The Planning Paradox
Why Most Big Goals Fail — And How to Avoid It
“Most people overestimate what they can achieve in a year and underestimate what they can achieve in 10 years.” — Bill Gates, Founder of Microsoft
In 2012, I stood before my 20-person team and declared: “We will grow from $4 million to $15 million in revenue in three years.” If we pulled it off, we’d sell at a strong multiple — and everyone would share the upside.
The excitement was contagious — until progress stalled.
Eighteen months later, we were still stuck at $4 million. Quarter after quarter, we missed our targets. Confidence — theirs and mine — was fading, and the goal felt increasingly out of reach.
I remember walking into our Monday morning meeting one day, scanning the faces around the table, and feeling the spark was gone. The jokes were fewer. The updates were shorter. It wasn’t just the numbers that were flat — the energy was too. And I knew it started with me.
Some of my greatest lessons came from painful experiences — this was one.
Over the past decade, I’ve shared this lesson with dozens of leadership teams. Predictably, those who embrace it achieve — and often exceed — their greatest ambitions. Those who ignore it? They stall, struggle, and sometimes fail completely.
The hard-earned lesson from that failure is my gift to you — one that can save you years of frustration. It’s the lesson that turned my own trajectory around — and it can do the same for yours.
The Paradox
Here’s the paradox: The mindset that fuels bold, long-term vision — ambition, creativity, optimism — often clashes with the discipline, focus, and realism short-term execution demands.
Long-term vision rallies your people around a meaningful goal. It inspires. It gives permission to dream big and engineer the path to get there.
In my experience, 10 years is the sweet spot.
But short-term execution is a different game entirely. It’s about clear priorities, achievable milestones, and relentless follow-through — quarter by quarter, year by year.
Master this paradox, and you’ll see the difference between burnout and breakthrough. I’ve seen it firsthand.
It’s one of the most important shifts a leadership team can make — and one of the easiest to get wrong.
Building a Long-Term Vision
Long-term goals have been called many things — BHAG (Jim Collins), Core Target (Gino Wickman), The One Thing (Gary Keller), and more.
Some of the most well-known examples include:
Put a man on the moon by the end of the decade — NASA
Connect 1 billion people — Facebook
Achieve full self-driving capability — Tesla
Crush Adidas — Nike
I’ve seen equally inspiring goals from leadership teams I’ve worked with — even if they never make headlines:
24,000 units and 1 million commercial square feet by 2027 — Property Management Firm
$100 million in revenue by 2035 — Investment Banking Firm
Help create 4,000 families by 2031 — Donor/Surrogacy Matching Agency
Become Los Angeles’s next leading architecture studio by 2030 — Architecture Firm
These goals do more than look good on a slide. They align. They inspire. They focus an organization.
Why Big Goals Require Big Time
Big goals need long timeframes because big change takes time. Along the way, expect to rethink or rework:
Strategy
People
Processes
Systems
Capital structure
Change is messy — and rarely unfolds as expected. If you’re leading a small or mid-sized business, you don’t have the deep bench of resources large enterprises can throw at a problem to smooth the disruption.
The 10-Year Economic Reality
There’s also the macroeconomic layer to consider. As I learned from Gino Wickman, the economy tends to follow a 10-year cycle:
2 great years — record profits
6 average years — steady profits and reasonable returns
2 bad years — if you’re not careful, they can take you out
If your big goal is tied to a tight timeline, those two down years can wipe out years of progress. But when you give yourself a 10-year window, you flatten the peaks and valleys. You're less likely to panic or run out of runway. And if everything goes better than expected? Celebrate early!
From Vision to Reality
Bringing a long-term vision to life means mastering a very different skill set — the discipline of short-term execution.
Short-Term Discipline of Execution
While long-term vision requires ambition, creativity, and optimism, short-term execution demands discipline, focus, and realism.
The truth is, as human beings, our focus starts to drift after about 90 days. Cognitive fatigue sets in. Life happens.
That’s why the best teams reset every 90 days using a repeatable cycle:
Evaluate performance from the prior period
Re-center on the long-term vision
Identify the most important objectives
Balance those objectives with available resources
Execute and stay focused
Repeat
Aim for flawless execution — but accept that perfection is impossible. Hitting 80% of your goals still builds meaningful momentum.
You don’t need perfection to make progress.
What matters most is the compounding effect of delivering on good decisions, quarter after quarter. That consistency — not intensity — is what brings long-term visions to life.
As Jim Collins explains in Good to Great, it’s the flywheel effect: disciplined people, disciplined thought, and disciplined action — these are the hallmarks of great companies.
The Trap — and How to Avoid It
Many ambitious leaders lean toward long-term thinking — fueled by what’s bold, exciting, and transformative. That’s essential for setting vision, but when applied to short-term execution, it becomes a liability.
Many failed long-term visions share the same pattern:
Lack of discipline to reset and refocus every 90 days
Overreaching short-term goals
A widening gap between ambition and execution — and morale slipping in step with results
The consequences:
Failure to deliver on commitments
Consistently falling short, which drains confidence and leaves you with a demoralized team
Erosion of accountability and trust
The good news? The solution is straightforward — and it lives in the paradox itself.
To succeed, you must shift gears. The mindset that fuels the long-term vision can’t fuel the day-to-day. Execution requires a different muscle: discipline.
When planning for the long-term, the sky is the limit. Dream big. Inspire. Cast vision. You can achieve anything in 10 or more years.
But when it’s time to advance that vision? Shrink the timeline. Bring discipline. Focus. Realism. Trade “someday” thinking for today’s most important step. Use a 90-day cycle to chip away at your big goals — one clear step at a time.
That’s how bold visions come to life — not in one giant leap, but through hundreds of small, intentional steps.
And when you do get it right, the results can be transformative.
The Turning Point
When I first learned this lesson after stalling at $4M, I didn’t master it overnight. But once I did, everything changed.
Shortly after, I merged my company with a like-minded firm. Together, we embraced both sides of the paradox — holding a bold 10-year vision while rigorously executing on disciplined 90-day cycles.
In just three years, we grew from $13M to $40M in revenue and sold the business to a publicly traded global IT services firm — in an all-cash deal.
That outcome wasn’t luck. It was the compounding effect of hundreds of disciplined decisions, made over time.
If you want to bring your boldest vision to life, don’t wait for the perfect plan or the perfect moment.
Dream big.
Execute small.
Do it again in 90 days.
Then again. And again.
Because in the end, your future won’t arrive in one big leap — it will be built in the next 90 days.
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