How Do You Reach the Other Side of Change?

EXPERT OPINION BY CHIP CONLEY, HOSPITALITY ENTREPRENEUR AND FOUNDER & CEO OF MEA

FROM THE WINTER 2023/2024 ISSUE OF INC. MAGAZINE

Retrospectively, it's easy to understand which parts of our education have most impacted us. I can't say my college European History 101 class helps me as an entrepreneur, but my seventh-grade typing class continues to serve me well, and the art class I took that same year opened me up to seeing the world in new ways.

But there's one class I never got to take, and it's one I desperately wish had been on offer. I'm talking about education on transitional intelligence. In the past, Americans didn't change jobs much: Half of Americans age 65 and older have stayed with an employer for at least 20 years. Today, the average worker holds 12 jobs throughout their career. Life is far less linear than it used to be, but we have no formal education process to help us navigate the many personal and professional changes we now face. It's as if we've moved from horses to cars but aren't being offered driver's ed.

I say this from experience. In 2007, after more than 20 years of running my boutique hotel com­pany, something shifted. My inspiring calling turned into a dreary job. I'd written my third book, and dreamed more about writing and speaking than I did about being CEO. I'd plow through my day job looking forward to the speech I was giving that night--it felt like I was cheating on my 3,500 employees.

I had no idea how to extricate myself from this situation. It took a major health crisis for me to find the courage and wisdom to not only welcome change into my life, but to master it as well.

I'd go on to sell my company, join a little startup named Airbnb, and ultimately create the Modern Elder Academy. And I can now deconstruct that transitional period of my life into three phases: the ending, the messy middle, and the new beginning.

All entrepreneurs experience these three phases at one point or another, whether you lose a major client, hire a superstar who transforms your business, or face the prospect of selling a company you've operated for decades. Each person's journey will be slightly different, but there are some universal truths I want to illuminate through my own story.

First, the ending: I needed to embrace the idea that something precious--my relationship to my company and my ego attachment to my business card--needed to end. One of the best ways to facilitate this step is to ritualize or mark it. My friend Marianna did this while winding down her branding firm. After five years of toying with the idea of closing, she invited her co-workers, former employees, clients and former clients, friends, and family to a cemetery to celebrate the 20 years her company had existed. By memorializing this change, she had a clear before and after. I did something similar: I invited six friends to dinner to brainstorm my future and burned a piece of paper with a list of everything I needed to let go of to successfully start my transition.

Next: the messy middle. This is the liminal period of the hero's journey. The earth feels shaky because we're on awkward, new ground. We're frightened, like a caterpillar that wants to retreat from its chrysalis mid-metamorphosis. There are two mechanisms for surviving this stage: social support and identifying the through line of your life to a post-­transition.

I leaned on my network for emotional support, but I also sought guidance from my best friend, who happened to be a leadership coach. She helped me see how my life experiences had prepared me for this new era. Being able to see that pattern, that through line, gave me confidence I was on the right path.

The final stage, the new beginning, is when the butterfly emerges from its chrysalis. As it first flutters its wings, though, it might struggle to get off the ground. The key is adopting a growth mindset, a willingness to learn and improve without self-­criticism or performance anxiety.

I thought my new career path would exclusively consist of writing and speaking, but when I was asked by Airbnb co-founder and CEO Brian Chesky to become his in-house modern elder, I realized I was going to be a mentern--an experienced mentor but a clueless intern when it came to the tech industry. I taped a question to my bathroom mirror: How can I turn my fear into curiosity?

These three stages are not taught in school or in the workplace. Often, we just become wiser upon witnessing our own mistakes (and others'). But truly understanding transitions--and knowing what tools are available to you in each phase--is one of the most valuable skills you can learn, and the key to thriving in our ever-changing world.

Photo Credit: Illustration by Antonio Giovanni Pinna.