Retirement Starts Today: 10 Key Retirement Concepts

This is part two of my series on the book Retirement Starts Today by Benjamin Brandt.

The first post was Retirement Starts Today: Why I Think Rehearsing Retirement Is a Great Idea. If you haven’t read it you should go back to check it out as this post builds on that one.

The first post was about the main point (at least IMO) of the book: start planning for retirement life now. Think about who you want to be, what you’ll do, what it will look like, etc. while you are still working. Try and test out as many activities as you think you might enjoy in retirement while you are still working, so once you retire you can hit the ground running, knowing you have a bunch of pursuits you enjoy.

Today I’m going a bit broader to give you 10 key concepts the book touched on that I thought were worth sharing. Most of these aren’t shared much in the book, but instead things I thought of as I read it.

Let’s get started…

1. Retirement Looks Different in Real Life Than It Does in Your Head

One of the problems with retirement is that many people build a fantasy version of it in their minds.

When you’ve been working for decades, retirement can start to feel like a magical finish line where all stress disappears and every day becomes amazing. You imagine endless freedom, endless relaxation, endless travel, endless golf, endless whatever-it-is-you-think-you’ll-love.

I can’t say this is a completely absurd feeling. I’ve shared many times how thrilled I was in retirement, especially once the realization hit me that I was FREE! Free for the rest of my life! How awesome is that?!

But it’s not one big vacation either. Normal life is still there. You still need to mow the grass, take out the trash, deal with family issues, help sick parents, and much more. Life goes on.

And you also start to get used to the retirement awesomeness (eventually) that was originally made it feel like Christmas morning every day. Human beings adapt to almost everything, including freedom. Granted, it took me 5+ years to get used to it…but still, I eventually did.

Since it’s a mix of greatness, the unknown, and real life, I think it’s dangerous to assume you’ll instantly know how to build a satisfying retirement lifestyle after decades of working full time.

Some people do know. But most (or at least many) don’t.

I’ve seen this over and over through the millionaire interviews and from retiree emails over the years. The financial transition into retirement is often easier than the emotional or lifestyle transition.

2. Work Provided a lot More than a Paycheck

It provided structure. Routine. Social interaction. Identity. Momentum. Goals. A sense of usefulness. Sometimes even purpose.

Then suddenly all of that disappears.

That can feel wonderful at first. But eventually many retirees realize they need to intentionally rebuild parts of their lives.

That’s one reason I’ve long been an advocate of testing retirement life before retirement officially begins.

And part of that testing involves creating a life outside of work. If it’s your all-in-all and you leave it, you’re going to have issues. You need to minimize its impact in your life before you’re ready to move on.

3. You Should Experiment Before the Stakes Are High

One thing Brandt discusses in the book is experimenting with retirement activities before retiring. I strongly agree with this idea.

In fact, I think people should begin doing this years before retirement if possible.

The traditional retirement model is strange when you think about it. People spend 30-40 years working, then one day simply stop and hope everything works out afterward.

That’s a massive life change.

Yet many people spend more time researching a refrigerator purchase than they spend preparing for the practical realities of retirement life.

I think a much smarter approach is gradually building your retirement life while you’re still employed. Take some time to:

• Try various activities.
• Explore interests.
• Develop hobbies.
• Build routines.
• Learn what energizes you and what doesn’t.

Most importantly, learn what your day-to-day life actually feels like when work is no longer the center of everything.

People often think they know what retirement will feel like. But imagining retirement and living retirement are two completely different things.

For example, many people say they want to travel constantly in retirement. Then they discover that nonstop travel gets tiring pretty quickly. (Travel was never a retirement focus for me thankfully as I abhor it now.)

Others dream about golfing every day until they realize that playing golf seven days a week eventually starts feeling repetitive. Hahaha. I met one guy in The Villages who became the president of a big membership group. His new position required a lot of volunteer time and activities. When he was asked why he had taken on this position late in life he said, “I’ve played all the golf I can take.” lol

Some think they’ll happily sit around relaxing forever until they discover that too much unstructured time actually creates anxiety or boredom.

The main point is: you don’t really know how retirement will hit you until you test it.

That’s why I think “practicing retirement” is such a valuable concept.

4. Retirement Is Easier When You Already Have a Life

One thing I’ve noticed is that the happiest retirees are usually people who already had meaningful lives outside of work before they retired.

Work may have been important to them, but it wasn’t their entire identity.

They already had:

• interests
• relationships
• routines
• hobbies
• fitness habits
• community involvement
• personal goals
• passions outside the office

As a result, for these people retirement becomes less of a cliff and more of a transition.

I was in this group. I didn’t have a plan for how to spend my time in retirement (which is a big risk and why I’m such an advocate for trial retirements these days — you can learn from what could have been a disaster for me.) I thought I had enough going on outside of work plus I was a curious and adaptive person, so I could add/adjust as needed.

Thankfully I was right and I was able to take what I already knew I wanted to do (ramp up exercise, read, write, play video games, spend time with family, etc.) and add a couple new things (pickleball, an extra business — first Rockstar Finance and then MMM) and I’d be set. It all worked out well.

But retirement can be much harder for people whose lives revolve almost entirely around work.

I’ve known people who spent decades saying:

“When I retire, THEN I’ll start living.”

Personally, I think that’s risky.

None of us know:

• how long we’ll live
• what our health will be
• how much energy we’ll have
• what physical limitations may arise later

That’s why I think it’s wise to begin integrating parts of your retirement life into your current life whenever possible.

What that might look like:

• developing hobbies
• traveling more
• joining groups
• volunteering
• learning new skills
• exercising consistently
• reconnecting with old interests
• spending more time with family
• experimenting with flexible work

The point isn’t to fully retire early necessarily.

The point is to build a richer life now instead of postponing everything indefinitely.

5. One of the Most Important Retirement Questions

As I read the book, I kept coming back to a question I think every future retiree should answer:

“What does a good Tuesday look like in retirement?”

Not vacation. Not a once-a-year trip. Not a fantasy.

Just a random ordinary Tuesday.

Some questions to consider:

• What does that life actually look like?
• What time do you wake up?
• What do you do during the day?
• Who do you spend time with?
• What gives the day meaning?
• What are you excited about?

I think many people struggle with retirement because they only imagine the big exciting moments. They picture cruises, beaches, travel, and freedom. But retirement is mostly made up of ordinary days.

So the real question is whether you’ve built a life you actually enjoy living on ordinary days.

That’s where trying out retirement ahead of time becomes incredibly useful.

It allows you to begin answering those questions before your paycheck disappears and before your old structure vanishes.

I often tell people that instead of traveling to enjoy life I created a life in and around home that I enjoy more than any travel. 😉

6. Retirement Is Not Permanent Vacation

Another point the book touches on that I strongly agree with is the idea that retirement is not the same thing as an endless vacation.

Vacations are fun partly because they are temporary.

If every single day becomes pure leisure with no structure, no goals, no purpose, and no momentum, many people eventually become restless.

This is the issue I experienced in part in The Villages (where every day does seem like a vacation day.) It’s just not real life.

What is real life: any random Tuesday. 😉

7. Structure Matters More Than People Realize

One thing the book reinforced for me is how important structure can be in retirement.

Not rigid schedules. Not turning retirement into another job. But some level of rhythm and structure.

You could also call it a routine.

Work naturally provides structure whether we realize it or not. It tells us when to wake up, where to go, what to focus on, and what needs to get done. Once that disappears, some retirees feel surprisingly untethered.

That’s one reason I think anchor activities are important.

Many successful retirees naturally create routines around things like:

• exercise
• sports
• volunteering
• church
• hobbies
• classes
• reading
• social groups
• mentoring
• projects

These activities create momentum and rhythm.

I have said previously that exercise is a great anchor for me. It’s what I do almost every morning and it accomplishes so many things — builds my body to help me stay healthy, gets me an early, big win, gives me energy for the day, connects me with others (gym/pickleball friends), and a few other things. Then once that’s done, the day is my oyster to do with as I want.

It’s the combination of partial structure (exercise in the morning) and the rest of the day being flexible that I think makes for a great retirement (at least for me).

A lot of retirees underestimate how psychologically valuable that can be.

BTW, there’s nothing magical about the structured part being exercise or in the morning. It could be a volunteer opportunity you do every afternoon. The concept is to have part of the day set for most (if not all) days and then let the rest flow as you want.

You can also determine how much time you want to set as a routine and either ramp it up or take it down from what I have (mine is about a two-hour block).

8. Retirement Often Magnifies Who You Already Are

One observation I’ve had for years is that retirement tends to magnify existing personality traits.

People who are naturally curious, engaged, social, and proactive often do very well in retirement because they continue building interesting lives.

People who struggle with boredom before retirement often struggle with boredom afterward too.

That’s another reason trying out retirement early makes so much sense.

It allows you to discover:

• what energizes you
• what drains you
• what interests you
• what feels meaningful
• how much social interaction you want
• how much activity you need
• what type of routine fits you best

And importantly, it gives you time to make adjustments.

Retirement becomes far less intimidating when you’ve already started building the life you want.

9. The Book’s Discussion on Spending Reinforced What We Already Knew

Another theme in the book is that many retirees struggle to transition from saving money to spending money.

As we’ve discussed before (and will again), I think this is very real issue.

After decades of living in accumulation mode, many people become so conditioned to save and invest that spending money feels emotionally uncomfortable even when they can easily afford it.

I’ve seen retirees continue acting like they’re one step away from financial disaster despite having more than enough assets to support themselves.

As a result, they delay:

• travel
• experiences
• hobbies
• family gatherings
• generosity
• enjoyment

Then eventually age or health limits what they can do.

Brandt argues that retirees should focus more intentionally on using money to create meaningful experiences and memories instead of endlessly maximizing net worth.

Overall, I think he makes a good point.

At some stage, the purpose of money should shift from accumulation toward enhancing life.

Otherwise people can fall into the trap of protecting money they’ll never actually use.

That said, I would add one caveat.

I do think retirees need to remain realistic about longevity risk, inflation, and healthcare costs — especially early retirees.

Someone retiring at 52 potentially needs their assets to support them for four decades or more. That requires a different level of planning than retiring at 70.

So while I agree retirees shouldn’t become excessively fearful about spending, I also don’t think the answer is careless spending.

The sweet spot is intentional spending.

Spend confidently on things that genuinely improve your life while still maintaining reasonable financial flexibility and margins.

If you need help in this area, see Math Hacks to Help With Spending Decisions 

10. Financial Independence is the Start

The biggest thing this book reinforced for me is something I’ve believed for a long time:

Financial independence is not the end goal.

It’s the foundation.

Money buys freedom, flexibility, autonomy, and options. Those are incredibly valuable. But once you achieve them, you still need to build a meaningful life.

This is something no retirement calculator can solve it for you.

You have to discover through experience:

• what fulfills you
• what excites you
• what kind of pace you enjoy
• how social you want to be
• what gives you purpose
• what kind of structure works best for you

That’s why I think “practicing” retirement before retirement is such an important idea.

The earlier you begin experimenting, the smoother your eventual transition is likely to be.

Final Thoughts

Overall, I thought Retirement Starts Today was a decent retirement book because it focuses on the side of retirement many people ignore.

The financial side gets most of the attention, but the lifestyle side is often what determines whether retirement actually feels satisfying.

I especially appreciated the emphasis on experimenting with retirement life before fully retiring. Longtime readers know this is something I’ve advocated for repeatedly over the years because I think it helps retirees avoid the “now what?” problem that catches many people off guard.

Retirement is a huge life transition. In many ways it’s one of the biggest transitions people ever experience.

So it makes sense to prepare for it intentionally instead of assuming everything will automatically fall into place once work ends.

The people who seem happiest in retirement are usually the ones who gradually build lives they enjoy long before retirement officially arrives.

That’s it for this time. Stay tuned as I’ll share the third part of this series soon.