Chapter 1: The Cost of Regret
The Climb to Significance
When Success Is Not Enough
A Practical Guide for Business Owners, Leaders, and Executives Moving from Achievement to Enduring Impact
For those who've achieved success—and now want what truly lasts.
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Launching February 28, 2026
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The Leadership Crossroads
You've Achieved What You Set Out to Build
The business is thriving. Your leadership is recognized. The results are undeniable. Yet a question persists.
The Achievement
The business is profitable. The team is strong. Your influence is growing. You've built something that works.
The Question
Yet beneath the metrics and milestones, a question persists: Does any of this truly matter beyond my tenure?
This question can feel uncomfortable—especially when your business is performing well and your leadership is making an impact. You don't want to appear ungrateful or uncertain. So you do what successful leaders do: you set new goals, drive better results, and push toward the next level.
But here's what many leaders discover: professional success can postpone the deeper questions—but it cannot answer them.
The question doesn't fade with time—it intensifies. Not because you've failed, but because you're ready for something that endures beyond your current role.
Understanding the Difference
Legacy vs. Significance
L
Legacy
What remains when you're gone. The monuments. The achievements. The things people remember about what you built.
S
Significance
How you live—and who you build—while you're here. The people you develop. The culture you shape. The impact that compounds through others.
"The real trap isn't failure—it's spending your one life building something impressive that never becomes enduring."
The Climb Framework
A Practical Framework for Turning Success into Significance
Three phases designed to build in sequence—giving you alignment, momentum, and integrity on the climb.
Phase 1: Map the Climb
Alignment
Get clear on who you're climbing with, what you're climbing toward, and why it matters. Phase 1 sets your direction.
- •People: Build the circle that shapes you
- •Passion: Fuel with direction, not distraction
- •Purpose: Name the mission you're living for
Phase 2: Make the Moves
Momentum
Translate clarity into action—habits, decisions, follow-through. Phase 2 builds your movement.
- •Move: Execute what matters
- •Measure: Track what actually counts
- •Multiply: Grow impact through people
Phase 3: Navigate the Traps
Integrity
Even with momentum, the trail has traps—especially for high achievers. Phase 3 keeps you honest.
- •Camouflage: Significance that doesn't look impressive
- •Cost: The price of what lasts
- •Control: The lie that you can manage outcomes
For Owners, Leaders & Executives
This Book Is For You If...
You've achieved the success you set out to build—but the satisfaction keeps slipping away
You're asking whether your wins will matter beyond you, beyond this quarter, beyond your tenure
You've checked the boxes—title, sale, security—yet feel oddly empty
You want your accomplishments to become enduring impact—shaping people, culture, and legacy
You're ready to stop performing and start building something that truly lasts
You sense that hesitation costs more than action—and you're prepared to make the climb
"Our greatest fear should not be of failure, but of succeeding at something that doesn't really matter."
— D.L. Moody
Where Are You on the Climb?
Take the 2-minute Significance Assessment to discover your current position on the journey from success to significance—and get personalized next steps.
Free • 9 Questions • Instant Results
It was another hot August, and it was time to start planning the annual trip to Lima, Peru—my 12th time making the journey. As I mapped out the itinerary, a familiar thought surfaced: Should I finally take time to go to Machu Picchu?
It had been on my bucket list long before my first trip to Peru in 2010. But like every year before, I started doing what I do best—rationalizing why this wasn't the time, and telling myself it would be smarter, wiser to do it "someday."
I had grown comfortable living with regret.
Each year I came home from Peru excited and energized by the trip, but there was always a subtle, gnawing disappointment underneath it all: I had missed another chance to live out a dream. Now I realize my hesitation wasn't just about a trip—it was a pattern quietly stealing significance from my life.
The Book
The Climb to Significance
When Success Is Not Enough: A Practical Guide to Building a Life That Matters Beyond Achievement
This book is built to be used, not admired. Inside you'll find practical tools, field guides, and concrete steps that create real change—not someday, but in the life you're living right now.
What You'll Get:
- The 3-phase Climb Framework with actionable steps
- 9 Field Guides and practical tools you can use immediately
- The RES Loop: Recognize → Establish → Score
- The Significance Scorecard to track what truly matters
- The First-Hour Playbook and Seven-Day Launch
- Real stories of transformation and breakthrough
Available Now on Amazon:
📖 Hardback📚 Paperback📱 Kindle
🎧 Audiobook launching April 2026
About the Author
Joshua K. Howard
Founder & Managing Principal, Bluefin Capital Advisors & Cor Leo Advisors | CM&AA | CEPA
Josh Howard is the founder and Managing Principal of Bluefin Capital Advisors and a Founding Partner at Cor Leo Advisors. A Certified Exit Planning Advisor (CEPA) and Certified Merger & Acquisition Advisor (CM&AA), Josh has trained over 3,000 executives, business owners, and leaders through seminars and leadership programs, working with hundreds of businesses—both for-profit and non-profit—across industries and sectors.
With executive experience in both public and private sectors—and deep expertise in manufacturing and distribution—Josh brings a global operator's perspective, having traveled to 50+ countries and directly managed business in 90+ countries across six continents. As an entrepreneur involved in 12+ companies, he understands the realities of growth, risk, and execution firsthand.
Beyond business, Josh personally invests in humanitarian mission work and mentors college students, helping leaders build a life of significance—defined by enduring legacy, the people they develop, and impact beyond the balance sheet—so the exit is not the finish line, but a launch point for greater purpose.
What Leaders Are Saying
"As a multigenerational family business, we feared losing who we were. Instead, Bluefin Advisors led exit planning and drew multiple strategic and PE offers. Four of five family members stayed, and we closed the sale with generational wealth."
— Business Owner, Central Florida
"We started with a $10M offer tied to a 45% earnout. After engaging Bluefin Advisors and overhauling sales, operations, and financials, we exited at $25M in just 24 months—preserving our family legacy in the process."
— Robinson Family
What Makes This Book Different?
Unlike typical business books, The Climb to Significance is built to be used—not just read.
Most Business Books
- Theoretical concepts without implementation
- Focus on external metrics and revenue growth
- Generic advice that applies to everyone
- Inspiration without actionable tools
- Read once, shelved forever
The Climb to Significance
- 3-Phase Framework with step-by-step implementation
- 9 Field Guides you can use immediately
- Significance Scorecard to track what truly matters
- First-Hour Playbook to start today
- Real transformation stories from business leaders
Real Transformation
From Success to Significance: Mark's Story
Mark had built a thriving distribution business over 30+ years. Revenue was strong, the team was capable, and he'd received multiple acquisition offers. By every external measure, he'd succeeded.
Yet as he approached his planned exit, Mark felt a growing unease. His children had no interest in the business. His leadership team was transactional—capable, but not invested in carrying forward his vision. And the potential buyers saw his company as an asset to be optimized, not a legacy to be honored.
The turning point came when Mark completed the Significance Scorecard and realized he'd been measuring the wrong things. He'd built a successful business, but he hadn't built significance.
Using The Climb Framework, Mark made three decisive moves:
- Phase 1 (Set Direction): He identified his 3-Seat Roster and invested deeply in two emerging leaders who shared his values
- Phase 2 (Build Movement): He restructured the business to multiply impact through people, not just systems
- Phase 3 (Keep Honest): He delayed the exit by 18 months to ensure the culture and leadership would endure beyond his tenure
The result? Mark sold the business at a higher valuation—but more importantly, he sold it to a buyer who committed to retaining his leadership team and preserving the company culture. Two years post-exit, the business is thriving, his former team still reaches out for mentorship, and Mark has launched a nonprofit that extends his impact into the next generation.
"The Climb Framework gave me permission to stop chasing the next milestone and start building something that would outlast my career. The exit wasn't the finish line—it was the launch point for greater significance."
— Mark, Distribution Business Owner (30+ Years)
Your Climb Begins Now
Not someday. Not when things slow down. But in the life you're living right now.
If you feel that low hum, you're not crazy—and you're not alone. You may simply be paying attention. This is your permission to stop performing, stop chasing the next win, and start telling the truth about what you really want your life to mean.