Why Waiting for a Second Chance Holds You Back from Building a Fulfilling Life
- 11 hours ago
- 6 min read
Written by Rachael Chestnut, Builder of Iconic Brands
Rachael Chestnut is a former military strategist turned brand builder, creating iconic brands engineered for cultural impact through human-centered strategy. She is the Founder of The Play Nice Agency and a frequent contributor to marketing and media publications.
A few months ago, I was standing in my kitchen, hovering over the espresso machine (impatiently waiting for my jet fuel to brew), when my partner walked into the room, exhaling an audible “ugh!” The “ugh-sigh” is a primary form of communication in our household. I’m a business marketer and entrepreneur, and she’s a property manager, barista, and semi-professional dog wrangler. Often, in tandem, we’ll let out audible sighs, pleading to the universe, “Can we catch a fu*king break, please?” Some days, simply existing in the world, while having to do things like wash your hair and fold laundry, can feel like an impossible ask.
The relentless demand of the “daily churn” is something we’re all familiar with, and as Americans, it’s hardly the worst part of our shared experience. The backdrop of our professional lives is marred by a constant state of tragedy.
To make the “ugh” even more warranted, as working Americans, our collective understanding of who we are was founded on the concept of progress. We’re the quintessential roll-up-our-sleeves do-ers, builders, and leaders who thrive on productive frenzy. And today, our output is overshadowed by a cultural landscape that feels increasingly untenable.
Our daily lives are marred by a 24-hour news cycle covering stories about war, tyranny, acts of violence, and social upheaval, yet we remain at our computers, forcing productivity, while the world splits at the seams.
When I talk to clients, friends, neighbors, and fellow business leaders, I hear the same quiet confession again and again, I feel untethered. There’s a shared undercurrent of exhaustion and uncertainty, a sense of striving without clarity, pushing forward without a clear north star.
For many, each day feels less like purpose-driven progress and more like survival. There’s an anxious, low-grade pressure to “make it” somehow, financially, personally, without a clear definition of what it even is. It’s draining. It’s also deeply human.
The reality of life on earth isn’t very forgiving. It’s true. There are no “pass go, and collect $200” cards handed out here. The macro-arc of our existence doesn’t offer redo’s. There’s no extra inning waiting for us to finally decide to live well.
It took me nearly two decades to fully realize that not getting a second chance to build a life rooted in joy, fulfillment, and peace is the greatest motivator I’ve ever known. Having one shot changes everything. It forces intention.
So we ask, “What’s the point of all this?” We all want the same answer. And we want someone else to give it to us. In the absence of certainty, we distract ourselves, chasing performance, productivity, optics, anything to avoid the uncomfortable truth.
Most of us operate under the assumption that we’ll get a second chance to do it better. And we won’t. Once I stopped banking on the myth of second chances, I started building a life that felt sustainable now, one that moved me away from doomscrolling and quiet existential spirals toward something steadier, abundance. ownership. agency.
What emerged were ten intention-based practices (part mindset, part action) that dramatically changed how I navigate both my best days and my most “ugh” ones. I call it my yolo execution plan. At its core, it’s simple.
Mindset shifts in life
Turn obstacles into opportunities: When you’re in “the shit,” instead of wallowing in the experience, focus on the outcome of the experience. Choose to view challenges as opportunities to further your career, intimacy, knowledge, and personal growth.
Stop letting fear dictate your strategy: Sometimes, fear can be a great motivator, however, it shouldn’t perpetuate anxiety that governs your decision-making. If it’s not being used productively, it’ll only block you from reaching your full potential.
Build your self-worth like it’s an empire: I once had a therapist who, every week, asked me the same rhetorical question, “Whose butt is more important?” Answer, it’s always yours. (Unless you have children. In that case, your butt is the second most important.) Don’t devalue yourself because others have done that to you. Healthy boundaries are a brand positioning for your life.
Stay intellectually curious: The more we learn about the world, the more engaged we become, which propels further curiosity. And curiosity fights things like depression and hopelessness. You don’t have time to feel hopeless when you’re too busy learning about soil minerals or the health benefits of ice baths.
Stop believing your own lies: Most of our internal narratives have very little to do with reality. Living in your head means you’re not living in the world. Unless you’re knee-deep in writing a fiction novel, get out of your noodle and into the fresh air.
Action shifts
Let shit go: (Sings Blink 182’s "All the Small Things" in my head). The minutiae? Let it slide off you like water off a duck’s back. Save your limited energy for the big-ticket items that directly impact you and compound over time.
Choose hard paths: The more you challenge yourself to take the path less traveled, the more emboldened and unfuckable-with you become. Reward yourself for choosing challenge over comfort. I promise, it’ll make you feel like a superhero every day.
Say “yes” to calculated discomfort: So many of us have a knee-jerk reaction to say “no” to things that feel uncomfortable and unfamiliar, because these feelings require you to relinquish the illusion of having control. Let yourself feel uncomfortable. Growth rarely feels comfortable or convenient.
Build a five-year plan: To drive feelings of progress and purpose, it’s helpful to set actionable and measurable goals for our lives, which helps us build not just a more intentional life but serves as a reminder that we’re consistently working toward something.
Make your own luck: This is the most important skill I’ve ever learned. When life presents you with a “no,” know there is always a “yes” somewhere to be snatched up if you’re bold enough to find it. Finding the “yes” requires creative problem solving, relentlessness, and an unshakable faith in your ability to transform your reality. But if you’re looking for a “yes,” there’s more than one way to get it.
Here’s what I’ve learned: Moving from “UGH” to aligned, energized, and forward-moving in life and in business requires the same thing, the willingness and courage to stop waiting for better conditions to make your move. And this isn’t just my personal philosophy. It’s how I approach branding and business strategy.
It’s true. We’re living in a volatile, fast-shifting market and culture. The rules of the game are changing. Attention is fragmented, and trust is fragile. And so many leaders and businesses are quietly asking the same question individuals are asking, "Where do I fit now?"
If you’re feeling that tension, you’re not alone. If you feel like your business needs reinvigoration, your brand feels misaligned for this moment, or your personal positioning no longer reflects who you’ve become, that’s not a failure. It’s a signal. It may be time to evolve.
If you’re ready to reposition your business for stronger growth and cultural relevance, or refine your brand strategy to move more purposefully in this climate, I’d love to have a conversation. Think about where you are and where you want to be. Think about what’s standing in the way.
Because just like in life, there’s no second chance at this particular moment in your business. But there is an opportunity to build something with more intention, resilience, and alignment.
One day soon, you’ll find yourself moving from the “UGHs” to the “HAHAs.” And when you make this shift, you’ll realize you didn’t need a second chance. You just needed to make a move. If that resonates, let’s talk.
Read more from Rachael Chestnut
Rachael Chestnut, Builder of Iconic Brands
Rachael Chestnut is the Founder and CEO of The Play Nice Agency, working with Fortune 500 powerhouses to scrappy startups, helping leaders build iconic brands with high cultural impact. Before her brand-building days, Rachael cut her teeth doing "secret squirrel" work for the government as a trained military strategist and applied international economist, experience that shapes her disciplined, high-stakes approach to brand business strategy. Rachael regularly leads seminars and workshops to support new business leaders in her local community, and is a frequent contributor to digital marketing outlets that aren't afraid to publish the "f-word," which she always uses both sparingly and strategically.
