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  • Kerri Cummings

The Art of Overthinking: Confessions of a Successful, Middle-Aged Adult

As I sit in my impeccably organized home office (and by impeccably organized I mean messy), sipping on a freshly brewed cup of coffee, I can't help but reflect on the journey that brought me here. You see, I've always been a successful person. A high-achiever, a go-getter, a Type-A personality, call it what you will. But little did I know that my penchant for success would also come with a hidden side effect: overthinking.

Ah, overthinking. The art of over-analyzing, over-worrying, and over-complicating even the simplest of tasks. It's like a relentless mental loop that plays in my head on repeat, as I dissect every decision, anticipate every possible outcome, and weigh the pros and cons of every situation. From choosing the right outfit for an important meeting to planning the perfect vacation, my brain can spin into a vortex of endless thoughts, leaving me mentally exhausted and emotionally drained.

As a successful, middle-aged adult with a thriving career, a loving family, and a well-managed social life, you'd think I have it all figured out. But little do people know, behind the polished exterior lies a mind that's constantly buzzing with thoughts, worries, and doubts. It's like having a mental circus in my head, with multiple acts competing for attention - the lion of work deadlines roaring, the trapeze artist of family responsibilities swinging, and the juggling clown of social obligations tossing tasks in the air.

One might think that with age and experience, overthinking would subside. But no, it only seems to have gotten worse. As I've climbed the ladder of success, the stakes have gotten higher, the decisions more complex, and the responsibilities greater. I find myself second-guessing my every move, fretting over the smallest details, and playing out worst-case scenarios in my head like a broken record.

Take the recent incident of choosing the perfect gift for my friend’s birthday. What started as a simple task of buying a present turned into an epic quest for the ideal present. I researched, read reviews, compared prices, and analyzed every possible option, only to end up feeling overwhelmed and exhausted. In the end, I settled for a gift card, feeling defeated and drained by my own overthinking.

And don't even get me started on my work-related decisions. From choosing the right projects to take on, to navigating office politics, to making strategic career moves, my mind becomes a labyrinth of endless possibilities and potential outcomes. I often find myself playing out scenarios in my head like a movie director, meticulously planning every scene and analyzing the potential risks and rewards.

And do you know what comes of all of that? NOTHING. NILL. ZILCH. I end up not doing much of anything.

But overthinking doesn't just stop at work or personal decisions. It seeps into every aspect of my life. From fretting over what to wear to a social event to obsessing over the right words to say in a conversation, my mind is a whirlwind of thoughts, worries, and what-ifs. It's like having an overactive brain that refuses to take a break, constantly on the lookout for potential problems and pitfalls.

One of the most frustrating aspects of overthinking is that it often leads to analysis paralysis and … PROCRASTINATION.

The more I think, the less decisive I become, and the more I procrastinate. It's like being stuck in a mental quicksand, unable to make a move without drowning in doubts and uncertainties. And as a successful professional who's used to taking charge and making things happen, this lack of action can be infuriating.

But amidst the chaos of overthinking, there's one thing that has been a game-changer for me: mindfulness. Yes, that seemingly elusive state of being fully present. It sounds really foo-foo or esoteric, but it is not folks. (yes, you businessman in the back scoffing, saying stuff like “I don’t do girly stuff like meditating”, yeah I’m looking at you.)

When I first started practicing mindfulness, I was skeptical. I mean, how could just sitting there and observing my breath make a difference? But the more I did it, the more I realized how powerful it was. Instead of getting lost in my thoughts, I was able to observe them without judgment. I could acknowledge my worries and anxieties, but not let them control me.

Now, it DOES takes practice (a lot!), and there are still plenty of times when I get caught up in my thoughts. But I've found that the more I practice mindfulness, the easier it is to let go of those thoughts and come back to the present moment. And that's a pretty damn good feeling. And what’s more, it helps me get more done because I’m spending more time taking action and less time THINKING about it.

Here's a small exercise ANYONE can do (yeah, Mr. Business man in the back, even YOU have time for this:


You simply sit with your eyes closed (or open if you want) for 60 seconds, paying attention to your breath. That’s it.

Try it. You’ll be amazed at how one single minute can feel like a tiny little vacation!


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