Leadership. Parenthood. Work. Life. They all come with expectations—often ones we place on ourselves. We’re supposed to have it together, show up as the calm in the storm, and always know what to do. But what happens when we don’t?
When you’re the one in charge but feeling totally lost.
When you’re the parent but aren’t sure how to parent.
When you’re the boss, but you’re looking to your team for direction.
When you’re supposed to be the thought leader, but clarity is nowhere to be found.
When people depend on you to be the calm in the storm, but inside, you’re battling your own panic.
When you’re promising to take care of others’ families while your own feels like it’s slipping through your fingers.
When you say you don’t need affirmation, but you find yourself searching for it in all the wrong places.
When you’re sitting at a bar on a work trip, talking up your company while fighting back the feeling of being an impostor.
If any of this resonates with you, know this: You’re not alone.
This Is My Story, But It’s Likely Yours Too
In fact, I’m there right now. These last few months have been some of the hardest of my life.
Everywhere I turn, there’s another challenge demanding more of me than I feel capable of giving. Work has been a whirlwind—exciting but relentless. At home, the weight of being the dad my family needs feels heavier than ever. And internally, I’ve been wrestling with a deeper struggle: Who am I when I feel like I’m falling short?
The truth is, leadership, in all its forms, can feel isolating. When people look to you for guidance, you feel the pressure to perform, to deliver, to have all the answers. And when you don’t? It’s easy to spiral into self-doubt.
I’ve asked myself questions like:
It’s in these moments that I’m learning—slowly and imperfectly—what real leadership looks like.
Real Leadership Means Admitting You Don’t Have It All Together
There’s this myth we tell ourselves: To lead, we have to be invincible. But what if the opposite is true? What if real strength is found in admitting we’re struggling? What if true connection is built in our vulnerability?
I’ve had to remind myself that it’s okay to ask for help. It’s okay to tell your team, “I don’t have all the answers, but I’m committed to figuring this out with you.” It’s okay to tell your spouse, “I feel like I’m failing, and I need your grace.” It’s okay to pause, breathe, and let yourself feel the weight of it all without judgment.
It’s also okay to confront the shadows that whisper lies about our value and purpose.
The Shadows We Face
Jon Tyson talks about the lies that creep in during these moments—the Shadow of Futility and the Shadow of Apathy.
The Shadow of Futility tells us: “My work doesn’t matter.” It convinces us that the effort we’re pouring into our work, family, or community is meaningless. But the truth is this: “You have a calling to serve and heal the world.”
Even when you feel like you’re stumbling, your work has meaning. The care you show your family, the leadership you provide your team, the ways you contribute to the world—they all matter. The fruit of your labor might be hidden, but it’s never futile.
The Shadow of Apathy tells us: “There’s nothing worth giving yourself for.” When the pressure mounts, it tempts us to disengage, to stop showing up. But the truth is this: “You were born to live a life of consequence.”
Even when it feels overwhelming, you were created for impact. Leaning in—even when it’s hard—shapes a legacy that matters.
Life Is Messy, Leadership Is Hard, but You’re Not Alone
I don’t have all the answers. But I do know this: The moments we feel most lost are often the moments we’re growing the most. The times we feel like impostors are usually the times we’re stepping into something bigger than ourselves. And when we’re brave enough to admit we’re struggling, we create space for others to do the same.
So if you’re reading this, feeling like you’re barely holding it together—take heart. You don’t have to be perfect to lead. You don’t have to have all the answers. You just have to keep showing up.
We’ll figure this out together.
Justin has a proven track record of delivering results for clients across a range of industries, including hospitality, technology, retail, and non-profit.