#15: The Top 7 Regrets of Mid-Career Professionals
If you’re like me, when you hit 40, you may have had an awakening...like you’re suddenly in a new “club”--it’s not a “Gives Zero Fucks” club...but, rather, a “Gives More Considered and Aligned Fucks” club. A club that helps you to be more courageous and bold...that fuels your chutzpah to stop wasting your time and start living a more satisfying life on your terms.
Seeing that the number of years you have ahead of you in life is roughly equal to what’s behind you becomes motivational fuel...it catalyzes an urgency to course correct that which makes you sad, frustrated, or angry.
Whether your desired changes are radical or smaller, there are consistent themes that emerge: failure, loss, pain. Do these sound familiar? If so, you’re not alone.
I get to spend my days helping mid-career professionals--people roughly 35 to 55 years old--look inward and embrace curiosity to discover their best professional good. Through my conversations and coaching sessions, I’ve seen several core themes emerge around what makes mid-career professionals (and, generally, people in midlife) feel the deepest regret. Today, I’ll share the top seven regrets.
My hope is that by exposing what others are most disappointed about in their professional lives, you can maximize your chances of minimizing professional regret in your life.
So...what do you regret most about your career?
Instead of suppressing your career regrets with a pint of Haagen-Dazs, it’s time to fly your regret flag, my friend. Why? Because regret can be a powerful catalyst for change...one that far outweighs the short-term emotional downsides you might’ve tried to eat your way through with last night’s pint of Dulce de Leche. Which, for the record, is the best premium caramel ice cream ever...and I should know. I ate it almost daily back when I was a marketer for Haagen-Dazs. It was my first job out of college and, while fun, it set me up for a lifetime of disappointment when I later learned no other employer has a stash of free ice cream 10 feet from my desk.
Recently, I’ve been on a mission to explore the awkward but powerful question of, “What would you do if you could magically rewind your career?” I surveyed and interviewed scores of mid-career professionals between the ages of 35 and 55, and I asked each of them what they regretted most about their careers to date. It was a diverse group: a 42-year-old new mom looking to make a career pivot, a burnt-out teacher, a seasoned tech expert, a corporate director. You see...disappointment doesn’t discriminate. No matter the industry, role, or relative success, a few key themes emerged that I’m happy to share with you today. Because I know that you might be fearing leaving your “comfort zone,” and yet you see that perpetuating your “Jo/e Midlife” status quo is excruciating...even damaging.
You can become the Mid-Career Change Champ you secretly long to be. And you can create a rewarding career change without sacrificing what you’ve worked so hard to build.
But it requires us to articulate and celebrate our disappointments, understanding that it’s our capacity to experience regret deeply, and learn from it constructively to ultimately frame our future success. You see regret isn’t all bad--it can be a helpful, even inspiring emotion. Don’t bother with that “No Regrets” tattoo!
And with that unintentional pep talk out of the way, let’s get to those top seven regrets of mid-career professionals.
Regret #1: “I wish I had acted on my career hunches.”
“Now or never” moments appear from time to time in our careers. Like that time I had dinner with Richard Branson on the roof of the SoHo House in Manhattan, despite the fact that I’d just spent the entire afternoon vomiting from next-level motion sickness and didn’t have time to shower before meeting him. That was definitely a “now or never” moment--in all my puke-y glory! But I’m so glad I acted on my hunch with that one--he’s one of my idols. Psychological research suggests the importance of identifying these sometimes unpredictable but potentially rewarding moments of change and jumping on these nonlinear opportunities to enhance your professional life. So the question to ask yourself is, “What’s a career hunch I’m currently ignoring?” Go ahead, take 5 minutes to write it out.
Regret #2: “I wish I hadn’t listened to other people about what to pursue.”
So many people think that when you reach 40, you’ll be living your own life and making your own choices. But this isn’t always the case. Living someone else’s life is a bigger theme than you might suspect. Mom, Dad, Mrs. Johnson from 10th-grade English, and so many other influential authority figures..you hear me? There are a lot of people who realize they’re in the wrong career because they listened to someone else about what would provide the stability and maybe even status. To say nothing of the unspoken prestige we confer upon someone who chooses to become a doctor, lawyer, engineer, architect, etc. There are a lot of people who haven’t yet mustered the courage to change directions...and are still living life on someone else’s terms. I say this with sincere knowledge...the first time I went to grad school was absolutely based on the ideas and encouragement of others. And while other people are probably operating from a place of love and trying to help... I wonder if they’d also like to take responsibility for my school loans…?
Regret #3: “I wish I hadn’t worked so hard and missed out on so much.”
So many mid-career professionals regret what they’ve missed out on in life by working so hard: children’s activities, the chance to have children, intimacy with loved ones, adventure and travel, spiritual growth, and even simple relaxation. In contrast, their pursuits now feel almost meaningless and empty. Of course, we know from the Harvard Study of Adult Development -- one of the world’s longest-running longevity studies -- 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. Again, this resonates for me, too. As anyone who’s worked at a startup can attest, you grind over some SERIOUSLY long hours. Having worked for 3 different startups, I definitely did my time. And as a 42-year-old woman who’s never been married or had children, I’ve occasionally second-guessed my decisions to throw myself so fully into my career. Today, I have tremendous clarity about what I want for my life...and how I choose to spend my time. But even 5 years ago, I was unsure about whether my window of opportunity for kids was closing without my consent.
Regret #4: “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 our biggest fears tend to be around failure, loss, and pain. The fears mid-career professionals have, particularly women, often emerge from a lack of healthy boundaries, from intense people-pleasing behavior, and from a drive toward “perfectionistic over-functioning” – 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. Just like facing our regrets head-on, we’ve got to do the same with fear. While these themes have never consciously been a big concern for me post-college, I suspect they’ve loomed large in my subconscious...which is bound to happen for someone who was a big fish in a very small pond throughout my upbringing. And these fears are everywhere among my clients when we first start working together. But watching my clients move beyond these patterns is one of the most rewarding aspects of my work.
Regret #5: “I wish I had the confidence to start my own business.”
For many midlifers, as personal finances shore up, there’s a yearning for more control in life. One obvious answer to this is to become an owner, instead of an employee. But there’s a big gap between wanting and doing: a recent study found that 70% of workers wished their current job would help them with starting a business in the future, yet only 15% said they had what it takes to actually venture out on their own. This is even true of Fortune 500 CEOs. If you’ve been wanting to venture out on your own, there’s so much opportunity right now. It’s an exciting time to start your own business! And the resources to help you make it happen are easier than ever to access. Let’s talk to get you moving in the right direction.
Regret #6: “I wish I had quit earlier.”
Almost uniformly, those who had actually quit their jobs to pursue their purpose wished they had done so earlier. But it can be hard to do, even when you’re dissatisfied. And especially during the COVID pandemic. But making your switch needn’t be a zero-sum game--there are ways to pursue your career reinvention without having to quit first. Nevertheless, it’s nice to hear what lies on the other side of quitting, isn’t it?
Regret #7: “I wish I hadn’t become trapped by the money.”
Unsurprisingly, the top regret was moolah. This plays out in a couple of ways: Either people feel they need to keep making exactly the same amount as they are today, so they won’t change direction or leave their toxic jobs...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. So many people out there are sick and depressed about it, but they simply can’t see a way out. Those golden handcuffs are real, y’all. But they don’t have to be. I promise.
Hopefully, you see yourself in these regrets (remember, that’s a good thing) so you can begin to overcome them. Because this is such a big theme for people in midlife. And it’s also a big theme when looking back on life at age 65+. Research shows that our oldest generation is telling us to live a life with “yes” as our bias...and that we’re much more likely to regret a career move we didn’t make than trying and having it not work out. Like the “better to have loved and lost than to have never loved at all” mantra -- but with your career!
So if you’re seeking career change or career reinvention, then let’s talk. Just go to meghankrause.com to learn more about how I can help you do precisely this!
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