Make It Last – Ep 8 – A Widow’s Guide with Anna Byrne

Losing a spouse is a traumatic event. No matter how it happens, you’re never really prepared for what happens afterwards. This week you’ll be introduced to an author and estate planning attorney who has written the guide for navigatingnthe next steps you have to take after losing your spouse.

Anna Byrne is an estate planning attorney and investment advisor. She is also a widow herself and shares her personal story about the loss of her spouse and the advice she has for taking the next step forward.

Make It Last with Victor Medina is hosted by Victor J. Medina, an estate planning and elder law attorney and Certified Financial Planner™. Victor provides 360º Wealth Protection Strategies for individuals in or nearing retirement.

For more information, visit Medina Law Group or Private Client Capital Group.

Here is the link to the show:

Make It Last – Ep 8 – A Widow’s Guide with Anna Byrne

Click below to read the full transcript…

Bert:  Welcome to “Make It Last,” helping you keep you legal ducks in a row and your nest eggs secure with your host, Victor Medina, an estate planning and elder law attorney, and certified financial planner.

Victor J. Medina:  Everybody, welcome back to Make It Last. It is Saturday morning, June 3rd. I’m going to be talking to you today about some mistakes that people make in retirement. I’ve got a special guest today. Her name is Anna Byrne. She has written a fantastic book called “A Widow’s Guide ‑‑ Your Legal and Financial Guide to Surviving the First Year.”

She is a friend of mine, as well as a very just accomplished estate planning attorney and investment advisor. She’s written a fantastic book. I can’t wait to get to that interview.

In the meantime, I wanted to say thank you to everybody that has been listening to the show and sharing all of their kind comments about how well it’s going. We think it’s been going great as well.

I’ll tell you something. If this is something that you like, I would appreciate it if you share it with your friends. This show is about helping you keep your legal ducks in a row and your financial nest eggs secure.

If you know somebody who could benefit from doing that, I think you ought to send them the link to the show and tell them to tune in, or what you could do is even give them the link to the iTunes podcast. We’re on all of the podcast catchers that are out there, on iTunes, or you can get it on Android, you can get it on Stitcher.

If you share that link or if you make search for Make It Last, you can subscribe, and not only listen to this show but listen to all the prior shows as well. If you have any ideas for any shows that you want to hear more about, I’d ask you to go ahead and send it to

If you do that, you’ll suggest them show topics for us and we’ll bring them in to what we have to talk about. Thanks so much for all of that.

I don’t want to waste any more time. I want to go right into the topics because we have lots to cover today. The topic that I wanted to cover first in the first segment before we get to our special guest is, I read this fantastic article about mental mistakes that people are making with their retirement spending.

It struck me as being very, very accurate because when we come in and meet with retirees…My job, what I do with clients is try to help them preserve their wealth. We might think of ourselves as wealth preservation or wealth protection strategist.

What we’re trying to do is make sure that whatever they have accumulated during their lifetime, they don’t lose and that they pass it on as effectively and efficiently as possible, as protected as possible. That has led to some mistakes that come in thinking about before they get to retirement that carries through until we help educate them differently.

We’re going to go through eight of those of mistakes. We’re going to go through them as quickly as possible.

One of the ones that I think hits people hard and it comes up a lot is the idea of longevity and how long someone is going to live. It turns out that the studies are suggesting that you will die sooner than you think. I’m just trying [laughs] to think of a nice way of saying that but there’s no nice way of saying that.

According to the data by the Social Security Administration, a man who reaches 65 today in 2017 can expect to live on average until about age 84. A woman turning 65 today can expect to live on average until about 86.

That’s a little bit younger than most people think. They think they might get it to 90 or later. It turns out that only about one out of every four 65‑year‑olds today will live past age 90.

That contrast with they study on people’s belief because that reveals that while younger people underestimate their longevity, older people overestimated it. On a survey, there are 68‑year‑old men, 71 percent of them believe they have a chance of living to 78, but they have an 82 percent chance of actually reaching that age.

They overestimate that by almost 10 percent, by 10 percent thinking that they’ll get there but the numbers don’t suggest that. That overestimation relates back to a mistake in retirement spending because people also overestimate how much they will need in retirement and underestimate how much they can spend.

We’re certainly not suggesting that people go crazy and try to coast in at 95 not owning anything. On the average, people can actually increase their spending habits in retirement a little bit more than they think.

They have to do that smartly. If they’re constantly liquidating their account to spend that money, if they haven’t put a plan around this retirement spending, they could actually run out of money a little bit sooner. Depending on market conditions, it may not work out well.

You have to have a smart plan. I think that’s what I’m trying to leave you with. You have to consider your retirement income spending as part of different buckets that you have. You’re going to have in certain buckets that you spend on, somebody’s guaranteed income, somebody’s money that you can use.

The idea is that you should probably increase your spending if what you’re calculating is that you’re going to live to 95. Another mistake that people make in retirement spending is a delaying that gratification to spending on the good stuff.

My parents are an example that I like to highlight because I have been encouraging them to do things like take trips now. They’re a little bit younger on the younger side of retirement. They’re on the upper side of 60.

While they’re certainly not saving money for retirement, they haven’t thought about, “I’m going to do that later.” I’m trying to impress upon them this idea that you’re not going to have the opportunity to do that later. You’re not going to be able to walk the cobblestone streets of Spain when you’re 80.

That’s not going to be something that you’re going to want to do. What we ought to be thinking about is actually enjoying that stuff today and not worrying about so much being financially prudent and delaying the gratification because people who get older suffer physical limitations that makes them less capable of spending that money.

For personal reasons, the older that they get, a spouse may pass away. If they do, they’re less inclined to spend money. They’re less inclined to take those trips around. I think it’s important to remember that you could be spending more money. You could be doing it sooner rather than waiting for later. That’s what we’re thinking about here.

There are other mistakes that have been made. I’ll give you some of them. Some have to do with investing. One of them has to do with trying to time the market and doing their investment management as they get older.

Trading in your retirement portfolio and managing that and not asking somebody to help, I think, is one of those major mistakes. In fact, “The Wall Street Jounal” article agrees with me. Trading by amateurs is akin to baking by amateur bakers.

You’ll never get a good loaf of bread because you’ll constantly be opening the oven door all the time if you don’t have the experience to understand how things work.

All of the research suggests that in fact investors are notoriously bad at evaluating the risk they’re taking with their portfolios. That’s because they’re thinking the way that they were when they were still in the workplace.

They don’t realize that the wealth of young people is in their income. When you’re retired, it’s in your savings. You can’t afford to take as much risk because you can’t fall back on the human capital that it took to essentially make that money. That makes sense. You can’t go back into the workforce and make it up by saving more and letting that time.

You need to be thinking about taking your retirement savings and putting them in a well‑diversified portfolio which includes in many cases guaranteed retirement income because if you miss out on that, if you miscalculate that, it can have serious impacts because you neither have the time nor the ability to make that back up.

You can’t go back into the workforce, you don’t have time for that market to come back on you.

The last one we’re going to leave you on in terms of the mistakes is that it’s often better to give with a warm hand than a cold one. When we ask clients, “What do you want to leave behind?” They always say that they want to leave their stuff to their children in equal shares. I said, “Is there anything that you want to give them now?”

While people also over estimate how long they’ll need money and they’ll under spend on that, leaving that gift for after you’re gone is probably less enjoyable than doing that during their lifetime. There’s a lot of joy that’s related to giving. You may want to think about doing that while you’re still around as opposed to after you’re gone.

Those are the major mistakes in retirement. When we come back from the break, we’re going to talk with Anna Byrne, an author…

Victor:  …who’s written A Widow’s Guide ‑‑ Your Legal and Financial Guide to Surviving the First Year.

I think this is going to be a great topic because many people do have to deal with the loss of a spouse and moving on from that and understanding what steps they have to take. I think it’s going to be great because people get so lost at that period of time.

Anyway, join us when we come back with special guest, Anna Byrne, here on Make it Last with Victor Medina.


Victor:  Welcome back from the break. I have our very special guest, Anna Byrne. Anna Byrne is an estate planning attorney as well as an investment advisor, so a little bit like me except that she hails from the great state of Massachusetts.

She’s our guest today because she’s written a new book. That book is called A Widow’s Guide ‑‑ Your Legal and Financial Guide to Surviving your First Year.” Welcome, Anna, to the show.

Anna Byrne:  Hi, Victor. Thanks so much for having me. I’m delighted to join you.

Victor:  Thank you for making time in your schedule to talk about it. As you may know, this show is about helping people through the retirement journey. One of those steps for our married folks unfortunately always deals with the loss of one of the spouses.

This idea that there are things to do and that there’s a journey involved in that, I think is something that’s underserved in the counseling that goes on. I want to get to the book, but before we do that, just give listeners a little flavor of your professional qualifications like what got you to where you are and what do you do today besides being an author?

Anna:  I started my career. I have to do the numbers, but it’s about 22 years ago. During these last 22 years, I’ve been a trusted advisor in several capacities. I started out my career as a tax attorney working around the dot‑com boom.

I was advising business owners, entrepreneurs tax strategies around liquidity events that they were anticipating whether it was through an IPO or a sale. After my first husband passed away, I pivoted and I was hired to be a corporate attorney for an incubator where I started companies.

I basically was on the other side of company stock where I was creating the company stock and understanding how all of that works and how it’s all structured, and advising the CEOs whose companies I was either helping fund or getting going.

After the whole dot‑com boom went belly up, I ended up back in the world of investment financial tax advising where I had a firm called Kirkland Advisors. I worked with a couple of public companies where I was advising their employees on their stock options, on their restricted stock, on the tax implication of that.

Finally, I ended up in the practice of law for the first time in a private practice working with more main street business owners, main street mom and pop shops businesses, as well as individuals. I realized that they were very, very underserved in terms of advice on tax on estate planning.

About 2008, 2009, I realized that I had a personal story, a personal story that came from the loss of my first husband who died very suddenly. I realized that in order to serve my greatest purpose, I needed to marry that professional experience with my personal experience.

That was when I decided to start my own estate planning practice where we do planning a little differently. We know that our days are numbered on earth. We know that’s going to happen. It’s very scary. We’ve created a process whereby clients become partners in the process of planning, become invested in planning.

More recently, I decided to create a financial services company or actually resurrect Kirkland Advisors as Kendall Wealth. The birth of that company comes from the fact that once you have your estate plan, it’s time to have a good life. I am very much focused on helping people have a good life especially those that are going through transitions like divorce and death of a spouse.

Victor:  You let the cat out of the bag a little bit in terms of your qualifications to write this book about A Widow’s Guide. You said that you lost your first husband. Set the timeframe for us about how long ago did that happen.

Anna:  It will be 18, 19 years this October.

Victor:  You wrote this book about a year ago. Can you talk a little bit about what brought you to the point of wanting to share that story, when share the lessons that are in the book about some of the practical steps that people can take afterwards? How did you get to writing this?

Anna:  I have been working with women in my practice for, I don’t know, since 2009 and well before that. I saw a common struggle but they all were experiencing in their journey from the initial shock to three years later feeling stronger, feeling more empowered in some way.

I felt that every woman in particular, but every person who certainly goes through this needs to have some framework to go through this journey. In my personal experience, it took me 18 years to get this book out.

This was a big hurdle. There was a lot of fear associated with writing the book, fear of a lot of different things. What ultimately led me to write this book was the desire to help people and to coach people in a very supportive way through this extremely difficult journey.

Victor:  Do you mind sharing how much of the lessons that you share in the book are things that you knew when you lost your husband? Are they all things that you had to learn the hard way over the course of the 18 years? How much of this was something that you personally experienced?

Anna:  I would say that when Ron died, I was an attorney already for, I guess, four years. He was an attorney. I had already worked in tax and estate planning. My exposure to this area was already there.

I was paralyzed after he died. I felt like any discussion around money, anything dealing with estate was just this horrible stab back in my heart. Any money, any life insurance, anything that dealt with money was just blood money. It was somehow meant to replace my wonderful husband who I miss terribly.

When I wrote the book, I wrote it from the perspective of I have walked in his shoes. I’ve had to go through all of these steps on my own and make these difficult decisions on my own.

The framework, I didn’t have when I was going through it myself. That framework is one that I have created over the years in working with my clients.

Victor:  Let’s do this. We’re going to take a quick break. When we come back, I want you to talk a little bit more about some of the practical lessons that are in the book and things that listeners can take away from that including where we’re going to find this book and why we should buy it. Do you mind sticking with us through the next segment?

Anna:  Sure.

Victor:  Sounds great. Listen, we’ll be right back with Make It Last…

Victor:  …where we are joined today by Anna Byrne, estate planning attorney and investment advisor. She’s written A Widow’s Guide ‑‑ Your Legal and Financial Guide to Surviving your First Year. Stick with us on after the break. We’ll talk about what you can take out of this book and use in your own lives.


Victor:  Welcome back from the break. I’m joined today by a special guest. Her name is Anna Byrne. She’s an estate planning attorney and an investment advisor. She runs her law firm through Eckert Byrne and her financial advisor firm through Kendall Wealth. She’s a practicing estate planning attorney and an investment advisor in Cambridge, Massachusetts.

She’s authored a book called A Widow’s Guide ‑‑ Your Legal and Financial Guide to Surviving your First Year.” Anna, you shared with us a very personal story of the fact that you are a widow and some of the struggles that you had dealing with the after effects of that.

I love this book. I got to tell you. I got the chance to read through it. It’s just wonderfully‑written. Personal parts about what you had to go through, and sympathetic ears to what other people need to go through, but there’s also this practical side in that and these action lists and journals.

Tell me a little bit about your decisions to marry those two things together, and what you think is important for people who’ve lost a spouse, and how they move on. Why do they need to keep these two things going at the same time?

Anna:  By the two things going, do you mean the legal and the financial?

Victor:  No. I actually mean the soft issues about journaling and dealing with the emotional after effects of the loss, as well as the practical steps of putting one foot in front of another. Your book marries those two things together.

Anna:  The book is a way for women to start conquering their fear and focusing their attention on positive small steps that they can take to move forward. The book is laid out in a way that…It’s hard to see the light. It’s hard to see that your heart will ever mend, that you will ever be able to focus again, that you will ever be able to wake up and feel OK.

I want to share my personal story as an inspiration, because I have come out to the other side where I have happiness in my life and I have a completely different perspective even though I remember those dark days.

The book is laid out with some very practical information to provide an understanding, a basic understanding of what is going on, because this is something that I have found that women in particular are so afraid that they don’t know what probate is, they don’t know how things work.

I wanted to provide an education about what the process actually is, but then also practically outlying tasks with a check box that you can go through yourself. You can have someone help you but the whole purpose of this book is to provide people this forward motion.

The journaling pages are part of that, because I recall when months after Ron died, my mom and dad forced me to go see a therapist, and I thought, “Jeez, I don’t need to talk to someone.”

To humor them, I went through this process, and I met with this therapist, and I said to him after a couple of sessions, “I feel like I don’t need you. Can you just explain why are you thinking this is a benefit to someone like me?”

He said, “Well, because I don’t have a personal relationship with you, and I cpi;d honestly give you a sense of how you’re moving along in your journey, and that you’re actually making progress.”

The journaling pages are represented about that. He was so right. He was so right, because I did not see my progress. I couldn’t see my progress. I was blind to it.

If you write it down, for example, you can go back a year later or months later, and look at that first entry, and see how you were feeling compared to how you’re feeling today, or the questions that you had that you’ve now answered.

It’s about giving women in particular this feeling of forward movement and an ability to go back and say, “Wow. Look at all these boxes that I’ve checked.” That’s all you do, or look at the journal pages that you’ve gone through and you can see that progress, because every single person going through this journey makes progress.

It might be small. It might be large, but you’re making progress and it’s wonderful if you can somehow document it so that you can see it and feel proud, because part of getting to the other side and of getting through this grief journey is overcoming all of your fears, and overcoming your anxieties.

That’s what I wanted this book to be, is this guiding light through this journey with practical steps as well as a personal way for you to document what you’re doing and of on a monthly step‑by‑step basis so that you can look back and feel proud of what you’ve accomplished.

Victor:  In your life, you have the help of the objective emotional support of a therapist, and then you brought the background or the legal and financial in large part because of your professional training. Do you think there’s a role in widows’ lives for that objective legal and financial advice? If so, what does that look like?

Anna:  Absolutely. There’s basic information that I provide in the book, but it’s certainly not enough to be able to make specific decisions on their particular situation. I feel very strongly that having a team of advisors working together in an orchestrated way is in the best interest of the widow.

Partly, where they need to begin is accepting the fact that they need help. That’s difficult, help in the sense of friends, help in the sense of professionals. I think one of the hurdles is how do you go about finding a professional that is the right professional.

Victor:  That’s what I was going to ask you exactly. How do we figure out who that’s right, right for them? Do you have advice on that?

Anna:  I do. In the book, I’ve actually offered a series of questions that they can use to interview an estate administration attorney, a financial advisor, things to ask. Things like how do you bill, how are you going to communicate with me, and all of those important things that you may not think of.

I wrote those all out. There are questions that you can take with you as you interview your professional. I would say the key advisors are obviously the attorney who’s going to be helping you make these legal decisions and taking you through the legal process of settling an estate.

Having a financial advisor is critical because the big question ‑‑ and I’ve seen this over and over whether you have a $25 million estate or a $200,000 estate, the biggest fear that someone is facing is, “Do I have enough money to pay my bills?”

Having someone who can sit down and objectively say, “You know what, Sarah? You are fine, because here’s what you have and here is the projection that I did for you in terms of cash flows, and so on, and so forth.” The attorney, the financial advisor, and the tax preparer.

Sometimes you have one, that’s great. Other times, you need to go out and find an accountant who can help with various other aspects of your financial life, dealing with taxes. Someone is going to have to help you with that. The book definitely has questions that you can use to interview these three different advisors.

Victor:  That’s great. Like I said, I love this book for no other reason. I mean, it’s substantively fantastic. I think it also has a great fanciful attraction, which is that the cover is made out as an adult coloring book. With nothing else, people can occupy their time [laughs] by coloring in the cover along the way.

If people want to learn more about the book, in fact even to buy it, where can they go to learn more about the book?

Anna:  I self‑published this book. It’s available on Amazon. You just have to search, Anna Byrne, A Widow’s Guide in the search bar on the Amazon website and you will find me.

You could purchase the book. You can preview the book a little bit as well. I believe the first chapter’s available for free preview. You can also go to my website that I have set up for my book, that’s called,

Victor:  What we’re going to do is we’re going to drop that into the show notes for people that are listening on iTunes and want to go to the website.

If you’re listening live on the radio, you can go to and check out episode eight, and we’ll put a link there that will give you the link. Anna Byrne is A‑N‑N‑A. Two Ns there and it’s B‑Y‑R‑N‑, and you can check out more.

Anna, I want to thank you for being my guest here today. This is great information to share with other people. I think that if there’s anybody out there who has personally experience a loss or knows of somebody who experiences loss, and purchasing this book and giving it to them, I think it’s probably one of the best gifts that they could give.

Thank you so much for spending this morning here with us and sharing this great information. You’ve been a fantastic guest.

Anna:  Thank you so much, Victor. I appreciate you inviting me and allowing me to share my story.

Victor:  Well, this has been Make It Last with Victor Medina. I want to thank you all for joining us. I want to thank our guest, Anna Byrne for joining us here today. Again, if you’re interested in learning more about that, you can go to That’s A‑N‑N‑A‑B‑Y‑R‑N‑

If you like this show as well as any of the other shows that we have, feel free to subscribe on iTunes so that you can get this show delivered to your email inbox, or your favorite podcatcher, as well as going back to listen to old shows. We covered things like annuities, IRAs, everything that’s important for you in retirement.

I want to thank everybody who helps produce this show. There’s a great team behind this that puts this show together. This has been Make It Last with Victor Medina, where we help you keep your legal ducks in a row and your financial nest eggs secure. Join us again next Saturday.

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