I recently finished Jerry Colonna’s mesmerizing work, Reboot: Leadership and the Art of Growing Up, and it has transformed my thinking about this period of transition in my life. I recently wrote about what I'm lovingly calling my “midlife existential crisis”, and I explained that following a period of one challenge, and one tough blow after another, I went through a career upheaval that left me reeling. It left me despondent and depressed. My usual ability to shake off the struggle and recommit myself to a positive vision of the future felt like it would never return. 

I spent several months consuming memoirs of people - mostly women - who reached similar points in their lives for one reason or another. Inflection points. Moments or times when something inside of them shifted. 

In this time I read:

• The Year of Yes by Shonda Rhimes

• On Being Human by Jennifer Pastiloff

• Maybe You Should Talk to Someone by Lori Gottlieb

• No Happy Endings by Nora McInerny

• Brave, Not Perfect: Fear Less, Fail More and Live Bolder by Reshma Saujani 

And these books filled me with wonder and inspiration while making me feel just a little less alone. All of this reading, all of this curiosity about how others cope with an experience like mine - one of feeling lost, while wondering “what next?” - helped me understand this state of despair was not just a routine depression resulting from yet another punch in the gut, towards my self-confidence and assuredness. 

No, this was a time for me to pivot. And yes, I’m purposely borrowing a term from the startup lexicon. As a company you pivot when you realize your current product, or your company’s current direction, needs to be adjusted substantially. You realize that if you continue down the current path, you won’t get to where you dream of going. No, you’ll sputter out, and run out of the gas and money and time it’ll take to make your dreams happen, and actually realize the vision you’ve held for so long. 

Life is like this. When you get a divorce, you don’t just lose a relationship. You lose your dream of the future. The vision you had for the next few years, for your old age. You aren’t just reconstructing your daily routine, your finances, or your romantic relationship. You’re recreating your entire life, and the hopes and dreams you held for that life. 

Inspiration from Leaders Who’ve Failed

These moments of change are all too common in our lives. We all experience hard losses that force us to rethink everything, to reevaluate every idea we had for our lives, and, if we’re brave enough, to forge a new plan for our future. Despite the fact that a life pivot is so damn common, Jerry Colonna helped me realize that our language around this transition needs to be changed. 

I had no idea how to describe what I was going through. The only term that seemed at all relevant was “Midlife Crisis.” And frankly, I used that term while having a consultation with a new therapist. I said, “It’s not like I’m having a midlife crisis or anything.” And she replied, “Why not? You are middle-aged.” Oof. 

Yes, if you look at the exact definition of “crisis”, it fits. But man, the connotation of that term is so doomsday, so full of despair, conflict, and devastation. And what’s more, it gives you no sense of what comes next. 

Why don’t we look at these periods of change, these inflection points in our lives, with hope, optimism, and positivity, instead of as failure? 

I often chalk up the lack of satisfaction and pride in our lives to the unfortunate power of social media - of being bombarded with images, videos, and stories of other people’s highlight reel while we’re living our own bloopers and B-roll. But this goes deeper than that. 

I’m currently listening to the book Range: Why Generalists Triumph in a Specialized World by David Epstein, and he dives into the power of being a generalist, and the limitations that come from being an early specialist. He tells stories about so many of our most lauded artists, leaders, and professionals of every stripe, sharing how they found their path, cultivated their career trajectory after multiple failures, or how they bounced around from one job, one direction, to another. 

So many of these sound like utter failures, where they were frustrated with their lack of early success, and tired of regularly hearing from family members and loved ones that they should just stick with something - even if they hate it. We are told from a very young age that the right way to grow up, the proper way to achieve success, is to pick a direction and pursue it with commitment, with fervor. 

Some people are able to do that. Their path to success is linear and logical. Other people strike gold early in their careers - achieving that now oh-so-tantalizing status of a unicorn while still in their 20s. These stories of successful young upstarts are pervasive. I think, perhaps, they always have been, but they are even more so today. They dominate our understanding of what success means today. College dropouts like Bill Gates, Steve Jobs, and Mark Zuckerberg cloud our perception of how one gets to the top. 

And when you don’t follow that model, choosing instead to bounce around, take your time shaping your own vision for the future, and charting your own path toward success - however, we’re defining it - we feel behind. Then, when we experience life’s inevitable setbacks, prompting us to reassess and re-envision our future, it often leaves us feeling even greater failure, despair, and frustration, rather than signaling that we are ever closer to the life we deserve. 

Celebrating Self-Discovery

I am increasingly aware and accepting of the fact that I am still very much in discovery mode, trying to navigate my life, opportunity, and future. I also own that life hasn’t been the easiest in the last few years, especially with health diagnoses, a divorce, and business decisions that just didn’t pan out. 

I have a long way to go before I will claim that I have figured anything out what I want to be when I grow up, but I have figured out one thing. This is not a crisis.

I’m realizing this is part of the process, a necessary step of the journey, and one that should be celebrated instead of mourned.

I’m not going to lie and say I’ve fully shed this idea, this feeling that I’ve come up short in life and have some serious catching up to do. That sense is too deeply ingrained in me to shake off so easily, but I am done feeding the idea that every single step of my journey and my self-discovery aren’t valid and worth celebrating. 

This is a pivot. A reboot. 

And it’s a sign that good things are coming.