The Power of Perseverance
What a 25-year boat project reminded me about staying the course
I met a guy on the dock in Trinidad. His name is Jack.
Over 25 years ago, Jack acquired a small sailboat. The boat had been wrecked and was in pretty rough shape. But Jack saw potential in the vessel’s clean lines and good bones.
Fast forward to today, and after many, many hours of work, the boat has been restored to glory. She’s all new wood and fresh varnish, still boasting those clean lines and good bones. A real beaut, as they’d say.
Jack is finally gearing up to leave the dock. He has a million adventures planned and can’t wait to set sail on a dream that’s been more than a quarter-century in the making. It was a joy to meet him.
And I haven’t been able to stop thinking about him.
Jack—and his beautiful boat—have stayed on my mind for the past couple of weeks. I keep returning to his more-than-average dose of perseverance. Because that’s really what Jack’s story is about, isn’t it? The ability to doggedly stay the course, even when it’s difficult, even when it feels impossible.
I bet he questioned himself at times. Why not scrap the vessel and buy one in better condition? Why not take an easier path forward?
But he didn’t. And now, he’s been rewarded with the palpable excitement that comes with a job well done and a future deliciously full of the unknown. Because he chose to persevere.
Why perseverance matters
Here’s the truth: the good stuff—making bold, intentional changes in your life, learning new skills, achieving goals that matter—never comes easy. Those truly worthwhile things cost us time. They cost us effort. They require belief, consistency, and yes, perseverance.
I think Jack’s story is sticking with me because these past six months professionally have been an act of perseverance in my own life. And looking forward, it seems like that theme will continue.
I’ve written often about my journey building a more intentional relationship with work. It’s deeply fulfilling, but also deeply challenging. There are days filled with euphoria over new opportunities and cup-filling interactions, and there are days when I wonder if I’m out here alone, and if anyone is even listening.
The voice that suggests returning to something more familiar, even if it brings less joy, is always near. And I know from talking with many of you that I’m not alone in that tension. The tension between who we want to become professionally and who we’ve been. Between courage and comfort. That tension is real. And it can be hard to admit.
Which is why meeting Jack hit home.
What kept him going, I wonder? How did he stay motivated when he saw other fully formed sailboats gliding by while his own sat in pieces? How did he continue on when it seemed too expensive or too slow? I wish I’d asked. I bet he’d have fascinating answers.
But it got me reflecting on how I’m persevering. How I’m staying on the hard path that leads to the good stuff.
What I’ve learned about perseverance
1. Roll with the punches.
As I drafted this post, I found myself researching the difference between perseverance and persistence. Both speak to tenacity in the face of difficulty, but perseverance includes a willingness to adapt. Persistence is rigid: continuing on the same path, even if it’s not working.
I’ve learned that rigidity won’t get you far. A plan that refuses to flex will sink the whole effort.
So I’ve been adjusting as I go. I’m trying new tactics to reach decision-makers for contract work. I’m building different tools here (including a resource I’ll launch this weekend) to support my audience. These aren’t the exact steps I imagined taking, but they’re the right steps for now and importantly, they still align with my north star, which is a perfect transition to my next point.
2. Reconnect with your goals frequently.
If you’ve read my writing before, you know how much I believe in returning to your own compass. It’s worth repeating. Perseverance demands that of us. To achieve a goal worth fighting for, you must stay connected to that goal in the first place.
Document what you’re working toward. Write it in a journal. Save it in Google Doc. Revisit it when you start to lose your way. Without that grounding, it’s too easy to drift. I can’t tell you how often I’ve gone back to the documentation I’ve built for myself and recentered. It has been incredibly helpful.
3. Celebrate along the way.
Rethinking your relationship with work is a journey. And journeys have milestones worth pausing for, even the small ones.
Jack shared that his boat ended up in a country with limited resources to complete the restoration. For a long time, progress stalled. But eventually, he got her to Trinidad, where he found the right people, the right tools, and the right time to complete the work. And he celebrated that win.
When he told me that part of the story, Jack’s joy was palpable. Getting the boat to the right place was a win and he marked it. It was a key moment of momentum that kept him on track towards his goal.
We need to do the same.
As we head into another golden summer weekend, remember Jack. Remember his long view. Remember the dream he didn’t abandon.
And remember this: you can stay the course, too.
Here’s to perseverance, to the hard path to the good stuff. Happy weekend ahead, friends.
Hi, I’m Ashley. I write Beyond the Break—a space for women navigating career transitions with intention, honesty, and heart. Through storytelling and reflection, I explore what it really means to build a sustainable, meaningful relationship with work. I’d love to hear from you.
Do you need a reminder to persevere through a big change? Are you struggling to remember where your center is? I can help. Check out my section on coaching and mentorship to learn more or shoot me a message to chat.
Love this focus on perseverance, with a critical side order of alignment. Keep going, but also keep coming back to your foundational goals to make sure where you are going is aligned with where you want to be.