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I’m regretting the bad decisions I made during my Midlife Crisis and paying for it now.
At 52 years old I’m starting my life over. After making a horrid romantic decision that resulted in my complete financial ruin, I’m having to rebuild from zero.
Here’s what happened and how I’m fixing it using ancient knowledge from the Stoics and good old fashion pragmatic advice.
The Regret Overwhelmed Me
It’s 3 PM on August 20, 2024, the north facing view out the window over the Colorado Rockies at 42,130 feet filled me with wonder and awe. I had traveled these mountains for years in my RV, and even backpacked them for over 100 miles on the Colorado Trail. I found myself rather privileged to have experienced them from below and above.
Yet as the Boeing 737 glided through the air in and out of white fluffy clouds I felt the rush of deep regret. I once lived free moving about these mountains yet I let a romantic partner manipulate me out of my dreams.
I didn’t want to leave Colorado. After a couple of weeks there, I had a positive mindset recharge and felt strong physically after hiking quite a bit. Yet as the plane headed west, deep down I felt I was headed back to something I never wanted for myself.
When Life Was Grand and Free of Regrets
In July 2020, I headed out for my maiden voyage in my new-to-me RV. I was free. No financial burdens. My kids were on their own. I could make every decision for myself.
That summer I venture into Colorado, driving that lumbering RV down forest roads, solo, the world had opened up to me.
Read also : Amazing Camping in Colorado During my Maiden Voyage
As I looked down on the terrain from the plane 4 years later, I tried to be hopeful of my future but that summer in 2020 kept playing in my head. The vivid memories of camping in the woods brought saddened tears to my eyes, will I ever experience being truly me again? Will I recover mentally and financially from letting a toxic man take all that from me?
Last time I was free of burdens while in Colorado. This time the burdens in my head weighed so heavy I almost couldn’t enjoy the gorgeous sights below.
I pushed back the sadness and regret and decided to live in the moment, at least for the next 2 hours to Las Vegas I won’t let him control my life.
Feeling Regret at Midlife
It’s a common occurrence to have regrets between the ages of 45 and 65. With the vigor of youth gone and the imminent approach of old age around the corner many people at this stage of life begin to reassess their past decisions.
Some react by making, what many would consider, irrational decisions to reclaim that youth. We see this in the cliché of the middle-aged man buying the red convertible and even marrying a younger woman. The image of Clark Griswold in National Lampoon’s Vacation classic scene comically epitomizes this phase of life as he fumbles eating a dog urine soaked sandwich as a beautiful, younger Christie Brinkley flirts with him.
I was no stranger to making horrific decisions in midlife while trying to regain the fun of being younger with no worries or burdens.
At 49 years old and 6 months into living solo in my RV, I got into a relationship with a man who would later prove to be the most toxic person to have entered my life.
Deep down I knew he was toxic, I classically ignored my gut to experience what I thought was love.
He portrayed youthful fun, yet later I realized it was masked narcissistic irresponsibility. Over the years his mask fell away to reveal his true nature but it was too late for me to recover, the damage was done. By the time I figured out what he truly represented, I was psychologically and financially ruined.
After the Midlife Crash : Feeling Regret for the First Time
Approaching Las Vegas, flying over Utah and then Nevada strong turbulent air shook the plane causing sudden, frightening drops in elevation. I couldn’t help but find parallel in this moment with my last 4 years during what I like to call my Midlife Crisis.
Those years were filled with beauty and strength yet strong setbacks as I made bad decisions in my love life. At times I was flying high and others I’d drop into depressive states with the feeling I had no future.
Then the crash. The break up and financial ruin in 2024.
Read also : When I Realized It was a Midlife Crisis
I thought to myself, “I do hope this flight doesn’t end with a crash like my life did this year.”
As I landed in Las Vegas, looking at the landscape of the treeless desert, I felt empty inside. I gave away my freedom to a toxic man and now I’m starting over my life at 52.
I’m regretting ever meeting him. I regret ever feeling like I missed out on my youth and fun that lead me to making the horrific decision to be with a toxic person.
For the first time in my life I was feeling regret. I didn’t want to go back to the Arizona heat and being locked inside a house until at least October. This wasn’t the home I made for myself, that home was on the road and now it was gone.
This thought made my stomach turn. After 4 years of freedom on the road, living what I felt was my best life, I was going to be locked in a prison.
Solutions to Midlife Regret
Below are 3 solutions I’ve decided work most days to help me stop regretting the bad decisions I made and move forward in a positive manner.
- Stoicism
- Forgiveness
- Advice to myself
Will Stoicism Solve My Problems?
“No person has the power to have everything they want, but it is in their power not to want what they don’t have, and to cheerfully put to good use what they do have.”
– Seneca
In the last year or so I’ve started to study Stoicism.
With the help of Ryan Holiday and his book The Obstacle is the Way, I’ve begin my study of how to live a better live through the philosophy and virtues of the Stoics.
Facing the facts without judgment and emotion is what my life is right now. I can cry and feel sorry for myself. Or I can use my mind and body to get out. The decision is mine.
Most days I can apply Stoic philosophy to my daily life and move forward not letting emotion dictate my actions, like I did 4 years.
Do I Need to Forgive Myself to End the Cycle of Regret?
Forgiving myself for the bad decisions I made is yet to happen.
I know letting go of past mistakes knowing I’m only human will release me from mental burdens I carry and just might help me build myself back up again financially.
Yet I feel I need to be financially stable and prove I’m mentally strong to be able to leave this in my past. For now, I’m working 7 days a week online get back on my feet.
Some days I’m in this viscous cycle of needing to lift out of my hole yet without forgiveness it may never come.
Giving Myself the Advice I Would Give Others May Work
Frankly, there are days I just need to trick myself. “What would I say to a reader or a dear friend if they were in my situation?” And then follow that advice.
I’d tell them the following:
“These middle years don’t need to be full of regrets, they can be a positive time to pivot. Men and women can and do find that life between 45 and 65 is enlightening. Reveling in the fact that we have life experience and intellect under our belts, many people dive into new hobbies, change careers or revamp a love life that went stale. Midlife can be a time of exploration and rejuvenation of who we truly are, something that most of us suppressed for years during career building, child-rearing and holding our marriages together.“
When all else fails, I advise myself. And then maybe I can find my way back to being Allie again.
To You : How do you deal with Midlife regret?
Please leave a comment below to share your experience with conquering that aching feeling that you truly messed up and can’t get out of the hole.
Helpful Resources
Life Reimagined : The Science, Art and Opportunity of Midlife This book has helped me understand Midlife a little better and knowing I’m normal.
The Mindful Path to Self-Compassion: Freeing Yourself from Destructive Thoughts and Emotions I once constantly carried self loathing and negative thoughts, until I decided to stop. A book I read a few years back that gave me permission to give my self some compassion. And begin healing.
Every Challenge Presents a Choice by Jon Brooks. A stoics view on how nature has given us the resources to make good decisions and use challenges as opportunities.
Stoicism 101 by Holstee (They created the manifesto that changed my life years ago, see image below)
My Complimentary YouTube Video
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I’m Allie. At 48 I set out solo to live in my RV. That journey is on hold but my passions for hiking and living well in my 50s still live on! Join me below for more inspiration and adventures. We’re older but even stronger!
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