14 Tips From Chip Conley For Finding Your Purpose In Midlife And Beyond

Millennials are known as “the purpose generation.” Research indicates that the vast majority of people under 40 are motivated more by their passion for making a difference than by their salary. But what about older generations?

Chip Conley, the cofounder and CEO of Modern Elder Academy – the world’s first midlife wisdom school – says that we are defined by purpose throughout our lives. People who feel aligned with their sense of purpose tend to live longer, and during those extra years of life they also generally are healthier, feel happier and are less lonely.

Conley founded and ran the highly successful boutique hotel chain Joie de Vivre for over 20 years before accepting, at age 52, a position as the in-house mentor to Brian Chesky, the youthful co-founder and CEO of Airbnb. At the time, Conley was twice the age of most of the employees at the rapidly-growing company. During his years working there, he discovered how sharing wisdom and swapping ideas with Chesky helped them both to thrive. He honed his own sense of purpose for his second half of life: “To build a community of inspired and empowered midlifers.”

All older adults have wisdom to share, Conley saw – but often their contributions aren’t valued. In today’s tech-savvy working world, ageism is rampant. An AARP survey revealed that over three-quarters of older workers have experienced age-related discrimination.

Conley coined the term “modern elders” and began building a campus where people could come to “turn their midlife crises into a calling.” The Baja, Mexico beachfront retreat center opened in 2018. Efforts have grown since to include online courses and a regenerative community for modern elders in Santa Fe, New Mexico.

Here, Conley shares 14 ways to connect with your life purpose in midlife and beyond:

• View purpose as a verb rather than a noun.

In modern times, purpose has become a possession. We’ve all heard people say, “I can’t find my purpose,” as if it’s a backpack they left in a roadside gas station bathroom. As a noun, purpose is something you possess—a valued asset in your grasp that you can show to others. As a verb, it’s a deliberate and conscious way of being. You show up being purposeful and, magically, you become a magnet for the possibility that your purpose may come to you.

• Calculate what percentage of your adult life is still ahead of you.

In the modern world, if you make it to 65 years old, there’s a better than 50% chance you’ll make it past 85. Make a guess of how long you’ll live and determine how many years you have left, then compare that with how many adult years you’ve lived since age 18. For example, if you think you’ll live till 90 and you’re 54, you’re exactly halfway through your adult life. Are you surprised by how much life you still have ahead of you? Chances are, your life is far from over. Let that be your motivation to embrace change now.

• Think about your regrets.

Think about something you just recently learned or started doing that you wish you’d known or done ten years ago. Once you’ve locked that in your mind, think about something you’ll regret ten years from now if you don’t learn or do it as soon as possible. How can you make a commitment to learning or doing that now?

• Be the beginner.

What if someone walked up to you at a cocktail party and asked, “In what ways are you a beginner right now?” That’s quite an opening line, but it’s a beautiful window into a growth mindset. What hobbies, skills, or topics have you started exploring for the first time in the past year? What if, for the rest of your life, you made a commitment to yourself that you would always be the beginner at something?

• Consider your gift.

It has been said that, “The meaning of life is to find your gift. The purpose of life is to give it away.” What is your gift? Maybe one way to discover this is to ask yourself the question, “What are five pieces of proprietary sage advice I can offer a younger person?” Focus on your personal, hard-won wisdom as opposed to something more generic. For example, “Be yourself, everyone else is taken,” is a beautiful sentiment, but Oscar Wilde already said it. What gift of wisdom has your singular fingerprints all over it?

• Focus on service.

As we approach the second half of adult life, we move from our “can do it” spirit of rugged individualism (often fueled by the ego) to a “conduit” desire to collaborate and serve those younger than us. How might your purpose be focused on serving those who are younger than you? It doesn’t matter how old you are – there are always those younger than you who could use your wisdom. Find a purpose project that will live far beyond your years. Commit yourself to planting your seed of wisdom into a fertile ground of younger people with no sense of pride or ego in wanting recognition for your contribution.

• Ask yourself: “Where is purpose lacking in my life?”

If you’re feeling a lack of purpose in your life right now, ask yourself: Is it in your individual job function or the team you work with, or is it in your company’s mission and culture? If the answer is the former, maybe the solution is repotting yourself in a different part of the organization or retooling what you’re responsible for. If your issue is more about the company’s mission or culture, what has changed since you joined?

You might be surprised if you approached HR leadership and, in a gracious manner, outlined what you’re seeing. Maybe you could help develop a Culture Club within the company that advises on both what can reignite the culture as well as how could the company’s mission might become more of a magnet, not just for you but for new employees as well? But maybe you’re just bored or our priorities have changed. Assuming you don’t think this can evolve, then it’s time for the next step.

• Create a “mentern” relationship.

A mentern is part-mentor, part-intern — and you can create one with anyone from a different generation. I truly enjoyed having this kind of relationship with Airbnb CEO Brian Chesky. I offered him leadership emotional intelligence and he offered me tactical digital intelligence. We were both better off for it. You might also call this “mutual mentorship.”

• Foster intergenerational connection.

If your workplace has Employee Resource Groups (ERGs), create a co-generational ERG dedicated to fostering a new generational compact of how older and younger employees can solve vexing problems in the workplace, for your customers, and in the world. Think of it as an “ideas potluck” across diverse generations.

• Redefine what “success” means to you.

The first half of adult life is often defined by three mantras: “I am what I do” (achievement), “I am what others say about me” (display), and “I am what I have” (status). Midlife is our time to stop trying to impress. Junk the old "success script" and own your own wisdom. Which of these three mantras most haunts you and how can you write a new success script for yourself?

• Journal.

At 28, when I was struggling as a young CEO of my boutique hotel company, I repurposed an empty diary into My Wisdom Book. Each weekend, I would reflect upon some of my most challenging lessons of the past week. Afterward, I’d dutifully add a few bullet points, reflecting on what I had learned from these lessons. Metabolizing these life experiences helped me accelerate my wisdom.

This coming weekend, pull out an unused journal and jot down a few sentences about three or four different circumstances you encountered during the week, including how you handled them – even if you made a mistake or two. Then note what you learned. If you do that every weekend for a year, you’ll be shocked by how much wisdom you will cultivate.

• Get creative.

Sometimes, the most cathartic thing you can do in your messy middle is to tap into your creativity and cultivate your ability to seek awe. Break out of the dark neighborhood of your mind and explore cooking, gardening, painting, or anything that lightens you up. Go for an “awe walk” in nature as a means of helping you to see beyond your own predicament. When I was going through a particularly dark time, I started scheduling three 3-hour nature walks weekly with my dog Jamie. I noted these in my calendar as my “Spying on the Divine” appointments.

• Explore the parts of your life that feel “unlived.”

Ultimately, midlife is not about the fear of death; it’s about the fear of not truly living. We all have a box of “unlived life,” almost like a time capsule from the future. How can you explore that box of unlived life? Was there a dream you had early in life that feels “unlived” today? Our development as a human can happen unevenly. You might be 75-years-old in terms of your experience and wisdom when it comes to leadership, but 17 when it comes to romantic relationships. Or vice versa.

• Take a gap year.

These days, many high school graduates are taking a year off before starting college, calling this a “gap year.” Are you willing to take a gap year, at minimum, once per decade until the end of your working life? If you could go back to school for a year, what subject would you study and how might you utilize that knowledge in your life? Where would you travel? Do it.