The Top 5 Regrets Of Midlife Professionals

Part of Kathy Caprino's series "Becoming the Most Powerful You"

I’ve spent 16 years now focused on career coaching, teaching and training mid-to high-level professionals across 6 continents to “dig deep, discover their right work, and illuminate the world with it.” And in this work, I’ve seen a number of powerful repeating themes and patterns about what makes professionals experience the deepest pain and regret. Strangely, these patterns of regret are the same no matter where these people are from, their socioeconomic levels, education, roles, industries, and more.

Below are the top five regrets thousands of midlife professionals have shared. These are the same regrets I personally experienced when I was locked in my unhappy 18-year corporate career.

The top 5 regrets are:

1. I wish I hadn’t listened to other people about what I should study and pursue.

Many people believe that when you reach 40, you’ll certainly be living your own life, and making your own authentic choices. Sadly, I’ve found that it isn’t necessarily -- or even often -- true. Many people feel deep regret because they’re actually living someone else’s version of a "good" or "successful" life – not their own. Most typically, they’re living a life their parents or peers told them they need to live and are engaging in careers their authority figures demanded or strongly encouraged them to pursue.

I’ve heard from so many people aged 40-60 who now realize they’re in the completely wrong career, pursuing the wrong goals because they studied in college what their parents and "experts" told them was the right thing, for security, stability, money and status. They also admit that there was some unconscious or "hidden" cultural mandate they felt, to become a doctor, lawyer, or engineer, etc., for the recognition and status that their parents thought would be achieved in these fields. 

The reality is that these professionals didn’t believe they could challenge these mandates, or they could never muster the courage to change directions and say “No, I don’t want this!” And now, many years have passed and they’re still not living the life they want.

To live a happy, rewarding life on your own terms, it’s critical to starting saying “yes” to your authentic beliefs and values, and stop living someone else’s life that feels so wrong, even if it’s the life your beloved parents wanted for you.

2. I wish I hadn’t worked so hard and missed out on so much.

So many midlife men and women share that they regret what they’ve missed out on in life by working so hard. They missed being in the fabric of their children’s lives, being emotionally and physically present. Or they missed the chance to have children. They missed the opportunity to build true intimacy and closeness with their spouses, family and friends. They missed experiencing adventure, travel, enjoyment, vitality, learning, spiritual growth – not having the chance to stop and relish life, nature, good health, peace, or relaxation. They missed out on so much and sacrificed so much precious time to pursue work goals that now feel meaningless and empty.

I’ve seen that too that when people get to the end of their lives – in their 80s and 90s -- they’re not thinking at all about the work goals they strived so hard to achieve. They’re thinking about love and family, about the people that matter deeply to them, and how they made a difference to these people. And they deeply regret what they didn’t do with and for these loved ones.

For a potent glimpse into the top five regrets of the dying, which midlife people also begin to feel more acutely, listen in to the amazing and powerful wisdom of Bronnie Ware on my Finding Brave podcast:

We can learn so much from these top regrets of the dying, and finally, take action to change the trajectory of our lives today.

3. I wish I hadn’t let my fears stop me from making change.

We have many different fears that stop us from taking action, but the biggest fears are around failure, loss, humiliation and pain. Mid-career professionals share with me that they have so much fear and resistance around making change, particularly if it means they have to stretch out of their comfort zone, speak up and stand up for themselves, or risk losing things that they spent so long accumulating. They fear looking like a loser, going broke, not being able to care for their families financially, and having to start over. 

And they desperately fear leaving their “comfort zone” yet they see that perpetuating the status quo is far from "comfortable." In fact, it's often crushing.

The fears that seem to hit midlife professional women the hardest often emerge from a lack of strong, healthy boundaries, and from intense people-pleasing behavior and a drive toward “perfectionistic overfunctioning” – doing more than is healthy, appropriate and necessary and trying to get an A+ in all of it.

This is societally-trained behavior that includes teaching girls not to be assertive, outspoken and confident, and this training begins when girls are very young. For instance, research has shown that girls lose one-third of their confidence by the time they are thirteen years of age.

As adults, until we can get in the cage with our fears, close our power gaps and address what holds us back from living bravely and authentically -- and stop killing ourselves trying to live up to an impossible, unhappy standard -- fear will continue to lock us in quiet desperation.

4. I wish I had learned how to address toxic situations and people.

Back in 2014, I wrote a LinkedIn post "6 Toxic Behaviors That Push People Away" that went viral (over 3 million views) and I was shocked at the outcome. I heard from over 1,000 people who shared how toxic their lives and relationships had become. And they admitted with amazing candor that they themselves were toxic to be with, and often had no idea what to do about it.

Toxicity is rampant today, and so much of it comes from stress and from negative, damaging ways we were raised and shaped, and what we were taught (or not taught) about acceptable and unacceptable behavior. It also emerges from people whose self-esteem has been severely hurt– through childhood pain, trauma in later life, and crushing experiences at work that shattered them.

Toxicity – at work, in relationships, and in our own thoughts -- hurts us terribly, but often we don’t see it clearly enough until our bodies break down, or other crises hit that focus us to take brave new action to learn to love, protect, and heal ourselves.

5. I wish I hadn’t let myself become so trapped around money.

Finally, the money issue – this comes up in almost every coaching conversation I have with mid-career professionals. Their concerns around money, even if they have an abundance of it, generate deep regret. People share that they know they’re not living the life they long to, and they’re sick and depressed about it, but they simply can’t see a way out because they’re trapped about money.

Either they feel they need to keep making exactly the same amount as they are today, so they won’t change directions or leave their toxic jobs or careers, or they’re desperate because they’re not making enough, so they want to pursue something “safe” that they know will make them miserable in the end.

Often, they have huge misconceptions too about the "cost" of changing careers or jobs, and those misconceptions stop them from even exploring change in a risk-free way.

I’ve learned that our relationship with money goes very deep, and stems directly from our wealth programming and what we learned from childhood about it. 

The negative, fear-based stories we tell ourselves about money keep playing out in our lives, despite all our best efforts. If we don’t get to the bottom of our own money story and heal it, we remain trapped in unhappy situations for the entirety of our lives.

Money is often at the root of why we lose connection to the thrilling dreams we once had for our lives and careers. This is one of what I call the 7 most damaging power gaps that professionals face today. In fact, 76% of the over 1200 women I've surveyed indicate that they've let go of the dreams they once had for joyful, thrilling work and have no idea how to reclaim that dream.

Here's more on that power gap:

If you’re like me, when you hit 50, it was a huge awakening. I felt as if I were suddenly in a new “club” and that club allowed me to be stronger, braver, and bolder, and stop wasting my precious time. Suddenly, seeing that the number of years you have ahead of you in life is smaller than what’s behind you, is a very motivating experience.

For many, it elicits an urgency to address what’s wrong in our lives – what makes us sick, depressed and angry. It catalyzes us to muster the fortitude and commitment to stand up for ourselves and choose more authentic paths. We say "Enough!" to all those who pressure us to be someone we don't want to be. We have the tough conversations we need to. And we finally take the rights steps to build meaningful and impactful lives we can be proud of.

And for that, we need to find brave every day.

For hands-on coaching support to build a more rewarding career, join me in a Career Breakthrough coaching program, check out my book The Most Powerful You: 7 Bravery-Boosting Paths to Career Bliss and tune into my weekly Finding Brave podcast.