Old No. 2
A Business Leader’s Guide to Choosing the Right Strategy
A practical strategy guide for business leaders, using a real golf hole to explain how to choose the right path, manage risk, and finish what you start.
This guide explains how I help leaders choose strategies they can actually finish — using a golf hole I designed as the model.
Why This Guide Exists
I didn’t design this hole to punish mistakes.
I designed it to reveal how different people make decisions under constraint.
Business strategy works the same way.
The Guide
Start by Seeing the System (Not the Shot)
What the Hole Teaches
The green represents the outcome you want
Distance represents time and patience
Hazards represent constraints you can’t ignore
Fairway width represents margin for error
Out-of-Bounds represents decisions you can’t undo
How to Use This in Business
Before choosing a strategy, step back and design the system you’re operating in — not just the next move.
Coaching Insights
If we mapped your current business like this hole, where are your hazards and how wide is your margin for error right now?
Coaching CTA
➡️ In our first session, we map your business like a course — outcomes, hazards, and margins — so you can see the whole hole before you swing.
Choosing Your Path
Path 1 — The Clear View
Precision Strategy: High Reward, Low Forgiveness
Course Design
50 yards wide, straight at the green
OB on the right (homes)
7-foot weeds on the left that quietly eat mistakes
Business Meaning
This path favors leaders who:
Know exactly who they serve
Have deep expertise
Operate in environments with little room for trial and error
Risk to Watch
The clearer the strategy, the more expensive the miss.
Coaching insight
Where in your business do you have clarity — but very little forgiveness?
Coaching CTA
➡️ I work with leaders on this path to pressure-test assumptions and widen margin without losing focus.
Path 2 — Straight Down the Middle
Execution-Dependent Growth Strategy
Course Design
Looks safe off the tee
A massive hazard sits between 150 and 100 yards
Requires a committed, well-executed second shot
Business Meaning
This path fits leaders who:
Are scaling
Are transitioning from early success to sustained growth
Face mid-journey choke points (people, tech, capital, trust)
Risk to Watch
Most failures don’t happen at the start — they happen at the commitment point.
Coaching Insight
What obstacle are you approaching that won’t be solved by vision alone?
Coaching CTA
➡️ This is where coaching focuses on execution discipline — aligning team, timing, and capability before the hazard shows up.
Path 3 — Up the Left Side
Resilience Strategy: Forgiving, Slower, Survivable
Course Design
25 yards wide
Rough until the last 100 yards
Clean approach opens late
Business Meaning
This path suits leaders who:
Are building something new
Are pivoting careers or markets
Value learning and survivability over speed
Risk to Watch
Progress feels slower — but failure is rarely catastrophic.
Coaching Insight
Where might rough early actually protect you from bigger risks later?
Coaching CTA
➡️ Coaching here focuses on momentum, learning loops, and confidence — without rushing the process.
Reaching The Green Complex — Where Strategy Is Finally Judged
Course Design
Fairway and rough inside 100 yards
Two deep bunkers guard the left front
One bunker is protecting the back right
Business Meaning
Late-stage execution matters more than early momentum.
Success near the goal requires restraint, not aggression.
Coaching Insight
As you get closer to your goal, where are you at risk of overconfidence?
Coaching CTA
➡️ I help leaders slow down near the finish — where precision and judgment matter most.
How to apply this to your situation.
Identify which path you’re currently on
Name the hazards you’re pretending aren’t there
Decide if your strategy matches your actual skills and margin
Strategy isn’t choosing the best path.
It’s choosing the path you can finish.