Creative Something, developer of some of the top creativity apps, blogger on Medium, contributing author for Inc., and a former writer for Adobe's 99u. 

Back when I was in grad school and began really diving into the study of creativity I found Tanner on Twitter and eventually discovered his incredible blog Creative Something. Tanner was creating inspiring, thought-provoking stuff centered on creativity. And he was doing it with a fresh perspective and approach that didn't feel stuffy or overly academic. He's done a lot in a short amount of time and he’s also a major dabbler--but we’ll get to that.   

I think you’ll find Tanner’s perspective on creativity, Facebook, and the digital landscape fascinating. Without further ado: meet Tanner Christensen. 

HS: What does creativity mean to you? 

TC: Creativity is the mental capacity to generate novel and useful ideas.

HS: What piqued your interest in creativity? How did you come to study it and research it?

Creativity is this really alluring thing just on its own, isn’t it? Even if you don’t understand what it means to be creative or how it works, the notion that anyone, anywhere, can generate unique ideas from seemingly nowhere is a real type of magic that you can see and touch and be a part of.

It first captured my attention when I was very young. My friend’s father at the time ran a successful graphic design business and whenever I visited that office, full of colorful prints and futuristic gizmos, I always felt some type of magic in the work they were doing there. That’s what inspired me to pursue a career in design.

For some years I worked as a freelance visual designer, eventually landing a job at a real design agency, and everyone there kept talking about creativity but could never explain what it was they were talking about. I found that strangely captivating.

I decided to start pursuing the answer for myself; what is creativity and exactly how does it work? What makes novel thinking so powerful? If we could learn more about it what possibilities might we unlock?

HS: So you’re a product designer/creative strategist. Can you tell me about what you do and how the two intersect? 

TC: My first job at that design agency wasn’t actually in design. I was hired to do online marketing — which I didn’t know how to do. I spent a lot of time having to teach myself about search engine optimization, computer science, and all that.

So while I was learning about these strategic, mostly analytical practices, I was also spending a lot of time on the side researching and writing about creativity.

After about three or four years I started to develop a really comprehensive understanding of creativity. What I learned was that what I — like many others — had been led to believe about creativity simply wasn’t true. It isn’t about art or design, writing or music, creativity is fundamentally about ideas and how we develop, understand, and communicate them. Not just in terms of the arts, but in every realm of thinking and work.

I was able to take this perspective and apply it to my work, to the point where I’ve done everything from leading creative teams of designers and engineers, to creating hit apps, and writing on this fairly renown blog called Creative Something.

Most recently I landed at Facebook where I work as a product designer and am able to do a lot of other fun things with my knowledge of creativity.

HS: We’re all on Facebook. But you work there. How is creativity woven into the Facebook culture?

TC: Some of the most remarkably talented and highly intelligent people I have ever met work at Facebook. When I first joined the company I was amazed to discover that one of the cognitive neuroscientists I had looked up to over the past decade, Paul King, worked there too.

It’s the kind of environment that makes you really appreciate the bridge between logical thinking and creativity.

The problems we solve at Facebook are really difficult, even at the smallest scale. What seems like a straight-forward challenge to outsiders — creating an experience that connects people all across the world — is actually highly complex. You have to figure things out like how a design pattern will scale for a hundred different screen sizes in a hundred different languages, some of which change direction or break the layout of a product.

What’s culturally acceptable and understood in one part of the world is abnormal or shunned in another. How do you create something as simple as a button when it’s not going to be looked at or understood the same way for any two people? Getting that right is really important when it comes to connecting the world.

At Facebook we rely not only on data and formal logic to solve problems or to empower people, we have to think creatively too. Because nobody else is designing at the scale we are. Nobody has ever really had to think about the things we’re creating at the scale we’re creating them.

The culture of the company is really about how to bring highly intelligent and overly creative people together — both groups highly ambitious — in order to achieve the same goals. I’ve written a little more about how Facebook achieves this here.

HS: Did anything surprise you about Facebook once you began working there that you didn’t anticipate prior to joining their team?

TC: Everything about working at Facebook has been a surprise. Even now, a few years into the job, I stumble on things that surprise me.

For one, the utter intellect and talents of those I work alongside is awe-inspiring. It’s really hard to put into words just how smart some people can be. I thought I had some idea of intellect but when you work alongside people who are programming machines to do things humans can barely do that’s really humbling.

Another thing is just how complex the work is being done at Facebook. It can sometimes be easy to look at the website or app and think that the goal of Facebook is something it’s not or that our priorities are misaligned, but the reality is so far from that. There are a lot of people doing a lot of really difficult work to help connect and empower people around the world, and it takes a lot to make it happen in such an effective way.

HS: You recently had a book published. Congrats! Can you tell us what “The Creativity Challenge” is about and what inspired you to write it?

One day in 2015 I got a call from Adams Media, my publisher, they had been reading my blog and were interested in seeing if I wanted to write a book.

Together we came up with the idea of The Creativity Challenge in an effort to create a small book that could empower anyone who flipped through the pages to think creatively.

The book is filled with 150 activities that I was able to piece together through my years of researching and writing on creativity. Some are fun and quirky while others are fairly straight-forward. The point of the book wasn’t to radically alter how people think about creativity, it was more of a way to provide an easy-to-reference guide for shaking up your routine and dusting off mental cobwebs.

HS: What are your creative habits? What do you do to sharpen your creativity?

TC: I dabble. If I wasn’t a designer I’d be a dabbler. The absolute best way to remain creative is to have many diverse hobbies, and so that’s what I’ve tried to do.

If you want to quickly energize your creativity, find something interesting in the world and learn how to do it yourself. Twitter, YouTube, and Quora are great ways to do this by the way.

For example, right now I am in the middle of: writing a second book, learning Arduino in order to make an tangible product, picking up tools for fine metal jewelry making, coding my seventh app, writing for Inc.com, getting into videography, leading public design critiques for Facebook, painting, ceramics, cooking, world travel, and probably a dozen other things I’m failing to recall.

All of these things do wonders for helping me think about solving problems and working in different ways.

I actually recently wrote about this  and state:

"Taking a break to work on something else helps us avoid fixating on existing solutions or patterns of thinking."

It isn’t easy and it’s definitely time consuming, but any time I can do something new or different I try my best to do it. Though it’s worth mentioning I often encounter fear at the beginning of these things. I don’t think the fear of failing at a new endeavor, or getting hurt or lost while traveling, or embarrassing yourself, ever goes away. You just learn to push past it after some time.

HS: What is your advice to a multidisciplinary creative who might aspire to one day do the kind of work you do or achieve what you have achieved?

Two things I’d tell my past self:

1. Keep going. Whenever you feel like it’s all a waste of time, or like nobody’s listening, or like you haven’t gotten the things you’d hoped to get by now, just keep going. Grit is a tremendously powerful thing, and many people don’t have it, so learn what it takes for you, personally, to keep trading through. If you’re doing things you love or find stimulating, then at least you’re getting fulfillment from that.

2. Be loud. Write, make videos, do a podcast, lecture, do gallery shows, publish your work, do whatever it takes to make people hear you. Even if what you say is wrong, or even if your work isn’t the best, people will start seeing you for the things you put out into the world. People who keep their work and their thoughts to themselves aren’t perfectionists, they’re indifferent. Show people you care — about the work or process or whatever — by being loud with it. Even if people come out and chastise you for it, the world is a big place and there will always be someone out there cheering you along because they need what you can share with them.

3. And, of course, I'd say pick up a copy of The Creativity Challenge.

A huge "thank you" to Tanner for taking the time to talk all things creativity. Do you know someone who should be interviewed for Conversation with a Creative? Drop me a line. 

If you're ready to make more space in your life for creativity, download my free eBook, More in Less: 21 Productivity Hacks for Creatives.