‘Much of my past identity was wrapped up in all the admiration associated with being on centre stage’
After setting up and later selling a chain of boutique hotels, Chip Conley took up a role with Airbnb and discovered he had to learn to guide and advise to help the startup flourish. His experiences of a midlife career change inform his self-help book, Wi
Ifyou’re 55 now, there’s a good chance you’ll live another 40 years. You’ll want to spend that time productively, yet myths about older workers persist. Many companies are (rightly) embracing calls to become more diverse in terms of race and gender, but are laggards when it comes to recognising the value of age diversity. People assume older workers are more expensive, less loyal, less healthy, less trusting and less committed – most of the research demonstrates that this is not the case.
But there’s one myth that is worth investigating further, because it’s crucial for anyone looking to reinvent their career at 50+: the idea that elders aren’t motivated to change as we age; that we get set in our ways. Well, do we?
Reinventing ourselves in mid-life means introducing ourselves to new environments which may inflict change upon us. This can be unsettling: our career can be an existential anchor, tethering us to our identities. That’s why some of us can feel so unmoored when we lose a job or feel disoriented in a new one. It’s also why we may feel angry that ageism or youthful cronyism (the young hiring the young) derails our career just when we feel at the top of our game. Yes, obstacles can grow as we age, but so can our ability to weather the storm.
Maybe our growing selfawareness, and our willingness to change our costume, can allow us to start lifting the burden of too many shed identities. When you’ve worn out all your past roles, cast aside all your costumes, and relinquished your customs, you’re left with yourself, in its purest form. That’s when it starts getting interesting. After a lifetime of accumulation, we can instead concentrate on what we do best, what gives us meaning, what we want to leave behind. We become unmasked – in a good way.
I know this from my own experience. I set up my own company aged 26 and spent nearly two dozen years as a hospitality disruptor, expanding my little empire (or so I saw it) to more than 50 boutique hotels before selling Joie de Vivre Hospitality at the bottom of the Great Recession. I thought I’d be CEO of Joie de Vivre until I was 80 years old. But, virtually overnight, my calling became a job and the high wore off. I had to change. For many of us, there’s a gradual “moulting” that occurs before the world sees our new identity. During my own moulting period, I felt lonely and occasionally confused because it was hard to share my intention of a radical identity change. The way I had blossomed as a teenager was by collecting accomplishments. I was the youngest in my graduate business school class at Stanford and then started my company just a couple of years later. My first hotel, the funky Phoenix in San Francisco’s Tenderloin, became a worldfamous rock ’n’ roll motel where I served Linda Ronstadt breakfast in bed, and lent cuff links to JFK Jr for a wedding in our courtyard. By the time I was profiled in People magazine at the age of 30, I was already well on my way to becoming an admiration addict.
One of my first lessons when I joined Airbnb as a senior leader and mentor to its millennial co-founders was that I’d need to “strategically edit” part of my historical professional identity. Airbnb didn’t need two CEOS. Nor did they need me, the curious interloper who had only just recently learned the term “sharing economy,” pontificating wisdom from the elder’s pulpit. I was no longer the “sage on the stage” as I had been for years as an expert on entrepreneurship, but was instead transitioning into what might be better described as the “guide on the side,” counselling and advising the leadership team. In those first few months, I just listened and watched intently. I imagined myself as a cultural anthropologist, intrigued and fascinated by this new habitat: a modern, male Margaret Mead, an anthropologist amid the millennials.
Admittedly, much of my past identity was wrapped up in all the admiration associated with being on centre stage. Now I was behind the curtain, giving stage directions to the lead actors. I’d gone from headliner to acting coach. Fortunately, I learned as much from them as they did from me.
I also experienced a sense of liberation that surprised me. Back at Joie de Vivre, I
People assume older workers are more expensive, less loyal, less healthy, less trusting and less committed – most of the research demonstrates that this is not the case
was weighed down with “boss baggage”: the worry of whether I was venerated or loathed as the holder of power and the public face of the company. Plus, helping lead the charge with my younger comrades in the burgeoning movement to democratise hospitality – as the liaison and leader to millions of hosts and tens of millions of guests – gave me a profound sense of mission.
If you are looking to reinvent your career at 50+ there are a number of avenues open to you: including rethinking a gap year, entrepreneurship, working at a non-profit, relocating internationally. All of these are ways of donning that new costume and evolving your identity. As you embark upon the next stage of your career, here are some stratagems that helped me, and may be helpful to you:
Build a collaborative bridge:
You may have industry connections that your colleagues don’t have due to the fact you’ve been on the planet a few more years. As the only senior executive at Airbnb with a decades-long travel industry background, it was essential that I take on the role of an elder statesman, or in modern parlance, a secretary of state.
Be humane and humorous:
Writer Henry Miller suggested the most comforting thing about growing old gracefully is the ability not to take things too seriously. In a company that was doubling in size every year, and under a microscope for all kinds of reasons, it was easy to lose our sense of humanity as well as our sense of humour. So being accessible, real, and, occasionally, real funny was part of my evolving identity.
Be calm and curious:
I quickly learned that if I was the smartest person in the room, I was in the wrong room. Being a calm and curious presence and asking open-ended questions that helped us to see our blind spots became part of my growing reputation in the company.
Be present:
Presence is far more intricate and rewarding an art than productivity. In a culture that often measures our worth as human beings by our efficiency, fast iteration, and answers, the cult of productivity has its place, but worshipping at its altar can rob us of our sense of curiosity, joy, and wonder.