Today is our third (and last) day covering thoughts shared in the book Retirement Starts Today by Benjamin Brandt.
If you missed either of the first two parts, you should check them out before reading this post.
Part 1 was Retirement Starts Today: Why I Think Rehearsing Retirement Is a Great Idea and part 2 was Retirement Starts Today: 10 Key Retirement Concepts.
As we discussed in part one, I strongly agree with the idea that people should “try out” retirement before they actually retire.
I’ve long believed this is one of the smartest ways to prepare for retirement because the reality is that many people spend decades preparing financially for retirement while doing almost nothing to prepare for retirement life itself.
They assume they’ll naturally figure it all out once work ends.
Sometimes they do. Sometimes they don’t.
The problem is that retirement is a much bigger lifestyle adjustment than many people expect. Work provides far more than a paycheck. It provides structure, routine, social interaction, goals, momentum, identity, and purpose. Once that disappears, some retirees thrive while others feel surprisingly lost.
That’s why I think future retirees should begin experimenting with retirement life while they are still working. You want to discover ahead of time:
- what you enjoy
- how much structure you need
- what gives you purpose
- how social you want to be
- what hobbies actually stick
- what a satisfying ordinary day looks like
The good news is that this doesn’t require fully retiring early or making massive life changes overnight.
In fact, there are a number of simple and practical ways to start trying out retirement long before you officially leave the workforce.
In part one we gave a couple ideas how to practice retirement, but this post will go deeper — with ten practical ways to test-drive retirement before retirement officially begins.
One thing I liked about Retirement Starts Today is that the “practice retirement” idea isn’t just “think about retirement more.” It’s much more practical than that.
The core idea is:
Start gradually building your retirement life while you still work instead of waiting for some magical switch to flip later.
In that spirit, here are some practical ways people can actually do that.
1. Take Longer Breaks From Work
One of the most obvious ways to test retirement is to simulate it temporarily.
That could mean:
- taking a two-week vacation and living more like a retiree instead of a tourist
- using a sabbatical
- taking extended PTO
- trying a month between jobs
- negotiating unpaid leave
- working remotely from another location for a while
The key is this:
Don’t fill every minute with vacation activities.
Instead, try living normal life without work.
That means:
- waking up without an alarm
- creating your own schedule
- figuring out what you naturally want to do
- seeing how much structure you need
- testing hobbies and routines
I think this is hugely valuable because many people discover they either love the freedom immediately or feel strangely lost without structure.
Both are useful discoveries.
2. Start Developing Hobbies Before Retirement
This is probably the biggest practical step.
Many people retire with no hobbies besides watching TV, browsing the internet, and perhaps occasional travel. That’s usually not enough for a satisfying 30-year retirement.
Brandt talks a lot about experimenting with interests, and I strongly agree. Start trying things now.
If you need suggestions of what you could potentially try, read my series on the top seven retirement activities as well as see my huge list of retirement activities.
If you can’t find a handful of ideas from those two, you’re probably a lost cause. Hahaha.
The important thing is not finding “the perfect hobby.” It’s building engagement and curiosity into life.
One thing I’ve noticed is that retirees who stay mentally and socially engaged tend to do much better emotionally.
3. Practice Having Unstructured Time
This sounds simple, but it’s actually difficult for many workers.
A lot of people have not had meaningful unscheduled time in decades. Their lives are almost entirely driven by work schedules, meetings, commuting, and deadlines, plus personal demands like family obligations and kids’ activities.
Then retirement arrives and suddenly nobody is telling them what to do anymore. That freedom sounds great until it actually happens.
One practical exercise is simply leaving chunks of time intentionally unplanned and seeing how you respond.
Do you:
- naturally find meaningful things to do?
- feel anxious?
- get bored?
- waste the day?
- feel energized?
- feel restless?
Those reactions tell you a lot about what retirement may feel like.
4. Build Social Connections Outside Work
I think this one is massively underrated.
Many people underestimate how much of their social life comes from work. Then retirement happens and they slowly become isolated.
Brandt touches on this and I think he’s absolutely right to emphasize it.
People should start building social connections outside work before retiring:
- clubs
- church
- sports
- volunteer groups
- classes
- hobby groups
- neighborhood relationships
- recurring lunches or breakfasts
- mentoring groups
The happiest retirees I know usually have strong social rhythms already established.
Retirement is much easier when you already have people and communities woven into your life.
5. Try “Retired” Weekdays
This is one of my favorite practical ideas.
Take occasional weekdays off and live them the way you imagine retirement would look.
Not vacation. Normal retirement life.
What’s that? Some things that might include:
- Go exercise in the morning
- Read
- Run errands during off-hours
- Meet someone for lunch
- Work on projects
- Relax
- Volunteer
See what the pace feels like.
One thing many people discover is that they love weekday freedom more than they expected.
Others realize they need more stimulation and structure than they assumed.
Again, both are useful discoveries.
6. Reduce Lifestyle Dependence on Work Identity
This is harder, but very important.
Some people’s entire identity is tied to career status, titles, income, achievement, being needed, and all the other trappings associated with working. Then when work disappears, they feel psychologically untethered.
That’s why I think people should gradually build identity outside work.
You could become…
- athlete
- mentor
- volunteer
- writer
- traveler
- teacher
- church member
- grandparent
- hobbyist
- community member
The broader your identity becomes before retirement, the easier the transition usually is.
7. Experiment With Different Retirement Activities
One thing Brandt emphasizes that I agree with is experimentation.
Don’t assume you already know what retirement will look like. Test things. Find out what you like and what you don’t. Shoot for having a total of at least five go-to activities that you know you enjoy in retirement.
Mine currently are:
- Exercising
- Pickleball (which is a form of exercise but also enjoyable — as opposed to the StairMaster which is exercise but not enjoyable)
- Writing
- Managing businesses
- Mentoring (online)
- Time with family
- Reading
Plus there are a few others — which mostly happen now and then. Examples would be taking local trips and playing video games (I only play certain types of games, so when there are no new ones out I like, I don’t play.)
Retirement becomes much easier when you enter it with self-awareness. And self-awareness usually comes from experimentation, not imagination.
8. Build Physical Fitness Before Retirement
I’d personally emphasize this even more than the book does.
A huge percentage of retirement enjoyment depends on mobility, strength, endurance, flexibility, energy, and pain levels.
People often focus entirely on financial preparation while ignoring physical preparation. That’s a mistake.
One of the best ways to practice retirement is to start living more actively now:
- walking
- swimming
- lifting weights
- stretching
- sports
- mobility work
- balance training
You want to enter retirement physically capable of enjoying the freedom you worked so hard to create.
I currently do the following:
- Swim
- Cardio (Stair Master, though swimming is also cardio)
- Pickleball
- Lifting Weights
- A stretching/balance/strength routine (ChatGPT helped me put it together)
I mix these by day as well as intensity by day (some days are easy and some are hard).
9. Gradually Shift Toward a Retirement Lifestyle
I think the best retirements often happen gradually rather than abruptly.
Instead of:
work nonstop → instant retirement
…it can be healthier to slowly transition toward retirement life.
That might mean:
- consulting
- part-time work
- remote work
- reduced hours
- more vacation time
- flexible schedules
- semi-retirement
- seasonal work
This gives people time to psychologically adapt instead of slamming into a completely different lifestyle overnight.
We talked about two great ways to do this in part one of this series, so check that out if you missed it.
BTW, you could argue that I’m in a 10-year “gradual” shift myself, as I’ve continued to work in retirement (for myself, of course.)
10. Learn How You Actually Like to Spend Time
This may be the most important practical takeaway of all.
Most people are surprisingly disconnected from what genuinely makes them happy on ordinary days.
That’s why I often think retirement planning should include this question:
“What would I naturally do if nobody required anything from me?”
The only way to answer that honestly is through experience. That’s why trying out retirement early is so useful.
You learn:
- how much structure you need
- how social you are
- how active you want to be
- whether you enjoy slower living
- what actually energizes you
- what gives you purpose
Those lessons can dramatically improve retirement satisfaction later.
And honestly, many of those changes improve life before retirement too.
Final Thoughts
One of the biggest mistakes people make with retirement is assuming that financial preparation is the same thing as retirement preparation. It’s not.
Money is obviously critical. Without enough savings and investments, retirement freedom becomes much harder to achieve. But once the financial side is reasonably in place, the next challenge becomes figuring out how to build a life you actually enjoy living.
That’s where “trying out” retirement before retirement can make such a huge difference.
The goal isn’t to perfectly engineer every aspect of your future life ahead of time. Retirement is still going to involve adjustment, surprises, and evolution no matter how much preparation you do. But the more you experiment ahead of time, the more likely you are to enter retirement with momentum instead of uncertainty.
You’ll have a better sense of:
- what activities energize you
- how much structure you need
- what hobbies actually stick
- how social you want to be
- what gives your days meaning
- what a satisfying retirement lifestyle looks like for you personally
And perhaps just as importantly, you’ll avoid the trap of building your entire future around assumptions that may not actually fit you once retirement becomes reality.
One thing I’ve consistently seen among happy retirees is that they usually don’t retire into a vacuum. They retire into lives that already have substance, relationships, routines, interests, and purpose built into them.
They don’t wake up on their first day of retirement and suddenly try to invent an entirely new life from scratch. Instead, they gradually build that life over time.
That’s why I think testing retirement early is such a smart idea.
In many ways, the best retirements aren’t created overnight after someone leaves work. They are built little by little for years beforehand.
This ends our mini-series on this book. What did you think of it?
Leave a Reply