When people think about retirement planning, they often assume it’s a straightforward process. Save consistently, invest wisely, and when the time comes, start pulling money out as needed. Simple enough—right?
That assumption is one of the most common misunderstandings about retirement income planning.
During a recent client meeting, I was asked a question I don’t hear very often—but one I know many people are thinking:
“Is retirement income planning really that complicated?”
It was an honest, direct question. And it deserved an honest, thoughtful answer.
The short explanation?
Planning for retirement income is very different from saving for retirement. One is relatively simple. The other requires strategy, timing, and the ability to think several moves ahead.
The best way I’ve found to explain the difference is through a familiar analogy:
Working years are like playing checkers. Retirement is more like playing chess.
The Simplicity of the Working Years (Checkers)
For most people, the accumulation phase of life—the years spent working and saving—is fairly straightforward.
You’re focused on a few primary objectives:
Earning as much income as reasonably possible
Saving consistently
Contributing to retirement accounts
Managing day-to-day expenses
Supporting a household and raising a family
This stage of life is busy, but financially speaking, the goal is usually clear: build as much as you can while you’re earning a paycheck.
That’s why I compare the working years to checkers.
Checkers is simple. The rules are easy to understand. You don’t need to think ten moves ahead to enjoy the game. Most decisions are linear and reactive. You move forward, capture when you can, and focus on the next step.
Financially, that’s how many people operate during their careers. Save more when possible. Spend less when necessary. Make progress over time.
And for the most part, that approach works.
The Transition Period Most People Underestimate
Where things start to change is in the years leading up to retirement.
This is often a unique financial window:
Children are out of the house
Household expenses may decrease
Income may be at its highest point
Retirement feels close—but not immediate
Big decisions start appearing on the horizon
This period typically extends from peak earning years through the first year or two of retirement.
And this is where many people underestimate the complexity of what’s coming next.
Because at this stage, you’re no longer just saving money.
You’re preparing to use it.
Why Retirement Income Planning Is Like Chess
When you enter retirement—or even the years immediately leading up to it—you’re no longer playing checkers.
You’re playing chess.
In chess:
Every move affects future moves
You must think several steps ahead
You consider both opportunities and consequences
One decision can change the entire board
Timing matters just as much as strategy
Retirement income planning works the same way.
Decisions around income, taxes, Social Security, savings, and withdrawals are interconnected. A choice made today doesn’t just affect this year—it can influence your financial flexibility for decades.
And unlike checkers, there’s rarely a single “right” move. There are trade-offs, variables, and long-term implications.
A Real-Life Example: Social Security Decisions
One of the clearest examples of this “chess vs. checkers” dynamic is Social Security planning.
I often share a personal story about a conversation I had with my father when he was approaching retirement.
Like many people, his initial instinct was to claim Social Security as soon as he was eligible. On the surface, that decision made sense. More income sooner felt reassuring.
But when you look beyond the immediate benefit, additional considerations emerge:
Would he continue working?
How would early claiming affect his benefit amount?
What would happen if he outlived expectations?
How would this decision impact my mother if he passed first?
In my parents’ situation, my mother had limited Social Security benefits of her own and would eventually rely on spousal benefits. That meant my father’s claiming decision didn’t affect just one life—it affected two.
If he claimed early, the reduced benefit would eventually become the income my mother relied on later.
That’s not a one-move decision.
That’s chess.
Thinking Beyond the First Move
This is where many retirement plans fall short—not because people make bad decisions, but because they don’t realize how many future moves are tied to the current one.
Some common examples:
Claiming Social Security early vs. delaying
Deciding when to retire versus when to stop working
Choosing which accounts to draw from first
Rolling over retirement plans or leaving them in place
Considering Roth conversions without fully understanding tax implications
Coordinating income sources alongside required distributions later in life
Each of these decisions has ripple effects.
And once a move is made, you can’t always undo it.
The Emotional Side of Retirement Planning
Another theme that frequently comes up in client conversations is confidence—or the lack of it.
Many people say things like:
“I think I’m in a good position.”
“I should be okay.”
“I feel like we’ve done enough.”
Those statements aren’t wrong—but they’re often incomplete.
There’s a difference between hoping things will work and understanding why they should.
One of the most important roles of financial planning is helping people move from uncertainty to clarity. Not through guarantees or promises—but through education, preparation, and perspective.
Retirement planning isn’t about predicting the future. It’s about preparing for multiple possibilities and understanding how different choices may play out over time.
Why Education Matters More Than Advice Alone
One of my personal goals—both in client meetings and through my content—is to challenge the way people think about financial decisions.
Not to overwhelm. Not to confuse. But to help people ask better questions.
Questions like:
What happens if this decision doesn’t go as planned?
How does this affect future income flexibility?
What are my alternatives?
What trade-offs am I accepting?
How does this decision affect my spouse or family?
You don’t need to be a financial expert to ask these questions.
But you do need to understand that retirement planning is rarely one-dimensional.
Checkers Is Easy to Learn. Chess Takes Time.
I often use this analogy when explaining the value of working with a financial professional.
You can learn checkers in a few minutes.
Chess takes longer.
Even though the board looks similar, the rules, strategies, and consequences are very different.
Retirement planning works the same way.
Many people reach retirement with solid savings but without a clear income strategy. They know how much they’ve accumulated—but not how it’s meant to work together over time.
That doesn’t mean they’ve failed. It simply means they’ve reached a stage where a different skill set is required.
Why One-Size-Fits-All Advice Falls Short
Another important point worth addressing: comparing your situation to someone else’s.
It’s tempting to rely on advice from:
Friends
Family members
Coworkers
Online forums
Well-meaning relatives
But no two financial situations are identical.
Income sources, tax considerations, health factors, family dynamics, and personal goals all play a role.
What worked for someone else may not be appropriate for you—and vice versa.
That’s why education and context matter so much when making long-term decisions.
Watch the Full Conversation on YouTube
This blog is based on a recent video where I walk through this analogy in greater detail, share real client experiences, and explain how these concepts show up in actual retirement planning conversations.
Watch the full video on my YouTube channel: JasonBowersFP
In the video, I expand on:
The chess vs. checkers analogy
Real-world retirement income decisions
Why timing and sequence matter
How to think beyond the next move
Be sure to subscribe so you don’t miss future videos focused on retirement planning, income strategy, and financial decision-making.
Final Thoughts: Think Several Moves Ahead
Whether you’re years away from retirement or already approaching it, the key takeaway is this:
The closer you get to retirement, the more important it becomes to think several moves ahead.
That mindset applies beyond finances—to career decisions, family planning, and even everyday choices.
When you understand that retirement planning is more like chess than checkers, it becomes easier to see why education, preparation, and thoughtful decision-making matter so much.
You don’t have to navigate these decisions alone—and you don’t need to have all the answers today.
But understanding the game you’re playing makes a meaningful difference.