In his new book, The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture (Portfolio, an imprint from Penguin Random House, 2018), entrepreneur Scott Belsky reveals that the volatile middle of any path is not just something to get through, but a richly challenging stretch you should mine for its valuable lessons. In this excerpt, he reflects on separating personal identity from work and how difficult it is to do so.
One common struggle among successful entrepreneurs and artists is that their identity is wrapped up in their work. Whether its a musician feeling forever defined by his band's success a decade ago or a business leader known for a particular venture earlier in her life, great work tends to hijack one's sense of self.
I saw this with my grandfather Stanley Kaplan while I was growing up. Stanley began tutoring kids for standardized tests like the SATs in the basement of his parents' home in the late 1930s. The son of immigrants, he took it upon himself to help provide for his family and ultimately purchase their first car.
For the fifty years he was running his tutoring business, my grandfather was "that Kaplan." I recall getting into cabs with him when I would visit New York City as a child. He would always ask the driver if they or their children had taken the SATs. "How did they do and how did they prepare?" he would ask with a grin, waiting for their response. He taped every interview he gave and relished the identity he shared with his company. Upon his death, I remember rummaging through hundreds of old cassette tapes chronicling every interview he had done. My grandfather Stanley was his business.
More a tutor than a businessman, he sold his business in the early 1980s to the Washington Post Company and put most of the proceeds into a nonprofit foundation. The Washington Post Company went on to transform Kaplan into the global enterprise it is today, with more than one hundred physical schools and a vast online business that has generated billions in revenue. It was an extraordinary achievement for the son of an immigrant plumber, who only became a tutor when he wasn't accepted into medical school because of the limited quotas for Jewish students at the time.
But when he sold Kaplan in the mid-1980s, just as it began to really grow, no amount of money would make up for the part of himself that he lost with the sale. In his old age, he suffered from a depression that I later learned he likely struggled with to some degree throughout his life. I remember his extreme melancholy, and how his eyes would only light up when I asked about the early days of his business. It was as if the sale of his business--the end of something that had so powerfully defined him--was his end as well.
These memories weighed on me as I considered the prospects of selling Behance. I had spent only seven years building Behance, not my whole life, but like my grandfather, my identity was wrapped up in it. Many of my friends were in my industry, and any fanfare I received was because of Behance more than any other part of my life. I was afraid of becoming like my grandfather and being defined by it.
I've seen many friends leave their high-profile jobs or the companies they founded and face similar struggles. Homebrew's Hunter Walk, one of my favorite early-stage investors, wrote a candid blog post after leaving a senior role he held at YouTube for a number of years, which he was widely known for in his industry. He wrote about trying to acknowledge his own struggles with "separating 'where I work' from 'why I matter' and self-worth." As he explained it, "Careers are sets of decisions where you have the chance to emerge from the chrysalis every so often and show the world, show yourself, how you've evolved. You are not your org chart, your department budget, or your title. Don't let success at a company prevent you from pursuing scary and wonderful new opportunities to build. It took me a little longer than it should have, but from the other side, it's pretty awesome."
Having the confidence to leave your previous identity behind is easy to say, hard to do. Having endured a journey that nearly sucked the life out of you, that journey becomes a part of you.
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 Behance 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," he 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. And you are not your work. 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 successful final mile requires letting go of what you made and returning to who you are, your values, and your curiosities that are kindling for whatever comes next.
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