What is one piece of advice you would give to someone who is struggling to let go of their career identity in retirement? How did you define yourself outside of work?

Redefining Retirement: It's Not About Leaving Work — It's About Reclaiming Your Life Most people ask the wrong question: "How did you define yourself outside of work?" But the real question is, "How did you define work outside of yourself?" Because for a lot of people, work came first — and life got the leftovers. I've coached hundreds of clients through career transitions, and one of the most overlooked (and emotionally charged) shifts is retirement. Especially for those who wrapped their identity around their job title, their schedule, their income, or their perceived importance. Letting go of that identity can feel like letting go of themselves. That's why my first piece of advice is this: stop asking what to do with your time. Start asking who you are when you're not doing anything. That's where the gold is. That's where your values live. When I wrote my book, "Check! Your Guide to Creating a Life Transforming Bucket List," it wasn't because I wanted people to write down 100 things and check them off like a shopping list. It was because I kept seeing the same pattern in coaching: people couldn't figure out what they wanted, because they didn't know what mattered to them anymore. So I flipped the model. In the book — and in coaching — I ask people to write their bucket list not to plan a vacation, but to reverse-engineer a life. What lights you up? What have you always dreamed of doing? What would you regret not doing? Those answers don't just reveal your goals — they reveal your core values. And once you know those, you can rebuild your life to honor them — even in retirement. For me, I didn't stop working and suddenly discover who I was. I redefined work. I made it an extension of my values — service, meaning, impact — and I started showing up in new ways. I became a life coach. I run a farm animal rescue. I paddleboard with my dogs. I write books. I still work. But I don't live to work. I work in a way that supports the life I've intentionally built. So if you're struggling to let go of your career identity, ask a different question: What kind of life do you want — and how does work serve it, rather than swallow it? Because your legacy isn't your resume. It's how you lived. And it's never too late to change the story.

One piece of advice I would offer to anyone finding it difficult to let go of their career identity is this: give yourself time and grace. Retirement is a major life transition not just in schedule, but in how your body and nervous system adjust to a new way of living. For years, your days were likely shaped by work, responsibilities, and routines. Stepping away from that rhythm might feel disorienting at first. Now instead of seeing this shift as a just loss, try to view it as an opportunity to reconnect with parts of yourself that may have been set aside. For example, what dreams, hobbies, or experiences have been on an indefinite pause due to work? Perhaps, this might be the right time to explore them. It is also helpful to remember that your career (while meaningful) may have defined you in ways that did not leave much room for other aspects of who you are. Think of it like this: retirement is not about erasing your past, but about expanding your sense of self. Many of the qualities that served you well at work like your creativity, reliability, leadership etc., can be used in new and fulfilling ways. It is similar to using flour: the same ingredient can make both bread and cake, depending on what you wish to make. This is exactly like with your skills and values now. They still matter, and will simply be expressed differently and on your own terms. So dear reader, let's get baking. Your new identity is waiting for you to discover it.

I have a stepmother, who retired at the age of 57. She was a senior executive at Lehmann Brothers, which folded a few years after she retired. She once led as many as 300 people worldwide, and played a pivotal role in protecting the company from Y2K bug about 25 years ago. She was a rarity, as a high-level executive who built her career from the 1970's to the early 2000's. I watched her growing up and always had the feeling she was at war with someone every single day. When she retired, she had her immediate family and step-family now to deal with on a daily basis, not the 300 people worldwide who called her "boss". I remember having dinner with her one day on a vacation by a beach in Georgia. I gave her this advice, as she meticulously planned a family vacation and scheduled every day down to the minute: "Your family is not your staff. It is ok to simply relax and enjoy your time with us. You did the work. This is what you worked for." Needless to say, she did not want to hear that from me. But over time, she has traveled a lot. And it became her identity. She's been retired almost 20 years now, and between cruises and traveling through several countries and US states, she is no longer treating her own family like a team of direct reports.

One piece of advice I would give to someone looking to redefine themselves in retirement is this: stop defending who you were and start discovering who you can become. Often, we feel the need to hold on to our past identities from our corporate careers, which can prevent us from exploring new possibilities in this next phase of life. A simple way to embrace this idea is by going through your closet and trying on outfits in new ways. The styles you wore in the corporate world may not fit your new lifestyle, so think about how you can redesign your outward appearance to reflect your inner growth. This transition is an opportunity to let go of the idea that you must continue doing things the way you've always done them. Consider rearranging furniture in your home or making small changes to your environment. These actions can help you identify a new identity and discover talents you may not even realize you possess.

One piece of advice I'd give to someone struggling to let go of their career identity in retirement is to intentionally explore new passions and roles that give you purpose beyond your job title. When I retired, I initially felt lost without the daily structure and recognition my career provided. What helped me redefine myself was focusing on areas I'd always been curious about but never had time to pursue—like volunteering with local nonprofits and diving into gardening. These activities gave me a sense of accomplishment and community outside of work. I learned that identity isn't fixed—it evolves as you do. It's about finding meaning in new ways, not holding onto what was. Taking small steps to build a new routine around interests and relationships helped me rebuild my sense of self beyond my professional life.

When you no longer have a career identity in retirement, you need to find a new purpose. Your identity has been tied up with what you do for work, and now you need to discover what you care about, what is important to you. You will need to explore your values and then research what exists in the world that relates to these values. This new direction will replace your old work, motivating you to move forward with the next phase of your life. Change takes patience, most importantly with yourself, so allow this to happen at its own pace.

Your soul is here for a higher purpose. You've dedicated your life to everyone else. To your family, your co-workers, and your place of employment. You've sacrificed and made repeated choices for everyone else's benefit. You have this one life. You've come here to express the True you, in a way only you can. She is in there below the masks, the programming, the conditioned patterns, and habitual thinking that affirm you being someone you are not. What you do is not who you are. Where is that heartfelt dream that got stuffed in the back of the closet? That aliveness you felt for the thing you wanted when you were seven? The thing that animates your physical being. GO DO THAT! Engage with your life. Remember you are an ecstatic expression of life itself! You've got the goods, but perhaps you need a guide.

I did things differently from most. Instead of waiting until 65 to retire, I started investing in real estate at 23, which allowed me to retire from my pharmacy career at 31. I realized after retiring from my "official" career that even in retirement, you can make a difference. For example, real estate has had such a significant impact on my life that I decided to found a real estate coaching business to help others build more financial freedom themselves. My advice to anyone who's struggling to let go of their career identity is to think about ways they can keep contributing to causes that matter to them, even if they're not working 9-5 anymore. As I've learned firsthand, it's completely possible, and it makes retirement so much more meaningful.

The best way to build your identity outside of your career is to focus on what truly matters to you—your values, passions, and the things that bring you joy. For some, that might mean deepening relationships and getting involved in their community, especially if connection and family are core values. For others, it could be diving into a creative hobby or personal project that sparks curiosity. There's no single 'right' way to redefine yourself after work. The key is to explore. Try new things, stay open, and lean into what sticks. Letting go of a career identity starts with curiosity and following what lights you up.