Hope, Plans, and Surprises: Thriving Amid Uncertainty
Created at: September 15, 2025
You can hope for the best, plan for the worst, and prepare to be surprised. — Denis Waitley
A Three-Part Posture Toward Uncertainty
Denis Waitley compresses a full-cycle strategy into one sentence: cultivate hope to set direction, plan for worst-case scenarios to contain downside risk, and train for surprise so you can pivot. The triad admits that forecasts are fragile, yet insists action is still necessary. In this framing, hope supplies momentum, planning supplies resilience, and readiness for surprise supplies adaptability. Together they create a stance that keeps you moving without being blindsided. With this foundation established, we can see how each element amplifies the others rather than serving as a substitute.
Hope as Directional Energy
To begin, hope is not wishful thinking but directional energy that orients effort. Martin Seligman’s research on learned optimism (1990) shows that people who interpret setbacks as temporary and specific persist longer and problem-solve better. Consider a marathoner who reframes a bad training day as a data point, then adjusts pacing goals; hope keeps the mission alive while reality refines the method. In this way, hope identifies worthy targets and sustains the stamina to reach them. Yet optimism alone can invite overconfidence, so a wise next step is to confine risk through rigorous planning.
Planning for the Worst: Risk and Redundancy
Here, planning transforms aspiration into durable strategy. Techniques such as scenario planning, risk registers, and buffers convert uncertainty into structured choices. High-reliability fields use layered defenses—the Swiss cheese model described by James Reason (1990)—so that multiple safeguards prevent a single error from becoming catastrophe. Airlines file alternates; hospitals drill for power failures; engineers build redundancy into critical systems. Crucially, this is not pessimism but prudence: by deliberately imagining failure modes, we buy down the downside. Even so, no defensive stack is perfect. Therefore, the third element—preparedness for surprise—becomes the hinge between plans and reality.
Prepared for Surprise: Agility and Antifragility
Surprise readiness accepts that some variables will defy prediction and emphasizes the capacity to reconfigure quickly. Dwight D. Eisenhower is often credited with the line that plans are nothing; planning is everything, highlighting that rehearsal creates the flexibility to improvise. Practical tools include pre-mortems (Gary Klein, 2007), option-like small bets that are easy to reverse, and the OODA loop—observe, orient, decide, act—for rapid iteration (John Boyd). Nassim Nicholas Taleb’s Antifragile (2012) pushes further: design systems that benefit from volatility by limiting downside and harvesting upside. With this mindset, surprises become information, not paralysis. To see the triad in action, history offers a vivid case.
Apollo 13: Improvisation Under Extreme Pressure
In 1970, Apollo 13 suffered an oxygen tank explosion en route to the Moon, prompting the calm but chilling transmission, “Houston, we’ve had a problem.” NASA’s teams had extensive contingencies, yet they still had to invent new procedures in hours: devising a carbon-dioxide scrubber from plastic bags, duct tape, and checklists; repurposing the lunar module as a lifeboat; and choreographing precise engine burns. Hope defined the mission—bring three astronauts safely home. Worst-case planning provided redundant systems and disciplined protocols. Preparedness for surprise enabled rapid, collaborative ingenuity. In concert, these elements turned a near-fatal crisis into a landmark of applied resourcefulness.
Daily Habits to Embed the Triad
Finally, the quote becomes practical through routines. Begin with hopeful clarity: define success and set leading indicators so progress is visible. Next, constrain downside: run a pre-mortem before major decisions, add time and budget buffers, write explicit stop-loss rules, and keep checklists (Atul Gawande, 2009) for repeatable tasks. Then, rehearse surprise: schedule plan B drills, keep small reversible experiments in flight, and conduct weekly after-action reviews to update assumptions. A modest emergency fund, diversified income streams, and a personal network further increase adaptability. By cycling through hope, planning, and surprise-readiness, you increase your odds of good outcomes while staying ready to turn the unexpected into opportunity.