Hello Friend,

Today, I want to talk about something that doesn’t come naturally for most of us: embracing uncertainty. It’s uncomfortable, sometimes downright terrifying, but it’s also where some of the biggest breakthroughs happen. Learning to lean into the unknown isn’t just a business skill—it’s a life skill.

In March, I had a great conversation with Lukas Gage on the Let Me Save You 25 Years podcast. Lukas, an actor who’s chosen to build a career on quality over quantity, has faced more than his fair share of “leaps of faith.” In an industry filled with uncertainty, he’s had to turn down work, trusting that the right roles would come along. His story of taking risks and thriving in ambiguity resonated deeply with me. In fact, it reminded me of my journey with Lovesac.

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Why Embracing Uncertainty Matters

Learning to navigate uncertainty isn’t about ignoring the risks. It’s about acknowledging them while moving forward anyway. In business and in life, the ability to embrace the unknown helps us see opportunities where others see obstacles, pushing us to be resourceful, innovative, and resilient. This leap of faith isn’t easy, but it’s a critical skill in any path worth taking.

Three Ways to Lean Into the Unknown:

Break Down the Unknown into Smaller Steps
Big, unknown challenges can be overwhelming. Breaking them down into smaller, manageable steps makes the path clearer. Take one step forward, evaluate it, and then plan the next. Before you know it, you’re moving forward confidently, even in ambiguity.

Lean on Your Support Network
We don’t have to face the unknown alone. Whether it’s family, mentors, or colleagues, leaning on a support system can make uncertainty feel more manageable. Sometimes, just talking things through brings clarity.

Stay Present and Grounded
Uncertainty can pull us into future “what-ifs.” Staying present helps us focus on what we can control right now. You’re better equipped to handle whatever comes next when you're grounded in the present.

Recommended Reading

Ryan Holiday’s The Obstacle Is the Way – If you’re looking to build resilience in the face of challenges, this book is a great resource. It dives into the philosophy of Stoicism, offering practical advice for navigating uncertainty and adversity with calm and clarity.

One Last Thought

Straight up: uncertainty isn’t easy. It’s uncomfortable, and we often do anything to avoid it. But here’s what I’ve learned: leaning into the unknown becomes a catalyst for growth. You discover strengths you didn’t know you had. You find solutions that would have never surfaced otherwise. Embracing uncertainty is about moving forward even when the path is unclear—it’s about trusting that each step will reveal the next.

What’s one time in your life when taking a leap of faith changed everything? Reply directly to this email to let me know. I’d love to hear how embracing the unknown has impacted your journey!

Keep moving forward,

P.S. Don't miss these recent podcasts featuring Gary Vee and Garrett Gee!