The MapleMoney Show » How to Spend Money Wisely » Estate Planning

How to Plan a Regret-Free Life, with Jordan Grumet

Presented by Willful

Welcome to The MapleMoney Show, the podcast that helps Canadians improve their finances to create lasting financial freedom. I’m your host, Tom Drake, the founder of MapleMoney, where I’ve been writing about all things related to personal finance since 2009.

As I get older, I realize just how quickly life moves by. And in the end, I don’t want to leave behind many regrets. But how do you plan a regret-free life? That’s what this week’s episode is all about.

Jordan Grumet was a hospice doctor who discovered the personal finance community through a book called The White Coat Investor. Since then, he left his clinical practice to pursue his passion for deep conversations about money and life.

Today he hosts a podcast called Earn & Invest, and his upcoming book, Taking Stock: A Hospice Doctor’s Advice on Financial Independence, Building Wealth, and Living a Regret-Free Life, comes out on August 2nd, though you can pre-order it on Amazon today. I sat down with Jordan to talk about living for today as you plan for the future.

As a hospice doctor, Jordan encountered many dying patients of all ages. He talked with many of them about their life story, and he asked them about the regrets they had. One thing that always stood out – no one ever said that they regretted not working more, or not achieving the financial goals they set for themselves.

Jordan and I discussed the financial independence movement, often referred to as the FIRE movement. In recent years, several offshoots have developed – Barista FIRE, Coast FIRE, etc., because people are recognizing that they want to use their money for good today and not just save for retirement tomorrow. Jordan views this as a very healthy evolution.

Jordan and I also talk about the concept of time, and how it’s commoditized so often in our western society. We are constantly being shown ways to add time or save it. The truth is that we have no control over time. What we can control is the way we spend the time we have. It’s an intriguing conversation that isn’t as heavy as it sounds. 😉

This episode of The MapleMoney Show is brought to you by Willful: Online Wills Made Easy. Did you know that 57% of Canadian adults don’t have a will? Willful has made it more affordable, convenient, and easy for Canadians to create legal Will and Power of Attorney documents online from the comfort of home.

In less than 20 minutes and for a fraction of the price of visiting a lawyer, you can gain peace of mind knowing you’ve put a plan in place to protect your children, pets, and loved ones in the event of an emergency.

Get started for free at Willful and use promo code MAPLEMONEY to save 15%.

Episode Summary

  • Jordan shares the different regrets of the dying
  • Life regrets can vary depending on age
  • Three paths to financial independence
  • How Jordan used side hustles to reach financial independence more quickly
  • What’s your biggest fear about dying young?
  • A non-confrontational way to talk to your parents about their estate planning
  • Financial legacy documents vs. medical legacy documents
  • How an ICE Binder works
  • We try to buy and sell time, yet we have no control over it
Read transcript

As I get older, I realize just how quickly life moves by and at the end, I don’t want to leave behind a bunch of regrets. But how do you plan a regret-free life? That’s what this episode is all about. Jordan Grumet was a hospice doctor who discovered the personal finance community through a book called, The White Coat Investor. Since then, he’s left his clinical practice to pursue his passion for deep conversations about money and life. Today, he hosts a podcast called, Earn and Invest, and his upcoming book, Taking Stock, A Hospice Doctor’s Advice on Financial Independence, Building Wealth, and Living A Regret-Free Life, comes out on August 2nd. You can preorder it on Amazon today. I sat down with Jordan to talk about living for today as you plan for the future.

Welcome to the Maple Money Show, the podcast that helps Canadians improve their personal finances to create lasting financial freedom. This episode of the Maple Money Show is brought to you by Willful. Did you know that 57 percent of Canadian adults don’t have a will? Willful has made it more affordable, convenient and easy for Canadians to create a legal will and power of attorney documents online from the comfort of home. In less than 20 minutes and for a fraction of the price of visiting a lawyer, you can gain peace of mind knowing you’ve put a plan in place to protect your children, pets and loved ones in the event of an emergency. Get started for free at and use promo code maple money to save 15 percent. Now, let’s chat with Jordan…

Tom: Hi, Jordan. Welcome back to the Maple Money Show.

Jordan: I am so excited to be here and chat with you today.

Tom: You’ve got a new book that just came out called, Taking Stock. This is an interesting take in that you’re a hospice doctor. You kind of see this from a different view than others regarding how people might perceive all this at the end, how they might look back at their planning (or lack of planning) and how they kind of tally it up at the end. Both my parents had passed away and I kind of had a bit of that then—making sure they were properly prepared, last minute. I believe your father died when you were young, right?

Jordan: Yes, he died when I was seven years old.

Tom: Oh, wow. So, as a hospice doctor, what did you see there? Did you actually hear conversations, whether it was you with a patient or maybe just even overhearing conversations? I know in situations like that, relatives might come in and all of a sudden they’re sort of discussing what needs to be done next.

Jordan: Let me give you the background. I had gotten burned out in medicine and discovered financial independence. I kind of did the deep dive into personal finance and enjoyed it so much that I started writing about it, doing a podcast about it, etcetera. And the one thing I realized very quickly is the steps to learn about your finances are fairly straightforward. We can learn how to put money towards retirement. We can learn how to invest—all those types of things. But what I was stumbling on was the why. Once you have money, how does that integrate into your life? What do you do with it? That’s one part of my life. The other part of my life is I’m pulling away from medicine, the parts I don’t like, and I’m sticking with the one thing I do like, which is taking care of the terminally ill and dying—doing hospice work. Doing hospice work, there are many occasions where we talk to patients and families about the patient’s life. You do something called the “life” review. A lot of times part of that life review is talking about people’s regrets. As I was doing this more and more (because I was spending less time practicing general medicine) I was also delving into personal finance with my podcast. I realized the conversations were dovetailing together because when I was talking to the ill and the dying, they were telling me all these things they regret. They were never telling me they regretted that they didn’t work more, right? They didn’t work more nights and weekends. They weren’t regretting that they didn’t get to that big “net worth goal” that was big on their mind which is something people like us in personal finance think a lot about. They were really talking about the experiences, people and “bucket list” items that held importance in their life that they didn’t have the courage to pursue. That’s kind of how I found that these worlds came together. What’s the sense of having money and learning good money management if it doesn’t ultimately get you those things that are important in your life—things that dying people think very much about. That’s how those two worlds came together for me.

Tom: With these conversations did you see a difference between younger or older people. I’m assuming it’s mostly older people just because that’s usually the way things work. But there must be some cases where you had younger people with some kind of terminal illness. Did that change things? Because you kind of hear the YOLO (you only live once), does that change when you’re younger? Where maybe you spent too much time preparing?

Jordan: We definitely see, in hospice, different types of regrets depending on the age of the patient. I’ve definitely dealt with people in their 20s and 30s and 40s dying, and a lot of them regret exactly that. That they didn’t take more time to enjoy themselves and even enjoy their wealth by doing things that were important for them. On the other hand, when you get people in their 70s and 80s, it’s a lot more about relationships and legacy. People are looking back on what relationships didn’t they repair? Have they built their legacy? Do their family members and friends know their story? Have they left something of value to them? That may be monetary or it may be stories, objects, or experiences they want to live on after they’re gone. So, there’s definitely a difference.

Tom: The idea of leaving a story is interesting. When my parents passed away, there’s certain things I never asked them that I would have liked to have known. I just didn’t ask them. So, whether you’re that child wanting to ask something of your older parents or you are that older person wanting to make sure this is prepared, how do you do this? When you say stories, are you talking journal it down or actually just talk to people? What are we looking at?

Jordan: I think there’s several ways to do it. Some people do it exactly like that. They write down the story of their life. They put it into working order as they saw the world so that they can hand it down to their loved ones. And their loved ones can kind of see what viewpoint they had on the world and what was most important to them. That’s one way. But with storytelling, we don’t necessarily have to write things down. Sometimes it is sitting down with those people who are important in your life and telling them the stories of your life. We always figure we have more time, right? We always figure if don’t do it today, we’ll do it tomorrow. Then the days turned into weeks, which turn into months and years and then one day you might find yourself on your deathbed. But had you had those conversations with your children, grandchildren and your loved ones… There are multiple different ways to do it. It’s just being thoughtful about it. And again, kind of thinking about your legacy and what that means.

Tom: One more thing about the idea of talking to some of these people in the hospice situation. You said nobody really is going to say that they regret not working enough. I assume there are cases where someone didn’t prepare enough. Maybe they did work a lot, but they spent it all. Maybe they didn’t work enough and they didn’t have money at the end. Either situation, there’s got to be regret in that way. Maybe they were a little too much on the “you only live once” side or they were working really hard, but in the end still didn’t have the money they needed.

Jordan: I’ve certainly taken care of people who’ve been in dire circumstances. There’s a story in the book where I talk of a patient whose wife was in the nursing home and they spent a lot of their money taking care of her in the nursing home. In fact, he eventually had to get what’s called the Medicaid divorce. He had to get divorced from his wife, not because he wanted to divorce her, but because that would separate their assets so that she could get government support and they didn’t have to spend down all the money he needed to live on. After his wife died, he ended up getting bad heart failure and really had very little. He had Social Security, which in the United States pays a certain amount of money. But he was really hand-to-mouth. Interestingly enough, he suffered. There was no question about it. He didn’t want to go back to the hospital. He didn’t want to go to a nursing home. He lived really with the bare minimum at home before he died. We were able to bring in some services to help him, but he didn’t complain about that. It was more, “I regret that I didn’t do other things.” So you definitely need enough for substance, there’s no question about it. But that usually isn’t what people really regret. You might ask them and they say, “Yeah, I wish I had a little more. I wish this was more comfortable.” And thankfully, in the United States, there’s still a safety net that even the poorest of the poor can eventually get something called Medicaid, which allows them to stay in a nursing home. There’s some safety there, even if you have very little money. But usually, it’s deeper things that people regret and not necessarily their monetary situation.

Tom: The safety nets are a good thing to bring up too, because here in Canada, obviously, we have health care for free, but there are certain things. Long-term care does (technically) cost money. There’s always some kind of program you might fit into if you don’t have the funds available for that. But to look at it as a bill without any programs, these things aren’t cheap. It’s not something you want to have to think about at that time. But I guess with proper planning, things—not just retirement savings, but things like insurance come into play where you can kind of make sure you’re protected for these.

Jordan: Yeah, most definitely. It’s a big part of the process, right? It’s planning financially for yourself, but also having the right protections and insurances to protect your family and to provide in the worst case scenario.

Tom: Speaking of planning, one of the more interesting things I found in your book was these paths to financial independence. Can you give an overview of these three different paths?

Jordan: Certainly. I describe something called, the parable of the three brothers in the book. It’s really kind of a story about how there were once three brothers. The eldest, kind of saw his path as a hindrance and wanted to get to the end as fast as possible so he skipped meals and skipped sleep to get there as fast as he could. He “grinded it out.” When he got to the end of his road, he had tons of time to enjoy his freedom, but he was fairly exhausted. The middle brother didn’t like his path either but didn’t have the strength and stamina that the eldest brother had so he would take these moments away from the path to go up into the forest or to hang out in the mountains, almost like a mini retirement. Then he would come back and finish his path. He got to the end of his path a little bit later than the eldest brother. He had less time to enjoy his freedom, but a lot more energy. And last but not least, the youngest brother was different than either of the two. He set off on this long journey of a lifetime, walked this long path. But he loved to hike. So as he was on the path, he was looking at the forest and the trees, enjoying the rivers and the sun beating down on his face. When he finally got to the end of his path, he did something that neither of the brothers could understand. This was years after they had arrived and they were enjoying the freedom. They looked over when he got to the end of his path and what did he do? He turned around and started to walk back the way he came. What’s the point of this parable? Well, when it comes to financial independence, I really think there are three main paths. There’s lots of other ways and detours to get there but the three main paths are the traditional FIRE (financial independence path), where we work really hard at front load the sacrifice, grind away, often at a job that we don’t like, make as much money as we can. And once we hit a certain net worth number, we quit, put our money in the stock market and let that support us for the rest of our lives. That’s the eldest brother. Some of those original FIRE practitioners that we often talk about, like Mr. Money Mustache or J.D. Roth from, Get Rich Slowly, that’s kind of their path. The path of the middle brother is more people who kind of don’t want to grind it out. They want to enjoy today as well as tomorrow yet want to support themselves. This is more like the side hustle or passive income path. These are people who define financial independence as making enough passive or side hustle income every month to cover their monthly needs. They want to enjoy the time they have now, even as they’re working. You see this often in people who do real estate or digital entrepreneurship. Those type of things are kind of a nice path of the middle brother. You can get to financial independence fairly quickly. You don’t have that huge net worth that maybe the eldest brother has. But you can support yourself, and you can set up your insurances and other things to protect you. And then last but not least—and I think this is the most controversial are the youngest brother’s. I almost define financial independence as when they find a job they love that fulfills a sense of meaning, purpose and identity. They would do it even if they weren’t being paid for it. If you can find a job you love, you’re pretty much financially independent from day one because you make enough money to do the thing that you want to do most. This we see a lot in artists or creatives—people who love their job and that’s what they want to do with themselves. The purpose of money, in general, is so that you can fill your time with things that are purposeful and meaningful for you. The youngest brothers do that immediately. In a sense, the money they make is to cover their daily needs, and they’re set. So those are kind of the three past the financial independence. I think if we can start thinking about what our sense of meaning and purpose are, we then can look at those paths and see which fits us best.

Tom: Where do you see yourself lining up in these? Because you kind of sound like you’re all three.

Jordan: I think this is very true. And nothing says you can’t switch from brother to brother depending on what time of life you’re in, or that you can borrow techniques from both. I used to think that I was the youngest brother and the reason why is, my father died. He was a physician. I, from a very young age of seven, decided I wanted to be just like him. I wanted to fill his shoes. So I was very passionate about going to medical school and becoming a doctor. I started very much like the youngest brother. I didn’t care about money. As long as I could support myself and I could get there, I’d be living my best life. Once I got there, though, I got really, really burned out and I started saying, “Boy, this thing I thought was my identity. This thing I thought I wanted to do with my life probably isn’t everything there is. How do I get out?” Then I became (very much) the eldest brother. How do I kind of grind this out? Work as hard as I can, make as much money as I can so that I can be done in a few years and then do whatever the heck I want. But within that, when I started to think about how do I make enough money? How do I be the best eldest brother I can be, I started doing side hustles. By doing side hustles and building businesses on the side, I was borrowing some of those techniques in order to get to my financial independence number faster. At different times in my life, I feel like I’ve been a little bit of each (brother) and I think that’s okay. I wrote this parable not to mean that you have to stick specifically to one path, but just to help delineate the clear points of each. We can pick and choose. And everything is okay, like I said, as long as you’re using those path in service of bringing more meaning into your life. For an eldest brother, meaning might be getting to financial independence as fast as possible so I can quit my job to do something else. For the middle brother, meaning maybe interlaced throughout work. Sometimes they like work, sometimes they don’t. But they’re trying to get meaning now as opposed to waiting like the eldest brother (until financial independence). Then the youngest brothers, they don’t want to do anything without meaning. They want meaning right now and they want that to be part of how they actually make money. So, it’s just a very different way of looking at things.

Tom: Yeah, I can see how different things fit different people. You said the third one—the youngest one, might be the most controversial, but I almost find that traditional financial independence one is the tougher thing to fully embrace. It’s this idea that you’re just going to put everything into retiring early because, if something happens to you, maybe you just don’t work 60 hour weeks for nothing and you die early and now you can’t do anything. It’s all for nothing at that point.

Jordan: And that was my dad. He died at 40, right? If he had been a traditional FIRE proponent, he would have died probably either right after he got there or even before. And if he hated his job and was just grinding it out to get there, it would have been really sad. For that reason, I really caution people. We don’t know how long we have left. No one can guess that. All we know are our basic fears. I often ask people the real important question, what scares you more? Are you afraid that you’re going to die young and wealthy without having those great experiences? Or are you afraid you’re going to die old and broke because you didn’t save enough money? Depending on how you answer that question, it’s going to help you toggle how fast you try to get to financial independence. People who are afraid of dying young, I say, instead of squirreling every single penny away in investments, be very thoughtful about maybe 10 or 15 percent goes to investments, and then another 20 to 25 percent goes to a YOLO (you only live once) fund. Live it up. Use that money for your time. Use that money to take more vacations or to have more meaningful experiences. Or, even if you really love things, to buy those things you love, if that’s your fear. Now, if your fear is like mine where I was going to grow old and eventually be broke, then grind away and assume everything will be okay. The best guess are our fears. We don’t really know what’s going to happen.

Tom: And beyond the worst case scenario of dying is, what’s my health going to be like? I have kids. Are they going to be too old? There’s no sense missing all that family time, all that ability to be active and spend all of it working. Maybe you want to do some more active adventures. You want to spend time with your kids while they’re young. It doesn’t necessarily just have to be this case of, are you going to die early. It could just be, do you want to do some things while you’re 30 and 40 or do you just want to save all of it for 50 plus?

Jordan: And the real cool thing about it is, I think people are realizing this, right? In the financial independence movement, you now have all these offshoots of ways of both pursuing financial independence, but also enjoying today. You have things like coast FI and slow FI and barista FI—all these cool names. But what they’re really saying is, let’s start working in purpose identity—let’s use our money for good now, as well as save up for financial independence. And it’s okay if it takes longer because we’re going to build the life we want today as opposed to just waiting for some later date. I think it’s a very healthy move. It’s a very healthy evolution.

Tom: Beyond just the money of how much you’re going to work upfront or later, another important thing to be prepared for are things like wills and beneficiaries and such whether yourself or you’re checking into it for your parents. How do we approach this? Is this something that you just do once and forget about? Do you do you check in occasionally on these? Again, both your own documents and everything—just making sure that people within your close family are taking care of this too.

Jordan: I think those are two separate conversations. One is, a lot of us are in that sandwich generation right now. We have kids that might be young, but we also have parents who are getting into their 70s and 80s and dealing with that. One of the big things is to start having those conversations with your parents. That can be very difficult, right? Because no one likes to talk about money. So how do we breach those subjects? In the book, Taking Stock, I talk about some of the different ways we can talk to our family members about that. One way, for instance, is you can start working on your own financial planning and your own legacy planning, as well as asking your parents. So you go up to your mom and dad say, “Hey, mom and Dad, I was thinking of possibly getting a will and trust. I know nothing about it. Tell me your opinions. What did you guys do?” It’s like a total non-confrontational way to talk to your parents about what their plans are, but instead you’re asking advice. They may come up with some great stuff, which is good advice you can use that towards your own plan. But even if you’re very savvy about this, it actually gets them talking about what they’re doing. It’s a great approach—ask for advice. Another approach is to tell stories about people you know who’ve had bad things happen. I tell a story in the book about a gentleman whose mom had end-stage Alzheimer’s. His dad had done this great job of doing all of the estate planning for the mom. But then his dad got COVID and was put on a ventilator. Then this guy realized his dad had all the financial power of attorney for himself and his mom and had never planned for something like this to happen. If the dad stayed on a ventilator and couldn’t make decisions and the mom needed extensive care, the son didn’t have the financial power of attorney to actually utilize the money. So telling stories like that, “Hey, mom and Dad, you know, this friend of mine went through this horrendous thing, can you believe it? What do you think of that?” It’s also a great way to start bringing up that conversation. I think another great conversation starter is to ask about legacy, “I’ve been thinking a lot about what legacy I want to leave for my children. Mom, Dad, what kind of things do you want to leave us? What stories?” But it also gets into financially. “That summer house. We go there every other year with the whole family. Do you want that tradition to continue? What is the legacy you want to leave to your children and grandchildren?” Those are three great ways to broach the subject. But you’ve also got to think about not only your parents estate planning and legacies, but your own. I like to call these “legacy documents” because I think what we’re really doing is creating a financial legacy for our kids and grandkids. There’s a series of documents that anyone who’s old enough to have any kind of property or do you have any kind of savings or has any dependents should start thinking about. The financial legacy documents are as simple as (first and foremost) making sure all your beneficiaries are set. Does your 401k have the appropriate beneficiaries? I’m using 401k and that’s obviously an American retirement savings. But do your retirement savings and your life insurance have all the appropriate beneficiaries? The other is the transfer on death. Lots of bank accounts, especially in the United States, when someone dies, you can fill out a transfer on death form so that instead of a bank account going to the legal system which we in the US call probate… Instead of having it to go to probate for a judge to decide where the money goes, you can actually specify with a lot of these accounts, transfer on death. After that, then we get into things like wills and trusts. Trusts are pretty complicated and if you really want to get into those, I suggest you get a lawyer or at least read an estate planning book. But wills are basically your instructions for what you want to happen to your material things. After the beneficiaries are set, after the transfer on death are set, you have this legal document which, in the United States goes to the court system in a process that’s called probate, you want to make it as clear as possible. You can DIY (do it yourself) will, but again, if you have any real assets or family independence, it probably makes sense to get an estate lawyer and to do a good job of writing out a will so you can make sure that your legacy, your things, whether they be monetary or objects, end up where you want them to. And that’s one set of things. Then they’re more of the medical legal legacy documents. And that has a lot more to do with your financial power of attorney, medical power of attorney, your living will. There’s a bunch of medical documents to consider in there. But I consider those two kind of separate categories.

Tom: Beyond those, the financial in the medical, there’s the third thing you mentioned in the book, this ice binder. Can you explain what that is and how this comes together?

Jordan: This is actually one of my favorite topics ICE stands for in case of emergency. What we’ve found in personal finance and especially in financial independence is usually you have one individual who’s really into it. They learn all about investing. They learn all about savings. They’re the ones who set up all the bank accounts, set up all the investments. They might even be the ones who are paying the yearly fees for everything having to do with the house. These are the people who are doing all the budgeting and paying all the bills. But that’s one person of a couple (if they’re married) or there’s children or parents or other dependents. What happens if that one person dies or gets in an accident and can’t speak for themselves or for their family? There’s all this financial information that could be lost or at least misplaced. So the “in a case of emergency” binder basically codifies all your accounts, all your passwords, all your different social media that you use. It creates a binder that’s a legacy binder for your family in case (God forbid) something happens to you so that all of the family, financial and important information is all in one place. Everything from the kids doctor’s—some people if they have young kids will put information about where the kids like to eat, who the kid’s best friends are. Any kind of information that would help someone if both parents died or one of the parents dies who holds all the information. You’d be amazed at how many people die without the financial information available. It just makes it difficult. I think in in my book, I talk about a case where a gentleman died and he had a safe in the house. He spent thousands of thousands of dollars on an incredibly secure safe. He had all sorts of important assets in there, a coin collection, all sorts of things of incredible value. But he didn’t tell anyone the combination to the safe, and then he died. And so an ICE binder is a good place to put all that information so it’s available for your loved ones. I think it’s a real important part of estate planning that we often skip over.

Tom: I would just add from my own experience, too, if the idea of listing all these passwords for all these accounts sounds like too much to keep on top of on a printed copy, it’s a great time to have a password manager anyways. That way, you just have to give them that one password. You might want to point out that these accounts exist but if you’re constantly changing passwords, this isn’t something you have to be printing out all the time. You could just make sure that one password is updated and maybe keep it along with that safe PIN and everything.

Jordan: Yeah. It’s a common thing that people will both have a protected digital copy with some type of password protection or encryption. Then they’ll usually have a hard copy which they put in their safety deposit box. So, as long as your loved ones know where the key to your safety deposit box is, you’re pretty much set. Then you just have to make sure you update it. But even an old version of it is so much better than nothing.

Tom: That’s true. Even just the idea that these accounts exist is a starting point, because in some cases you can have someone with some random account out there, either a bank account, investing account or just a social media account, but if people don’t know they exist, that’s already going to be a big issue, even if the password is expired, that can be taken care of later.

Jordan: Exactly. At least it’s an accounting of all the accounts and insurances and those kind of things.

Tom: There’s one more thing I wanted to touch on briefly. I grabbed this line from your book that I really liked. It said, “We are not trading hours or minutes, we are merely living through them.” It was an interesting thought on how we look at time. You do go into time quite a bit in this book beyond just the finance side of things. What’s your thoughts on this? How should people be looking at the time in their day and how to optimize that?

Jordan: Well, interestingly enough, we often try to commoditize time. We talk about it—and look at the words we use. You buy time, you sell time, you waste time. We like to feel like we can manipulate or change it. But the truth of the matter is, time is a constant and we have zero control over it. Time passes no matter what you do. So there are probably two things we have a little bit of control over. One is, if we think of our life broken into different size time slots, we probably have a little bit of control over what we decide to put in those timeslots. What activities do we do during those time periods? The time period stays the same. But whether I’m sitting at home playing video games or playing catch with my son, those decisions I have a little bit of control over. The other, more ephemeral issue is, we perceive time differently at different times of our lives. When we’re young, we feel like we have all the time in the world. And yet when we get older, we feel that time flies. Give me something that I hate doing, like planking and have me plank for two minutes and it feels like time screeches to a stop. On the other hand, put me in a restaurant eating pizza with people I and the time, the two minutes feels so fast. It was here and gone. So we can mess around a little bit with our perception of time, but in reality, our best way to control things is to have a little control over where we need to be and what we need to be doing during those timeslots. It’s one of the great ideas behind financial independence. If you can create some financial space in your life, it can take you away from things you might not want to be doing, like working in an office and fill those time slots with other things, like being with friends and family or doing a beloved hobby or even a side hustle—something you really like. The only mistake I think we make is we figure it’s binary. You’re either working or you’re doing what you like. I think we can get better at filling those timeslots with things we love doing, or at least like doing even before we’re financially independent. I think that’s a big struggle I talk about in the book. It’s learning that we can start doing this at a much younger age. We don’t have to wait until we’re retired. And certainly, we don’t want to wait until we’re on our deathbed to start realizing, “Oh, I had more control over my time and I didn’t put things in those timeslots that had meaning for me.”

Tom: That’s a great point, because I know before COVID, when I worked in office, there would be these watercooler talks where there’s people that are working 50 plus hours a week who say they have no time. But then when they’re talking about what they did in the evening, they were just watching TV. Maybe you really like TV. I’m not saying that people can’t watch TV, but it always kind of bothered me that people didn’t see that that time could be used for something else. Maybe it is that side hustle or spending time with your kids. You can be working your normal eight hours in a day, but if you’re so burnt out from work that all you’re doing is watching TV in the evening, you’re not really making the best use of that time. It’s not really that you have no time.

Jordan: And here’s what I love. People say, “I’m already working eight hours. The last thing I want to do as a side hustle at night when I’m not working.” But I like to flip that around. What if you found a side hustle that was something you were passionate about? Now, I did this when I was younger. I loved artwork and started a side hustle buying and selling artwork. I loved doing it so much. I didn’t really see it as work. Here’s the thing, if you happen to be lucky enough that you start making some income with that side hustle you’re passionate about, you might be able to start cutting back at work to such an extent where instead of spending that eight or nine hours in the office which you hate, maybe go part-time with work and then spend your time in the side hustle, which now you’ve built up and you’re passionate about. That’s a win. Let’s say the other thing happens. You work your normal eight or nine hours a day. You go home at night and you do your side hustle you’re passion about it, and it goes nowhere and you make no money. Well, guess what? It was probably time spent better than sitting watching Netflix anyway because it was something you were passionate about and liked. We seem to think that there’s this black and white tradeoff. But the truth of the matter is, there are lots of shades of gray there. How can we start intentionally making some of those tradeoffs to favor being more thoughtful about intention and purpose now, as opposed to waiting until some later date when we feel like we’re more financially stable?

Tom: Another thing I found with starting a side hustle, (being the blog and the podcast and everything) was an unexpected benefit. It made me like my job more. It wasn’t that my office job was something I was super passionate about, but it did give me some financial space to feel like I could speak up more at work. I didn’t feel like I was risking my job by giving a negative opinion on something to someone higher up. Just having some leeway like that financially kind of became a mental thing where I found I liked my job more just because I didn’t feel like I was completely reliant on it. You may not even have to find a different job that you truly are more passionate about. Sometimes just having that little bit of space can actually make it all come together where you’re kind of happy with everything.

Jordan: Yeah, I’ve seen that in several physicians. Being a physician myself, people were really burning out at work and started working more because they wanted to build up a plan towards being financially stable. When they realized instead of working more, why don’t I work 70 percent? They might not be able to retire for another 10 or 15 years, but their control over their time in that sense gave them such relief that they started enjoying work more. When they saw, “Oh, I actually have some control here. I can toggle how many hours I work. I can give up on retiring early and retire a little later but enjoy every day a little more and not feel so burned out.” It was that sense of control that made them actually enjoy the process. Even things they thought they weren’t enjoying, now felt better once they could control it.

Tom: Yeah, I love it. Thanks for walking us through your new book. I think people should check it out. There was a lot of inspirational stuff on how to handle all this from planning for retirement, planning your time, and just put it all together so you don’t end up in that hospice room regretting everything regarding the choices you made. Can you let people know about the book and where they can find you online?

Jordan: The book is, Taking Stock, A Hospice Doctor’s Advice on Financial Independence, Building Wealth and Living a Regret-Free Life. It can be found anywhere books are found, especially online at Amazon, Target, Books-A-Million. Wherever you can buy online, it will be there. It’s through Ulysses Press. It drops August 2nd and you can find me at That houses pretty much all of the things I’d use. You can learn about the book there. You can also learn about my financial podcast, Earn and Invest and my blog, Diversify. I also have a medical blog which I’ve been writing since 2005. I don’t write there much anymore but there are links to all those things. Or, if you want to just go to the podcast, it’s

Tom: Great, thanks to be on the show.

Jordan: Thanks for having me. It’s been a blast.

Thank you, Jordan, for speaking so candidly about what can be a sensitive subject. You provided a great reminder of the importance of enjoying every moment and balancing the future with the present. You can find the show notes for this episode at If you have a moment, head over to YouTube channel and subscribe there. We’ll be getting back to releasing never-before-seen content, soon. Either search for Maple Money or go to and subscribe today. Thanks, as always, for listening. I really appreciate it and I look forward to seeing you back here next week

When I was talking to the ill and the dying, and they were telling me all these things they regret, they were never telling me that they regret that they didn’t work more…that they didn’t get to that net worth goal that was big on their mind… - Jordan Grumet Click to Tweet