Losing a loved one is not just emotionally overwhelming but also legally and financially stressful. When it comes to the financial stress of grief, you should never deal with it all by yourself. Otherwise, you might find yourself broken beyond repair. I sit down with Chris Bentley of Wings for Widows who discusses why you should seek professional help when making major decisions regarding your assets after losing a loved one. He also breaks down the most common mistakes widows – and even widowers – are making after their partner’s passing and what must be done to finally correct it.

I am sharing my experience of loving the same man for 32 years, a mother to two adult children, a retired military officer, a breast cancer survivor, and my connections with others.  

Anyone experiencing suicidal thoughts should reach out to a suicide hotline or local emergency number in their country: Psychology Today Suicide Hotlines and Prevention Resources Around the World.

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Dealing With The Financial Stress Of Loss With Chris Bentley

Widowhood is complicated. The financial challenges that are involved in this process are daunting. Oftentimes, we may not be familiar with the finances, but we need help. What happens when your spouse passes, and they had a credit card bill only in their name? Do you know what to do in that situation? What if the house was in their name and not yours? What if the car? What if you are trying to go back to work and you are looking for childcare?

These questions can be answered in the conversation we are about to have with Chris from Wings for Widows. The information that he shared gives life. Tax return help, financial advisors, free help for the widowhood. I encourage you to share this episode with everyone that you know. Widowed or not widowed, the information that Chris is going to share is going to change your life. Let us get into this conversation.

Chris, welcome to the Widowhood.

Thank you, Tina. I am so blessed to be here.

The widowhood smile, what is the inside version in your head when you hear welcome to the widowhood?

In the beginning used to think of Mr. Rogers, Welcome to the neighborhood. That little song goes off in my head, and welcome to the neighborhood. Widowhood is not a group you want to welcome anybody to. There is that side of the coin. If they are part of that club, that is why we are here. That is what we are here to do is to try to help them out.

I am not a widower. I do not know what that experience is like, but I have a heart for widows and widowers. When I hear about widowhood, I immediately know that this is someone, regardless of where they are on their journey, who has suffered a lot of pain. Again, depending on where they are in their journey, they have struggled or have learned a tremendous amount about themselves and perhaps others.

It is a transitional experience that I would not wish on anyone. Over a million people experience it every year. It is a reality. It is something we have to deal with. I am just glad I am on this side of the coin. I am able to help folks who are making that transition and are in that part of the club. I am also fortunate that I have not experienced it.

When you talk about having a heart for the widowhood community, I do not know if that does it justice. Maybe in this question it will. What moment or realization led up to you hanging up your stocks and bonds for widows and widowers and the creation of Wings for Widows?

That moment of clarity was when I discovered there were no organizations that provided free services for widows and widowers to deal with the practical side of loss. There were lots of services paid or otherwise that were available around bereavement and grief. When I went to hunt for services for some folks that I had met, some widowed people that I had met, I thought for sure I would be able to come riding back on my white horse and share all of these resources for them.

That did not happen. That was when the light bulb went on that if these resources do not exist, A, why not? B, they are so necessary just on the surface. Is there something I could do? That realization materialized in this thought that once I did a little bit of digging, there were so many who do not have a professional network. Where are they going for help with the practical matters of loss?

Meaning budgets and healthcare, and claiming benefits, and changing titles of ownership, and all the things that have to be done after a loss that most people have to contend with on the spectrum of stuff to do after a household goes from 2 to 1, there is a lot of stuff to do. I realized that there is a very small segment of that population that actually has a professional network.

They are going to be okay. As a financial professional, I was working with those people, but what about all the other people? Where were they going? We found out they were going to places that were not giving them the correct answers, and the best advice. That was the moment of clarity, when folks need help the most, it is not available.

I wanted to do something about that. You are right, a heart for this mission or a heart for the plight of widows and widowers in this country, having a heart for it is a pretty good start, but it certainly takes a lot more than that. That a-ha moment for me as a spiritual person, as a man of faith, I really thought I was being called to do something, to act, not to just walk by and say, “It is a really big need out there. Somebody will fill it one day. I decided that I was called to be that person.” At least get it started.

When you say called, can you elaborate on your level of commitment and how your life changed in that call?

I did not see it coming. You rarely do when he calls. You do not know everything he has in store for you, naturally. Initially, it is like, “I will just see if this makes sense.” We will go out and meet with some widowed folks and see what their needs are, and see what advice I need to give them. I mean, it was so simple. They did not even have a checklist. That materialized one improvement after another until today, it is quite different.

Why Do You Need Professional Financial Help In Your Grieving Journey

Chris, during our pre-podcast conversation, you mentioned the need for every widow or widower to be able to have professional services. When you say professional services, what does that look like?

Much of the practical side of loss is financial in nature. Yes, there are generally some legal things that have to be done. It may not be just one professional. It may be a team of professionals. Frankly, a lot of people do not have a team of professionals. It might require a CPA or someone to help you with the taxes because the tax situation changes. It may be a state planning attorney to help with updating the will or the trust documents. Certainly, all the beneficiaries need to be changed. That might require some legal help, but generally, that can be done by a financial advisor. Those are the kinds of professionals that are most necessary for most people after losing a spouse.

Someone tuning in to this may say, “With my significant other, past or maybe my child or my mother, I had their last check and maybe the house and a car. What you are talking about is way too complicated. I do not need all of that.” What would you say to a person thinking that?

When folks think of financial advisor, they immediately assume there is an assumption that they have to have a lot of assets or they cannot work with a financial advisor. That is a misconception because it is not the case. If you have any assets, there are a lot of decisions to make around your financial wellness after a loss. It is nice to have someone who has been around the block and understands, even if there is not a whole portfolio of stocks and bonds, but making decisions about the house, should I refinance or not?

Can I afford to stay in my home? Should I be thinking about moving or downsizing? Those are huge questions to consider. Many times, those types of large decisions should not be made early on in widowhood, and certainly should not be made in haste. Rather than having the emotional tendency to get all these things done and perhaps move and do this and do that, to bring in a professional, like a financial advisor, that could sit down with you and walk through these scenarios, it takes some of that emotion out of the equation.

You are working with a third party that does not have that same level of emotion or desperation, or other concerns. It could be that third party with a clear objective about here are the scenarios, here are the things that we will work through, really making sure that you, the widow, have a very clear understanding of your entire current situation, what has changed as a result of your loss. For most, that is often the income. You had income. If that goes, and the average is 37% after a loss of a spouse, for some, it is 100%.

If the only breadwinner is the person who passed, then income could go to zero very quickly. That is a crisis. Crisis brings emotion. Rather than make these decisions at haste to bring someone in who can be objective and look at expenses and look at income or other sources of income or savings or assets, and how do I turn those into income, which is a treatment that we need to entertain sometimes. Is there value in the home? Can we take some of the value of that home and turn that into income for you and your family? You do not have to have a lot to learn a lot and benefit a lot from a financial advisor. I would say that the professional you start with is usually a financial advisor.

That question comes up with people very often. From my experience, as we are having this conversation in our voices of widowhood healing through the holiday season, if I have this right, this conversation will air in January. People are starting to think about their tax returns. They may have had a loved one who just passed during the holidays. It was just a few months ago, but it literally was last year.

How is that going to impact their 2025 tax returns being filed in 2026? There are a lot of decisions that need to be made. The emotional part of widowhood, I do not think people recognize a lot the way stress and trauma, and grief impact our body. I consider myself a high-functioning individual.

I was in the army for twenty years, an army officer, a lead team supervisor. My husband died. I could not remember what I did an hour ago. In my reading, understanding the neurological impact of grief on my brain, the idea that my prefrontal cortex was not operating strategically and I was in more of a fight or flight mode, I may have looked the same on the outside, but the tiredness of grief, the inability to sleep, now my brain is not operating at capacity and I am exhausted.

I am still trying to figure this out. Now making major life decisions, it is hard to function, let alone to find someone that I can trust to help me make these decisions if this is not a place I am familiar with. I have seen so many widows and widowers being taken advantage of in this very vulnerable state. How are you able to help them find a trusted individual, and what does that look like?

Those are all really great points. You said it so well, because it is like the perfect storm. Everything at once, because of the grief, the loss, the anguish, then having to make decisions, but you have got widow fog, and you cannot make the decisions, you cannot remember. You are supposed to make all these decisions, and that adds to the stress. It is a vicious circle. We see that, and we understand that.

I will get to your question, but one of the reasons that Wings for Widows only recruits certified financial planners because in their own practice, in their paid practices, they are known as fiduciaries. Meaning they put their client’s interest first, well above their own. That is just a requirement of earning that certification. We, Wings for Widows, do not just hire anybody who says, “I am a coach,” or “I am a financial coach.”

These are highly credentialed individuals who always put our clients, Wings for Widows clients, first. These are trusted individuals. That does not make it a whole lot easier, but it is true. Again, there is this myth that this is a professional with all these credentials, and I have never worked with a financial advisor before. Even though my brain is telling me to call this person or go work with this person or go to Wings for Widows and find a coach because it is all free, why wouldn’t you?

The reason is that there is a certain amount of whether you call it embarrassment or unfamiliarity. “What is going to happen? I have never worked with somebody like this.” Maybe some money shame. “I should have saved. I should have been a better saver.” Those sorts of things, or “I do not know enough to work with somebody. I just do not know. I was not part of those meetings, nor my husband and I, nor my wife and I. We never talked about it. Now I am supposed to know all these things, and I do not know them. I am supposed to share this with a stranger.”

It is a little weird. A little scary. Intimidating is a great word. We do see that. Yet if you can’t tuck that away and use a little bit of faith and trust in all the others that have gone before you, that have come to Wings for Widows in particular, that had nothing but great things to say. This massive wave of stress is gone. There is hope again. We just worked on a story with a 33-year-old widow in Florida, who speaks five languages, has only been in the US for a few years, and was just weeks away from getting her citizenship. Her husband died.

There was no money. We found out he canceled his life insurance. Nothing was coming to her. There was no money. The house was in his name, so she had to deal with that. She was not going to get her citizenship. The car was in his name, and she did not know how to drive and did not even have a driver’s license because she did not know how to drive.

Suddenly, she is at the helm of her entire life. She took a chance and reached out to us. We righted all of that, fixed it all. Worked with the VA, worked with the church to get her driver’s license, worked to get her a job, and all of these things. This incredible relief for someone who was left in such a really shaky, bad position with the clock ticking, going to run out of money, “What do I do next?”

She said, “I have got to get help. I do not know, I am going to lose it all if I do not go ahead and take a chance on Wings for Widows.” We jumped through hoops and turned things around for her very quickly. I am fortunate that she came to us. Not everybody is ready to do that, which is why we offer some of our other services that are less perhaps intimidating. Go at your own pace. You can get a lot of good information, but you do not have to talk to a stranger about your finances.

Services And Programs You Can Get From Chris

What are some of those other services?

We have WidowWise University. That is a complete online education service. It has 60 lessons over 10 sessions that cover just about every topic that is relevant to a newly widowed person. Each course is about 8 to 10 minutes long, so they are relatively quick. It is just the most important things. What you need to know, what you need to do, here are the action items, here are the things to think about, and there are worksheets if you need a worksheet.

For every course, there is a closed caption video. If you are hearing impaired, you can still get the help that you need. That is a great place for folks to go. We give a scholarship. There is a small charge for that just to cover our expenses on that. We also give Project CARE Scholarships if someone cannot afford them. It is $19. If somebody cannot afford it, we will forego the $19.

Your university charges $19 for each class.

$19 to have access to it all. We have over 100 scholarships now for folks there doing that work. That is one option. You do not have to go speak. The only thing that the university does not give you, it tells you all the things you can do, but it does not tell you exactly what you and your situation need to do. Each course, each lesson is siloed. Everything you want to know about applying for healthcare, or Medicare, but it does not tell you what you need to do in your situation, with all the other factors that need to be considered. That is the difference.

When you are working with a financial advisor, they look at everything, your entire situation holistically. Sometimes the advice is different based on having the full picture. The third is just our website is just chock full of resources. It is about 100,000 visitors a year, which is growing. This year, we launched what we call six specialty hubs. There is just a ton of information at no cost. For example, taxes, you mentioned.

Our November newsletter will be about taxes and getting ready for the new tax season. What has changed? What might impact you as a widowed person in 2025? What are some of those things to think about in 2026? You can sign up for our newsletter. There are twelve monthly issues. We tackle a new issue every month, with about 10,000 subscribers for our newsletter. That is completely free as well, which is really great, the first year or two to get that advice coming into your mailbox every month.

The website, like the hubs, has a tax hub. Between now and April, it will be one of our most heavily visited places on our whole website because there is not as good place anywhere else on the internet for widows to come and learn all about what would apply to them in terms of taxes. That is our tax hub. We have a social security hub because it is very confusing to people when they lose a spouse, what are their benefits? What am I entitled to?

We cover all of that on our social security hub. We have a solo parenting hub for solo parents to look at all the considerations and things to do as a solo parent, and on and on. One for debt management. “Why do I have all this debt? I need help. Where do I go?” You can come work with a coach, or you can go to our hub and learn about all the things that you should be considering, or you can go take a sign into WidowWise University and learn about debt management there. Lots of options. Everyone learns differently. We have a service that will meet most of those folks looking for help. They will find it one way or another.

Worst Financial Decisions Grieving People Do

What I am hearing you say, if you are not ready to connect 101, you can use the university style, learn the information, and gather. Maybe that is the first step, feeling less intimidated, an intro into that. Now I have gone through the university. Maybe I can just start and reach out and go, “I have all these different things, and I need someone to help.” When people come to you for assistance, have they shared what items or what process, or what thoughts kept them from asking for help quicker or sooner?

We do learn that, but we learn that at different times. We learn it when they actually become a coaching client. We will get some of that information because we do provide some client surveys to just find out before, during, and after. We get some of that knowledge. Most of it was that I was just too busy, and I did not make time to go figure out what you were all about. I remember there are several comments where “I wish I had found you sooner.” They found us a year later. “I wish I had known about you sooner.”

We wish that would happen too, because often some really bad mistakes happen in that first year. After all, decisions are made in haste. You have got that widow fog going on. You have got children you are trying to manage their grief. You are trying to manage your own. Sometimes we just make these decisions to check the boxes. I just want to I have got to get this off my plate. I have got enough on my plate. I want to just get this off my plate and move on. It turns out that was not a good idea.

You talk about decisions you found that were bad for people to understand. Maybe they are on the cusp of that. What are some of those bad decisions that you have seen that people have made?

The one that I see over and over is that they do not understand what their legal responsibilities are for paying bills. That is a big one because the bills come in. Maybe it was John who was paying the bills every month. John is gone, unfortunately, and now I am paying the bills every month. I just keep paying the bills even though some of those bills were John’s responsibility. If John took out a credit card in his name only at Home Depot, and John is gone, that is between John and Home Depot.

I do not have to pay that Home Depot bill. What you do have to do is call Home Depot and tell them that John has passed and would like to have the account closed. They may or may not do that. If there are enough of those accounts out there, then usually what happens is there is some sort of probate process, which ensures that if there are assets that the creditors are fairly equally or fairly paid before those assets are used by the surviving spouse.

That is all probate is. It is a very scary thing. Everybody thinks, “There are lots of ways to avoid it.” That is a very common one. “I did not know I was supposed not to pay that bill.” They pay it. We had one case where the husband, the spouse, was a consultant, had a whole consulting business and had that business for 30 years. He got sick, and the prognosis was not good.

As his health was failing, his wife kept asking, “What are we doing with the business? What is going on with the business? I do not know anything about the business. Are there things I need to do or learn about the business?” Finally, this individual said, “No, it is all taken care of. It is all closed down. You do not have to worry about it.” Lo and behold, this individual does pass, and a few months later, a notice from the post office comes in the mail.

She is now opening all of her mail. What is this, some business PO box for this individual’s business? “Why am I getting this?” It was all shut down. She goes to the post office and finds out that it was not all shut down. There was a box full of demand letters and letters and overdue, and past due notices. Now she takes this box home. She felt it was her obligation to settle up the score with all these business accounts of her past husband.

None of that was her responsibility. Unfortunately, she had taken her only life insurance money, a term life insurance policy, and paid off all of his debts and then was left with nothing. We met her after she had done all this. She wept when we explained that she did not have to owe it. Once you pay it, it is too late. You cannot get it back. Those are the kinds of mistakes. It is not knowing what should be paid and what should not be paid, and what you own and what somebody else owns.

You cannot just sell your spouse’s car if there is a loan out on that car. That loan needs to be satisfied, and the title needs to be changed, and all these legal things have to happen before you part with that car. It is very tempting. There is a car sitting in the driveway. I am not using it. I have never used it. I am going to sell it because I need the money. It is not good. There are all kinds of problems when that happens.

Thank you for sharing those because those are huge. The person with the credit card, and tell me what you have seen. I want to make sure their name is good. I do not want them to be dead. People feel like, “I made their name look bad.” Have you ever run into people with that concept versus the idea that business is done? They are no longer here. I am living, and I need funds to continue managing my life, which makes me have to make a business decision. At the cusp of our grief and our emotions, logic does not always prevail.

Logic does not always prevail. You have never been in this situation before. How would you know? Who would expect you to know the right way to approach bills coming in for your spouse who is gone? You just do not know legally. As good people, we have been raised to take care of our debts. I have not had anyone that I am aware of, maybe other coaches have heard it, where they have said, “I paid all those bills because I wanted to make sure that John’s name was in good standing.”

I have never heard anybody say that. They just do not know that they are not responsible, just morally. Legally, they are not responsible. If it were a moral issue, that would be different, but it is not. It is illegal. There is no legal responsibility for this survival unless it is a joint bill. When I am talking about just the bills that belong or credit cards liabilities liabilities that belong to the decedent, those are not legally the surviving individual’s responsibility.

No one has to feel bad about not paying those bills. It is okay. You are going to be fine. For those who have enough assets, they often will pay the bills because they just want to get the score settled and take care of all of that. They are sitting in an excellent financial position, and they want to do that. They certainly can.

For those and about 40% of the folks who walk through our doors, they are not in a financial position to just pay off all of those old bills. The one that always comes up, that is a bit of a mystery, is old medical bills. We get questions a lot. Those seem to be the last bills that not only do they show up after the spouse has passed, but they also come in late. They come in forever, and they keep coming in.

It is an emotional trigger. “You had the nerve to send me a medical bill? I cannot wait to get on the phone to tell you how this is not going. If anything, you want to trigger someone, they died. It is later, and I have sorted my mind and settled, and you are asking me for money for killing them.” That is what your mind is.

We do not handle that. We see that all the time. That is not handled. It is rubbing salt in the wound. “You have got to be kidding me. You did not save them, and now I am still paying this bill. Shouldn’t there be a contract that you save them? I paid the bill. You do not save them. I do not pay.” Unfortunately, the law does not work that way, and it is considered a joint asset. You are working together to pay off, paying whether it is medical devices or doctors or hospitals or anesthesiologists, whatever it is.

Why You Should Get Someone To Advocate For You

Unfortunately, they do not die with the passing spouse, which is unfortunate. I wish that the law would change, but not likely to change anytime soon. However, what we have learned, and again, going back to your earlier question about having an advocate, having a person, it is more than just a financial piece and sort of monitoring or helping you mitigate the emotional piece of making those decisions.

Having someone who can advocate for you is, you do not get at WidowWise University. You do not get that by just going to our website. I mentioned the 33-year-old in Florida, our coaches, we had two coaches working together, trying to get her a job, advocating for her, not just, “We are done with you. Thanks a lot,” but actually trying to close that loop because she needs a job, and they are going to help her get a job.

That is not really something that we do at Wings for Widows, but they are advocating for that person. That is the beautiful thing about working with financial coaches. It is more than just about the money. It is holistically everything that is involved in your household, including children’s and their welfare, but it has an advocate sometimes. An example of that is I was working with a woman named Joe. They worked for four years to save her husband, Kyle.

It was pretty bad. It took four years, but they did end up losing Kyle. By the time they lost Kyle, they were broke. They had nothing left. All the 401(k) plans were gone. They had been dropped by both of their companies for insurance. They had no insurance. They were paying out of their own pocket, and everything was gone. At the end of the day, Joe still owed $250,000 to the Mayo Clinic. Everything is gone, and she owes $250,000.

Joe is a realtor. It is like, “I know I can go back to work, but you do not just get a paycheck.” You have to go sell a home, and she is just lost, Kyle. She needed a break. As her coach, we were working together, but her biggest concern was this giant medical bill and how we could handle it. I just decided, “I am just going to advocate for you. I am going to take your eight-page letter. I can write a better letter. I am going to take your eight pages. We turned it into a page-and-a-half letter.” We sent that off.

They reduced the bill by $220,000. She literally had $27,000 left to pay. They set up a whole pay arrangement and delayed it until she was back to work. They worked with her because someone was willing to advocate for her. That is what we do. Sometimes, when it looks hopeless, having someone who has some of that experience can turn that hopelessness into hope. That is another reason why putting a little bit of trust into a coach versus some of the other options can really pay off.

Working With Families That Have Children

That is a life-changing experience. If I heard you correctly, did you mention some services or ways that you assist with children who are grieving?

Not directly. About 51% of the families we work with have children. We are very sensitive. That situation is probably the most difficult, the most challenging, unless it is a much older person and they are adult children. Now that is actually a benefit. That could be helpful. When they are young children, minors at home, or even younger children might require childcare. We know how expensive childcare is.

Trying to make this decision to go back to work just to pay for childcare. How is that going to help me pay my mortgage? It is really critical that young widows and widowers, because we serve both. By the way, they may grieve differently, but they are both in pain, and they both need good advice. It does not matter if you are a man or a woman. Unless you have been through this before, it is best to get good advice. We provide that to both.

That situation is so sensitive with young children that I say we go over and above making sure that that family is stable, and that in this role of an advocate for childcare, and helping them find the resources in their local area. Again, perhaps churches or other resources are available. There are ways to find these resources by zip code all over the country.

Not everybody knows about these resources. We will help them. We know where you are, and we will find whatever resources are right there. Many times, it is a referral to the county services. Sometimes it is a referral to other services. There are a fair number of services that do provide for children in this country. Usually, we can find some resources for them locally to help them out.

Raising Awareness About Working With Bereavement Professionals

This is some really good information. Are there any other nuggets in Wings for Widow that you want to mention, or services or ways in which you show up for the community that we have not addressed?

We are just here about walking alongside. We do not offer grief-specific services, bereavement services. We felt when we started nine years ago, that it was available pretty much in every community, one way or another. We work with a lot of community partners that provide those programs and those services.

We love referring to these groups, whether they are national or regional or local. Just because we are focused on the practical matters of loss, it does not mean that we try to isolate that from the grief. We do understand grief. We do understand how that affects an individual for not just for a few weeks or a few months, for years. The way that we come and walk alongside is different from how we typically work with clients or other clients that are not going through this widowhood journey.

I did not join that club. It is very different. It is a very different approach. We train our coaches in this style. I speak all over the country about how financial advisors could do a better job working with their widowed clients. The model that we use traditionally with our typical client does not work with our widowed clients. Really raising awareness with the professional community, including the bereavement side, about how important it is to get the practical matters addressed quickly so that healing can begin.

It is really impossible to heal. Even think about my own grief. If I am worried about where the next meal is going to come from, if I am worried about losing my home. If I do not have a car and I need to go to work, and I have to figure all these practical things out so that I can live, then I can grieve. We are educating the bereavement professionals because that is often left out. That is not even part of the initial conversations around grief.

What would be holding you back from healing? The fact that I do not have a job, and there is no money coming in, and we do not have a safety net or a cash reserve. It is important to know that Wings for Widows is not a grief-centric organization. We are very sensitive to grief and have a very different approach when working with widows, clients, so I would think that one of the very first things that we do in our process is have a collaboration meeting. There is no obligation.

There is no resigning of any documents. There is no obligation. There is no cost. Even if there is some shame, some intimidation, some embarrassment, some fear and uncertainty, it is just a meeting with someone who could maybe really be helpful. I always tell everyone, “If you are not sure, just go to the very first meeting with your coach. You get to pick your coach, find a coach that you look at that you like, and then meet with them and see what happens.” That would be my advice to your listeners as well.

Get In Touch With Chris

As they are tuning in and they realise I need help, whether it is a widow or a widower, or maybe a financial advisor that would like to make their services available and partner with you, how does one reach you? What is your website?

It is www.WingsForWidows.org. You can Google us. You can Google financial help for widows, and we will pop right up at the top. We do advertise on Google. If you Google the right words, we generally pop up and can find us. Just coming to the website and getting familiar with our services and what we do is a great place to start. For financial advisors, they can find us in a number of ways. Different organizations were available as resources in those organizations, through the pro bono side.

If a financial advisor is thinking about volunteering, they can go to the Foundation for Financial Planning. It is a 501(c)(3). Their mission is to provide financial advice to those who do not have access to it. All of our coaches come through there to get to Wings for Widows. We have a very close relationship there. Any financial advisor who would be interested in learning more about Wings for Widows or volunteering with us can just come to the website, or they can go to the Foundation for Financial Planning website.

Experiences In Serving In The Army And Navy

Thank you. I try to make this a little interesting. I give my guests an opportunity to be the show’s host and see if they have any questions for me.

I did not see that one coming.

That is why it is different.

I do have one. I am a naval veteran. You mentioned your time in the Army. From our other conversations, I am not sure we knew that. I do not recall you telling me that you had been in the Army for 21 years. Is that what I heard?

Yes.

Tell me about that. What did you do in the Army?

I was a logistician. I remember being this very young private in Fort Dix, New Jersey, going to boot camp. I went to Fort Lee, Virginia, for my technical training. I was stationed at Aberdeen Proving Ground was my first duty station. I remember being at a police station there.

In Maryland, at Aberdeen?

Yeah. Actually, that is where I met my late husband. I was in Korea for eighteen months and then came back, and I was stateside at Fort Eustis, Virginia. I did five and a half years of active duty and then the remaining of my reserve. We started having children. I just could not commit to that and being there. I still had a love for serving. I am glad for it.

That is fantastic. Thank you for your service.

How about you?

That is wild. I have a funny story about Aberdeen. I was actually arrested in Aberdeen with two of my friends. We had gone to Aberdeen. They had a runway there. One of our friends has just gotten his private pilot’s license. We went to Aberdeen to all jump in his aeroplane. While he was making his flight plan, the other friend and I wandered outside. We are just killing time. We wandered inside of an open gate into an old plane on the property.

It was easy to get on the plane. We climbed into the plane. We are just sitting in the pilot seats. Next thing we know, the military police with the flashing lights, there were three cars that came up, drew their weapons and told us to get down and handcuffed us and took us in and interrogated us. It turns out that the open gate should not have been open because of the way it was opened. The sign that said keep out, restricted area could not be seen.

Eventually, they let us go. It was a lot of fuss over nothing. It was a very old plane. It was all rusty. That is my Aberdeen story. I never went back to Aberdeen after that. That is funny. I went to the Naval Academy. I spent much like you, fifteen years active. I was known as a Naval flight officer. I had planned to be a pilot, but at the Academy, my eyes went bad. I was basically like a goose. I wanted to be goose-like with Maverick. I wanted to fly jets and do all of that.

I was the last class through the fiscal year, going through Pensacola, and that was not available. I could not fly jets. I went and flew P3S. They were sub hunters. I chased Russian submarines for the better part of my career. Spent time on a couple of carriers, some shore commands. At fifteen years, I took an early out. It was a drawdown in ‘93 after all of the Desert Storm activity. They were offering some pretty nice deals. I took it and joined the corporate workforce at that time. It was a great fifteen years. Almost all of my children have either been in active duty, are serving today, or are retired.

Thank you for your service. Both of our children have served in the Navy. Most of my siblings have been in the military also.

That is fantastic. Two military families. Thank you.

Episode Wrap-up And Closing Words

Chris, thank you for this conversation. Thank you for educating our community. I am going to make sure that if not already that your link is on our resource page. I do not want to just put Wings for Widow. I want to put the subcategory so people understand what services are available. I will work with you to make sure I have those listed correctly because between the university, the tax services of the SSI and all the different things.

I do not want them to just see this title and not get a real understanding of what is provided and how you can be of assistance to them. I would like you to close out this conversation with final words, maybe something you wanted to cover that we did not go over and repeat how they can locate you.

Final words are do not do this journey alone. It cannot be done. It should not be done alone. If you find yourself recently widowed, surround yourself with people who care about you, people who want to care about you. Do not make these decisions in a silo. Reach out, get help. This was never intended to walk this journey alone. I do not know how to say it any more eloquently. Do not walk this journey alone. We are happy to walk with you, walk alongside you for as much as Wings for Widows can do. We can be reached again at www.WingsForWidows.org. It is a great place to start.

Thank you so much.

Tina, thank you so much. I sure appreciate being here.

Important Links

• Chris Bentley on LinkedIn
• Wings for Widows
• Wings for Widows on Facebook
• Wings for Widows on Instagram
• WidowWise University
• Project CARE Scholarships

About Chris Bentley

Chris is a graduate of the U.S. Naval Academy and a Navy veteran. After leaving active military service, Chris spent a decade with Pepsi and Coca-Cola. After earning his MBA at the Carlson School of Management, University of Minnesota, Chris focused on financial services. After a stint at AEI Fund Management, Chris spent the next 15 years at RBC Wealth Management and Ameriprise Financial Services. He earned his CERTIFIED FINANCIAL PLANNER™ designation in 2013 and built a full service advisory and wealth management practice in the Twin Cities. Chris sold his practice in June 2022 to his partner to lead the company he founded in 2018: Wings for Widows, a public 501(c)3 charity, based in Wayzata, Minnesota.

Chris has authored two books. The Legacy Planning and Conversation Guide became an Amazon International Best-Seller in 2020. Later that year, he published The Newly Widowed Guide to Financial Wellness; the third edition was published in 2025.

Chris is also the Managing Director of WidowWise LLC, which founded WidowWise University, a one-of a-kind educational resource for widowed individuals. Wellness; the third edition was published in 2025.

The comprehensive curriculum encompasses 10 essential financial topics, delivered through 60 lessons that feature reading materials, closed caption videos, and downloadable worksheets.

As a national advocate and evangelist for widows’ rights, Chris regularly speaks to civic organizations, financial advisory firms, and professional associations such as the Financial Planning Association (FPA). Through his work with WidowWise and the Widowers Support Network, he creates educational content and awareness campaigns that illuminate the overlooked challenges faced by widowed individuals. He equips audiences with practical knowledge and emotional insight, empowering professionals and the public alike to better support those navigating life after loss.

In his spare time, Chris enjoys traveling, boating, sailing, music, craft beer, fine bourbon, and time with his wife Susie, family, and friends