What Scares Me the Most (and Why I Do It Anyway)

Hazards of the sea aren’t what keep me up at night—hardly shocking for a man raised on tales of whaling ships and rogue waves. What does strike fear into the core of me, though, is something far quieter, much more personal, and distinctly less cinematic: vulnerability. Yep, I’d rather weather a gale-force storm than say aloud, “I think I really like you.” But, as time and experience have taught me, the things that terrify us often hold the keys to the connections we crave. So, despite trembling like a leaf in the wind, I do it anyway. Here’s why—and how.

The Fear Factor: Why Vulnerability Spooks Us

Let’s set the scene. Vulnerability—whether it’s acknowledging a crush, owning up to a mistake, or opening up about your hopes for the future—feels a lot like walking into the ocean on a cold morning. The water is bracing, your body protests, and your instinct is to run back to the warm safety of the shore. But staying on dry land means missing out on swimming entirely. This delicate balance between safety and immersion is exactly where vulnerability lives.

My fear of it didn’t pop up out of nowhere. Growing up surrounded by the stoic practicality of Nantucketers, emotions weren’t exactly dinner-table conversation, unless the emotion in question was enthusiasm for saltwater taffy or disdain for certain tourists parking illegally on cobblestone streets. My parents were kind and loving, but I was taught, indirectly, that keeping things “steady as she goes” was best.

It wasn’t until years later, after my junior year in Edinburgh, where I was writing one tragically bad maritime-themed love poem after another, that I realized something: the only way to fully experience connection is to lean into the discomfort of being seen. And by “seen,” I don’t just mean your Sunday best—I mean your messiest, most trying, sailor-swearing self.

In the Trenches: How I (Reluctantly) Learned to Be Vulnerable

Learning to navigate fear is like learning to navigate a ship: trial, error, and the occasional bout of seasickness.

Bumbling Confessions

Remember your first real love? Mine happened the summer after boarding school. Back on Nantucket, I became hopelessly enamored with someone who worked at the coffee shop near my family’s inn. She had hair like a storm cloud and eyes the shade of the sea right before a squall—a poet’s dream, really. But one day, while attempting to confess my feelings, my words came out as something like, “Uh, coffee’s great. I think I love you. Um. Not coffee. You. Coffee’s great, though!” I left in a flash of panic.

Her response, if you’re wondering, was kind. She even asked if I wanted to sit outside with her and talk for a bit. Embarrassing? Sure. Humbling? Absolutely. But as we sat on that weathered bench sharing awkward laughs, I realized even bumbling vulnerability beats keeping everything bottled up.

Why It’s Worth It: The Unexpected Rewards of Fear

Turns out, there’s an entire treasure trove on the other side of fear (and no, I’m not about to compare it to buried pirate gold—but close). Vulnerability, despite its uninviting façade, is magnetic. When you share your fears, hopes, or truthfully admit you’ve spent more time in line at Trader Joe’s rehearsing a conversation than actual shopping, people respond. Because at the heart of it, your bravery gives them permission to put down their own armor.

Here’s why it’s worth the discomfort:

  1. Freedom from Overthinking: Speaking your truth saves you from mentally replaying the “What if I had…?” scenarios at 2 a.m.

  2. Deeper Connections: Genuine moments foster trust faster than perfectly rehearsed lines. It’s not perfection people fall for—it’s humanity.

  3. Self-Respect: Just as you admire someone who’s bold enough to ask for what they want, you’ll find respect for yourself when you do the same.

Anchors That Steady Me—And Can Steady You

Of course, just because I’ve learned to put myself out there doesn’t mean it’s a breeze. I still get second thoughts before initiating touchy conversations, amending a mistake, or worse yet, attempting modern dating (a story for another time). But I’ve cobbled together a few strategies that help me push past the fear, and they might just help you too.

1. Embrace the Awkward

Getting vulnerable with another person will lead to awkward moments. Prepare for this like you’d prep for bad weather: with patience, humor, and plenty of dry towels (metaphorically speaking). Remember, awkward isn’t failure—it’s just the sound of growing pains.

2. Lower the Stakes

Not every vulnerable conversation has to be grand. Start small. Share a quirky childhood story you’ve never told anyone, or admit to a fear that won’t rock the boat too hard. These “practice rounds” build the muscle.

3. Lean on Humor

Historical fact: humor has always been my life raft. Even in the messiest moments, a little well-timed levity keeps things afloat. Think of it as tossing a buoy to lighten the weight of the serious stuff. (But avoid self-deprecating too much—it’s a slippery slope.)

4. Pause for Perspective

If I’m dwelling on whether I’ll say or do the “wrong thing” while trying to share, this quote from Teddy Roosevelt pulls me back into place: “It is not the critic who counts…The credit belongs to the man who is actually in the arena.” You’re in the arena. That deserves credit.

5. Remember: Rejection Isn’t the Villain

Here’s the truth—sometimes it won’t work out. But rejection is not the fire-breathing antagonist it’s built up to be. It’s just one more character in this grand comedy of errors we call life. You can grow from it. Trust me. (And if you can’t, at least there’s wine.)

Conclusion: Cast Off the Bowlines

The fears we face when it comes to vulnerability might not look like storms or serpents, but they’re just as daunting. (Frankly, I think our brains are sneakier villains than any leviathan from old sailor tales.) Still, each vulnerable step is worth it. Whether it’s love, forgiveness, or deeper understanding you’re seeking, it’s waiting on the other side of that boat you’re so hesitant to leave.

So here’s my challenge to you: take the plunge, one toe at a time. Confess something small. Speak an unspoken truth. Tell someone you care about that, despite your stoic demeanor, they actually mean the world to you. Sure, it’s terrifying—but then again, aren’t the best views always at the end of the most difficult climbs?