Reboot Podcast Episode #180 – Navigating Darkness, Perfectionism & Purpose as an Entrepreneur – with Melissa Berstein

The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.

#180 // October 23, 2025

Guests

Melissa Bernstein

Melissa Bernstein

Author & Co-founder of Melissa & Doug

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Episode Description

At the heart of entrepreneurship lies not just innovation and ambition, but a deeper journey of self-discovery, resilience, and embracing our most authentic selves. Entrepreneurship, often glamorized for its successes, can just as easily lead us into the depths of uncertainty, loneliness, and self-doubt. Yet, as we face these challenges with open hearts, we discover the possibility for profound transformation—both in our work and in ourselves.

In this episode, we welcome Melissa Bernstein, entrepreneur, creator, and co-founder of Melissa & Doug. With candor and warmth, Melissa shares insights from her latest book, The Heart of Entrepreneurship, reflecting on her lifelong dance between creativity and perfectionism, passion and patience, success and existential struggle. Together, Jerry and Melissa unpack what it means to persevere through the “rollercoaster” of building something meaningful, the importance of embracing imperfection, and the healing power of making our inner journeys visible.

Show Highlights

Memorable Quotes:

“Your journey shows that entrepreneurship isn’t only about ideas, but about learning to bear uncertainty, to temper ego, to stay aligned with what matters most. It’s one of my favorite phrases. And to do so in a way that sustains not just the business, but the human being at its center.” – Jerry Colonna

“The heart of entrepreneurship is at the intersection of finding something you’re passionate about and that gives your life enough purpose that you’re willing to have the patience to see it through to fruition.” – Melissa Bernstein

“If you don’t have a mission that you are so passionate about, that you are willing to eat that glass every single day, you won’t have the resilience to last more than a few months, much less decades.” – Melissa Bernstein

“We are wired for homeostasis. We are wired for comfort, safety, and familiarity with things that are known. So entrepreneurship is actually counter to being human. Our humaneness wants safety, and entrepreneurship throws all that into flux. So to truly be an entrepreneur, you have to actually overcome what is endemic to being human, which is why it’s so difficult and it’s so challenging and it takes such courage because ultimately you have to transcend yourself to be an entrepreneur.” – Melissa Bernstein

“I agree it’s about transcending the human tendency towards safety and certainty. And in doing so, I think you get the chance to be even more human, even more adult. Just like romantic relationship, just like parenting presents an opportunity for us to confront the parts of ourselves that we’d really rather not, in our bid to stay safe, entrepreneurship is an opportunity to put it all out there, to confront the insecurities that arise when you put a product out there.” – Jerry Colonna

“Perfectionism is a curse and will ultimately lead to breakdown because, as humans, we are imperfect. And if we are striving for something that we are not, then it’ll make us so we don’t try anything out of the box. And even thus, we will still constantly fail because we’re that’s the beauty of us. We have lots of foibles and cracks.” – Melissa Bernstein

“You realize when you do show your truth that so many others are feeling exactly the same way, and you’re not alone. And that is a revelation to those of us who believe in our despair that we’re entirely alone.” – Melissa Bernstein

“People who are high achievers have existential meaning crises more often and more acutely than people who aren’t achievers. And it’s because they realize that all these achievements actually don’t fill the void.” – Melissa Bernstein

“I do think it’s possible to get to a point where the striving is a kind of striving for your personal best.” – Jerry Colonna