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Planning for Retirement

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April 16, 2026 By ESI 18 Comments

Today we’re going to continue sharing thoughts from the book How to Retire by Christine Benz. It’s a great book and I highly recommend it. And as with the last article, I’ll be giving away a copy of the book at the end of this post.

We’ve already covered this book once in the post titled How to Retire. You may want to check that out if you missed it since this post builds on it.

Today’s chapter is Christine’s interview with my friend (and Millionaire Money Mentors member) Fritz Gilbert from The Retirement Manifesto. It covers an extremely vital part of retiring well: planning for your retirement.

We discussed this a bit when we covered chapter 1, but chapter 2 (this one) is completely about planning for a great retirement: first setting a date and then detailing what to do five years out, three years out, and so on.

I’m not going to walk through the chapter step-by-step like I did with the first one, but instead I’ll share each of Christine’s summary bullet points at the end of the chapter along with my thoughts.

It’s a Big Job

We’ll begin with this point on how overwhelming planning for retirement is for many:

Getting ready to retire involves lots of activities that, taken together, can seem daunting. Breaking it down into smaller, phased tasks-jobs at year three, jobs at year two, and so on, can make it more manageable.

My thoughts:

  • If you take nothing else from this post it should be this: you need to plan for retirement. If you don’t, you’re simply rolling the dice with your post-work life and the odds of it being a disaster are as great (or greater) than the odds of it being a success.
  • Another way of saying it is if your retirement plan is to just “go with the flow,” you will get go with the flow results. And no one wants to leave something so vital up to chance, luck, fate, or whatever you want to call it.
  • Which is why I’m surprised how few people plan for retirement. It’s a multi-million dollar, decades-long decision and many people give it as much thought as they do what’s for dinner tonight. After all, who needs to plan for 24/7 free time? We all know how to do that, right? No, we do not. Not for weeks, months, and years on end. Some people can’t even manage a Saturday afternoon of free time — how do they expect to survive in retirement?
  • When people do plan for retirement about 95% of it revolves around the financial side of the equation…do they have enough money to support themselves? If the answer is “yes”, then most stop planning at that point, leaving out the other big question for a successful retirement: what am I going to do with all my free time/life? Getting this right is just as important as having the money side handled.
  • You can tell when people failed to plan for retirement because they are unhappy in it. They are bored, don’t know what to do with themselves, etc. Many go back to work simply because they don’t know what else to do. These are not failures of retirement itself but rather failures of not planning in advance for something they knew was coming.
  • Breaking down any large project into bite-sized pieces is a great way to tackle it (after all, you eat an elephant one bite at a time, right?) and retirement is no different. In particular, you can test out all sorts of fun activities, side hustles, volunteering opportunities, etc. while you’re still working and keep the winners with you into retirement. This way you know you’ll have some well-tested, enjoyable tasks to fill your free time…which is a huge step towards having a great retirement.

Now let’s move into an area that’s not discussed much.

Not Just for Workers

In the next point Christine notes that there are some particular sub-groups who need to plan for retirement (though they might think they don’t need to):

Retirement isn’t just a transition for people who do paid work. People who have been caregivers for elderly parents, for example, might feel a loss of purpose when they’re no longer doing that “job.” They need a retirement plan just as much as the person who’s retiring from paid work.

Basically, anyone who’s doing something and moves into doing “nothing” (not that they literally do nothing but they have an abundance of free time in retirement) needs to think about and plan for what their life will look like in retirement.

My wife had to deal with this when she went from homeschool teacher to “retirement.” Back then we (and the world) knew less about planning for retirement, what makes a great retirement, etc., so my wife had to figure out what to do with the void in her life.

Fortunately she’s always had a lot of interests in life so when time opened up she expanded those and added a few others. But even so, it wasn’t as smooth of a transition as it could/should have been if she had planned for the change in advance.

Moving in Retirement

Next Christine broaches a topic that I’ve been living through the last three years — moving in retirement:

If you’re pondering relocation for your retirement, trial run it before you officially move.

Lots to say on this one. Having retired in one spot, lived there seven years, then moved to another city across the country, and didn’t like it so moved to another part of the country, I feel I am uniquely qualified to offer some perspective on this issue. Hahaha.

I recall Wes Moss noting in his book on happy retirees that moving in retirement was associated with an unhappy retirement. I think his point was more around buying a new home with a mortgage (adding debt in retirement), but perhaps some of it was for a few of the reasons noted below.

Moving in retirement is complicated. As in all things in life, it’s not just about you (if you have a family). I had my wife’s preferences to consider in our moves as well as those of my daughter and son-in-law (we lived near them in Colorado and wanted to be close to wherever they were).

My wife was done with winter…at least any substantial winter. She grew up in Erie, Pennsylvania, we lived in Grand Rapids, Michigan for 14 years, and we lived in Colorado for seven years. So she had her fair share of cold and snow. She wanted to move somewhere warmer.

The kids were “done” with Colorado Springs as they felt they had experienced everything there they wanted to do — plus it wasn’t close to anything new they wanted to try (like other major cities, attractions, etc.) In addition, they felt the city was declining over the past few years. They apparently were on to something as US News dropped The Springs from third to 406 on their list of best places to live. Crime, affordability, and job opportunities were listed as the reasons for the decline.

I was up for trying something new. Since we’d been to The Villages for three months the year prior and my dad had moved there, that seemed like a good place to consider. The kids had some plans that looked like they would end up in Florida as well, so it appeared to be a great choice.

Given all that, let me share a few tips for moving in retirement:

  • Don’t visit your perspective new location at its best time of year and then compare that to your current home’s worst time of year. Try the new place at its worst too so you can see how bad it gets.
  • Try out the new location for at least six months. Three months is not enough. You can live almost anywhere new for three months, especially when the weather is terrible at home. The longer you can try out your new potential home, the better.
  • Remember that plans are just that…plans. They can change, and in our case they did (for our kids). It turned out to be for the better in our case, but it could have easily gone the other way.
  • Some thoughts on how to do research on a possible new location: talk to locals, watch YouTube videos (there’s a channel on everything these days), and read as much as you can about the place. Live there a good amount of time during different seasons as well.
  • If you don’t have to, don’t sell your home in the old city until you are 100% sure that the new place is a winner. That way you can always go back if you want to.
  • Consider very carefully the impact of what you give up when you move: relationships with friends, organizations (church, gym, etc.), doctors, and so on. You likely built those over years or even decades and they aren’t easily replaced.

It eventually worked out for us as we all ended up in a place we (as a group) prefer to Colorado Springs, but it was a rough two years to get here (especially for me.) But who knows if we would have ended up here if we hadn’t gone through what we did — it’s hard to say. Everything happens for a reason, but if I had to do it again, I’d follow the tips above more closely.

Next we move on to a money issue…

Retirement Budgeting

Christine offers this thought next:

Be ultra-specific about what you expect your in-retirement budget will look like and consider trying to live on your projected spending amount. Is it realistic?

My thoughts:

  • We had a budget the first 10-15 years of our marriage. We needed it when we wanted to pay off debt and lay the foundation for growing our net worth. And I recommend one for anyone just starting out — to get a handle on their finances.
  • During this time it got progressively less detailed as we got a better and better handle on our finances (especially spending). I started by updating it every month, then it was every quarter, and then twice a year.
  • Eventually we just went to an annual estimate (which we always met because we had established our lifestyle and didn’t deviate much from it.)
  • But even then, we still tracked everything in Quicken. So we knew down to the penny what we were spending and where.
  • When I decided to retire, I created a budget and reviewed/managed it for a year or so. I developed it using all the data I had from Quicken, then adjusted it for various changes we wanted to make in retirement (more travel costs, no “costs” for saving, etc.) Once we lived it that first year, I knew we were good, so I stopped creating an annual budget (though we still track everything to this day.)
  • If you have been tracking your finances like we did and/or if you have been living on a budget in the years prior to retirement, you shouldn’t have any problem setting up a retirement budget. That’s why I recommend you begin tracking your money five years out from retirement (if you haven’t been doing so) if you can or at least two years out at a minimum. Otherwise you’re going to create a budget that might not be even close to accurate.

No one wants to run out of money in retirement, so this is a very important part of creating a successful retirement.

Now we move to a very common retirement “problem.”

Moving from Saving to Spending

Christine shares this next:

Transitioning to spending from your portfolio after a lifetime of saving can be psychologically difficult. Start the process by steering new investment contributions to cash in the two to three years leading up to retirement.

My thoughts:

  • This is a HUGE issue — even for people who have way more than enough resources. We talk about it often in the Millionaire Money Mentors forums (where everyone gets a lot of encouragement to spend on things that bring them joy.)
  • It’s an issue because no one becomes wealthy and is able to retire comfortably (and especially retire early) without having been good at saving. It’s just not mathematically possible. So you have a habit (keeping spending in check) that has been developed over decades that now needs to be relaxed at least a bit (if not more). It’s difficult to reverse those tendencies after all that time.
  • In addition, you have a hard time even thinking what you might spend extra money on. That’s because most people who are successful financially have become content with what they have. Which leads me to this point…
  • While encouraging others or ourselves to spend more in retirement, we shouldn’t make the false assumption that all additional spending will make you happier. It could, in fact, make you less happy. It’s common in America for people to try and buy happiness by spending more — on everything from technology to trips to designer clothes to new, fancy clothes. But we’ve seen again and again that this never fills whatever void the person has in their life…and it just makes them broke. So if some spending doesn’t make you happier, why do it?
  • My best example of this is getting a new car. I could easily afford one and sometimes it seems like a great idea, but in the end I think it would make my life worse. It might not be as comfortable as my current car. I certainly would worry more about nicks and dings on the paint by other cars — and now I couldn’t care less. And would it have the room and style I like? I’m not sure if I could even find something close to what I have. So why buy a new car if it makes life worse?
  • Those who retire with less than a boatload of money have other worries — about running out of funds. This is why you see them working “just one more year” (which often turns into 3+ more years). They want to be extra careful with spending to avoid draining their savings too quickly.
  • There are two things that help cushion the blow and make the transition from saver to spender easier: cash and income.
  • Cash makes it better because you’re not spending your investments…those are left to grow, so people feel like they are still making financial progress. That’s why many suggest retiring with 2-3 years of spending in cash (as well as being a buffer for sequence of returns risk). Even today, we keep a few years in cash as a cushion should we ever need it.
  • Income is great because it’s a renewable resource (compared to spending out of your assets). You spend knowing that you’ll be earning more in the future. This is yet another great reason for a part-time job or side hustle in retirement.
  • I’m not sure there’s a great way to get past this issue other than to try and make higher and higher spending commitments (assuming you can afford them), basically walking yourself up the spending ladder as you learn to flex that muscle a bit.

And now to one of my favorite topics…haha.

Working in Retirement

Here’s how Christine ends her summary of this chapter:

Paid work can bring relationships and purpose, but so can pursuing a passion project like the charity that Fritz and his wife started. If you don’t need to continue working for money, brainstorm about what other activities can replace the things you enjoyed the most about your job.

My take:

  • I’ve said a lot about the benefits of work or work-like (volunteering) activities in retirement. If you’re interested in my thoughts, read The Top Seven Retirement Activities, Part 3.
  • Both jobs (either part-time or side hustles) and volunteering opportunities can be tried out prior to retirement so you know what you want to take with you into retirement.

Lots of great stuff from this book again today!

For the next post in this series, see Strong Relationships Make a Successful Retirement.

——————————————

As I said above, I’m giving away a copy of How to Retire on every post I do about the book. Here’s how to you can enter:

  • Leave a comment below telling me what you liked best about this post, what you think you can use, or something you learned from it. Basically just share anything meaningful related to the content above (note: “please enter me to win” and similar comments will not be considered out of pure weakness! At least put a bit of effort into it!) This should be fun!
  • Be sure to leave your email address when you leave the comment so I will know how to reach you if you win (the email address will not be visible to anyone other than me).
  • The winners will be selected by me at random a few days after this post goes live. I’ll announce who wins in my own comment.
  • I’ll email the winner, get their address, and send them a book from Amazon.

As with most giveaways, there are rules. Here they are.

Good luck!!!!

Filed Under: Books, Retirement

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Comments

  1. BERND G DOSS says

    April 16, 2026 at 4:02 am

    This segment awakened some aspects of planning that was not considered when I entered the final days of my previous working life. Although I considered moves to various parts of my current State, I did not investigate thouroghly many of the cities and this created issues that I am still facing today. Primarily issues with health care availability created the largest concerns. Looking forward isn’t always easy.

    Reply
    • Scott says

      April 16, 2026 at 9:53 am

      Sometimes if you have talents or resources continuing to work in some capacity allows you to comtribute to things of value to you. I wish my taxes could go to things I favor rather than those decided by a bribed politician. Retirement is often thought of as living to a certain standard until you die. Most don’t need much and self indulgence isn’t necessary to add happiness. Making the world a better place for those who follow, is a great goal.

      Reply
  2. CinRedMan says

    April 16, 2026 at 5:49 am

    Wow, this post touches on so many “fallacies”, especially in retirement; trying to buy happiness, relocating or buying that “dream home”, spending after spending a substantial portion of your life SAVING.

    My GF and I have had many discussions on all these fronts. Especially the topic of buy v rent(we currently rent a home and our property owner is FANTASTIC).

    For me, being around friends/family and the support structure, such as doctors and healthcare is such an important aspect of longevity. In a time of need, having more than one person you can call is so reassuring. Because, as we age, life has a way of throwing wrenches into the well oiled machine.

    Reply
  3. BSue says

    April 16, 2026 at 6:19 am

    With one son in LA and the other in Stockholm, I rather doubt we will be moving in retirement, but who knows? Having a major volunteer role has been perfect for my segue into retirement, and my husband still works half-time as a lawyer because he has fewer hobbies or interests. Of course, he says he hasn’t fully retired because I won’t let him just sit in front of the tv or his Kindle. We are in our early 70s and may live to our nineties based on our parents. That means there is no need to lie down and grab a lily yet.

    Reply
  4. Elkay says

    April 16, 2026 at 8:04 am

    I’ve been thinking about buying Christine’s book, and am enjoying your summaries and analyses.

    I especially liked your wise words about moving in retirement and have put it in my “Retirement Moving” folder for my husband to read when he has time (since he’s still working a little, he doesn’t even like the word “retirement”). We talk a lot about moving (he actually said, “I don’t want to die *in name of town we’ve lived for 25 years*”) but are very stuck about exactly where to go, for a lot of the reasons you mention, with the added issue of we don’t have kids to draw us somewhere, like so many of our friends do.

    I honestly think the biggest issue is that a couple is two people with undeniably different dreams and expectations for their third act. Friends say to compromise, which of course we are used to doing as a couple, but at this later phase of life, I can tell we both feel a little like “this is my last chance to get what I want.” Now, if only we could pin down those “wants” a little better!

    Reply
  5. M169 says

    April 16, 2026 at 9:45 am

    Having retired with more than enough, I am still straggling with the spending part. Over the years I learned to appreciate and enjoy what I have (and I think I have a lot), and I rarely lust after something I see others having. I have no problem replacing things when they wear out or become obsolete, such as laptops or cell phones, but when it comes to upgrades, the frugal side of me usually wins. My car is a 2003 model, most of my furniture was purchased last century, I still use stereo components bought during college years. I can spend hours and hours researching and comparing items that are not so expensive because I am yearning for best value.

    Reply
  6. Pete says

    April 16, 2026 at 12:10 pm

    Your experience and recommendations about moving in retirement really resonated with me as we are in a similar situation that you experienced over the past few years. We currently reside in a 55+ community and it doesn’t really fit with what we thought when we first bought. Additionally, we want to be closer to our kids who live on the other side of the country. We are in the process, as you have mentioned you went through, of identifying new areas that may fit our desired next living location. However, it is hard as we are not in a position to try it out for 6 months. We have decided that if we are able to sell our current home, we would probably rent for a year in order to try out a new location. We haven’t really built much community in our current location so not too worried about that aspect. Good to know that others have run into similar situations as we sometimes feel like we failed to do our research prior to moving to our current location. However, as you implied, sometimes it just doesn’t work out and we need to be flexible in adapting to what will make us happy.

    Reply
  7. Phillip says

    April 16, 2026 at 3:42 pm

    The section I like most is about moving in retirement. Real world examples from those who have been there and done that like ESI are more useful and credible than generic advice. Although our situation is different and we are considering a temporary move overseas to be close to my in-laws, the thoughts on living through multiple seasons before taking the plunge and keeping your home base if you can afford it (we can) were a couple of things that I didn’t think of very much. There are probably many other things I should consider and Christine’s book reads like a great resource.

    Reply
  8. Mick says

    April 17, 2026 at 4:33 am

    Very wise advice on relocating in retirement. I appreciate your candor and sharing lessons learned from your experience. The advice of staying in the prospective location for 6 months is a good one and seems long, but I think it helps get past the euphoria phase and shows what real life would look like especially across weather seasons. Being closer to family is definitely a key consideration. Our kids are dispersed across the country and are building careers. I don’t think they’ll stay in their locations long term so that definitely drives our decisions on relocation locations. Right now we are staying put (no sudden moves!) and enjoying more travel in this early phase of our retirement.

    Reply
  9. K D says

    April 17, 2026 at 5:45 am

    I like your coverage of life in The Villages. We must be cut from similar cloth. I am not good at the always on vacation lifestyle/mindset.

    Thank you to for covering saving to spending. We are approaching retirement and I suspect it will be a big issue for us.

    Reply
  10. Nick says

    April 18, 2026 at 2:20 am

    I agree that it has been difficult to switch from saving to spending. So I decided to take money out of my pre-tax savings for the first time (in my third year of retirement) and drop it on something I wanted but didn’t need. Our second new car and first in 20 years. It hasn’t made my life worse.

    My 2006 Honda has 251,000 miles and is starting to have issues. Now we have a 2026 Honda hybrid that I have already driven across the country. No payments, higher income tax bill. This was a useful exercise in spending and showed me what I might have to deal with in the 2040s with future RMDs and potential IRMAA costs.

    Now I am planning to take annual distributions from my 401k and put it in a brokerage account for flexible post-tax growth and for some international travel for the whole family. From a total net worth perspective this doesn’t make sense but we get a lot of pleasure from taking our family to far-flung places. In fact, we are currently at an airport making our way home from Bali. After the long flights over the Pacific in cramped seating we might even consider better seats in the future…but only if we can get a deal on the upgrade.

    Reply
    • Thalia Lima says

      April 26, 2026 at 6:37 am

      That’s contradictorand a little ironic “long ✈️, cramped seating, consider better seats ONLY if we get a Deal on and upgrade😁

      Reply
  11. ESI says

    April 18, 2026 at 5:37 am

    This giveaway is over and the winner is Phillip. (I’ll be emailing you!)

    Reply
  12. Nancy says

    April 18, 2026 at 6:28 am

    I’m planning on retiring within the next year and have thought about what I will do with my free time but haven’t put anything down on paper. Just thinking about not having the stress of a daily job seems enough for now and I don’t have a problem filling up my spare time on days off. But I can see how more planning could be helpful especially since my husband, who is already retired, is a couch potato!

    Reply
  13. Ann Baldwin says

    April 18, 2026 at 12:36 pm

    I loved your comment that your wife had “had It with winter”. I considered weather an important factor in planning my retirement. I liked four seasons, but without the drama of snow/ice and scorching hot summers!! So I moved from N. California coast to mountains of NC. Works fine!!
    Please enter me in the drawing for a copy of the book.

    Reply
  14. James Hahn says

    April 19, 2026 at 12:48 pm

    This is a great and very personal article on retirement. I have determined to retire to Palm Springs, a move from the SF Bay Area. I had an investment property in San Francisco which I recently sold in a 1031 exchange to two investment properties in PS. They have to be rented out for two years before I can move into one of them. I have spent a lot of time in PS over the last 10 years or so and have more friends there than I do in the SF area. Most of those friends are people I knew here, but moved there over time. I have not spent time in PS during the summer but am assured that you adapt and learn how to cope with temperatures of 120 or more. Because the PS area is 50% plus retirees where is more to do and more times (other than nights and weekends) in which to do it. If I do need a heat break, there are multiple places in the world where I can spend two to three months living like a king for just SS or less, Bali, Indonesia being a great choice. It’s a place where with just my SS, I can rent a two bedroom villa near the beach, hire a cook, maid, driver and still have plenty left over.
    In PS there is a quilt shop where I hope to get a part time job. It’s not for the money, but a opportunity to share my expertise, get an employee discount and soak up some time.

    Reply
  15. James Hahn says

    April 19, 2026 at 1:05 pm

    This is more of a request. Have you considered writing an article comparing a “savings” approach to retirement versus a “cash flow” approach?
    I’ve studied retirement for the last 10-15 years and I find the latter approach a much more practical way to think about it. My basic advice to friends regarding retirement (financial) planning, is to create the most accurate budget you can, including an emergency fund, subtract your social security from that and then come up with a consistent source of income to cover the difference.
    In my case, SS plus income from investment properties is enough to keep my retirement accounts reserved for emergencies and fun.

    Reply
    • ESI says

      April 19, 2026 at 4:28 pm

      I’ve mentioned it several times in posts (that I prefer income over withdrawal) and I have a retirement email series that compares the two: https://esimoney.com/email-series/

      Reply

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