Read from “Never Play It Safe” (pg 11):
I kept letting myself get talked out of living my dreams by people who had given up on theirs. And it became a pattern that I repeated well into adulthood. I’d discover something unique and different about myself that I truly loved—go deep into that thing that made me come alive—and then like clockwork I’d put someone else’s idea of what I should be doing above my own. I let myself be pulled toward convention and the illusion of safety again and again. A willing concession of my unique- ness and my power.
In college I traded studies that I loved—art and literature— for premed because it was more impressive when someone asked what I was studying.
I traded a career in professional soccer for medical school at first, and then graduate school later, because I was conditioned to believe it was safer to align around a respectable, well-paying job than make a bet on myself, risking rejection or a blown-out knee.
I even walked away from a dream career as one of the world’s top photographers to run a venture-backed startup because it was trendy and because people kept telling me it was the “next logical step in my career.” But let’s be honest. I also knew my decision would garner near-universal approval from my peers. Looking back, it’s clear that although I loved the work and the impact our company made, what played a huge role in my decision to change directions was that founding and building a platform that would be used by millions and would create the possibility of a significant financial exit had the makings of the next great milestone to check off in a life based largely on achievement.
These are just a few of the easiest self-betrayals to describe in a sentence or two. But I made dozens, perhaps hundreds, of other such trade-offs in my careers, relationships, and other areas of my life where I willingly, even if unknowingly, swapped my authentic heart and soul for the tidy, well-worn ruts of others. The reasoning was always the same: either my dream plan wasn’t reasonable or practical or I wasn’t.
To be fair, I narrowly managed to navigate my way through, over, and around each of the escapades above, but each came at an exceedingly high cost. During one particularly difficult period, I found myself exploring ways to unwind and stumbled upon the world of ohne jede Verifizierung online zocken, where the simplicity and ease of access offered a momentary escape from the pressures of daily life. Some of these escapades came with debilitating illnesses due to stress. Others came with $100,000 in student loan debt. Others still resulted in family fights, lost friends, wounded egos, and some serious scar tissue.
All of this suffering on one hand, and yet, on the other, a set of remarkable recoveries. I always bounced back . . . perhaps not in a way I could have anticipated. These, I have come to realize, are the unexpected victories that will ultimately define my life— each allowing for an incrementally healthier, harmonized, and fulfilled chapter beyond the one before it. For example, bailing on medical and graduate school gave me the time to pursue photography full time, and I’ve earned a hundred times the student debt since then. Leading the startup allowed us to serve tens of millions of students, generate hundreds of millions in revenue, and be acquired by a public company, which provided a financial outcome for the team that made me feel as if the long road was worth the effort in spite of the downside. The family and friends I’ve bonded with along the way were orders of magnitude more valuable than those I lost, and the bruised ego and scar tissue are what enabled me to take the next step toward this moment. I’m much faster now at recognizing the temptation to put my own sense of right and wrong aside in order to do whatever everyone else thinks is best. I’m still not batting a thousand—and I never will be—but I’ve finally been able to (mostly) short circuit the swing between playing it safe and then needing to course correct.
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That excerpt is from my new book Never Play It Safe, and it’s available – TOMORROW! Wow, cannot wait to finally get this book into the world because we’ve all been there, haven’t we? We feel the pull of something exciting, a dream that makes us come alive, only to be talked out of it by someone who insists it’s “unrealistic,” “impractical,” or just plain “too risky.” And more often than not, these voices come from people who have already given up on their own dreams, who have chosen a path of safety and conformity. But their paths don’t have to be yours.
Here’s how we break free from that.
Recognize the Patterns of Self-Betrayal
Here’s the hard truth. Most of the time, the person talking us out of our dreams isn’t out there. It’s in here. Inside our own heads. We let those outside voices echo in our minds until they become our own. This isn’t just about the big moments either. It’s those little moments that add up, when you choose the “safe” route—taking that stable job instead of starting your own thing, swapping out the passion project for what “looks better” on paper.
It’s easy to fall into these patterns. I did it for years. And every time, it took a toll. The question is: where in your life are you trading your real desires for what others think is “reasonable”?
Understand Where This Advice Comes From
Most of the time, people who discourage you from following your dreams aren’t trying to harm you. They think they’re helping. But here’s the catch—they’re often speaking from a place of fear, not possibility. They’ve made their choices, usually choices that led them away from their own dreams. And they need to believe those were the right choices, so they project that onto you.
Next time someone offers unsolicited advice about your life, take a beat. Ask yourself: Is this person living a life I’d want? Do they know what it takes to go after what I’m pursuing? Or are they just afraid, trying to keep me on the same safe, predictable path they chose?
The Real Cost of Playing It Safe
Listen, taking someone else’s path can cost you more than you realize. Stress, debt, missed opportunities, and even your health can take a hit when you’re not living true to yourself. And it’s not just about missing out on what you could have done. It’s about missing out on who you could have become.
What have you traded for the illusion of safety? Was it a creative project? A relationship? Or maybe it’s a version of yourself that you never got to know? These are real, tangible costs, and the longer you keep paying them, the further you drift from the life that’s truly yours.
Course Correcting: It’s Never Too Late
If my story proves anything, it’s that there’s always room to course-correct. Sure, I made some choices that didn’t line up with who I really am. But I learned, adapted, and moved forward. And you can too.
You don’t have to burn everything down and start from scratch. Sometimes, it’s about small adjustments—starting to dedicate more time to what lights you up, or slowly phasing out the things that don’t. It’s about making deliberate choices to align with what you truly want, step by step.
Build the Courage to Trust Your Own Path
Here’s the thing—courage isn’t about not feeling fear. It’s about feeling it and still stepping forward. It’s about holding onto your vision when others doubt you. That’s where the magic happens.
Start by listening to your gut. Make small choices that reflect your true desires, even if they’re just baby steps. And find people who’ve walked a similar path and can provide some guidance and inspiration. The more you lean into those decisions, the stronger your trust in yourself becomes.
Find Your True Support System
It’s critical to surround yourself with people who push you to follow your dreams, not just play it safe. You may have to seek out a new community, a new tribe. And that’s okay. It’s all about finding those who see the world as you do, who understand the value of choosing passion over convention.
Take a look around. Who’s in your corner? Who’s there to support you when the going gets tough? Build those connections and lean on them when you need it.
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Embrace Growth Over Perfection
Let’s face it—you’re going to mess up. You’re going to make choices that don’t work out. But that’s not a sign to stop. That’s a sign to learn and keep going. Growth is messy, and it’s rarely a straight line. It’s more about resilience than perfection. Keep moving forward, keep learning, and keep evolving.
Your Life, Your Choices
At the end of the day, the choice is always yours. You can stick to someone else’s script, or you can tear it up and write your own. The question is, are you ready to reclaim your path and make it truly yours?
Think about it. Reflect on where you are. Are you living your dream or someone else’s idea of what your life should be? Decide now to take back your power. The world needs that unique version of you that only you can bring.
And remember, when you look back, it won’t be the risks you took on yourself that you’ll regret. It’ll be the times you didn’t.
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