The Retire Sooner Method: Secret #4, A Written Plan

Welcome back to my series on the great retirement book The Retire Sooner Method: The 5 Secrets Behind America’s Happiest (and Unhappiest) Retirees.

So far we’ve had the following posts in this series:

• The Retire Sooner Method: Overview
• The Retire Sooner Method: Overview, Part 2
• The Retire Sooner Method: Secret #1, The Money Green Zone
• The Retire Sooner Method: Secret #1, The Money Green Zone, Part 2
• The Retire Sooner Method: Secret #2, Core Pursuits
• The Retire Sooner Method: Secret #2, Core Pursuits, Part 2
• The Retire Sooner Method: Secret #3, Social Connections
• The Retire Sooner Method: Secret #3, Social Connections, Part 2

If you missed any of those posts, you’re going to want to go back and read them before you read this one, since today’s post is a continuation of the others.

Today we’re discussing Secret #4: Mapping out your future by having a written financial plan and/or a happy retiree life map.

I must admit I was skeptical about this secret at first. I’m still a bit on the fence as to whether or not it’s needed completely, which I’ll cover below, but it’s not what I thought it was based on the summary at the beginning of the book.

I thought this was going to be a “you must have a financial plan” recommendation from a financial planner.

How convenient, right?

But now that we have the details, I see that’s not really what Moss is saying. In fact, what counts as a “plan” is pretty broad, and much of it is something I agree with.

So for the most part, we’re on the same page.

But before we get too deep into this topic, let’s share his thoughts before I give mine.

Written Financial Plan

This chapter begins by sharing this finding:

Happy retirees are 2.25 times more likely to have a written financial plan than unhappy retirees.

That’s right: more than twice as likely. They’re also about half as likely to be anxious about their financial future. If you’re wearing nerdy glasses and have a pocket protector, you might say, “Wes, correlation does not imply causation.” Okay, nerd. But it’s pretty clear to me there’s a connection.

Think of retirement planning as having two complementary sides of the same coin. The financial side deals with the numbers: income streams, rates of return, inflation assumptions, withdrawal rates, tax rates, and more. It answers the question “Can we afford the kind of retirement we want?” But the life side is equally crucial — it maps out your daily and yearly sense of purpose, your core pursuits, your relationships, and how you want to spend the freedom that financial security provides. To know whether you can afford it, you first have to determine what life you actually want.

Without the financial side, even the most inspiring life plans remain fantasies. Without the lifestyle side, even the most sophisticated financial projections feel hollow and meaningless. But when you’ve got a plan where both sides work in harmony, something powerful happens: You stop merely hoping your retirement will work out and start actively designing it instead.

Earlier in this series the author said about this secret, “This isn’t just correlation; it’s causation.” Now it appears he’s backtracking on that a bit.

It actually might be causation, but I just don’t think they can prove that. So we don’t know for sure.

That said, the logic does seem to flow pretty well:

• When you are less stressed out, you have a better retirement.
• Having a plan, which we’ll define in a bit, helps you feel less stressed out.
• Therefore, having a plan helps you have a better and happier retirement.

That makes sense to me. And given that what constitutes a “plan” is pretty broad, I’m inclined to agree with the conclusion.

This is also where I think a lot of retirement discussion goes wrong. People often talk about “the retirement plan” as if it’s only a financial plan. What are your assets? What are your expenses? What’s your withdrawal rate? When will you claim Social Security? What’s your tax strategy?

Those are all important questions, of course.

But they are only half the plan.

The other half is figuring out what you’re actually retiring to. What will your days look like? Who will you spend time with? What activities will give your life structure? What will you do when the long-awaited freedom finally arrives?

If you don’t answer those questions, you may win the money game and still end up with a retirement that feels empty.

As I share more, you can see for yourself what you think.

The book moves on and uses an example of what can happen when you don’t plan for retirement:

Lawrence assumed retirement would simply “happen.” He figured his family would fill the space, his hobbies would magically blossom, and the rest would fall neatly into place.

Unfortunately, it didn’t. Without the scaffolding of work, his days sagged. The social interaction he thought would come naturally never quite materialized. Instead of walking into a full calendar, he walked into long, unstructured mornings and afternoons. At first it felt like a vacation. Eventually it felt like drift. And with drift came frustration, loneliness, and the creeping sense that something had gone wrong, though he couldn’t quite put his finger on it.

The implication was clear: It isn’t just financial planning that lays the foundation for retirement success; it’s the lifestyle choices. Without addressing and preparing for the financial reality of retirement, you won’t have the resources to support the lifestyle you envision. And without thoughtfully designing that lifestyle, even substantial savings can leave you feeling adrift and unfulfilled in what should be your most rewarding years.

Several thoughts from me:

• If you go-with-the-flow into retirement with no plan, you will get go-with-the-flow results, which is basically a coin toss at best. Sure, things might turn out great. Or they might be a disaster. Are you willing to let a multi-million-dollar, 30-year decision hinge on a coin flip? I’m not.
• I am continually amazed at the low level of retirement planning many people do. Many, and maybe even most, spend more time planning a vacation to Disney World than they do planning their retirement. And the results often show it.
• So yes, you need a plan. But the plan needs to address both the money side and the life side of retirement. If either one is missing, you could have trouble.
• The money side tells you whether the retirement you want is financially possible. The life side tells you what kind of retirement you’re trying to build in the first place.
• The more you can create your plan and test it IN ADVANCE of retiring, the better off you’ll be. See my series on Retirement Starts Today to get details on how to do this.

The book reinforces this final point with the following:

The Harvard researchers identified “adaptability” as a key factor in successful transitions, but I’d take it a step further. The happiest retirees I’ve studied don’t just adapt — they proactively design their purpose portfolio well before the retirement party. They start building those daily purposes while still working, gradually cultivating activities that will seamlessly roll up into yearly purposes.

We’ve heard this suggestion from a few retirement books now. I hope those of you reading who are in the process of planning for retirement are paying attention and taking action.

You’ve been warned.

What Constitutes a “Plan”

When I initially read that this was one of the five secrets, I thought it would morph into a pitch for financial planning services (from a financial planner — which is the occupation of the author, BTW).

And while that may be implied or slip in here and there in some readers’ thoughts, the book actually takes a low-key approach to “planning” and what counts to qualify.

It starts with these comments:

But planning doesn’t require complex platforms or expensive tools. It can be as simple as putting pen to paper, forcing yourself to think concretely about your future. In my work with families, I often begin with something deceptively simple: Draw a line from where you are today to a date you want to plan toward in the future.

Now it’s time to draw your timeline.

Step 1: Draw Your Basic Retirement Timeline — Number of Years You’re Planning For, Your Target Retirement Zone, and Assets Today

Step 2: Add Key Financial Years/Ages and Assets Tomorrow

Step 3: Add Up Your Income Streams

Step 4 (If Needed): Add in Other Important Financial Goals

The beauty of this timeline exercise is that it works with whatever tools you prefer. There’s the old-school approach we just outlined: large sheets of paper, colored pencils, highlighters, a calculator, and the tactile experience of drawing by hand. There are digital options, like eMoney or MoneyGuidePro, that provide sophisticated modeling if you’re working with a financial advisor. There’s even good ol’ Excel spreadsheets that offer calculation power and easy updates. Modern Al tools can help model complex cash flow scenarios given your inputs, running multiple what-if analyses to stress-test your assumptions. And you’re always welcome to join me on a Microsoft Surface or reMarkable drawing tablet as we map out the future, one hand-drawn timeline at a time.

So as you can see, there’s a wide range of what a plan can look like.

My personal plan involved both the old-school pen-and-paper option and a more detailed version in Excel. I would rough out my assets and spending in my journal, then use Excel to plan out a retirement budget for a few years into the future.

There was no in-depth analysis or paying $5,000 for a plan from a financial planner, which one actually offered to do for me at that price.

I did get a free review of my retirement plan at Vanguard, and they basically told me I was doing everything right. They had a few nitpicks here and there, but nothing meaningful and, in my opinion, nothing that added much value.

A few thoughts on the financial side of my plan:

• I wanted the finances to be completely battened down because I knew I didn’t want to trade work stress for money stress. I wanted finances to be a non-issue for us in retirement, and the results have been vastly better than I could have imagined.
• For me, the financial plan did not need to be fancy. It needed to answer the major questions: What do we own? What do we spend? What income sources do we have? What could go wrong? What would we do if markets dropped? How much cushion do we have?
• Once those questions were answered well enough, I didn’t need a 100-page binder. I needed confidence.
• That’s what a good plan does. It turns vague worry into concrete numbers and decisions.

The life/time side of the equation was completely different. It was closer to the coin toss I mentioned above, which is why I now advocate for a life plan for my readers.

At ESI Money, you can learn from both my successes and my failures!

I went into the life side of retirement thinking several things:

• Retirement would be a gazillion times better than work because I could do whatever I wanted rather than being told by a crazy boss what to do. This turned out to be so, so true.
• I knew I had a few things I already liked doing that I could expand upon and that could fill some of my time, namely exercising, writing at ESI Money, reading, and playing video games.
• I knew I was naturally adaptable and curious, two traits that would allow me to experiment and find other activities that would make me happy. It was these traits that led me to ask, “What’s going on there?” as my wife and I walked by a new park in our neighborhood and discovered pickleball courts for the first time. The rest was history! Hahaha.
• Since the financial side of life was handled, it allowed me to be a bit more creative and think about doing other activities, like buying and running Rockstar Finance. That was a fun but wild ride that turned more into a job than I had ever imagined, which is one reason I sold it. But the itch to create another business still needed to be scratched, and Millionaire Money Mentors was started shortly thereafter.
• I’m still adapting these days, adding and subtracting as I go along. I only play pickleball twice a week now, which is a subtraction, and I’m considering applying for a volunteer position on one of our town’s committees, which would be an addition. I’ve also all but eliminated long travel that requires a plane ride and extended stay, in favor of closer-to-home travel like the mountains and beaches of North Carolina.
• I also have a list of future “interests” that I may or may not pursue one day. Time will tell. But I imagine I’ll be adding and subtracting retirement activities all throughout my retirement.

Looking back, the financial side was very solid before I retired. The life side was good enough to get started, but it has evolved quite a bit. That’s probably normal.

Moss continues this line of thinking:

The tool matters less than the thinking process. You’re training your brain to think systematically about your financial future rather than squeezing your eyes shut and hoping it will all work out.

When you complete this exercise, you’ll have something most people never create: a visual representation of your financial journey through retirement.

More importantly, you’ll have transformed abstract anxiety about “running out” into substantial knowledge about your financial trajectory.

Instead of losing sleep over vague money worries, you’ll know specifically what adjustments might be needed and when to make them.

This financial roadmap becomes the foundation for everything else — from deciding when to retire to determining if you can afford a second home to calculating whether you can help with your grandkids education.

It’s the difference between financial hoping and financial planning.

I think “losing sleep over vague money worries” is the key here.

The plan helps you sleep well at night, which is the next secret, by the way. These all work together, as we’ll soon see.

A financial plan does not need to eliminate every possible worry. That’s impossible. Markets can crash, inflation can rise, health problems can happen, tax laws can change, family needs can shift, and the future can always surprise us.

But a plan can turn unknowns into scenarios. It can give you options. It can show you what levers you can pull if needed. It can tell you whether you’re in good shape or whether you need to make changes before retiring.

That is much better than simply hoping things work out.

Life Plan

That’s the background on the financial plan. Now let’s talk about the life/time plan — creating a plan for what you’ll actually do in retirement.

This section begins with the following:

While the financial timeline gives you the means to retire, the life side of mapping ensures you’ll have compelling reasons to wake up each morning. This time, you’re mapping meaning rather than money.

Specifically, you’ll be creating core pursuits/activities/hobbies on steroids — whatever you want to call these.

There’s an actual process the book recommends for doing this. Here are some highlights:

Step 1: Warm-Up Lists

Take a piece of paper — or open a fresh screen on your tablet — and start with some warm-up brainstorming.

Start by identifying your core values — what matters most deeply to you?

Underneath each value, begin brainstorming specific core pursuits or commitments that would honor that value in retirement.

Next, organize these possibilities into daily purposes (activities that could provide regular structure and meaning) and yearly purposes (bigger projects or goals that give shape to longer time periods).

Step 2: Spot the Alignment Gaps

This is where honest self-assessment pays dividends. Compare your current weekly activities against your core values. Many people discover significant gaps — perhaps they value creativity but have no creative outlets, or they prioritize family relationships but spend more time on solo activities than connecting with loved ones.

Identify these underrepresented areas now, while you still have time to address them gradually rather than scrambling to fill purpose vacuums after retirement.

Step 3: Draw Your Map

Now that you’ve brainstormed the things you love and the gaps you’d like to fill, it’s time to make the actual map. This time, grab a large sheet of paper and your colored pencils or fire up your digital whiteboard anew.

Now write out the most important things that come to mind. I find it helpful to use different colors for different categories. These may include family, church, your social network, and your favorite core pursuits. There’s no particular structure, except to start scribing the most important variables you see in your future. Once you start drawing these out, more specifics will come to mind. If they’re important to you, write them down and/or create a visual for the activity.

It doesn’t have to be pretty, just meaningful to you. The goal is to create a visual representation where you can quickly see whether you’re balanced across all your values. Include both continuing pursuits (activities that build on your existing expertise and passions) and new adventures (those curiosities you’ve been putting off for decades). Draw arrows or timeline elements showing when you’ll start different activities — which can begin while you’re still working versus what requires full retirement.

The key is making it visual and specific enough that anyone looking at your map would have a good idea of what your ideal retirement looks like.

Lots to comment on here:

• It’s a decent process, in my opinion. I’d probably make it a bit simpler, but I think the general idea is good.
• This reminds me of two things: creating a vision board and creating a Get-a-Life Tree.
• I think many here know what a vision board is, but in case you don’t, Google says, “A vision board is a collage of images, words, and affirmations that represent your goals and dreams. Designed to serve as a daily source of inspiration, it helps you clarify your priorities, stay motivated, and focus your energy on the life you want to create.” Sounds like what this is, doesn’t it?
• A Get-a-Life Tree is a bit more obscure than a vision board. This was created by author Ernie Zelinski in his book How to Retire Happy, Wild, and Free, which I covered in a three-part series starting with How to Retire Happy, Wild, and Free, Part 1. You can see an example of a Get-a-Life Tree here in case you’d like to create one of your own. I know at least one mentor in the MMM forums who uses this extensively.
• Whatever you call it, all these are thought-out plans for how you’ll spend your time in retirement, which is something I highly recommend you do. They also serve as visual reminders of what you want to do with your life and encouragement to actually do it.

Personally, my simpler version is a bit more bare bones and would include the following:

• Look over my list of Awesome Retirement Activities and write down those you think might interest you. Also refer to my Top Seven Retirement Activities because these are the best-of-the-best activities that I highly recommend you consider.
• Have a chat with your favorite AI to see if it can generate any additional ideas.
• Divide the list into items you currently do and want to keep, ones you’d like to try now to see what can be added, and the rest, which you can save for the future.
• Then start to schedule these. Add and subtract from there to create the retirement life you want.

In the end, all these approaches are really trying to accomplish the same thing. They help you identify retirement activities, think through what matters to you, and make sure the life side of retirement is a happy one.

They also force you to get specific, which is important.

“I’ll stay busy” is not a plan.

“I’ll spend Monday and Friday mornings playing pickleball, write three mornings a week, volunteer twice a month, have dinner with the kids on Sundays, attend church, lift weights three times a week, and take one local day trip a month” is much closer to a plan.

You don’t have to schedule every minute, and I wouldn’t recommend doing so. But you do need enough structure that retirement doesn’t become a long, unstructured drift.

Moss then wraps up this discussion with this:

When your map is complete, place it somewhere you can see it — on your office wall, next to the microwave, or on the fridge. The point isn’t to outshine your three-year-old grandson’s crayon drawing of Jesus; it’s to give you a daily reminder of the happy retirement you’ve mapped out.

Hahaha. Move over, sonny, grandpa’s drawing goes there! lol

And to wrap up this entire secret, Moss says this:

You’re not trying to eliminate all uncertainty. Life will surprise you regardless of how well you plan. The goal is to enter retirement with both the financial security and the sense of direction that allow you to adapt confidently to whatever comes next. When you’ve mapped both sides of the retirement coin, you’re not just calling heads or tails; you’re making change.

When you combine this visual life map with the financial timeline we explored earlier, you create something powerful: a comprehensive vision for retirement that addresses both the means and the meaning of your post-career years. You’re not just hoping your golden years will be golden — you’ve actively designed them to shine.

So as you can see, this is a very low-cost and low-effort way to attack the two major areas of retirement in a meaningful way, and it’s one I can completely endorse.

A few final thoughts from me:

• I started this chapter skeptical because I thought it might be a thinly veiled push for people to get a formal financial plan from a financial planner. But that’s not really what this is.
• I do think a written financial plan has value, even if it’s simple. It helps you understand where you stand, what income you’ll have, what expenses you expect, and what decisions you need to make.
• I think the life plan may be even more underappreciated because many people assume retirement happiness will happen automatically. It might, but I wouldn’t count on it.
• If you’re still working, start testing both sides now. Run the financial numbers and rehearse the lifestyle. You’ll learn a lot before making the leap.
• If you’re already retired and not as happy as you expected, this exercise could still be very useful. You may not need more money. You may need more structure, more connection, more meaningful activities, or more clarity about what you want your days to look like.

What about you?

If you’re retired, did you do both of these? If you aren’t retired yet, are you planning to?