As the Baby Boomer Generation is Aging, common regrets revolve around Relationships, missed opportunities, and the pursuit of fulfillment. Many of us regret not being more present and loving with Family and friends, not taking risks or pursuing passions, and not fully living life to the fullest. Regrets also stem from missed career opportunities and not prioritizing Health. Our Experts in this area of the site explore what has led up to us accumulating all of these regrets.
A major regret following most of us is in how we developed relationships. We may not have spent enough time with loved ones. We could have been a better spouse, parent or even child. We have not yet resolved family estrangements. We have lost touch with friends, and we may not have expressed feelings of Love and appreciation throughout our decades. Other regrets may have been the courage to live a life true to ourselves, or not taking more risks, or pursuing our dreams and passions or not prioritizing happiness. Not taking care of ourselves by making healthier Lifestyle choices when we were younger may top our list.
Regret Specialists & Contributors
Anne Bachrach Goal Setting and Achievement Podcaster and Author
You’ve been productive. Good for you! Maybe you watered the garden.
Maybe you took a gentle walk around the block. Maybe you decided that today was
the day to scrub the front porch steps because that moss was starting to look like
a shag carpet.
You come inside, feeling proud. You sit down in you…
You’ve been productive. Good for you! Maybe you watered the garden.
Maybe you took a gentle walk around the block. Maybe you decided that today was
the day to scrub the front porch steps because tha…
You’ve been productive. Good for you! Maybe you watered the garden.
Maybe you took a gentle walk around the block. Maybe you decided that today was
the day to scrub the front porch steps because that moss was starting to look like
a shag carpet.
You come inside, feeling proud. You sit down in your favorite
chair. You go to stand up five minutes later,
And your calf seizes up like a fist. Or your thigh cramps so
hard you yelp loud enough to frighten the cat. What in the name of all that is holy
just happened?
You’ve met heat cramps. They are not polite. They do not
send a warning card. …
You’ve been asked: “So, what are you going to do all day?”
You have an answer. But privately, you admit it’ll cover 2 to 3 hours a day.
You deserve a better, richer retirement.
Join our next Design Your New Life in Retirement small group program in September.
Learn more and sign up today.
…
You’ve been asked: “So, what are you going to do all day?”
You have an answer. But privately, you admit it’ll cover 2 to 3 hours a day.
You deserve a better, richer retirement.
Join our next D…
You’ve been asked: “So, what are you going to do all day?”
You have an answer. But privately, you admit it’ll cover 2 to 3 hours a day.
You deserve a better, richer retirement.
Join our next Design Your New Life in Retirement small group program in September.
Learn more and sign up today.
________________________
Dr. Jordan Grumet has crafted three books mapping the terrain between money, mortality, and meaning. His new book, The Healthcare Heist, opens with a story he rarely tells.
That experience became the seed of a much bigger argument: that insurers, pharmaceutical companies, pr…
“Fix or repair guy”
I’m a “fix-or-repair-guy.”
I differentiate this self-description from a “throw-away-and-buy-new-guy.”
Rapid replacement of broken items is, without a doubt, the more efficient course of action. I might spend two to ten hours repairing something that I could reorder …
“Fix or repair guy”
I’m a “fix-or-repair-guy.”
I differentiate this self-description from a “throw-away-and-buy-new-guy.”
Rapid replacement of broken items is, without a doubt, the more …
“Fix or repair guy”
I’m a “fix-or-repair-guy.”
I differentiate this self-description from a “throw-away-and-buy-new-guy.”
Rapid replacement of broken items is, without a doubt, the more efficient course of action. I might spend two to ten hours repairing something that I could reorder from Amazon in under 30 seconds. Silly.
There is evidently some other criterion at play here. Questions of efficiency and pricing my time never rise to the surface. I’d just rather fix it. It’s fun.
This week, the cleaning ladies dropped a hand painted tile made by Billie’s now thirty-somethin…
I've sat with 100 retirees, and the biggest regret almost never has anything to do with a bad investment. It's something I call the momentum trap. At 62, every single signal tells you to keep going, and almost nobody sees it coming until it's too late to get those years back. This v…
I've sat with 100 retirees, and the biggest regret almost never has anything to do with a bad investment. It's something I call the momentum trap. At 62, every single signal tells you to ke…
I've sat with 100 retirees, and the biggest regret almost never has anything to do with a bad investment. It's something I call the momentum trap. At 62, every single signal tells you to keep going, and almost nobody sees it coming until it's too late to get those years back. This video is what I tell every client who walks in at 62, the trap, the blind spots, and how to actually manage what comes next. We're going to cover: - the momentum trap that convinces smart, disciplined people to keep working long after they don't need to- why delaying Social Security to 70…
There is a particular
kind of silence that falls over a life when it arrives at a fork in the road. It
is not the quiet of peace, but the hush of a held breath. You stand at the junction
of two paths leading in opposite directions: to tell or not to tell, to leap
or not to leap, to leave or not to l…
There is a particular
kind of silence that falls over a life when it arrives at a fork in the road. It
is not the quiet of peace, but the hush of a held breath. You stand at the junction
of two paths …
There is a particular
kind of silence that falls over a life when it arrives at a fork in the road. It
is not the quiet of peace, but the hush of a held breath. You stand at the junction
of two paths leading in opposite directions: to tell or not to tell, to leap
or not to leap, to leave or not to leave.
In these moments,
time seems to stop, but the heart does not. The heart races. Because you know the
truth that all the platitudes about “new beginnings” try to hide: every real choice
is a double loss. Even the necessary losses, leaving a job that has died
inside you, ending a love that h…
She Left Her Body at 15: Laura Hoorweg on Grief, Mediumship, and the Other Side Episode Description What happens when your consciousness leaves your body, but you are still fully aware of who you are? At 15 years old, Laura Hoorweg was standing near the edge of a cliff in the Canadian wilderness whe…
She Left Her Body at 15: Laura Hoorweg on Grief, Mediumship, and the Other Side Episode Description What happens when your consciousness leaves your body, but you are still fully aware of who you are?…
She Left Her Body at 15: Laura Hoorweg on Grief, Mediumship, and the Other Side Episode Description What happens when your consciousness leaves your body, but you are still fully aware of who you are? At 15 years old, Laura Hoorweg was standing near the edge of a cliff in the Canadian wilderness when she says she suddenly found herself looking down at her own body. Moments later, she was above the Earth, then surrounded by galaxies, before being abruptly pulled back into her physical body. That experience changed the way she understood death, consciousness, and the human soul. In this episode …
Send us Fan Mail Most people already know what it takes to get healthier. Eat enough protein. Exercise consistently. Get quality sleep. So why aren't more people seeing results? Because the problem isn't a lack of information—it's a lack of execution. In this episode, I expla…
Send us Fan Mail Most people already know what it takes to get healthier. Eat enough protein. Exercise consistently. Get quality sleep. So why aren't more people seeing results? Because the…
Send us Fan Mail Most people already know what it takes to get healthier. Eat enough protein. Exercise consistently. Get quality sleep. So why aren't more people seeing results? Because the problem isn't a lack of information—it's a lack of execution. In this episode, I explain why so many of us keep searching for the next podcast, YouTube video, book, or fitness hack instead of simply doing the work we already know we need to do. We discuss: Why information has become a form of procrastination The difference between learning and taking action Why your first a…
In today's episode, Gina discusses the role of time in our anxiety healing journey, and specifically, our thoughts and perceptions of time. Urgency and the role of technology, constant notifications and information overload in exacerbating our anxiety are important factors discussed in this show. …
In today's episode, Gina discusses the role of time in our anxiety healing journey, and specifically, our thoughts and perceptions of time. Urgency and the role of technology, constant notifications …
In today's episode, Gina discusses the role of time in our anxiety healing journey, and specifically, our thoughts and perceptions of time. Urgency and the role of technology, constant notifications and information overload in exacerbating our anxiety are important factors discussed in this show. Listen in for tools and strategies you can use to reduce the effects of these factors that seem to rob us of our time and space. Start feeling better today!Stillpoint Fridays is my once-a-week Friday note — a slower, more personal reflection that’s different from what I share on the podcast.…
Many people dream of making a living in the arts. They imagine the performances, the applause, the recording sessions, or perhaps seeing their work displayed for the world to enjoy. What they often don't see is the entrepreneurial mindset required to sustain a creative career over decades.On a recen…
Many people dream of making a living in the arts. They imagine the performances, the applause, the recording sessions, or perhaps seeing their work displayed for the world to enjoy. What they often do…
Many people dream of making a living in the arts. They imagine the performances, the applause, the recording sessions, or perhaps seeing their work displayed for the world to enjoy. What they often don't see is the entrepreneurial mindset required to sustain a creative career over decades.On a recent episode of the Power of After Show, I had the pleasure of speaking with world-renowned conductor, composer, producer, and entrepreneur Robert Emery. Although Robert began his professional music career as a child prodigy, his long-term success has had far less to do with talent than with his willin…
A Common Sense Guide (No Psychology Degree Required) Meta description: A common sense guide to emotional intelligence for leaders — what it really means, how to build more of it, and how to use it in everyday work situations. It’s 4:45 on a Friday. You just got an email from a client t…
A Common Sense Guide (No Psychology Degree Required) Meta description: A common sense guide to emotional intelligence for leaders — what it really means, how to build more of it, and how to use i…
A Common Sense Guide (No Psychology Degree Required) Meta description: A common sense guide to emotional intelligence for leaders — what it really means, how to build more of it, and how to use it in everyday work situations. It’s 4:45 on a Friday. You just got an email from a client that makes your stomach drop — the project’s in trouble, and it’s not really your fault, but it’s about to be your problem. Ten minutes later, you’re walking into a team meeting and everyone’s watching your face to see how bad this is. What you do in the next sixty seconds sets the tone f…
Royce Shook
July 14, 2026
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Alan Cay Culler 
James Conole 
Stephanie Wautier 
Scott Friedman 
Gina Ryan 
Deborah Johnson 
Doug Thorpe