Illustrated Wisdom For The Middle: A Collaboration With Jessica Hische

Excited to launch a collaboration with Jessica Hische, an amazing lettering artist and illustrator I deeply respect and have known since the early days of Behance. Alongside the launch of THE MESSY MIDDLE, Jessica transformed three of the book’s 100+ insights into a limited series of illustrations. (and if you want one…read your way to the bottom).

THE MESSY MIDDLE distills 5+ years of interviews with legendary founders, artists, and executives about their middle journeys down to 100+ insights for founders, artists, and leaders of bold projects and new ventures. If you missed it, I shared an introduction to the book here and talked about the special “optimizing products” section here.

I sent Jessica an early version of the manuscript a few months ago, and she selected the three insights that resonated most with her. Today we’re thrilled to reveal the final illustrations…

“DTFW: Do The Fucking Work.”

Every journey has heavy, all-consuming moments. Firing employees. Extremely difficult clients. Solving a PR crisis. Weathering legal battles. On such occasions, you’ll struggle to push through the muck. You’ll fret the aftermath of confrontation. You won’t want to upset people, especially those who may be left without jobs because of your decisions. You’ll find every reason to analyze further, delay action, and blunt the blow. But most of the time, the right answer is clear, and the next step is yours.

You have a job to do. You just need to do the fucking work. DTFW.

This is what I would tell myself before going into a tough meeting, nail-biting negotiation, or making a tough decision rather than just talking about it. Whenever I needed to force myself to take action that would be painful in the short term but was for the greater good, I would whisper to myself, “Just DTFW.”

Don’t blame yourself for feeling skittish. Avoiding conflict and hesitating before you disappoint others is not a weakness, it is having a conscience. Relationships matter, and the cost of upheaval in any relationship or team culture is very real. But just as a common cold can become full-blown pneumonia if left unchecked, infections in a team grow when not addressed. Your job is to detect infection, determine whether it is viral, and nip it in the bud if it is.

In THE MESSY MIDDLE we explore the tactics that some great leaders use to keep their heads down, keep breathing, and endure wild bouts of volatility. I’m glad Jessica selected this section of the book, because it’s a helpful visual prompt for the steps leaders must take to unleash a project’s potential. Here’s the final illustration. I love it.

“Friction brings us closer.”

Our aversion to obstacles, setbacks, disagreements, and other forms of resistance is a bit ironic, because these frictions are what build our tolerance for future friction. We expend so much energy avoiding friction rather than inviting and leveraging it.

The old adage “Friction polishes stones” is true: Friction not only reveals character it creates it. By avoiding conflict, we don’t smooth out the rough edges of our ideas and plans.

The aspiration for a “frictionless” experience is shortsighted. A truly frictionless experience, where you avoid or deny every ounce of struggle, is mindless. Friction makes you feel the texture of a process, and the texture helps you remember what you’ve experienced. Without friction, teams are liable to move too fast, and edges that are too smooth fail to form sustainable bonds.

Hardship brings your team together and equips you to endure for the long haul. The upheaval of ordinary life causes a group of people to overlook their differences and unite around common causes.

In the section titled “Friction Brings Us Closer” in THE MESSY MIDDLE, I talk about some of the psychology and research around group behavor and shared calamity. Friction unlocks the full potential of working together. When triggered, your ancestral preference for group survival though collaboration over isolation aligns interests in a powerful way. If I had to pick a favorite illustration among the three, this would be it. I love how Jessica juxtaposed the beauty and stark struggle of friction so strikingly in her illustration.

“You are not your work.”

I close the book with a section of insights about “the final mile” of bold creative projects and big ventures — and how to not screw it up. We explore the common pattern of self-sabotage experienced by leaders at the end of projects as well as common challenges around your identity becoming coupled with your creations. One of these insights is titled “You are not your work.” Like many other well-known artists, Jessica is known for her work and I am not surprised that this insight resonated with her.

Detaching your self-worth from what you create is complicated, especially for creative people for whom work is very much self-expression. I remember one talk at the 2015 99U Conference from Rohan Gunatillake, a deep thinker in the world of mindfulness and meditation, and a serial maker of products related to mindfulness, including Buddhify, Kara, and Sleepfulness. His talk was about fear in creative careers, and his last point was the fear of decoupling self and work (which is an essential step in developing generativity). How do you build something that is a creative expression of yourself but not fail if it fails? Rohan gave the audience a suggestion for an important first step: recite a few affirmations while paying attention to how they make us feel.

He put up the first affirmation on a slide: “I am not my Twitter bio.”

The audience laughed. “This is an easy one,” Rohan explained — of course you’re not your Twitter bio.

Then he showed the next affirmation: “I am not my résumé.”

People laughed again, but a little less.

Then he switched to the third affirmation: “I am not my company.”

Backstage, this one made me gulp. So much of my life was my career, and Bēhance felt a part of me. Other entrepreneurs probably rolled this one around in their brains a bit, too. As founders, when you dedicate yourself to something for so long, the company ends up looking a lot like yourself. It’s an extension of your own interests, strengths, and faults. It is therefore hard to detach from something that is, by its very definition, your creation.

Rohan had one final affirmation: “I am not my work.”

The audience fell dead silent. “Hold that statement in your mind,” Rohan said. “Notice yourself thinking, ‘But I am my work, I put everything into it.’ The practice of decoupling yourself from your work is noticing that movement, noticing the struggle and the pain of that movement.”

When you’re finished, your fate and your work’s fate diverge, but your identity belongs to you. Your work, or your art, is something you’ve made. It can fail, be sold, or be left behind, but it can’t be you.

A Limited Edition Collection & A Fun Little Lottery

I hope you want one of these posters as much as I do.

Jessica has printed a limited edition of 50 of each, and they are on sale at her online store for $125/each or $300 for the set of three. They are likely to disappear quickly. BUT GOOD NEWS: We’re holding and giving away 20 single posters and 3 sets of all three of them to a group of winners. Go pre-order your copy of the book now, and you can enter the contest using this link.

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