"Always be able to take care of yourself." - Alison Winter
Alison Winter is the Co-Fonder and CEO of Gracious Exit LLC, a web-based resource for individuals and families to prepare for the end of life.
The workbooks and articles and resources provide t...
"Always be able to take care of yourself." - Alison Winter
Alison Winter is the Co-Fonder and CEO of Gracious Exit LLC, a web-based resource for individuals and families to prepare for the end of life.
The workbooks and articles and resources provide the roadmap to navigate this last stage of one’s like, and do it in a way that is positive, eliminates a burden for those left behind, and leaves a full picture of one’s positive contributions.
In 2006, Alison retired from Northern Trust Corporation, completing a markedly successful thirty-five year career, where she held leadership roles with increasing scope since 1987. She served on the Management Committee for the last five years of her tenure with Northern Trust. When she retired, Ms. Winter was the founding President and CEO of Personal Financial Services-Northeast based in New York, where she established the Northern Trust’s presence in that highly attractive and competitive market. Prior to that, she served as Co-President of Personal Financial Services for Northern Trust. In all, she expanded the Northern Trust franchise as a leader in managing the wealth of the affluent in 20 new markets, on the West Coast, The Midwest and the Northeast. Technology innovation, strategy, brand management and customer focus are hallmarks of her career.
In 2001, together with Susan S. Stautberg, they co-founded WomenCorporateDirectors (WCD), the only chapter-based international organization for women serving on Corporate Boards with over 3500 members serving on over 6000 Boards globally. She established the framework for scaling up, domestically and internationally, and there are now 80+ chapters on six continents. The organization has now been transitioned to Women Corporate Directors Foundation for Education and Research.
Ms. Winter received her MBA from the University of Chicago Graduate School of Business, earned her Chartered Financial Analyst designation, and is a member of the CFA Institute. She holds a BA from San Francisco College for Women. Over her career, she served on dozens of charitable and civic organizations, including Los Angeles Metro YMCA, New York Metro YMCA, The Joffrey Ballet of both Los Angeles and Chicago, Steppenwolf Theatre, and United Way Women’s Leadership Initiative. In 1998, she became the first woman to be Chair of the Los Angeles Area Chamber of Commerce in its 110 year history.
She lives in Pasadena with her husband, Joe. Her daughter, Leigh, lives with her husband and three sons in Los Altos, CA, and her son, John, lives in Chicago, IL.
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Your liquidity event is the most important financial transaction of your life. You have one chance to get it right, and you better make it count.
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Steve Wells: [00:00:00] I'm Steve Wells.
Jeffrey Feldberg: [00:00:01] And I'm Jeffrey Feldberg. Welcome to the Sell My Business Podcast.
Steve Wells: [00:00:06] This podcast is brought to you by the Deep Wealth Experience. When it comes to your liquidity event or exit, do you know how to maximize the value of your business? You have one chance to get it right, and you better make account. Most business owners believe that business value is determined during the liquidity event.
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Jeffrey Feldberg: [00:01:39] Welcome to episode 32 of the Sell My Business Podcast.
Alison Winter is the co-founder and CEO of Gracious Exit LLC, a web-based resource for individuals and families to prepare for the end of life. The workbooks, articles, and resources provide the roadmap to navigate this last stage of one's life and do it in a way that is positive, eliminates a burden for those left behind, and leaves a full picture of one's positive contributions.
In 2006, Alison retired from Northern Trust Corporation, completing a markedly successful 35-year career where she held leadership roles with increasing scopes since 1987. Alison served on the Management Committee for the last five years of her tenure with Northern trust.
When she retired. Ms. Winter was the founding president and CEO of Personal Financial Services Northeast, based in New York, where she established the Northern Trust presence in that highly attractive and competitive market. Prior to that, Alison served as co-president of Personal Financial Services for Northern Trust.
In all, Alison expanded the Northern trust franchise as a leader in managing the wealth of the affluent in 20 new markets on the West coast, the Midwest, and the Northeast. Technology innovation strategy, brand management and customer focus are hallmarks of her career.
In 2001, Alison together with Susan Stautberg co-founded WomenCorporateDirectors, the only chapter base international organization for women serving on corporate boards with over 3,500 members serving on over 6,000 boards globally. Alison established the framework for scaling up both domestically and internationally. There are now over 80 chapters on six continents. The organization has been transitioned to Women Corporate Directors Foundation for Education and Research.
Ms. Winter received her MBA from the University of Chicago Graduate School of Business, earned her Chartered Financial Analyst designation, and is a member of the CFA Institute. She holds a BA from San Francisco College for Women.
Over her career Alison served on dozens of charitable and civic organizations, including the Los Angeles Metro YMCA, the New York Metro YMCA, the Joffrey Ballet of both Los Angeles and Chicago, Steppenwolf Theater, and United Way Women's Leadership Initiative. In 1998, she became the first woman to be chair of the Los Angeles area chamber of commerce in its 110-year history.
Alison lives in Pasadena with her husband, Joe. Alison's daughter Leigh, lives with her husband and three sons in Los Altos, California, and her son, John lives in Chicago, Illinois.
Alison, it's an absolute pleasure to have you on the podcast. Thank you so much for taking time out of your schedule to be with us.
Why don't we start things off by having you give us a background of who you are, where you've been and what got you to where you are today, because you're doing something unique, valuable, and interesting. We'd love to hear that.
Allison Winters: [00:04:54] First of all, thank you Jeffrey for having me on your program here.
I'm delighted to be here. I was born in Omaha, Nebraska. Home of Warren Buffet and my father and the Buffets were friends. So, I learned early on about investments. I went to college in San Francisco, fell in love with California. Ended up coming back to the Midwest, and working for Northern trust, but in investments and learned a lot about everything pertaining to individuals and family’s wealth. The trust side of the business tax implications, transfer of assets to the next generation and all the planning that's involved in that. So, I saw a lot of things over those years. Ultimately, I moved into management and my first transfer was out to California. We opened our franchise and grew it substantially to be one of the largest trust companies in California.
And then they asked me to come back and expand us into the Midwest. We were just in Illinois at that point. So, I extended us into a number of States with a good concentration of high net worth individuals and was added to the management committee.
One day the CEO said, how would you feel about going to New York? This is the time we think to start getting a foothold. That was 2003 and there was so much aftermath of the crash, and all the scandals that came out on Enron.
And so, these institutions were reeling. I said I would love to do it. We went back to New York and, were very successful there. And we went into Boston and Delaware and Connecticut as well. And that's when I finally said I've got a great successor it's time for me to bow out or I'll have to keep working till I develop another successor.
So, that was, sometime ago that was in 2006 that I retired and we came back to California. About five years earlier, a friend of mine was having a group of women quarterly just around her dining room table. She was inviting women who served on corporate boards, generally fortune 500 boards to share in a confidential setting what they were doing, what did they learn from different things that were in the press? All the things you would expect they'd have questions on, but maybe not want to ask out in the open. She said to me, just off hand, why don't you start one of these in Chicago? And the more I thought about it, I thought, if we're going to start one in Chicago, we should really look at all the big cities.
And so, we need a name, we need a logo, we're going to need a website. This all went through my head and I went back to her and she agreed. So, that was the beginning of Women Corporate Directors. We had two chapters. By 2006. When I went to retire, we were then in Boston, Washington, DC, Atlanta, and a couple of other places.
And it was just starting to get such momentum. We were getting inquiries from all over the country saying they wanted to start a chapter. So, the timing was perfect. I was on the Nordstrom board at that time, I spent about 15 years on that board and also on their bank board. We really began to ramp up just one after another, by the end of that year, we were up to 10 chapters.
In another several years we had 20 chapters. By 2012, we had over 70 chapters around the world and we were holding conferences four times a year, one in the Americas, one in Asia, one in Europe, and then one in New York for the United States and they became a big deal. But ultimately it was very time consuming and it was time for us to institutionalize it and not just have it be run by us.
So, we got KPMG involved. We had a educational and research foundation within our business. So, we folded everything into that not-for-profit and, KPMG brought us out. And today they have something like 85 chapters around the globe. And it's doing very well.
I started doing speeches about something I learned when my dad was a widower and lonely and he knew I was his executor. So, he wanted to educate me on what I needed to do.
Once a month, I would come into Omaha and we'd sit and talk Friday night. And at first it was mainly on financial things, but over time, we really started to get into what kind of a funeral do you want? I remember asking him one time, who do you want to, talk at your funeral. And he named two people I'd never heard of.
So, that got me searching and really realizing we don't know our parents very well. Everybody is a little self-centered and I think the parent child relationship is very centered around you, the child. And even if you're 40 years old and you're busy with your job and your kids, I began a search to see what I could find about him.
That is what led to launching Gracious Exit. First my brothers and sister wanted to have some help with their estate plans. And then I started giving some talks and word of mouth spread, and I did a lot of, sessions with YPO forums. And I spoke in front of CEO at their global Institute.
And it's just a subject that is very much on the minds of people who are, whether they're in the early or mid-stage of that third stage in life. They're thinking about it. They may not have acted on it yet because they don't know where to start. And that is what Gracious Exit does.
Jeffrey Feldberg: [00:10:47] So, Alison, it's a wonderful story. And, thank you for sharing it. A Deep Wealth, we focus exclusively on exits, but a very different kind of exit. There's one thing that this all has in common, at Deep Wealth, our focus is preparation that you need to prepare well before an exit or liquidity event.
You're talking about a different kind of exit, but the preparation for that as well. And so our listeners may be wondering, okay, I understand a business exit of why you'd be talking about that, but why are we talking about, an uncomfortable topic for many people, about one's passing and what does it have to really do with anything in what is it all about?
And I know offline when we were talking, it just came to be the importance of having your affairs prepared ahead of time and in order. And when you think about it, when you're preparing for your own business, exit, a part of that focuses on you as well of taking care of your family, the day that you may not be there and what that looks like.
You're very modest because you sent a number of materials and we're going to include this in the show notes. Some of the, booklets that you have and the presentations that you've done, but why don't you take us through, step-by-step of what someone should be thinking about when it comes time for how do you prepare for your own life exit?
Allison Winters: [00:12:08] I think there's four areas that people, when they're. 60. Let's say they're about the time they're 60. Although I will say people whose parents died earlier, they start thinking about this is that number looms ahead of them in their own life.
But most people don't really think in earnest beyond their estate plans with their attorney about what happens when I die. When you sell your business, yes, you put things in the title of the trust, but did you put everything in the title of the trust and the trust deals with the financial assets, but is everything in there?
It's amazing how many things don't make it into that trust. Do you have an investment club or do you have every partnership you've ever invested in titled in the name of your trust? And you could go down a list. Most people over time, once they start thinking about it and putting it together, they periodically, especially in that first year, find themselves adding to that list of assets.
Then you've got to make sure what's the title and what is the appropriate title? Many people, who are clients of yours, particularly Jeffrey, have very good estate planning attorneys and they're dealing with all kinds of specialized trusts, but at the very least they have a living trust, or some call it a declaration of trust and everything goes into there so that you avoid probate and you have a pour-over will that advances it. Attorneys nowadays when they're updating estate plans, make sure there's a durable power of attorney signed on your behalf. In my case, it's my husband's and my husband's case. It's me. We both have, living wills, that document that, gives your instructions of what you want in the event of a serious illness that can lead to death, but you're incapacitated and someone needs to speak on your behalf about what you want, not what they're medically capable of doing.
The next thing is where are those documents, but not only where are those documents. If somebody's going to step in and take care of things, let's say you're incapacitated and you for six months, can't handle your own affairs. There are housekeepers to pay, things go wrong in a house.
It seems to me every day or every week. So, there's who do you call that knows this house and can come out and fix that problem. What medications are you on? Who are your doctors? When you get into your sixties, unfortunately, you've got a list of doctors, not just one and depending on how your health is.
So, what's their phone number? What practice are they in? What medications are you on? And when do they run out and how do you order them? All these things need to be looked at to have an orderly transition. And there's a final piece in that is thinking through what do you want to leave behind for your heirs?
When you're younger, you think you want to leave behind the material things, but as you get older, they're getting older too. And over time they have the material things they need. They're far more interested in the memories that they maybe don't have, but you were created with them.
I've done a whole series of photo books that are family for my kids and our grandkids like to look through them. I'm extreme in this preparing your legacy. Even with my siblings, we did a movie. we hired in a film crew and, in a long weekend, we filmed individual and group interviews around subjects that were about our growing up and who our parents were and the values they taught us.
And we talked about each other as well. So, there’s a really thorough look at who we are, who we were. We did a photo montage to music at the end of each of the individual videos. And my brother, said, now you've got your video for your funeral. So, they, then they will be used that way probably, but it creates a broader picture.
But more than that, we had a ball doing it. And when we get together, we watch sections of it. And I've made one of the DVDs available on the website because I think for some people it's a great way for a family to share memories. It's not cheap, but it's worth the price of a great vacation.
Steve Wells: [00:16:41] Alison, when Jeffrey and I sold our business, it was a huge financial windfall for us. And, I'm a little bit older than Jeffrey when that happened. And so I had our only child and a daughter in college. She graduated and advanced and got married and now she's got two grandkids.
I'm wondering if you can comment on something that I'm doing and see if you've see that with other clients you have. So, every year I meet with her and her husband and I bring her into my team, my financial advisor, the estate planning attorney, we use, accountants and CPAs. And we have a board meeting where I've shown them more and more about how the financial structure of my estate is and what am I investments are and get them involved. And I give them some money that they can give to the foundation every year to practice philanthropy so they can understand how hard that is. Because. From a lot of business owners, at least for me, it was huge.
It was like the day after your closing, all of a sudden you have more money than you've ever had to manage in one shot, and that's going to affect yourself. It's going to affect, obviously your finances and possibly your family. And I've tried to incorporate that in. Do you have any tips for me or people like me that find themselves in that situation?
Allison Winters: [00:17:54] Actually, you're doing the very best thing you could be doing.
And I applaud you for starting her out right at the get-go and meeting your advisors. She has I'm sure already picked up that this is serious. It isn't just fun. Oh, look at where we're well to do. We can do whatever we want. It's there's a responsibility to it. And as you said, she didn't grow up that way.
So, I think the fact that you're educating her in this very serious way and she understands and will more, so and over time, the value of having good advisors who work with each other and with you and her, I can't think of a better thing to have a smooth transition to the next generation.
For those who are listening, who have more than one child, they still should think of this seriously, because it's a great way to help your kids mature into understanding all the ramifications, legal, financial, and technical of having this kind of wealth. But when there are multiple children, there are multiple personalities, they've married, different people.
There might be even some tension within the family, even worse than that there might be some real feuding and that's when you have to be careful and think out what are the problems when we're gone and how do we head those off before we go. For some, it might be the decision to sell a beloved beach house because two of the four kids are married to somebody they're struggling financially.
There'd be no way they could chip in their fair share. That is bound to generate, some, conversation amongst others of how they're not picking up their fair share, et cetera. A family business, when you transfer a business and there's one child who is going to run it, they're getting more than the others because they need a majority ownership.
So, that has to be talked out with your heirs way in advance so that, where there's tension and then you can fix it. If you wait until you die, you can't fix it. But if you talk these out with your kids, like you're doing, you just have the one and that's great. But if you've got multiples, you're going to be in for some trouble.
If things at all look unequal to them. To this day, my siblings will say, you were mom's favorite. And sometimes we're joking, sometimes we're not. And we like each other. Families don't get along. And I've seen so many lawsuits and families broken apart. So, that's the one big thing I would say is anticipate problems and get them out in the open and discuss them and see if you can fix them before you go. But you're doing a fabulous, it's a gift to your daughter and granddaughter really. And your granddaughter then will grow up. Not as a kid whose grandparents can buy her anything she wants, but as somebody who sees I can help that other kid through our foundation. She can go on the group trip, there rather than be the only one that stays at home.
Jeffrey Feldberg: [00:21:13] Alison some terrific insights from you. I'm wondering though, if you can walk our listeners through this wonderful system that you've put together, otherwise known as the Gracious Exit, and I know you've put together Gracious Exit workbooks.
And what was interesting. I really like how you approach this, because you looked at it from a child who is really a grown adult in the forties or fifties, but taking your workbook and speaking to the parents and having those difficult conversations now, as opposed to later, when it's even harder, because you may not have that information.
All the way through to, people to take those workbooks and do it themselves, and to go through that process and the checklist and the different areas that are there. So, why don't we take that first group, which is a difficult conversation of a child, you're speaking to your parents.
What do you recommend to our listeners of how they broach this topic and how they can make the most of the conversation?
Allison Winters: [00:22:08] Part of it depends on the age of the adult child.
I can remember my mother approaching me, I just graduated from college. She had a very serious illness and it wasn't clear that she would, make it long, but she was home and she was going through her closet and bringing things out. And she was walking me around the house, trying to show me this has value.
This has value. Don't just give it to the, to charity. And I was like, mom, I don't want to listen to this. You're going to be fine. At 22, you can't picture that. Now, if she really had gotten there, my dad was the one who did all the planning in the family, and he was not ill. The more usual case is when the child is in their forties, fifties, generally in that era.
And I think the best time to do it is when your parents start going to funerals of their friends. Because you probably will talk about it on the phone. That's the perfect time to say. Have you thought about what you want for a service, what you want in your program?
And I bet they might say, I've begun to think about it. And that's a good opening to say, let's talk about it. There is this feeling that elderly parents don't want to talk about dying I think there is a generational shift between the baby boomers and the older generation that came before boomers that really was so private and they did not discuss these things.
Even with my dad, he didn't discuss them with me until he was in his eighties. And I was running a business and, had an MBA from Chicago and did all investments and everything else. He didn't want to talk about it until he got into his eighties, but he was doing well. He was fine. And he did start to send me things, but that was it.
He was an estate planning attorney. So, he would do that. I know lots of people whose parents did not want to talk about it, but every boomer. I know. And I'm in that first wave. We've all heard about horror stories about not knowing anything about it.
And you're actually seeing a lot of things in the press that are on that subject, because it's a lot more common than you would think. So, I think it's going to be easier for our kids to talk to us about it. But my daughter is in her forties, I talked to my kids, but the first time I started to talk to her about, she was in her thirties.
She didn't want to talk about it. And, gradually I'm sharing with them what I'm doing. I think this is the time. And with, with the foundation is another perfect example. You can begin to have these conversations around philanthropy as opposed to their own what they're going to inherit. But at some point, I think it's important to give them at least a low-ball idea of what they're likely to have down the road. And I'll tell you why. I had a client. She, had a trust that had been set up, it was about $30 million. She never spent any money out of it and she inherited it and it just kept growing and on her 80th birthday she decided to surprise her children and tell them about this money.
They had no idea this was coming. And they were furious with her. Absolutely raving furious with her because every decision that they made that was important to them was based on the fact that they had no money. And so, they could have sent their daughter to a better college and their son, and help their grandchildren out.
There were so many things that they said, the decisions I would've made would be much different if I knew I didn't have to, for example, save an extraordinary amount for retirement. And so, I think it's not a good idea to keep them in the dark about what's coming. But you also don't want to give them an amount and then down the road for a number of reasons, It's a far less amount.
We meet once a year and for the first time, the last year, and we go over this and I told them this is what you're likely to inherit. And they're like, okay. Now it's half of what I think it will be. It's enough that they know that. Okay. I'm not as worried about, when we build that new house, I know that I'll be able to afford it, long after you're gone.
There's not one answer. A lot of it is the maturity of your child who they're married to the pressure they might be under from a spouse.
Steve Wells: [00:27:01] Alison, I think we got to be careful, who hears this broadcast now that you just disclosed, you're discounting your, inheritance by 50%.
Allison Winters: [00:27:09] That's true.
Steve Wells: [00:27:11] You know what you said? You've lived through so many of those things. And when I look at my wife's parents who are passed and what we had to do at the end and take care of everything, my mom's still alive, but that generation really doesn't want to discuss it and I'm a boomer.
My daughter's 31. She doesn't really want to talk about my death and passing. And, we tell her we've bought a grave site and all this, but what I, I found and I just, when I knew you're coming on and you shared your workbook and I've been through this and I thought, wow, I actually saved it.
And the way I put it under my estate planning on my Dropbox, I said, Kristi asked my wife, we get to go through here and look how organized this is. And there are things that we haven't even thought of. And I thought we were pretty prepared. I wish we could actually show this on the podcast, but I think it's a valuable thing for everyone, particularly the business people who are going to be going out of their business and may have some wealth. They're going to have a lot of things to deal with. Is there anything you can tell us about the outline of that or sections, or how did you, first of all, even put that together?
Allison Winters: [00:28:13] I spent a lot of time, many years with my dad understanding his wishes. Once a month I went down there and as a result of that, I took all this information and I tend to write things so that I have it down and, then I looked at it and I thought, no, I want to change this now into a form.
The workbooks I have in an order to me are what you need to do as you're gathering information. The first two are financial and medical. You really need to get those down, but when you finished all the workbooks, you need to put it in the order of the person who's going to pick up the instructions and know what's the first thing that I do. Call the doctor.
Call the attorney that you didn't need to call the attorney that first day, but if you're donating your body to be cremated to a medical school, call them they'll come and pick up the body. I took all that information, but I put it in order and the first is getting ready for the funeral. Second section is the estate.
What is the order in which you deal with this, getting it, open, so that you're named officially the representative of the estate, whatever it might be? Getting checking accounts, your name on checking accounts for the estate. There's a lot of details. The third stage is the distribution and there’s plenty of time for. So, that's what that the very last workbook is it's called an appendix, but once you finished all these workbooks, it's very easy to fill that out.
Because you have it on some other workbook. I advise people to do the financial one first, as you saw, there's no place for dollar amounts. All we want to give whoever is stepping in our place is the name of every advisor we work with. Attorney accountant, property manager, partnership, interests, business manager, the company president, if you still have ownership in a company. All of those things are assets and you need to have what's the name of the contact? What's the phone number and where's the document that shows that you have this interest, for me, it still says file drawer. I'm not going to tell you where, because I don't want it on tape, but a file drawer under this label. So, that's the first one, because you have to know what is in the estate.
And there are so many nightmares for the person who steps in and has to wait until statements or bills come in to know what they're dealing with.
Steve Wells: [00:30:56] And Alison if I could interrupt you for just a second, I'm looking at it right now. What's so great about the outline, I've done some of these, but some of my habit, and if most business people are like me, I have 14 different, financial checking accounts. You got other business interests. So, they're all listed there. And if my daughter and son-in-law could understand the structure, it would be helpful and I don't really have that organized for them.
and just going through your list, I think that would be really, really helpful. And I just recently had a friend who was only in his early sixties and he had a stroke and, he was unconscious for, weeks. His wife could not get into his accounts. She didn't know the passcode of so many things. For me, it'd be all the different electronic files. How is someone going to find them if they need to grab this.
Allison Winters: [00:31:44] One of those workbooks. I can't remember the numbers right now, but it asks you to list out all your key, digital accounts and services and what the passcode is.
You don't have to give an account number, but I, have mine typed out. I have it in a place I can get to it electronically. And, this is something that is challenging for everybody because of hackers and so forth. But if I forgotten the password, I can go to this list and look at the password. The earlier part of your question, we used to do back in the days when I was working with trust, we used to do diagrams of an estate plan to show under what pocket each one was.
And, then there'd be a diagram under that who were co-owners and so forth. I think that you might even talk to your estate planning attorney to see if he has somebody in his office who could do that for you as a map of what you've got. The more complicated the estate plan, the easier it is to track for your heirs is if there's a map and it would be useful just in these meetings with your daughter, to understand this map of the different pockets and their purpose and where they're going.
Jeffrey Feldberg: [00:33:08] Alison, I like the organization. And let me briefly try and describe this for those that are listening, that don't have the benefit of seeing this.
And by the way, in the show notes, what Alison does is just incredible, but she took it to the next level because you can get the simple version of the Gracious Exit workbook. You can get that completely free. And so, she's paying it forward. and thank you so much for that. We'll put that in our show notes and you can click on that link and get that if you want to get a more complicated version as she calls it. it's a rounding error as a mere twenty-five dollars, and it's a fraction of a fraction of what you would pay in speaking to a professional advisor to help get that all in order. And so, I love what you've done. So, in the five workbooks, your first one, which is an Excel spreadsheet.
You have a total financial picture, then you move through to the medical history, your home team, your digital life, your wishes. And then you have, as you call them a appendix or maybe bonus sections, your friends and family to notify and then a to do list. And so, you've really covered the gamut from start to finish of what you should be looking for.
And Alison that as I was going through that, it also had me think you don't have to have this just for a passing. Heaven forbid something happened; some kind of medical situation happens. In a blink of an eye, you have all the information that you need for the medical team on hand, or, what the history is.
That can be just so crucial at that time. But here's what I was wondering. You've spoken to a lot of people about this, and you've been speaking to different presidents’ groups and CEO groups. From your experience and your conversations, what would be some of the top two or three things that people just tend to not even think of but are important, and they need to start thinking about that now, if you had to look back and think about that, what would that be?
Allison Winters: [00:35:01] You're right. Somebody has to step in if you're incapacitated, you don't have to die to be, unable to take care of things in your house. Most people don't really have anything written out on their medical situation. Even my husband. He lays out his bottles, and he knows what he has to take. But it wasn't written down anywhere. My dad, he did the same thing. Nothing was written down about who his doctors were and that was one of the first things I did with him.
I think those first two are the most important, those workbooks, where all the assets and what's your medical situation. The reason these things are so valuable to you even while you're alive and in charge of everything. When I go to a doctor, I take an updated sheet with me.
I only have to update it twice a year after I've had a doctor's appointment on the medical side, but rather than filling out those forms, I just say see attached and I give the doctor the list shows all my doctors, all my medications, any procedures I've had vaccinations. The works. I think the thing that, people really have to think hard if, what have they left off that financial list.
People have a lot of investments if they've been very successful. They enter partnerships. one, we thought of recently my husband has some interest in some horses we don't have that mentioned any place we realized. You can't just sit down and say, here's everything I have an ownership in. It comes to you because some of these things, you only think about a couple of times a year. In terms of an investment, you think of a displeasure, horse racing is his love. So, he doesn't think of that as an asset. It probably isn't an asset either, but, it's more of a liability, but he loves it.
If you can fill out those two things and then over time, keep thinking if there's something missing and part of the way you find that out is, and that's something I talked about in one of these other conversations that I had is simplifying your life. And as you go through files to see what you can throw away; you find things that you may be a forgotten about.
They're not very big, but you had them. I have a $1,000 insurance policy that my dad took out for me when I was a baby and I can't let that thing go. My dad took that out on me just to be sure I was covered. So, we all have things like that. I don't get a dividend. I don't think about it.
But once in a while I remember, oh yeah, I have that. There's not a failsafe in remembering everything. It takes a while to go over it.
Steve Wells: [00:37:41] You know what, it reminds me of Alison is when we coach business owners on how to make an exit. And when we talk about building their virtual data room, getting this data room together, because you've got to get all this information for the potential buyer and how, it seems like a simple thing, but how they can begin that process because, you want to sell tomorrow.
If you don't have that data room ready it could take you a long time. So, you're actually asking us to build our own personal life data room, which is very helpful. And, we talked to business owners about, how do you find the skeletons in your closet that you could make sure that you can take do something about, or those Rembrandts in your closet?
Our heirs they're there probably some skeletons, not, I'm not saying scandals. What I mean are issues that we've had to deal with that we may be passing on to them maybe need a backstory or information, or there's some opportunity that we haven't really discussed. And that could be a great opportunity to them.
Do you see that?
Allison Winters: [00:38:38] I haven't run personally across it, in these informal things I've talked about, but I did through a friend and, she has a beautiful antiques and collections of things in their home. Every time you go over and you compliment something, there's a story around that.
And she said, I want my kids to know the story of this, because it makes it so much more valuable to them to know that backstory to that Rembrandt as you called it. So, I said, if you got an iPhone, yes. All right. Do you know how to turn the camera around?
Take a room a day and just walk around the room slowly and videotape that piece of porcelain where you bought it, what it is, why it's special to you. Do you know how old it is, that kind of thing? And she has finished doing her whole house and she feels so good about it and comfortable with it. And I just had a similar experience.
A couple of weeks ago, my daughter was down and I. Hadn't had her look at my jewelry and I did love jewelry. I still love it, but I don't wear it as much anymore. And I wanted her to have some, she doesn't wear much jewelry in the kind of work she's in, but I was going through and I'd say, this your dad gave me.
And she said, mom, I really, if I knew the stories behind these different pieces, it would mean more to me. So, now I'm got that on my to-do list of what is the story behind key pieces of jewelry that she'll inherit and she'll know that she's wearing something that her dad picked out,
Jeffrey Feldberg: [00:40:16] Alison what I really like about what you're doing and Steve had referenced a moment back, but it's so true.
You're really preparing people for their final exit, if I can use that term, but in preparing people for that final exit, it's also a celebration of life. And as they go through your workbooks and as they begin that preparation. You're helping them find the Rembrandts in their attic that can become the stories of family lore and be passed on from one generation to the next that otherwise wouldn't have happened.
That's an incredible gift that you're giving to us. And, thank you. Thank you for putting that out there and being able to get that done, it's easier said than done. A quick, personal story since we've been sharing some personal stories. My grandfather was from the generation where they just didn't talk about anything.
And, at one point in time, when he was still in terrific health, I sat down with him and I said, grandpa it's amazing that you're here and you're healthy and you're with us, but there's going to be a point in time where that's not the case. Can we talk about this? Tell me what you want and what that would look like for you and what your preferences are?
And he just found that, for his own reasons that he didn't really share, he couldn't do that. And so I'm wondering as we begin to wrap things up here and, our listeners will hopefully take these wonderful resources and apply them for themselves, but also speak to their loved ones. Is there any advice you have in a situation like that, where it's just difficult for someone to share what their wishes are for their passing?
Allison Winters: [00:41:44] I do have something. This is something called the Go Wish Game. It's a deck of cards. What could be possible wishes that someone would want? To have my family, with me. To be able to talk about what death means. To meet with a clergy or chaplain, to be able to talk about what scares me, to have my funeral arrangements made, to keep my sense of humor.
These are all things that they want to make sure that they're hoping they have. when they die, or in those weeks or days or months leading up to their death. You're trying to get to how do you want the end of your life to be, do you want to do anything possible to prolong living?
Or do you want to just be comfortable and have family around and anything in between? Do you want visitors? Don't you want visitors? but that's maybe one thing and I'm happy, as I said to send each of you a deck of these cards. There's not a simple answer.
My dad wouldn't talk to us about anything, and it wasn't until I was, in my late forties. and he was in his late eighties. He did tell me when I was in my late thirties, that I was going to be the representative, because I had that background. And that took him a long time because he had four sons and then I had an older sister, but I had the background for it.
But he finally did want to open up and he is of that generation that never talked about anything. He was from that greatest generation and they gave back, but they didn't talk about themselves. Then they definitely didn't talk about money.
Steve Wells: [00:43:22] Alison, there's always a question we ask every guest and it's a fun question. and I'd like to ask it to you now. What would you tell the young Alison, the young woman, maybe even the girl, if she were there in front of you right now, after you've lived this valuable and enrich life? Any advice you'd give yourself from back then?
Allison Winters: [00:43:42] I think I'd give the same advice as my mother gave me. And that is always be able to take care of yourself. There's so much encapsulated in that always be able to take care of yourself, some might think it's too self-reliant at times, but that resonated with me because her, father had abandoned the family and, during the depression and my grandmother had a very tough time.
Her older siblings had to leave college so they could, help out. and my mother had to change high schools from the private one she so loving and to a public one where she thrived because it was what it was. And she dealt with it. That's the biggest advice that I would give to myself, is always be able to take care of yourself.
Jeffrey Feldberg: [00:44:32] That's wonderful advice and a terrific interview. Alison one last question for you. As we wrap this up. If somebody would like to find you and get in touch with you online, what would you suggest?
Allison Winters: [00:44:45] email@example.com and that gets forwarded to my personal email.
Jeffrey Feldberg: [00:44:50] It's been a true pleasure. Thank you so much for your time, your wisdom and your insights. And as we wrap up this interview, please stay healthy and safe.
Allison Winters: [00:45:00] Well, this was a lot of fun talking to both of you and, I love the suggestions and things that you came up with as well. So, thank you for sharing with me.
Steve Wells: [00:45:09] Thank you.