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Make a Checklist of Your Wishes For Your Family

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For the last decade of my father-in-law’s life, every time we visited him, he would find an hour to chat with us about his final wishes. It was never on the first day or the last. It was never over dinner. But at some point, he would find a few moments to talk about what he wanted his final days to be like and how he wanted his matters handled by family when he was gone. 

Keith and I came to expect these little chats every time we visited him. 

Now that we’re getting older, we’re trying to figure out when we should start having those chats with people. First of all, it’s a great reminder that if you haven’t already thought about the executor of your estate…now’s a good time. And don’t let that term intimidate you. Whether you have $1 or $1M, somebody is going to have to handle your final affairs. 

AARP Publishing has a book out titled, “Checklist for My Family” by Sally Balch Hurme, J.D.. This 250-page book outlines ten areas of our life that we might want to consider documenting. Some of them are very predictable like life insurance, investments, and real estate. Others are more surprising such as items to destroy, rewards programs, and pet care. 

I’m sure for many, the task of handling a person’s final affairs is given to a child. Keith and I have an interesting dynamic to consider because we don’t have children. I found this book to be something that we could complete and leave it in a place for the executor of our estate to review. I love that everything is in a single book, so our executor only has to find one thing – the book. And we can keep the book in a safe place or mail it to our executor.

The book has two parts. The first part is my “to-do” list. This is where I need to review items, make decisions about how I would like things handled by family, etc. The second part is where I document those decisions. Looking back, my father-in-law was quite the planner and there were plenty of things he forgot to tell us. This book reminds me that while there are several major decisions to make, there are lots of smaller decisions to consider as well. 

If I have one criticism about the book, it’s that the author doesn’t put enough emphasis on technology. The book does reference digital assets, but most of us have multiple social media accounts, emails, etc. and at some point, somebody will be given the task of deleting my digital life. In future editions, I could see technology being a separate chapter versus just a few pages.

At some point in time, we have to start making plans for our final days. I can’t speak for anyone else, but I don’t want to rush those decisions. Having a checklist for family that I can pick up and put down at my leisure makes me feel in control. And isn’t that want we’re trying to do – be in control of how our affairs are handled. 

Decision Making: What Underthinking Looks Like

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If you spend time on social channels, there’s a good chance you’ve seen the meme GIF about “what overthinking looks like”. It shows a young child crying in a pool, appearing to desperately cling to a lane marker rope to keep his head above the water. The mother rushes in to help him stand up in water that only barely comes up to his knees. The somewhat humorous intent, of course, is don’t overthink things – deal with the reality of a situation and you will be fine.

It’s a cute little message. But it made me wonder – where is the cute GIF about underthinking? There really isn’t one. Nor should there be. Because the result of underthinking is just bad decision making. And there’s nothing humorous or cute about that. 

The business world has always placed emphasis on decision making and its importance in organizational success. In fact, our consulting firm worked with a number of companies, teaching an adaptation of the Blake Mouton Managerial Grid – a way of evaluating decisions relative to the task that needed to be performed and the people that are impacted. I won’t go into the details here. The point is, business success often depends on a systematic approach to decision making. We should carry that forward into our personal decisions.

A simplified version of systematic decision making is a 5-step process:

Step 1: Identify the Goal. This may be the most important step since it is the basis for all the rest. For this exercise, let’s say your goal is to retire comfortably as early as possible. There are some parameters here (“comfortably” and “early as possible”) that can help us identify the best options.

Step 2: Weigh Your Options. For this, you will need information. Given the goal, some of the options may be drawing Social Security as soon as possible. Or maybe tapping into your 401(k) at first and waiting a few years so you can draw a larger check from Social Security. This is the time to talk with friends and experts to learn all opportunities.

Step 3: Consider Consequences. The previous step is so important because it will help us consider the consequences of each option. Will we deplete our nest egg too soon if we wait too long to file for Social Security? What will be our tax burden, and will that eat away at our savings? This step may even help to identify other options like part-time work during retirement.

Step 4: Make Your Decision. Remember the “overthinking meme”? At some point, you have to be satisfied that you’ve collected all the options you need and evaluated the consequences of each. That should lead you to the best decision that fulfills as many parameters as possible and gives you the best outcome.

Step 5: Evaluate Your Decision. Sadly, this is often the step that gets overlooked. But, even if you did a great job with the first four steps, you may be surprised with part of the results. The worst thing you can do is cling blindly to a decision just because of the effort you put into it. Evaluate your decision and make adjustments as needed.

One other thing to remember along the way is you don’t have to do this all by yourself. Of course you will have many conversations with family and friends. And AARP is full of planning resources. You can also check out The FIRE movement (financial independence, retire early) – a group that appears to be setting new standards in financial planning for retirement. Again, do your research!

We know that life is full of important decisions and retirement is one of the most critical. Unlike the “overthinking meme”, we can’t count on someone to rush in and rescue us when we make bad decisions. Fortunately, using a good system can go a long way toward helping us make good decisions.

8 Reasons to Learn About Social Security Early in Your Career

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I used to think the right time to learn about Social Security was right before I need it. No sense in learning about something and then having to learn about changes. Well, I’ve changed my mind on this. I received a copy of the book, Social Security Strategies: How to Optimize Retirement Benefits [3rd Edition]. Sad to say, I received this book over a year ago. And it’s been sitting on the corner of my desk for quite some time.

I finally started digging into the book and realized that understanding Social Security is going to take some time. And it’s possible that one book isn’t going to answer all of my questions. So instead of rushing to learn Social Security when I’m in my 60’s, maybe it makes sense to start learning about it when I’m younger. 

While I’m sure that I don’t know everything that I need to know about Social Security, I did learn a few things from reading about it. The book authors also have a website with additional information. Here are my takeaways:

  1. Social Security benefits are driven by age. I’m sure most of you already knew that. But it appears that for some individuals, the date when you can collect benefits is changing. For example, if you’re turning 62 in 2019, your full retirement age is 66 years, 6 months (that’s a two-month increase from last year).
  2. You will want to discuss Social Security strategies with your spouse or significant other. While many benefits are focused on the individual, the amount of your Social Security benefit can change depending on your marital status. You’ll want to decide as a family when each person might want to consider taking their benefit.
  3. You will want to plan your filing strategy years in advance. There’s a lot of writing about getting the greatest monthly benefit when you wait until you’re 70 to file for Social Security. But if your goal with Social Security is to draw as much money as possible, then it could make more financial sense to draw early and collect longer.
  4. If you don’t know how to manage cash flow, you’ll want to learn. Collecting Social Security means living on a budget. And budgets mean understanding cash flow. It’s about having money when you need it, and that includes for emergencies.
  5. You’ll want to monitor your estimated benefits. And start thinking about living within that budget. Speaking of budgets, another aspect of finances to think about is changing your lifestyle to live within your means. It’s possible that all of the things that are necessary right now, we won’t need to purchase in the future.
  6. If you’re planning to work while drawing benefits, you’ll want to understand the impact. If you’re planning to freelance or consult during retirement, you’ll want to think about how much money you’re trying to make while collecting Social Security. Because…see #7.
  7. Social Security doesn’t mean you’re no longer paying any taxes. There are limits on how much money you can make without incurring tax penalties. You’ll want to know what those numbers are because it will drive your unretirement strategy.
  8. Finally, you’ll want to know how to apply. And the necessary paperwork to bring. Don’t wait until the last minute to figure out how to apply. Can you apply online? Is it better to apply in person? What paperwork do you need to bring with you? 

Regardless of your financial position, chances are Social Security is a part of your retirement plan. Don’t wait until the last minute to start learning about it. And one other thing…if you’re thinking that you will need Social Security someday, then don’t ignore the conversations happening within government. I’m not here to tell you what to think. But if you don’t want someone to mess with your retirement without you getting a say…then learning about Social Security sooner (versus later) makes sense.

Image captured by Sharlyn Lauby at Lucky’s Lunch Counter in San Diego, CA

4 Unretirement Realities We Have to Face

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One of the things that I find interesting is how much retirement conversation is starting to creep into everyday life. And not because I’m talking about this on Unretirement Project. I’m hearing more people talk about retirement at conferences, etc.

On some level, I figured retirement would be something only discussed among people who are retired or very close to retirement age. And it would only be discussed in the context of simply not working anymore. But that’s not the case. Retirement conversations are happening with people of all ages. This is a good thing. We’re starting to demystify retirement. But that also means it’s opening our eyes to what the future holds – both the good and the challenging.

If you have a moment, I would recommend watching author Elizabeth White’s TED talk on the personal finance crisis. Because it has a direct bearing on retirement. And the notion of unretirement.

Regardless of where you are in your unretirement journey, I thought White’s talk had a few harsh realities we will eventually need to face.

  1. Being the first to “unretire” will be hard. Being the first at anything is hard. There are no rules or best practices. That’s one of the reasons we’ve started this blog. Hopefully along the way, we can document some of the great things people are doing and be helpful to future unretirees. But it’s important to keep in mind that we’re one of the first and we will need to use our past experiences to help us along the way.
  1. We will have to change. In her TED talk, White tells us that we need to “Get off our thrones.” We’ve always known that retirement would be a change. But the question becomes how much. Make no mistake unretirement will be a change too. Even though unretirement is designed to ease our transition, that doesn’t mean it eliminates change.
  1. We will need to develop a new relationship with money. Speaking of change, one of the biggest changes we will have to make is with money. In fact, it might extend to all of our resources. How we budget and spend our resources will change. We will need to prioritize our needs and wants. Many of us already know this, but we haven’t had to live it yet. It’s one thing to discuss “tightening the purse strings” and another to do it.
  1. Think retirement strategy, not money failure. So much of retirement is caught up in finances, I think it’s important to realize there are other aspects to retirement. Our retirement strategy includes quality of life, our health, etc. This could relate to money in terms of “Do I spend money on a trip or a pergola for the backyard?” Ultimately, we have to understand what’s important to us to develop a good retirement strategy.

I’m really excited that conversations about retirement and unretirement are more frequent. It tells me that people are planning for retirement as a new beginning. Because that’s what it can be. If we plan for it.

Image captured by Sharlyn Lauby while exploring the streets of San Francisco, CA

Unretirement: Create Your Own Aging Strategy

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I ran across a very interesting article on NextAvenue titled, “Let People Choose How They Age”. It’s a good read you might want to check out.

The gist of the article for me was that individuals should break some of those traditional stereotypes when it comes to retirement. You guys know I totally believe that. It’s what “unretirement” is all about.

But I think there’s a difference between saying, “I want to redefine retirement.” and actually doing it. Let’s face it. For decades, we’ve been told that, at a certain age, we stop working, and that’s it. We’re supposed to save enough money to take care of ourselves. Today is different. We don’t need to stop working at a certain age. We can earn money while collecting Social Security.

Again, if we’re trying to break the retirement mold and create our own unretirement, it takes time. And it means thinking about our aging strategy. And then being prepared to put those thoughts and plans into action.

How do we want to spend our time? There are so many different things we can do: traveling, volunteering, working, etc. And frankly, there’s no reason we can’t do them all. It seems to me though, as we age, we will need to reprioritize the ways we spend our time. We need to be prepared to do that on a regular basis. And communicate it to the people in our lives. That includes family, friends, managers, and co-workers.

What impact will health have on our plans? At some point, we have to confront our health. Even if we eat right and exercise regularly. As our health changes, can we find activities that we enjoy? Is it possible to still volunteer or work part-time? If possible, it could make some sense to take a personal skills inventory and identify some knowledge and skills that we want to work on now…when we have the time to do it at our pace and convenience.

Will our finances force us to change our retirement plans? It would be wonderful to say that when we retire that we won’t have to live on a budget. Chances are that won’t be the case. So, first, we must learn how to create a retirement budget. In addition, we must make some very adult decisions about things we might never do because the budget doesn’t permit. When we’re in our 20’s and 30’s, we figure the money will always show up. At some point, we have to address the possibility that it won’t.

As we think about our unretirement and retirement, we have the ability to pave our own path. But that doesn’t necessarily mean we will be able to do whatever we want. It will be necessary to balance our wants and needs with the resources we have available to us. That doesn’t mean we can make our unretirement and retirement an enjoyable and fulfilling time.

Image captured by Sharlyn Lauby while exploring the streets of San Francisco, CA

Choosing the Right Unretirement Gig

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One of the reasons that we started this blog was to share our experience with blogging. Little did we know when we started HR Bartender that it would become something that we love to do while making a little money.

And my guess is we’re not alone when it comes to retirees or soon-to-be retirees wanting to find a little something they can do and make a little side income. But I will admit, blogging might not be for everyone. So, how do you find what makes sense for you?

Well, one of my favorite career sites is The Muse. They recently had an article about “How to Choose the Right Side Hustle for You”. Of course, the article is focused on anyone, but I thought this could be perfect for individuals thinking about their unretirement.

Developing a side hustle or side gig (whatever you want to call it), takes time. Just because you’re doing to do it on the side doesn’t mean you shouldn’t put any thought into it. Having a side hustle still involves business plans, licenses, taxes, etc. Here are three things to consider when choosing the right side work:

  • What do you want to do? Not simply “What am I doing now?” Or “What am I good at?” You might choose to do something completely different in unretirement. Maybe follow a dream you’ve had for years. But it’s worth taking the time to think about where you want to focus your energy because that might give you some indication of skills you want to polish up.
  • What are you willing to invest? Starting a side hustle might take some money. Some side hustles take very little. When I began consulting, all I needed was a desk and a computer. Both of which I had at home. Other side gigs might take saving and purchasing equipment over time. If you begin the process while you’re working, then you can budget for the expense while you still have income from another source.
  • How much time do you want to spend? The main reason I’m bringing this up is because how much time you want to spend doing your side gig could tell you if a marketing investment will be necessary. If you don’t mind starting slow and working your way to greater income, then little or no marketing might be okay. If you want to have a certain amount of income right away in your unretirement, then it might take a more robust marketing plan.

And let me add, these questions also allow you to decide if you like the side hustle you’ve chosen. That way, if you decide that the side hustle you thought was going to be so fabulous…well, isn’t, you have time and resources to change it.

It’s perfectly logical to think about having a side gig during unretirement. But the time to consider developing one is when you’re still working. That way the pieces are in place when you’re ready.

Image captured by Sharlyn Lauby while exploring the streets of Denver, CO

Is It Possible to Flunk Retirement

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A friend of mine recently recommended the book “Don’t Retire, Rewire!” by Jeri Sedlar and Rick Miners. The focus of the book appears to be very similar to the concepts of unretirement, meaning that when we stop working full-time in Corporate America, we don’t have to sit around and do nothing.

I haven’t finished reading it, but one of the early sections that captured my attention was a list titled “The Top 10 Reasons Why People Flunk Retirement”. My initial reaction was “Can you flunk retirement?!” For me, the word “flunk” conjures up the idea that we failed, and we can’t recover. There were two interesting things about the list.

  1. Beyond “didn’t have a plan”, there was no mention of money, finances, insurance, estate planning, etc. While I don’t believe that retirement is all about the Benjamins, we do need to be realistic about having the means to live and take care of ourselves during retirement. Even if that involves living with a family member. And I could see individuals who don’t feel they’ve prepared enough financially for retirement feeling like they’ve flunked that aspect.
  1. There were several reasons that fell into the category of “assumptions”. For example, I assumed my partner would be my social life. Or I assumed that rest and recreation would be enough. And finally, that I didn’t know myself very well. I’m not sure these are mistakes that an individual can’t recover from. Now, I’m not saying it will be easy. The process of self-discovery can be hard. Not only do we have to come to our own conclusions, but we might have to share our feelings with friends and family.

But the real takeaway for me wasn’t to focus on the flunking part. It’s to figure out how to move forward.

In today’s business world, we appear to be much more accepting of failure than ever. Billionaire business people like Sir Richard Branson and Spanx founder Sara Blakely remind us that it’s okay to make mistakes. But I can see how people could feel different about flunking at 20 than flunking at 60. They also might choose to handle the situation differently based on their circumstances.

We have to view our unretirement and retirement as a journey. A journey that starts early in life. Will there be stumbling blocks and changes along the way? Absolutely. But that doesn’t mean we’ve flunked life or our retirement. It does mean that we need to find ways to adjust.

Image captured by Sharlyn Lauby while wandering the streets of Miami, FL