The Top 5 Regrets of Midlife Professionals

Part of Kathy Caprino’s series “Time to Brave Up” 

I’ve spent 11 years now focused on career coaching, teaching and training, helping mid-career professionals “dig deep, discover their right work, and illuminate the world with it.” I’ve seen several core themes emerge around what makes mid-career professionals (and middle-aged people in general) feel the deepest regret.

Below are the top five regrets I’ve heard from mid-career professionals around the world:

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 true.

So many thousands of people around the world feel deep regret and pain because they’re actually living someone else’s life – not their own.

Most typically, they’re living a life their parents told them to live, and engaging in careers their authority figures demanded or strongly encouraged they pursue.

I’ve heard from so many people aged 40-55 who now realize they’re in the completely wrong career, pursuing the wrong goals, because they studied in college what their parents and authority figures told them was the right thing, for security, stability and status. They also admit that there was a some unconscious or “hidden” cultural mandate they somehow felt, to become a doctor, lawyer, engineer, architect, etc., for the recognition and status that their parents thought would be achieved in these fields. The reality is that these professionals didn’t muster the courage to change directions, or say “No, I don’t want this!” And now many years have passed and they’re still not living life as they want to.

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 one your beloved parents wanted for you

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

So many men and women in middle age 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. 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 so much and sacrificed so much 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.

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, 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. They fear failing, going broke, not being able to care for their families financially. They fear leaving their “comfort zone” yet they see that perpetuating the status quo is excruciating and damaging.

The fears mid-career professionals, particularly women, often emerge from a lack of healthy boundaries, from intense people-pleasing behavior and a drive toward “perfectionistic overfunctioning”

– doing more than is necessary, healthy or appropriate. Until we can get in the cage with our fears and address them head on, fear will keep us stuck in quiet desperation.

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

When I wrote the post “6 Toxic Behaviors That Push People Away,” I heard from thousands of people (and still do) who shared how toxic their lives and relationships have become. And they shared that they have 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 parented, 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 shatter 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 conversation I have with mid-career professionals. Their fears around money, or their slavery to 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.

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, desperate situations for the entirety of our lives.

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 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, sad, depressed and angry. It catalyzes us to muster the courage, fortitude and commitment to finally do what’s required to start living the lives we long to.

And for that, we need to brave up.

To brave up and build a happier life, work with me, and check out my Amazing Career Project video training, my Facebook video on the top 5 regrets, and my TEDx talk “Time to Brave Up.”