When was the last time you really paused to look at your life, to reflect on your direction, your legacy, and the journey you’re creating?
During the EO Women’s Summit this summer in Lisbon, one of the speakers shared insights from Bronnie Ware’s book, The Top Five Regrets of the Dying: A Life Transformed by the Dearly Departing. This book offered such a powerful perspective on how we choose to live.
It gave our Founder and CEO Kara Roberts pause to reflect on her own journey and ask a different question: What can I do today to create a life I’ll look back on with gratitude?
Inspired by Bronnie Ware’s book, Kara found herself reflecting on her own journey through the lens of her Five Regrets of the Dying, not as a list of regrets, but as a reminder of how she wants to live. Five things Kara hopes will help her stay focused on creating a life that feels authentic, meaningful, and uniquely her own.
We hope this sparks a little gem of inspiration for you to pause, reflect, and perhaps make a small shift toward living more fully today.
Inspired by Bronnie Ware’s Five Regrets of the Dying, Kara Roberts personal reflection on each:
I wish that I had let myself be happier.
I shake my head when I think about all the stress and anxiety I used to tolerate. I worried about all the little things that really didn’t matter in the long run. Being happy has been a lot easier since getting the right support on my leadership team and becoming a nomad traveling the world. I have so much to be grateful for and find so much joy in exploring new places, cultures and meeting new people with different world views. Getting out of the day to day comfort of my life and shaking things up was a great choice for me. I had a moment when I was riding my bike past the Arena in Verona, Italy with fresh flowers and focaccia in my basket at sunset and thought “No need to romanticize my life.” I’ve built a life and a mindset that brings me joy. I know most people don’t have the opportunity to be a nomad but there are plenty of ways to add more whimsy to your day. Find what lights you up and allow yourself to fully enjoy the moment. Take an afternoon off and head to Pike Place Market to get some flowers and Oh My God peaches at Sosio’s. Head to Discovery Park (literally my favorite place in the world) and walk through the meadows listening to the birds, peer over the bluffs to take in the view of the water and the Olympics, hike down to the beach and try not to belt out Temple of the Dog lyrics in front of the lighthouse. Too niche?
I wish I’d had the courage to live a life true to myself, not the life others expected of me.
This one has been a long journey that I’ve recently made quantum leaps in. There are so many said and perceived expectations put on us. It can be scary to make decisions that go against the norm, can potentially hurt others or change their opinion of you. When I was separating from my husband I made unpopular decisions that friends and family struggled with. I’ve always lived outside of the box and believe that there are 26 letters in the alphabet so it’s never just choosing between A and B. I learned a saying that I still remind myself of 16 years later, “Your opinion of me is none of my business.” There is so much freedom when you realize that you have opinions of others without understanding the full circumstances so of course others will too. You are the only person who knows your heart and your needs and can make the decision that is best for you. Fast forward 16 years now that I am on the other side and the choices I made back then were the best ones for me and my family. It worked out beautifully. Was it easy and graceful? Not at all but I am so glad I had the courage to listen to my inner voice. Something happens when you start trusting your gut and things keep working out. It is a lot less work and a lot more happiness when you listen and act instead of ruminating and worrying.
I wish I hadn’t worked so hard.
This one is tough and one I am still processing. I worked so hard for 10+ years building my business. It felt like 24/7 stress because I would literally solve problems in my dreams while I was sleeping. It had a big impact on my physical and mental health. What if I would have had the tools for stress relief and mindset shifts? What if I would have set an hour a day aside for movement and meditation? As a mother of two and a leader of 20+ is that even possible? I’m not sure but I wish I would have known it was a good option to prioritize. One thing I am very proud of was my rule that if my sons walked in, I closed the laptop and gave them my undivided attention as much as possible. As they hit the teen years this time became even more valuable. Now I’m in an amazing season of being out of the day-to-day and have a lot of time for myself. I am grateful to be reaping the rewards of my hard work and I am slowly reversing the effects of chronic stress. If I could go back in time I would tell myself to slow down, breathe and that it is all going to work out.
I wish I’d had the courage to express my feelings.
This is a weakness for me that I am deconstructing. I saw a stand up comedian say, “My daughter asked me if I was in therapy as a kid. Therapy? I wasn’t allowed to have feelings. I wasn’t even allowed to be thirsty.” It’s funny because it’s true. I am learning to be brave and ask for what I need and setting boundaries that protect my health and happiness. I have a tendency to make up stories in my head of how people are feeling or why they make the choices that they do. I’m learning to let go of the responsibility of managing someone else’s emotions or reactions to my needs. It’s all about communication and trying to find a place that respects both people’s needs. Brene Brown has helped on this journey. A lightbulb moment for me was her saying niceness is about comfort, pleasing others, and avoiding discomfort, while kindness is rooted in courage, boundaries, and truth.
I wish I had stayed in touch with my friends.
I feel like I’ve always been good at this one due to being an Air Force Brat that went to a new school every year until high school. You learn to cherish people that you have a quick connection with. Back then we would stay in touch through letters and occasionally discounted phone calls in the evening if there was something really important to share. As an adult it is harder. We get caught up in our lives and responsibilities. You have to put a lot more effort into it. Being a nomad has helped me. When I’m “home” I’m much more intentional with reaching out to friends to make plans. Sometimes impromptu works the best. Recently I was thinking about old friends and I reached out to see if they wanted to join me at a Seattle Storm game in a hour. They already had tickets! I was able to get a seat right behind them and get caught up. Impromptu hugs are the best!
None of us gets to know exactly how our story will unfold. But we do get to make choices about how we show up for it. These Five Regrets of the Dying are less about looking backward and more about paying attention to how you want to live today.
