Investing, Parents, Estate Planning, and Purpose in Retirement

Today we’re going to continue sharing thoughts from the book How to Retire by Christine Benz.

It’s a great book which I highly recommend. 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 posted on this book as follows:

You may want to check these out if you missed them.

Today we’re going to cover the final four chapters from the book! Can you believe it’s come to an end? lol

Investing for Women

Chapter 17 is an interview with Jean Chatzky and the discussion is about how women’s retirement needs differ from men’s.

I won’t get too deep into this chapter as it’s fairly general, but I will share this:

When it comes to investing, some women are more security-oriented than men, which can lead them to build portfolios that are too conservative given their life expectancies. While stocks can endure steep losses over short time periods, over longer time frames they’ve been extraordinarily reliable. And with longer life expectancies, women need their growth potential and insulation against inflation even more than men do.

Need I say that once again the answer is index funds? Hahaha.

Talking Finances with Parents

Chapter 18 is an interview with Cameron Huddleston who has an excellent book (“Mom and Dad, We Need to Talk”) about financial conversations you need to have with your parents (and your kids).

This chapter is very informative and makes it worth getting the book for this chapter alone. Cameron’s book is also worth picking up (for even more details).

Here’s a great overview of the kinds of topics it addresses. Christine asks for best practices for how people should communicate with their children about their financial matters. Cameron responds as follows:

It is so important to share information about your finances, your estate plan, and your final wishes with your children. If you care about who manages your finances if you become unable to do so yourself, if you care about who gets what when you die, if you care about what happens to your body when you die, you need to make it known. Don’t count on your family members to know what you want unless you tell them. Even if you think you have a very simple financial situation, it’s still going to be complicated for your family if they don’t have any information.

If they’re getting involved because there’s some sort of emergency — because you’re sick or because you have passed away — they’re going to be stressed out enough. Having to play detective is that much harder when they’re coping with those emotions from your illness or from your death. I know people are reluctant to share information about their finances, because either they’ve been taught that you don’t talk about money or maybe they’re embarrassed about their finances. Maybe they never realized they needed to have the conversation. Sometimes they don’t like the idea of the role reversal, giving their kids some level of control.

But I really think the best way for you to maintain control over your own finances and your estate is to let your wishes be known. You have no control if you don’t tell your family members what you want. If you need long-term care like my mother did, if you develop dementia, and no one knows how to manage your finances, your family is going to make all those decisions, and they might choose to do things you might not have liked.

If you die without a will, or you don’t have a list of all your assets, and your family is digging through all of your financial details that you didn’t want them to know, they’re going to figure it out, tight? And they might miss something important. All those savings that you worked so hard to accumulate during your life if they can’t figure out where those accounts are, they’re going to get turned over to the state as unclaimed assets. So you need to have a paper trail and realize that you’re not giving up control by having these conversations. You’re maintaining control, and you’re letting people know what you want.

It’s really smart to talk to your kids and give them some information. You can control what information you want to give them. You don’t have to tell them down to the cent how much is in your checking account, how much is in your retirement account, and how much debt you owe. But it’s a good idea to give them a general idea of what your plans are for retirement. Are you planning to rely only on Social Security? Or do you have some savings or a pension?

A few comments here:

First of all, you need to be sure your spouse knows this information. The are so many relationships where one person knows everything and the other knows very little. That has to change…for us all.
We have been working on this issue. My wife knows how to get on my computer and open Quicken. From there, she can see every account we have, so at that point it’s just tracking them down and managing them. She also knows where to find my passwords, so if worse comes to worse and I die tomorrow, she will be able to get access to everything.
In addition, I have three people that are solid money managers — as good as or better than me — who she can call to ask for suggestions on what to do as issues arise, decisions need to be made, etc. (I got these people from the Millionaire Money Mentors forums.)
That said, we need to tighten things up a bit, so she’s not floundering for one second. We need to make sure she knows where it all is as well as has a game plan for what to do with it if I’m gone. That’s on the agenda for 2026…to get that settled.
I’ve already started the process with a clean-up of my passwords and my computer files…keeping only the important stuff and organizing them in a way that’s logical and easy to access. It will probably take me a couple weeks to get this completed.
In addition to making sure my wife is up-to-speed, we need to make sure our daughter knows more details of our finances as well. She has a very high-level view of them but it’s certainly not enough to get very far. As I type this I’m thinking I need to go through Cameron’s book again and make notes on what to share with our daughter. Maybe I’ll do a series and giveaways of that book!

The rest of this chapter digs into the details of what to do for end-of-life planning as well as what to tell your kids. Some of the highlights include:

The documents you need (will, financial and healthcare power of attorney, living will, etc.)
The help you’ll need (executor, trustee, etc.)
What to do/plan for if you don’t have kids (or can’t trust them)
How to organize your financial accounts to make it easier for someone else to manage
How to have a conversation about what’s in your will and why
How to communicate your wishes about your care, life-extending preferences, etc.
How you’d like to be buried as well as any funeral wishes

There’s much more, but these give you a great feel for the contents of this chapter.

There are two other comments worth sharing, starting with this one from Cameron talking about creating lists of accounts, passwords, etc. for others to use:

Have all of that information and keep it updated. I know it seems daunting to sit down and spend hours digging it up. So block an hour in your calendar each day for a week to get it done. Set a reminder once a year to go back and update it, because maybe you’ve changed your passwords, maybe you’ve paid off a credit card, maybe you’ve closed some accounts.

I love the method of “eating an elephant one bite at a time” and that’s just what this is.

It’s a daunting task to get everything in one place — so daunting that many people don’t even start because it seems insurmountable. But if you do a small part here and a small part there, it can be conquered over time.

This is what I’m doing with the items noted above, which is why it will take me a couple weeks to complete.

Christine digs into this topic a bit more with this:

I’m a big fan of creating a master directory — a guide to all of your financial accounts, including account numbers and passwords, people you deal with at each financial institution, and any important guidance you have on those accounts. (For example, “Use this account for ongoing spending,” or “Don’t sell during my lifetime; heirs should receive for tax reasons.”)

Because such a document includes a lot of sensitive information, encrypt a digital file or keep it under lock and key if it’s a physical document. Provide a copy to your trusted loved ones or let them know how to gain access to it if they need to. And keep it up to date!

I need to create something like this and I’m wondering whether it should be digital (which is easier to do but also more prone to being stolen) or hand written (which is harder but also less likely to be taken and used against you — assuming it’s stored in the right place.)

I still need to decide which of these to use.

Estate Planning

Chapter 19 is an interview with Jennifer Rozelle, an estate planning attorney.

This is probably the most-needed chapter in the book — and also the one most likely to be ignored.

A huge chunk of the millionaire interviewees don’t have a will…and unfortunately they are not alone. This from Google:

Fewer than half of Americans have a will, with recent figures from 2024-2025 showing percentages as low as 32% to 46%, depending on the survey, though older data from Gallup suggests closer to 46%. The numbers fluctuate, but most surveys indicate a significant majority (around 60-70%) of U.S. adults lack a will, with rates increasing with age and income, though procrastination and beliefs about not having enough assets are common reasons for delay.

Hey, if you’re ok with the state deciding what to do with your money, where your kids end up, etc., then carry on.

But if not, you need a will!

I’m also preaching to myself as I need a (new) will. I have one (of course) but it’s from Florida. I need a new one in North Carolina.

That’s also on my 2026 to-do list.

The sections they cover in this chapter include:

The basics of estate planning
Specifics of a last will and testament
How to name executors
Deciding who should inherit assets
Tax considerations
Power of attorney issues
Healthcare considerations
Trusts
The process of doing all the above

I’ll share a few highlights from the chapter starting with what Jennifer considers the basic components of an estate plan:

What I consider to be a very basic estate plan is primarily three sets of documents.

First, healthcare. We combine the appointment of a healthcare representative – the healthcare power of attorney — and advanced directive — which includes a living will — into a single document. Sometimes you’ll see a healthcare power of attorney and a living will declaration split out into two documents.

The second set is for financial power of attorney. The idea is to put someone in a position to make legal and financial decisions for us if you’re incapacitated.

The third is a last will and testament, which is going to dictate what happens after you pass away and who’s in charge.

We have all of these.

My mom had all of these as well, and I can tell you the living will was especially helpful when we were making her end-of-life decisions — because we knew her exact wishes.

Jennifer then adds this:

The only caveat I would put on those three sets of documents is that it’s prudent to investigate whether any additional planning through different kinds of trusts is appropriate given someone’s situation. I am not a believer that everyone needs trust planning, but you should at least ask an estate planning attorney whether you need to be looking at any further planning beyond these three areas.

Check. Will do. I have not yet decided whether or not we need a trust.

Here’s one thing that’s especially important…making sure your will and your beneficiary designations match. Jennifer’s thoughts:

If your will says that you want your assets to go to person A, and you list person B as the beneficiary on your retirement accounts or life insurance policies, the beneficiary designation is going to take priority. I’ve worked on many cases where people left ex-spouses as beneficiaries, yet their will says the assets should go to their kids. In those cases the parents inadvertently disinherit their own kids.

You can imagine the many, many mistakes that people have made regarding this. People think they’ve done a good job when they’ve done their estate plans, and they get their will in order, and they’re so excited. I think that’s a failure in the counseling that the estate planning attorney should be providing to those individuals about making sure the beneficiary designations and will sync up.

Christine adds this later:

Jenny’s point that beneficiary designations “trump” other aspects of an estate plan, such as what’s in a will, should be in bold type and underscored because so many people miss this. Your first step if you’re setting aside time for estate planning is to ensure that your current beneficiary designations sync up with your wishes and your current situation. If you go on to create a full-fledged estate plan, make sure that your beneficiary designations reflect that plan.

We’ve all been warned.

Finally there’s this — some things we don’t usually think about:

In addition to the legal documentation that Jenny outlines here, it’s valuable to think about the “softer” aspects of your estate plan. What’s the plan for your pets if something happens to you? Do you want certain individuals to inherit specific items that are meaningful to you, even if those items aren’t called out in your will? What’s your general take on how you hope that your friends and family will memorialize you when you’re gone? The nice thing about this type of estate planning is that it doesn’t entail hours in an attorney’s office. You only need to take some time to document your wishes and share them with your loved ones.

Our cat goes to our daughter and son-in-law. We left them an extra $10k in the will to take care of him.

We don’t have a lot of heirloom items, so we’ll just have our kids decide how to split those up.

To be honest, I really don’t care how I’m buried or memorialized though I suppose many will.

Purpose in Retirement

The last chapter (20) in the book is an interview with Jordan Grumet who discusses having a purpose in retirement (and life).

Here’s a comment that summarizes this chapter:

If you have a big-P purpose in mind for your retirement-something like starting a foundation or taking in foster children, go for it. But a group of little-p purposes is just fine, too-things like being a wonderful partner to your spouse, reading the classics, or starting a dining-out club.

I haven’t found a big-P purpose in retirement but a lot of things add up for me in the little-p purpose.

If you want more discussion on this topic, check out Finding Your Purpose in Life.

And here’s the final comment in this chapter:

It’s never too late to form a vision for what you want your life to be and take steps to get closer to it.

I’d also add that you can 1) have multiple visions/activities that give you purpose and 2) always change courses if you want — you don’t have to be stuck with one vision/purpose for the rest of your life.

In retirement I’ve had several phases/activities that have brought purpose/meaning to my life including:

Blogging/website ownership
Pickleball
Five year giving challenge
Travel (Grand Cayman, Hawaii, The Villages, etc.)

I’m currently in the process of determining what my next major activity might be. I have a few ideas…stay tuned to see what happens!

The Final Words

In the conclusion of the book, Christine makes five general thoughts about the book and what we all should consider doing in retirement. I’ll paraphrase her thoughts and give my take on them as follows:

“Be willing to entertain different perspectives” — There are countless thoughts, opinions, suggestions, etc. on the various topics associated with retirement. Many of them actually conflict with others. Be willing to listen to everything and open to new information. “Listen, ask questions, and stay open to new information.”
“Take your own path” — Retirement is about you, your family, your goals, and so on. “This is not the time to conform to how everyone else approaches retirement, or how your parents did it.” Don’t feel like you have to (or even should) follow some sort of traditional path in retirement. Instead decide for yourself what works best for you and your goals. Just like becoming wealthy, there are many paths to success in retirement (that’s not to say there aren’t some solid basics almost everyone should follow.)
“Forget optimization” — I LOVE this one! If you spend your retirement trying to maximize every dollar/decision and squeeze every penny, you’ll probably drive yourself crazy. “From a financial standpoint, the ‘optimal’ retirement plan is the one that you can stick with and that doesn’t create undue stress.” If you “settle” for “pretty good” in all the decisions/moves you make, you’ll be much better off than trying to make the “best” decision in every case.
“Experiment” — Christine suggests trying out retirement before you actually retire — a sentiment I completely agree with. Some suggestions: “Don’t quit your job; ask your employer if you could just do the parts of it you like. Don’t sell your house and move to Florida; rent a place for a month and make sure you like it first.” (I’d actually suggest several months in the summer on this one — I’ve been burned by Florida. Hahaha.)
“Find the simple pleasures in life” — From Christine: “The older I get, the more I’m convinced that success in life isn’t about ‘big-P’ purpose and bucket lists. It’s about what I think of as ‘micro-joys’ — a walk with a friend to get coffee, a perfect meal on the patio on a summer night, getting lost in a wonderful book.“ A few of mine are: doing the NY Times games with my wife every day, sitting in my recliner with my cat on my lap (listening to Christmas music), and looking out my window and seeing a herd of deer.

Well, that’s it! What a great book, huh? What was your favorite part?

I hope you enjoyed this series and will get a copy of the book for yourself. I’ve just scratched the surface of all this book has to offer so there’s plenty of new stuff even for those who read this entire series.

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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 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!!!!

Comments

BERND G DOSS says

July 2, 2026 at 5:02 am

As I look back on all the articles you have posted regarding this book and the commentary you included, I find many concepts that I have learned from, and still believe in. I think the most important aspect of our retirement life is to live it in a way that you desire and your families are willing to give you the best assistance they can. Thanks for the opportunity to learn more about life in peace through retirement.