“Throw Off the Bowlines”: A Note to High Performers Who’ve Been Playing It Safe
“Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do, so throw off the bowlines, sail away from safe harbor, catch the trade winds in your sails. Explore, Dream, Discover.” — Often attributed to Mark Twain
This has become one of my favorite quotes—but I didn’t discover it until later in life. By then, I had already done what many business leaders do well: built a career, chased results, hit targets, and provided for my family. On paper, it all worked. Promotions. Responsibility. Momentum. But if I’m honest, I also played it safe for a long time. Now I’m trying to catch up.
The Cost of Always Choosing “Later”
Business rewards discipline, consistency, and delayed gratification. Those traits build great companies—but taken too far, they quietly convince us to postpone living.
- I’ll travel when this season slows down.
- I’ll do that trip when the kids are older.
- I’ll take the risk when things are more secure.
The problem? There is always another quarter, another launch, another reason to wait. And before you realize it, twenty years have passed.
Safe Harbor Is Comfortable—But Nothing Grows There
In sailing, a safe harbor is exactly what it sounds like: protected, predictable, and low-risk. It’s necessary at times. But no sailor ever talks about the harbor as the highlight of the journey. The same is true in life and business. Growth—real growth—happens when you loosen the lines and trust the wind. When you choose experiences that can’t be optimized, controlled, or scheduled into neat blocks on a calendar.
- Adventure forces presence.
- Presence creates memory.
- Memory becomes legacy.
Give Your Children the Gift of Adventure
Your kids won’t remember how many emails you answered or how polished your LinkedIn profile was. They’ll remember:
- The trip that didn’t go exactly as planned
- The laughter when something broke or went wrong
- Seeing you try something new, even when it felt uncomfortable
Adventure teaches courage, adaptability, humility, and wonder—lessons no classroom or screen can replicate. You can show your children the world online. But you can only give them the world by stepping into it together.
Experiences Can’t Be Replaced by Content
We live in an age where you can watch a TikTok, scroll an AI-generated post, or see a drone shot of almost anywhere on Earth in seconds. But consumption is not experience.
You don’t smell the salt air through a screen. You don’t feel the exhaustion, the exhilaration, the stillness. You don’t grow the same way.
Some things must be lived to be understood.
A Challenge to Fellow Business Leaders
If you’re reading this and thinking, “This resonates, but I don’t have time right now,” that may be the signal you need to listen more closely. Ask yourself:
- What am I postponing that matters?
- What memories am I assuming I’ll create later?
- What would it look like to design a life—not just a career?
Success is a terrible thing to waste on a life that never gets fully lived.
Throw Off the Bowlines
Go create memories with friends and family. Say yes to the trip, the experience, the season of adventure. Let your children see you explore, dream, and discover—not someday, but now. Because one day, sooner than you expect, “later” will arrive. And the only thing worse than risk is regret.