What Great Minds Say About the Power of Planning and How Their Wisdom Can Improve Your Future

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Across centuries, cultures, and disciplines, the most accomplished thinkers and leaders have returned to the same insight again and again: the future doesn’t reward guesswork—it rewards preparation. From statesmen and generals to investors and philosophers, the lesson is remarkably consistent. The power of planning isn’t about predicting exactly what will happen. It’s about building clarity, resilience, and confidence before decisions become irreversible.

Here’s what some of the most influential minds in history say about planning—and why their wisdom applies to your financial future today.

Planning Prevents Failure

“By failing to prepare, you are preparing to fail.” (Benjamin Franklin)

Benjamin Franklin was making the most fundamental case for the power of planning there is. “By failing to prepare, you are preparing to fail” isn’t a warning about bad luck or poor timing—it’s a statement of cause and effect.

This is the core argument for having a plan. Not because planning guarantees success, but because not planning guarantees vulnerability. Without a plan, you’re left hoping the future cooperates. With one, you’ve at least thought through the terrain: the tradeoffs, the risks, the decisions you’ll face when options narrow and stakes rise. In personal finance and retirement planning, that preparation is everything. Markets will fluctuate. Life will surprise you. But having a plan means you’re responding with intention instead of reacting in panic. Franklin’s point is as relevant now as it was then: the real risk isn’t uncertainty—it’s facing the future without a plan at all.

Planning Is About Preparation, Flexibility, & Revision

“In preparing for battle, I have found that plans are useless, but planning is indispensable.” (Dwight D. Eisenhower)

Eisenhower wasn’t dismissing plans with this statement; he was elevating the idea of preparation, flexibility and revision. Planning forces you to confront tradeoffs, test assumptions, and think through consequences upfront. And, a written plan gives you a framework to make adjustments as your life evolves.

Plans are meant to evolve, not stay static.

TIP: Update your Boldin plan at least once a quarter. This check-in will boost your confidence and help you discover opportunities to do better.

The Future Will Surprise You

“Everyone has a plan until they get punched in the mouth.” (Mike Tyson)

“He who lives by the crystal ball will eat shattered glass.” (Ray Dalio)

“No plan survives contact with the enemy.” (Helmuth von Moltke)

The power of planning isn’t in predicting the future. A great plan is a framework that makes you comfortable with all the surprises that will reveal themselves throughout your lifetime. Good planning is about understanding ranges, risks, and responses—so you’re not forced into bad decisions when conditions change.

Planning is how you stay adaptable when reality deviates from expectations.

While you won’t likely be sparring in the boxing ring or facing an enemy army, you will need to grapple with big economic factors like inflation and market fluctuations. And, your personal life will have ups and downs too. You need a plan that evolves with you, and that is flexible enough to deal with whatever gets thrown your way.

And that is why running what-if scenarios is such a popular and powerful feature in the Boldin Planner.

Wishing Doesn’t Make Goals Come True

“A goal without a plan is just a wish.” (Antoine de Saint-Exupery)

Most of us have a goal of retiring. However, according to Fidelity, only a mere 18% of Americans have a written retirement plan. Retirees are more prepared, but new data suggest that only about 50% have a written plan.

If you want a secure retirement, you have to do more than wish, you need to plan for it.

Sure, many people manage their pre-retirement finances month to month or year to year. This is okay when you have income from a job. However, when your goal is to live off existing assets for 20-30 years (retirement), then you really need a plan.

Planning Demands Patience

“Someone is sitting in the shade today because someone planted a tree a long time ago.” (Warren Buffett)

Legendary investor Warren Buffett is known for making very long bets with his money. He demonstrates that financial security and growing wealth take a great deal of patience.

No matter your level of wealth, slow and steady wins the race. Returns can compound quietly over time, often invisibly, until one day they are obvious.

Plans Require Courage

“All you need is the plan, the road map, and the courage to press on to your destination.” (Earl Nightingale)

For many, the decision to retire is a courageous leap of faith. You’ve worked for most of your life, and all of a sudden, you retire and are without a paycheck and need to drawdown your hard-earned savings. That takes some courage.

A solid financial plan gives you the road map. But it’s courage that allows you to use it—to follow the plan through downturns, to revisit assumptions honestly, and to make changes deliberately rather than reactively. That courage comes from understanding your options and knowing why you made the choices you did.

In retirement planning, especially, the decisions are rarely binary. They’re about timing, taxes, spending, and tradeoffs over decades. Courage is what allows you to press forward without perfect certainty—confident that you’re prepared, flexible, and informed enough to adapt along the way.

That’s the role courage plays in planning: not blind faith in the future, but the steadiness to move forward with clarity when the future inevitably surprises you.

Planning Let’s You Glimpse at the Future

“Planning is bringing the future into the present so that you can do something about it now.” (Alan Lakein)

At its most powerful, retirement planning is an act of visualization.

It starts by imagining your future self—where you’ll live, how you’ll spend your time, what you’ll value, and what you’ll need to feel secure and fulfilled. But good planning doesn’t stop at imagination alone. It turns those ideas into projections you can actually see.

When you look at a financial projection, you’re not just reviewing numbers—you’re looking at a possible version of your future. You can see how your savings might grow, when work might give way to retirement, how spending could change over time, and how different decisions ripple forward. Seeing those outcomes makes the future feel real, tangible, and actionable.

The what-if scenarios and Monte Carlo analysis in the Boldin Planner take this one step further. Instead of showing a single, “perfect” future, it helps you visualize a range of possibilities.

That shift matters. Life doesn’t unfold along a single straight line, and your plan shouldn’t either. By seeing a range of outcomes, you can understand risk, test tradeoffs, and build confidence—not because the future is predictable, but because you’re prepared for variability.

This is what it means to bring the future into the present: to make invisible possibilities visible now, while you still have the power to adjust, adapt, and choose a path that works for you.

Here are 7 ways to bring your future into the present for a more reliable retirement plan.

Preparation Beats Urgency Every Time (But It’s Never Too Late)

A quote often attributed to Abraham Lincoln is one of the most enduring metaphors for preparation:

“Give me six hours to chop down a tree, and I will spend the first four sharpening the axe.” (Unknown)

The lesson here is simple: thinking ahead reduces overall effort and makes the goal easier to attain. This is certainly true of your financial life. Decisions about spending, savings, retirement timing, and more are far more powerful and make the goals easier to attain with a great deal of forethought.

Retirement can last 20 or 30 years or more. And, it is best if you spend 40 or 50 years saving and preparing for it.

Don’t despair if you’re just getting started

If you are feeling behind, don’t worry! There is a lot you can do if you are approaching retirement age, but feel like you haven’t been “sharpening the axe.”

Here are a few catch-up resources:

Goals Matter

“Begin with the end in mind.” (Stephen R. Covey)

“If you don’t know where you’re going, you’ll end up someplace else.” (Yogi Berra)

When it comes to your financial future, clarity of direction—when you want to retire, how you want to live, what tradeoffs you’re willing to make—makes all the difference in the details of your plan.

Planning Prevents Urgent or Desperate Decision Making

“Plan for what is difficult while it is easy; do what is great while it is small.” (Sun Tzu’s)

This insight is a reminder that the best time to deal with complexity is before it becomes urgent.

In personal finance, the hardest decisions—retirement timing, taxes, healthcare costs, income strategy—are far easier to plan for when they’re still distant. You can test scenarios, adjust the course, and make small changes that compound over time. Waiting until decisions are unavoidable often turns manageable trade-offs into stressful constraints.

The same is true of action. Small steps taken early—saving a little more, understanding tax implications, modeling different futures—can lead to outsized results later. What feels incremental today often becomes transformative over decades.

Retirement planning isn’t about solving everything at once. It’s about addressing the difficult questions while you still have room to maneuver, and taking meaningful action while the stakes are still small. That’s how preparation turns into confidence—and how complexity becomes something you can handle, not something that handles you.

Financial Plans Are About A Lot More Than Money

“To accomplish great things, we must not only act but also dream. Not only plan but also believe.” (Anatole France)

One of the most common retirement planning mistakes—beyond not having a plan at all—is focusing only on the finances and not on the life those finances are meant to support.

Too many people plan how much they’ll have in retirement, but not how they’ll spend their time. Yet retirement isn’t an ending—especially today. Modern retirees are starting businesses, launching second careers, traveling with intention, volunteering, learning new skills, and diving deeply into passions they finally have time to explore.

Planning for what you’ll do in retirement matters just as much as planning how much you’ll spend. Research and lived experience consistently show that having purpose, structure, and meaningful engagement is critical for maintaining physical, mental, and emotional health in later life. Without that, even a well-funded retirement can feel unmoored.

There’s also a practical side to this: clarity about how you want to live directly shapes your financial plan. Knowing your priorities—travel, creative work, family time, service, learning—helps you make better decisions about spending, saving, and tradeoffs. In many cases, it can significantly change your retirement budget and increase confidence that your plan aligns with what truly matters.

At Boldin, we believe the best financial plans start with life—not the other way around. To help spark ideas and support that kind of thinking, here are a few of our favorite resources on planning what comes next:

The Enduring Lessons of Planning

Across centuries and disciplines—from generals and presidents to investors and philosophers—the message is remarkably consistent: planning is how people turn uncertainty into agency.

That’s especially true for personal finance and retirement. Small decisions compound, tradeoffs matter, and the best time to think clearly about the future is almost always before you have to. When you take the time to imagine the life you want, visualize possible outcomes, and understand your options, the future becomes something you can navigate with confidence—not guess at.

If you’re ready to bring that kind of clarity into your own planning, the Boldin Planner helps you model your future, explore tradeoffs, and see how today’s decisions shape tomorrow’s possibilities.

Know where you stand. Plan what comes next.

Updated January 2026

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