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:
- How to Retire
- Planning for Retirement
- Strong Relationships Make a Successful Retirement
- Activities, Meaning, and Mental Health in Retirement
- Thoughts on Social Security
- Everything You Want to Know About Retirement Spending
You may want to check these out if you missed them.
Today we’re covering two chapters as there’s just a bit I want to share from each one.
The first is chapter 6 where Christine talks with Jonathan Guyton, a retirement researcher and financial planner who has developed the “guardrails” retirement spending system. Much of their conversation is about setting a retirement withdrawal rate, a topic that also gets lots of conversation in the Millionaire Money Mentors forums.
Determining Your Retirement Spending
The conversation begins with Christine asking the following:
What’s the starting point when creating a retirement spending plan?
Here’s Jonathan’s response:
A critical starting point is to know how much you need and want to spend regularly. You cannot have confidence in a retirement spending plan unless you have confidence in the core spending amount that you want to sustain over the rest of your life.
There are three ways to do it. First, you could use software to track what you spend and categorize it. Second, you could use a good old simple budgeting spreadsheet divided into categories.
If you really don’t like those first two, the third way works really well: Get ahold of your last six- to 12-months’ worth of checking account statements. Note what the balance was at the beginning. Add up all of the monthly withdrawals and then note what your balance was at the end. The difference is exactly what you spent.
Then go back and look at those line items to see if there were any unusual ones in there — things that normally wouldn’t be there. This is the biggest reason why we find that people who’ve done a good job of saving vastly understate their spending power in retirement: They assume that the spending they want to do in the next year needs to be repeated at that level every single year for the rest of their lives. But that isn’t necessarily true, because in the next 12 months there might be a child’s wedding or a home improvement or some bucket list travel. Even though you might spend at that level for the next ten to Is years, you are not going to spend at that level for the next 30.
You really want to identify the total of the expenses that are going to be there every single year for the rest of your lives. That’s the basic spending number to work from.
Lots to say here:
- I highly, highly, highly recommend that you begin tracking your spending at least three years before retirement. Five years is even better. If you can’t do this for some reason, please do at least two years. This will give you the best feel for what you’re spending pre-retirement (which will give the best estimate of what you’ll spend post-retirement.)
- This is important because knowing what you want/plan to spend in retirement is foundational to creating a solid retirement financial plan. Do you want to guess at something that’s vital to your success? I think not…which is why you want real-life data.
- Once you have 2-3 years of spending information, create a mock retirement budget using this data. Add and subtract spending that needs to be adjusted for your new lifestyle. For example, you can probably cut “saving” in retirement as you’re past that point and are moving towards spending. You can also cut work-related costs like clothing, transportation, and meals. You might need to add health insurance, travel, and leisure expenses.
- Project the budget five years out (take the initial budget for year one, adjust for inflation, and use this as the base for years 2-5.) Then adjust categories up or down if you have reasons to (like a big cruise every other year). Also add in one-time, major expenses like college, weddings, and auto purchases.
- Now you have a five year spending plan that you can use to determine your withdrawal rate as well as compare to actual spending. You can make adjustments along the way (to either the budget or actual) as you need/want to.
The rest of the chapter covers other spending topics including withdrawal rate strategies, which you can dive into if you get the book.
Income in Retirement
I’d like to share and comment on two of Christine’s takeaways from the discussion, both dealing with retirement income, starting with this:
The more you have in non-portfolio income sources like Social Security, the easier it will be to adjust your spending in line with how the market has behaved. I loved Jonathan’s point about having a pot for discretionary spending categories — especially travel, which is likely to be heaviest in the first half of retirement and apt to wane as you age. Having a pot provides a lot of flexibility about when to spend.
I’m going to adjust that first sentence to this: The more you have in income, the easier retirement finances are. This is why I’ve harped (through the years) on income being greater than savings in retirement…it just makes everything better.
If you have sources of income like Social Security, a side hustle, dividend income (on index funds or dividend stocks), real estate income, a part-time job, and the like, you have more wiggle room in case things turn bad, you don’t need as much savings, you have greater flexibility, and so on. Income just makes life better. I’m a big fan.
There are lots of discussions about spending being higher at the start (and the end) of retirement, so spending more early on (as long as you don’t go crazy) seems like a decent plan for most people. Then you “catch up” in those middle years where you don’t spend as much.
Christine next comments on income-focused investment plans:
Investment strategies that focus on current income can either lead to underspending or portfolios that are inadequately diversified. Instead, build a portfolio for total return and stay opportunistic about where you go for cash flows on a year-to-year basis. When yields are higher, you may be able to get the cash flow you need from spending income distributions. When yields are lower, you’ll need to rely more on trimming appreciated securities. Your portfolio won’t know the difference!
I don’t think you should focus primarily on income, just to be clear. I have most of my investments in index funds, then set aside some for dividend stocks and real estate (plus I have two decent side hustles at this point — which bring me challenges (in a good way — they keep me sharp mentally), enjoyment, a sense of purpose (helping people), and a decent income (especially for the time invested.) At this point I have no bonds, though I do keep three years of expenses in cash.
More Spending Encouragement
Now we move to chapter 7 where Christine talks with Ramit Sethi, financial author, podcaster, YouTuber, etc. He’s best known for his for his website and book both titled I Will Teach You to be Rich.
Ramit has always had a unique perspective on spending and has some interesting thoughts to share here. These pertain to non-retirees as much as retirees, so there’s something here for everyone.
We’ll begin with this:
A little technique I would suggest is to create something I call a worry-free number. When we were in our 20s, we’d go to the grocery store and a pack of gum was a dollar. “Okay, I’ll throw it in the cart. No big deal. It’s not going to change my life in any way. I’m not going to worry about that expense.”
But as we make more money, we forget to adjust our worry-free number. So I want everybody to create a new worry-free number. It might be $5. It might be $50. It could be $5,000. But now you have a new number, and anytime you’re making a purchase below that number, you simply don’t worry about it.
You and your partner can actually have a really dynamic conversation about what your worry-free number is. Do you need to be debating, discussing, agonizing over a $50 grocery store purchase? Probably not. So let’s make a rule. Let’s do it jointly, and then let’s try it out for a month and, if we find the number is right, never worry about that stuff anymore.
We always had “personal accounts” back in the day when we were more closely managing our finances. These were budgeted accounts where each of us had money we could spend on anything we wanted without the need to discuss it with the other person. I would always spend mine on books…my wife almost always never spent all of hers. Hahaha.
As far as talking with each other about purchases, it would depend on what the purchase was. The more one of us had expertise or control of an area, the more leeway we each had. Outside of that, we probably wouldn’t have spent more than $100 (maybe $50 even) without talking it over with the other one. We never had a hard and fast number…and didn’t really need one since we were both generally frugal.
That was back in the day…when $50 was worth something. These days I’ll spend a few hundred up to $1k without talking to my wife. She is still pinching pennies (she’s a spending work in progress) so she hardly spends anything (at least on herself — she’ll drop $200 to $300 on every trip to Costco.)
Next Ramit shares this:
Money is, starting at age 40, the number one thing that people worry about.
Yet if you talk to the average person, they have never read a single book about personal finance. Not one. How can we get to retirement age and not understand the thing that we worry about and agonize over every day? The first thing I would say is, it’s important to get educated. There are so many resources!
This is so true!
I think we can all agree that money has a pretty big impact on everyone’s lives.
After all, it is used to secure food, clothing, and shelter to survive plus provide any extras that can make life easier and more enjoyable.
And the downside of mismanaging money is huge. It could be homelessness, hunger, and even death. Or it could simply be a miserable life (which is pretty bad in and of itself.)
So…it’s pretty important.
But how much time and effort does the average American give toward educating themselves on even the basics of how to handle money? Sheesh, if people spent as much time studying money (over their lifetimes) as they spend on one season of Breaking Bad, watching football, or similar activities, we’d be much better off financially.
I searched but couldn’t find any accurate information on how much time people spend on educating themselves on personal finance. But it can’t be much based on the disastrous financial situations of average Americans (low savings rates, high debt levels, low net worths, rampant consumerism, etc.) And when I did find something close (where people reported what they did — which often differs from reality), the #1 place they said they educated themselves on money management is family and friends. Hahahaha. Like those people know what they are doing.
If someone would spend five minutes a day listening to a financial podcast, watching YouTube videos, reading a money book, etc., that would be 30 hours a year! That’s enough time to get a pretty good money education in just a couple years.
But how many do even that? Hardly any.
What they do instead is muddle through life, maybe seeking financial help when they have an emergency, but when that’s over, they move on with their lives.
I saw this back when we were coaching people and have seen it for 20+ years blogging. These days I see it all the time on Reddit — where I stop by and try to share wisdom with the crowd. People there are completely clueless of how to manage money and must resort to asking strangers on the internet (with dubious money management skills themselves) about what to do with their lives!
Most of these people (IMO) need to take responsibility and educate themselves about money management so they can make good decisions on their own.
This is so common that I’ve developed a standard Reddit reply which I copy and paste fairly often. It reads:
You need to educate yourself about how to manage money. You have a long life ahead of you so you’ll consistently have questions about what to do unless you learn the specifics yourself.
Start with a beginner book like Personal Finance for Dummies or the Total Money Makeover. Then read The Simple Path to Wealth, which will teach you about investing.
That said, the general steps to becoming wealthy are:
1. Earn as much as you can. This is generally through a career but can be a business (though it’s often riskier and takes longer to grow).
2. Save as much as you can from your earnings. Keep expenses low/reasonable.
3. Invest those savings in low cost index funds.
Hahaha. I am likely laboring in vain, but at least I’m trying to help!
Having Trouble Spending
Ramit shares this next:
I spoke to a couple who are part of the Financial Independence, Retire Early (FIRE) community. By age 50 they retired with $4.3 million. They’re very accomplished. But they struggle to spend money. They agonize over it. I shared this story on my podcast because many of us cover our financial anxieties by telling ourselves, “If I just had $10,000 more, or $50,000 more, or I retired, then I would be comfortable. I would feel good.” I routinely feature multi-millionaire couples who can’t shake their feelings of guilt and overwhelming anxiety. Many of them still drive five miles to save ten cents on gas.
That’s not a rich life. It can’t be a rich life if your entire focus is on how not to spend money instead of how to use your money to create meaning.
I think I know the people he’s talking about. They are great folks and are highly educated on money matters.
And yet, they have trouble spending what they have saved. And I can tell you, they are not alone.
I would say the majority of retired millionaires have issues spending money. They have built a fortune on being frugal (at least relative to income) and that habit is hard to kick. That’s why one of the most popular topics in the Millionaire Money Mentors forums is the “Let’s Spend Some Money” thread where we encourage and celebrate people spending money on things that improve their lives.
A few other comments on this before we move on:
- “Feeling of guilt and overwhelming anxiety.” I’ve never had feelings of guilt for having or spending money (I have felt bad after a terrible purchase, but not guilty). I only had money anxiety for the first week of retirement. It was really just fear of the unknown. Once I realized the world wasn’t going to collapse and the police weren’t coming to get me (because it felt like I was getting away with a crime by not going to work), my fear turned to joy and I haven’t looked back!
- This said, many people struggle with having enough (thinking they need more). It is very common for the answer to “how much is enough?” to be “just a bit more.” It doesn’t matter how much you have. Those with $2 million want $3 million, those with $5 million want $6 million, those with $10 million want $11 million, and on and on…there seems to be no limit where this stops. People think security is “just a bit more”, but once they get to that point, they raise the bar.
- “Many of them still drive five miles to save ten cents on gas.” Hahaha. We don’t do this, but my wife (in particular) does have a hard time NOT saving money, even if it’s inconvenient or requires additional expense elsewhere (like the cost of driving). But she’s working on it. lol
- “How to use your money to create meaning.” This is key. You want to spend in a way that makes something better — your life or someone else’s. Many times there’s a push from the “spend, spend, spend” crowd that seems to suggest that spending on anything is good, productive, and makes life better. This is not true. I could name a hundred things I could spend money on that would make my life worse. So the spending needs to create meaning…you can’t just spend for spendings sake and expect to be better off.
- What is meaningful is different for each person, so spending should be different from person to person. Some project what is meaningful to them on others, saying they should spend on this or that, but the spending has to have meaning for the individual. If it doesn’t, it’s worthless at best or at worst makes life less enjoyable.
- At this point in life, I don’t have a lot of spending that creates meaning relative to our income or wealth. I buy what I want and yet there’s plenty left over — which means I worked too long and should have retired much earlier, but that ship has sailed. What does create meaning for us is giving, so that’s our biggest “expense” these days by far.
Moving the conversation along, Christine then suggests this:
It sounds like you think people should practice spending, and spending on what gives them joy, well before retirement.
To which Ramit responds:
The years between age 40 and 60 are prime spending years.
Before 40, most people don’t have any money. After 60, many people have health issues that arise, whether with themselves or their family members.
If you haven’t started spending your money meaningfully before 60, it doesn’t mean it’s too late. But the message that I want to emphasize is that today is our best day. It’s our best day of health. It’s our best day of time. It’s our best day of relationships with the people around us. Tomorrow, it becomes just a little harder, and there’s a ticking clock.
Some thoughts:
- I should have spent more while working on financial independence. In particular, I wish we had started taking cruises as a family earlier. That’s the main spending thing we missed along the way. There’s not much else I would have wanted to spend on, but that’s a big one.
- “Today is our best day. It’s our best day of health. Tomorrow, it becomes just a little harder, and there’s a ticking clock.” This is a reason to retire asap. We have a few threads at the Millionaire Money Mentors that deal with this topic. Some share stories of people who put off retiring when they have more than enough (one more year syndrome is a real thing) only to have some unfortunate event happen (they pass away, their spouse passes, etc.), others tell of people suddenly passing away in their 40’s, 50’s, or early 60’s, and others recount lost hobbies and activities that people can no longer enjoy. Just remember that tomorrow is not guaranteed and anything you’re committing to today is the biggest cost time/life-wise that you’ll make for the rest of your life.
Thought-provoking stuff, huh?
To read the next post in this series, see Retirement Income, Asset Allocation, and Index Funds.
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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 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!!!!

ESI, another fine review of her book!
Yes, many of us retired folks worked too long and suck at spending once we do start Chapter 2.
We spend way more on taxes and giving than we ever have, at age 67. We will not expend our funds even if we try hard. A lifetime flow of income monthly that exceeds spending….well, we planned our retirement very well a few years before retiring at 57. 10 years later, our portfolio has grown and we have spent about $300,000 of it!
We find it easier to give to charities than our own children. I need to read up on this. It is not right in my mind. I will only spend money that I have earned. That will leave our children plenty when I return to dust.
Spending funds is hard when you grow up frugally and marry a frugal person as well. Good luck folks. I am just happy that I have a large amount of retirees that share my issues! ha.
Blessings to all from MO, Steve
Steve, some parents give a portion to children now when they are more likely to need and enjoy it rather than after we are dead and gone. People are living longer now! Education and travel seem like good venues for what I call Early Inheritance.
The sentence that today is your best day of health and relationships really hits me. I need to put that on a post it for the bathroom mirror!
My parents who had Depression era frugality had more money than they ever dreamed and were generous in funding their children’s and grandchildren’s educations and investments but little else. I noted that they enjoyed their money as much as they could stand. They were looking for sales and discounts all the way to pre-planning at the funeral home. I hope to enjoy my wealth a bit more and am already 8 years into retirement.
Our impulse spending limit is pretty low, probably around fifty dollars. Above that and we generally let each other know what we are doing. Its not getting permission, just communicating. I can’t imagine bumping that up to $500 or $5,000. Then again we rarely even spend the fifty, at our station of life we already own everything we desire and mostly are just buying replacement gear for things that wear out, like tennis shoes, tennis strings, tennis balls, fishing baits, sportswear, etc.
I am one year into retirement and have maintained ties with my previous job(which I do not hate) and still work on a casual on call type of basis. So I am following the advice of keeping the side hustle. I also feel pretty comfortable that I good spending plan in place and enough saved to cover future spending needs. Trouble is, any surprise expense or breakdown I feel the urge to cover by picking up more hours. I need to look into more of Ramits teaching and read the book you are reviewing to learn to relax more!!
Enjoyed the book and your follow-up analysis. All your comments really hit home, especially in regards to how many people in my circle of relatives have such limited knowledge of personal finance. Even more baffling to me, most have absolutely no desire to learn how to earn, save and invest for their future.
I love having my freedom since retiring from a stressful corporate job 4+ years ago. Despite having a higher net worth now than when I stopped receiving W2 income, I really enjoy spending more time reading and educating myself on these topics.
This sounds like a great book based on this and the previous posts. I can very much relate to the idea of “just a bit more” is needed to be enough. At some point, you have accept that you have enough.
Chapter 7 sounds like an important part of the discussion that isn’t always discussed in retirement planning. How to shift from accumulating savings to drawdown and spending, especially in the early years of retirement.
Who knew spending money could be so hard? It’s a taboo topic with my friends, who usually hit me with a sarcastic “poor you” when I bring it up. I need to expand my friend circle.
But after my Fidelity advisor told me my main problem is not spending enough—and online tools proved I’ll have millions left over even if I live to 95—I decided to take baby steps. I’m starting small, buying things I normally wouldn’t. My wife has already reaped the benefits; she gets a dozen roses every week or two now instead of just a few times a year. There’s hope for us tightwads yet! I should mention that for the past 5 years we have traveled to Europe every summer and take another 3-5 trips every year. Now if I could just breakdown and fly first class….not sure that will every happen.
Jim, ease into it by flying Business Class to Europe. You will feel so much better when you land you’ll probably get hooked. It’s a Gateway Drug to First Class…
The comments on ‘how much is enough’ and ‘just a little bit more’ stuck with me. I’m really struggling from moving from a saving-mentality to ‘can I spend a little and enjoy life’. I was always a saver but not overly frugal throughout my career, but never made an extravagant purchase. Now I’m struggling to spend $175-200K cash on a sports car I’ve dreamed of for most of my life. Ironically, I’m also concerned if I don’t buy it soon I may miss the opportunity to enjoy it.
As background: I (59) retired two years ago and believe we have enough saved $6M+ in the market, $1M in real estate investments, plus cash and paid off home; all totaling well over $9M. Additionally, our income stream is more than our expenses; spouse (53) still works, mainly for insurance and she likes it, plus I have a small DCP for next 9 years and RE income stream.
Side note, I checked out ‘Millionaire Money Mentors’ and was disappointed to see it closed to new members.
If you want to join, email me and I’ll let you in at the last sales price available.
I feel very similar to that couple that can’t spend. It’s difficult to break a 20+ year habit that has proven to be wildly successful.
Also, our inability to forecast our failing physical self hits hard. My mother is in her 70’s and her body is falling apart. A stoke, heart attack, extreme fatigue, decreasing eyesight… but she thinks it will get better. “I can’t wait until I’m back to normal,” she says. She sounds like a crazy person, but admiringly, I feel the same way. I’m healthy, I work out, my body will last forever.
Hard to bring something you’ve never known into your mindset.
Thanks for continuing this great series!
As I fine tune my bucket approach as retirement nears (5/31/26), your comment was very helpful: “At this point I have no bonds, though I do keep three years of expenses in cash.”
To supplement my pension until social security kicks in, I am using my traditional IRA as a retirement bridge account. It is 25% in cash, 40% in VWIAX (which is 60% bonds and 40% stock) and 25% in VTI (total market index).
I’m thinking of dialing down the bonds and increasing the cash, especially since my pension really functions like a bond. I’ll take suggestions any one has to offer on this portfolio composition.
I meant 50% in VWIAX!
This giveaway is over and the winner is Steve. (I’ll be emailing you!)
So many good comments. . I recently came across the concept of figuring out an am’oint I can depend which will have zero impact on our finances. I don’t recall the formula but our # came out to around $1300. It was likely similar to the .01% rule but there was more math to it. This idea has really given me a little peace – I, like many others have saved since I was a kid raised in a very poor home. Now I don’t think about the $100 for dinner out, don’t care really if I spend $300 at Costco.
I am more comfortable with my number being around $500 if it’s not in the budget.
Can’t really verbalise how impactful this has been. Has anyone else who struggles to spend tried this ?