Is This It?

Welcome to the very first edition of Is This It? 🎉 Mid-life "success" anxiety, ambition, and redefining what fulfillment looks like.

Before we dive in, let me set the stage: I'm 38, and I've been asking myself this question more and more lately. Is this it? Is this what I worked so hard for? The career, the achievements, the life I thought I wanted… why does it sometimes feel like I'm still waiting for the "real" part to begin?

If you've ever found yourself successful on paper but restless in reality, you're not alone. This newsletter is for anyone navigating the complicated territory between ambition and fulfillment, between what we thought we wanted and what actually brings us joy.

Now let's talk about the quote that inspired this launch:

"Doubt killed more dreams than failure ever did."

Let me start with a confession: this quote has been sitting in my iPhone Notes app for years. That's where I stash all the words of wisdom I stumble upon - whether from books, movies, friends, or the occasional wise housewife (Dorinda Medley is words of wisdom gold). It's my little vault of truths I turn to when I need a kick in the pants or a moment of clarity.

This particular quote has been whispering to me for months. Why? Because for as long as I can remember, I've wanted to share my stories - the messy, wonderful, challenging reality of building a life that looks successful from the outside while still questioning if this is really "it" on the inside.

For years, I let doubt hold me back. 🤔 Who am I to think anyone would care about my mid-life existential crisis? What if no one reads it? What if I fail? But then, I flipped the script: What if I don't try? What if sharing these questions creates connections with others asking the same thing? What if this leap, small as it seems, leads to something that actually feels fulfilling?

The truth is, doubt is a dream killer. It convinces you that you should be grateful for what you have, that questioning your path means you're ungrateful or lost. But sometimes, life has a way of forcing your hand—reminding you that the only real failure is not trying to find what actually matters.

Let me tell you about two moments from this summer that crystallized why this newsletter needed to exist now, not someday when I felt "ready."

The First Wake-Up Call: I was in Madison, Wisconsin, working remotely from my mom's house while I dropped off my daughter ahead of our summer getaway. My husband and I were preparing for a vacation to Spain - two weeks of pure escape. Then came the meeting invitation with a cryptic message. I knew instantly what was coming: layoffs. The entire team, gone. There I was, about to embark on an expensive European vacation, suddenly unemployed.

But here's the thing I didn't expect: I'd been unhappy in my role for nearly two years, passively exploring new opportunities but never quite finding the courage to make the leap. In a strange way, getting laid off felt less like a setback and more like the universe answering my question: "Is this it?" with a resounding "Nope, try again."

The Second Wake-Up Call: Ten days later, 35,000 feet above the Atlantic, our plane's engine failed. Mid-ocean, nowhere to land, passengers crying and praying. For the first time in my life, I genuinely thought I might die. I accepted it. I found peace in it.

But here's where life got beautifully complicated: we emergency-landed in the Azores; somewhere I'd never heard of, but suddenly felt deeply grateful for. What should have been just a traumatic pit stop turned into over 24 hours in one of the most stunning places on earth. Rolling green hills, cows roaming freely, dramatic cliffs dropping straight to the ocean, and the kindest, most hospitable people we'd encountered on our entire vacation.

The juxtaposition was surreal: near-death experience followed by accidental paradise. Instead of being consumed by trauma, I found myself present and grateful, wandering this whimsical place I didn't know existed. From terror to wonder in the span of a few hours. We landed safely back home, obviously, but something fundamental shifted - not just about mortality, but about what actually constitutes a life well-lived.

Those 10 days forced me to confront everything I’d been avoiding.

Here's what those moments taught me: We spend so much time climbing toward some imaginary finish line that we forget to ask if we're even running the right race. Getting laid off while on vacation should have been devastating. Nearly dying in a plane crash should have been traumatic. Instead, they became the push I needed to stop asking "Is this it?" and start creating something that actually felt like an answer.

I'm 38, married to my husband of 8 years (we've been together for 18!), and a proud dad since June 2023 when we adopted our incredible daughter. She's single-handedly my biggest blessing and the light of my life. Until recently, I worked in technology for a media and entertainment company (summer layoffs, thanks for that), and I'm navigating the journey to find work that balances financial stability with personal fulfillment… more on that adventure to come.

I live in NYC: the greatest city in the world, full of endless possibilities and constant reminders that everyone else seems to have it figured out. I'm competitive yet often crippled by self-doubt, ambitious to a fault with an entrepreneurial spirit, but increasingly aware that traditional success metrics don't always translate to actual happiness.

This newsletter is for anyone who's ever achieved something they worked hard for, only to find themselves asking, "Okay, but is this it?" It's about the gap between external success and internal fulfillment, the anxiety that comes with having what you thought you wanted but still feeling like something's missing.

Each week, I'll share one quote that's been sitting in my Notes app, paired with an essay exploring the messy reality of mid-life ambition, parenting, career transitions, and the ongoing quest to build a life that feels genuinely fulfilling, not just impressive on paper.

Some weeks, it'll make you laugh. Other weeks, it might make you think or feel a little less alone in your own "Is this it?" moments. My hope is that together, we can redefine what success actually looks like when you're brave enough to be honest about what you really want.

Think of me as your modern-day gay dad version of Carrie Bradshaw having an existential crisis. So to channel my inner Carrie:

I couldn't help but wonder... if this is supposed to be "it" why does it sometimes feel like I'm still waiting for my life to begin?

Don't let doubt rob you of your right to question everything. While I'm actively searching for my next role, I'm also choosing to invest this time in something that genuinely brings me joy: connecting with others who are asking the same uncomfortable questions about success, fulfillment, and what actually matters.

This transitional moment gave me something invaluable: the space to pursue something that felt fulfilling from the time my fingers hit the keyboard. Instead of viewing this period as just waiting for what's next, I'm seizing it as an opportunity to invest in what truly matters to me.

Whatever it is you've been holding back on - questioning your path, starting something new, or simply admitting that you want more than what you have - go for it. Life's too short and too unpredictable to wait for the "perfect" moment. Sometimes the perfect moment is right after everything goes wrong, when you finally have the clarity and courage to ask: "Is this really it?"

Thank you for joining me at the start of this journey. If this resonated, forward it to a friend who might be asking the same question. Let's build this community, one honest conversation at a time.

One small realization that shifted my perspective or taught me something unexpected.

Sitting at the Azores airfield after our emergency landing, watching my husband finally stop shaking, I realized something profound: We spend so much time worrying about the wrong things. I'd been paralyzed by the fear of starting a newsletter, while the real risk was never starting at all. Sometimes it takes almost losing everything to realize what actually matters… and what doesn't.

Is This It? will land in your inbox every Friday! Think of it as your weekly dose of honest reflection to kick off the weekend. If you know someone who might be asking the same questions, please share this with them and encourage them to subscribe. I'd love to connect with you too! Hit forward, hit reply, or just keep reading. Every bit of engagement helps build this into something meaningful.

Until next Friday, 

Chris

Next week: "The Things We'll Never Remember Learning" - what potty training taught me about growth, patience, and finding meaning in the moments that don't make it to your highlight reel.