Lessosn From Jack’s Story
- Why imagining your future self can help you avoid business decisions you’ll later regret
- How asking the right questions can reveal issues you hadn’t considered
- A simple way to evaluate partnerships: do they move you closer to—or further from—your long-term goals?
Thinking ahead isn’t just planning. It’s a way to protect your future self and make choices today that you’ll feel good about tomorrow.
Think About Your Future to Make Smarter Decisions
You’ve heard the following phase before:
“If I could go back, I’d do things differently.”
But what if you didn’t have to go back?
What if you looked forward instead?
By imagining your self—years down the road—you can make better decisions right now, which can lead to more pride, fewer regrets.
The Offer That Changed Everything
Jack Martinez had been running Coastal Bait & Tackle in Newport, Maine, for over 15 years. What started as a tiny shack by the harbor had grown into the region’s top fishing supply store.
His loyal customers—from weekend hobbyists to full-time commercial crews—came for the gear but stayed for the honest advice and friendly service.
Then came the offer.
Tom, a longtime customer and successful contractor, walked in with a proposal:
He wanted to buy 50% of the business.
His pitch? A big upfront payment—enough for Jack to pay off his mortgage and other debt—and a lighter workload so Jack could enjoy more of his life.
“I’ve been thinking about getting into something I really care about,” Tom said. “This shop means a lot to this town—and to me.”
Since Tom was younger, he added:
“When you’re ready to retire, I’ll buy out the other half. You’ll still keep half the control for now and stay active until you’re ready for the next chapter.”
“You’d still be doing what you love,” Tom said, “but with half the stress and more time off.”
Jack was intrigued. The money was tempting. And he’d been feeling stretched thin lately—managing staff, inventory, vendors, and everything in between.
Having a partner to share the load? That sounded appealing.
But something held him back.
He remembered a conversation a few months earlier.
Tom had suggested carrying cheaper rods from a discount brand. “Most customers won’t notice,” he’d said. “They just want a good deal.”
That didn’t sit right with Jack then—and it echoed in his mind now.
Casting for Clarity
Jack needed space to think.
Early Saturday morning, he took his boat out to a quiet cove—his favorite spot to clear his head.
As his line drifted in the water, his thoughts drifted to retirement. He imagined long days fishing, fixing up his cabin, maybe even starting a new business for fun.
Then it hit him:
“Why am I dreaming about starting another business? I already have one.”
The View from Tomorrow
Jack tried a new mental exercise.
He pictured himself at 75, looking back on his career.
He saw the younger version of himself—the guy who started with nothing but a dream and a small loan.
He remembered every milestone: adding rod repair, expanding the inventory, becoming the go-to shop for serious anglers across New England.
He thought of the customers he’d helped, the trust he’d earned, and the reputation he’d built by putting values ahead of quick wins.
Then he imagined what life might look like if he took the deal.
Disagreements over pricing.
Clashes over service.
A slow drift away from the standards that made his business great.
He pictured handing over the keys one day—only to realize he no longer recognized the place.
That regret—that loss of control—felt real.
The Decision Becomes Clear
By the time Jack got back to shore, he knew what he had to do.
The next morning, he called Tom.
“I really appreciate the offer,” Jack said. “But I’ve put too much of myself into this business to share control now.”
Tom was disappointed but respectful.
“I get it,” he said. “It’s your baby.”
Finding the Middle Ground
Still, the offer had stirred something in Jack.
He did want more time.
He did want help.
He just didn’t want to give up ownership to get it.
Two months later, he hired Ellen—an experienced retail manager who had worked in sporting goods for years.
She took over the day-to-day: staffing, inventory, vendor calls.
At first, it wasn’t easy for Jack to let go of the details. But Ellen earned his trust fast.
Jack focused on the parts he loved: strategy, customer relationships, and being the face of the business.
He finally had the breathing room he needed—without compromising what mattered most.
The Power of Future Perspective
Six months later, Jack watched Ellen run the store on a busy Saturday while he helped a young boy and his father pick out his first fishing rod.
He felt calm. Grateful.
He hadn’t just avoided a deal he might’ve regretted—he’d found a better way forward.
By stepping back and imagining his future, Jack stayed true to his values and found peace in the present.
Lesson Insights
Jack’s story isn’t just about turning down a partnership.
It’s about zooming out and asking the question:
“Will I regret this?”
Instead of chasing short-term relief, he stayed aligned with his deeper goals—his legacy, his values, and the joy of doing what he loved.
The big idea?
If you imagine yourself looking back, you can make decisions today that stand the test of time.
Applying the Lesson
Jack used a simple mental exercise—imagining his future-self looking back.
You can do the same.
Whether you’re leading a team, running a business, or facing a big decision, here’s how to use future-focused thinking:
- Project Yourself Forward
Picture yourself 10, 20, or 30 years ahead.
What choices would you be proud of?
What would you regret?
Let that imagined hindsight shape your judgment today.
- List What Matters Most
Before reacting, write down your non-negotiables—your values, your goals, your boundaries.
These will act as your compass.
- Pressure-Test Tempting Offers
Ask yourself:
“Would this still feel right even if it doesn’t work out?”
If the answer is no, pause.
Regret often hides in short-term wins.
- Create Space Before Deciding
Like Jack heading out to the cove—step away.
Time brings clarity that pressure clouds.
- Find Smart Alternatives
Jack didn’t ignore his needs.
He found a better way to meet them.
So can you.
Questions to Ask Yourself
Before saying yes to a big decision, ask:
- If I were looking back 10 years from now, what would I hope I had done?
- Am I chasing quick relief—or staying true to long-term values?
- What am I risking that I may not get back—like trust or control?
- Would I feel good about this decision if it went better than expected—or worse?
- Is there another way to solve this without giving up what matters most?
Sometimes, a few hard questions are all it takes to avoid regret.
Conclusion: Look Ahead So You Can Look Back Proudly
Jack didn’t avoid a mistake by luck—he did it by thinking forward.
You can too.
Every big decision—about money, growth, partnerships, or strategy—is a chance to pause, reflect, and protect what really matters.
So before you say yes, ask:
“What will future me think about this?”
That one question might save you years of regret—
and lead to choices you’ll still be proud of long after today.