Is It Time to Burn the Boats?

I’ve been thinking a lot lately about comfort.

Not the sleep-number-on-your-mattress kind or the La-Z-Boy kind, but the comfort that comes when you’re more or less set up in life. Life often ends up…fine. The job. The relationship. The day-to-day. And there’s nothing wrong with fine, except when it quietly becomes all we’re meant for.

So, like I do, I tend to wander into history when questions like this start nagging at me. I found myself mulling over the likely apocryphal story of Hernán Cortés. When he arrived in Mexico in 1519, he supposedly burned his ships so his men couldn’t retreat. No plan B. (It’s really a jerk move when you think about it). But if it is true, I love the moxie. I love the idea that the only way forward is forward. It’s like that scene in Gattaca when Vincent says “I never saved anything for the swim back.”

But there’s something in that idea that haunts me. Sometimes the thing holding us back isn’t lack of ability. It’s the safety net we’re clutching. It’s inertia. It’s the past or the cozy present making plans for our future by default.

And I get it, there isn’t necessarily anything wrong with comfort itself. Life is hard and being comfortable is nice. But what has been keeping me up at nights is this: Do golden handcuffs, cozy confines, and settling for “good enough” create a prison? Are we chained by something we mistake for security?

So this week, let’s talk about comfort and the chains that come with it, what it really means to burn the boats, why the safety of fine might be costing more than we think, and how you can know when it’s time to choose the leap into that great unknown.

The Comfort Trap (Or: Why Fine Feels Like Quicksand)

So yeah, about comfort: it's not a neutral thing. It's not just the absence of pain or struggle. Comfort is an active force. It wraps around you slowly, like layers of a soft, warm blanket, until one day you realize you can't move.

"Fine" has a way of stretching? One year becomes three. Three becomes five. You tell yourself you'll make a move after this project wraps up, after the bonus hits, after you've saved a little more. But there's always another milestone. Another reason to wait. The goalposts have legs, and they're faster than you think.

Your brain is complicit in this, by the way. It's wired to keep you alive, not happy. And alive, in your brain's estimation, means predictable. Known. Safe. So every time you think about leaving—the job, the city, the relationship that's run its course—your brain floods you with reasons to stay.

But there is a cost that compounds quietly in the time you don't get back. Energy you don't spend building something that matters. Versions of yourself you never meet because you were too comfortable to go looking for them.

The question isn't "Is this bad?" Most comfortable situations aren't bad. They're just... fine. The real question is: Am I staying because this is right, or am I staying because leaving is hard?

Because if it's the second one, you're not in comfort. You are trapped in a trap that just happens to have good benefits and decent snacks in the breakroom.

You Need the Fear a la Chandler Bing

There’s this moment in Friends when Rachel wants to leave Central Perk for a career in fashion but feels stuck. She’s scared and doesn’t know what comes next. Chandler tells her to quit first, because only then will she have the fear that forces her to figure it out.

He's right. Not in a toxic hustle-culture way, but in a deeply human way. Fear, the right kind of fear, wakes you up. It makes you resourceful. It activates a version of yourself that comfort keeps dormant.

Cause what if the safety net is also the thing keeping you from flying? What if knowing you can always go back is exactly why you never fully commit to going forward?

Burning the boats isn't about being reckless. It's not about jumping without looking or making stupid decisions because they feel dramatic. It's about making retreat harder than progress. It's about removing the easy outs so that the only way through is through.

Sometimes that safety net isn't protecting you. It's preserving the status quo. And the status quo, left unchecked, has a way of becoming your entire life.

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How to Know When It's Time (And What Burning Your Boats Actually Looks Like)

So how do you know? How do you tell the difference between comfortable and stuck? Between patience and procrastination? Between wisdom and cowardice?

Here are some signs you might be in the comfort trap:

• You’re bored more than you’re energized. If you can predict your next several months down to the weekly routine, and that thought makes you feel numb instead of grateful.

• Resentment is creeping in. At your job. At your routine. Maybe even at yourself. That low-grade irritation that shows up on Sunday nights or during your commute? That’s not just a bad mood. That’s your future self trying to get your attention.

• You’ve started using the word “someday” a lot. As in, “Someday I’ll start that business” or “Someday I’ll move to that city” or “Someday I’ll have the guts to try.” Someday sounds like a plan without requiring any action.

• The “what if it disappeared” test makes you feel relieved instead of devastated. Imagine the comfortable option vanishing, the job ending, the relationship breaking up, the lease expiring. Do you feel panicked or quietly, guiltily relieved?

Of course, burning your boats doesn’t always mean setting everything on fire in one dramatic gesture. Sometimes it looks like: Telling people your plan so backing out gets embarrassing. Setting a date and buying the ticket. Spending the money on the course or the equipment so sunk cost kicks in. Quitting before you have it all figured out. Making the decision public enough that retreat feels harder than progress.

Honestly, deep down you probably already know if it’s time. And I’ll wager you’ve known for a while. The question isn’t whether you’re ready, cause you’ll never feel fully ready. The question is whether you’re willing to trade the comfort of certainty for the possibility of something more.

In Conclusion

Comfort isn’t evil. But it’s not innocent either. It has an agenda, and that agenda is keeping you exactly. where. you. are. And maybe where you are is great. Maybe fine is exactly what you need right now. But if you’re reading this and feeling that familiar ache—the one that whispers “there’s more”—then I think you already know the answer.

You don’t have to burn everything at once. But you do have to be honest about what staying is costing you. Because the thing about burning boats is that it has nothing to do with the boats. It’s about what you’re willing to do when retreat stops being an option.

Cortés probably didn’t burn his ships, and Rachel is fictional—but the concept holds: sometimes you need the fear. Sometimes you need to close the door behind you to see what you’re actually capable of building ahead of you.

What comfortable exit are you holding onto? What would happen if you let it go?

The leap is scary. But so is looking back in five years and realizing you spent all that time standing on the shore, wondering what if.

As always, thanks for reading,
— Derek (AKA Chief Rabbit)
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