Part XXXVI: Estate Planning 101 — The Simple Path to an Estate Plan

Pull Your Head Out of the Sand 

By Vicki Cook and Amy Blacklock

Before I sat down to write this post, I re-read The Simple Path to Wealth. This quote from JL…

“As individuals we only have one obligation to society:  To make sure we, and our children, are not a burden to others.”

…is a great segue into addressing a topic that some people take in stride, yet others avoid for various reasons.

I also believe we should do everything in our power to avoid being a burden to others. That’s why a few years ago, I spent some time and money to create a “life & death plan” and make it legal. 

A “life & death” plan? You may have guessed that I was talking about an estate plan. I call it a “life & death” plan because the word estate causes some people to tune right out. 

They (wrongly) believe that estate planning is only for really rich, old, or sick people.  

The truth is that your estate plan protects you while you’re living and your loved ones when you die. It also safeguards the nest egg you’re working so hard to build and maintain. 

If you want the freedom to choose what happens to your health and wealth, you need at least some of the essential documents in an estate plan. This goes for every adult over the age of 18.

I’ll describe the documents you need in more detail below. But first I want to share what prompted me to stop procrastinating a few years back and get serious about finishing my plan.

Bad Things Come in 3’s

I made my last will and testament back when my kids were little. While it was a good first step, I never reviewed it over the years or completed advance medical directives (aka living will and health care proxy) or power of attorney documents. 

While I knew it was important (and should be a priority), my 40’s was an incredibly busy time with my family and career. I also thought the chances of anything bad happening to me were slim.

But within a year of my 48th birthday, something terrible happened to three healthy and vibrant women I knew very well. A colleague and two neighbors – all in their 40’s – whose kids went to school and played together with mine.

One died of an aneurysm. Another suffered a massive stroke. And the third underwent multiple brain surgeries to remove a large benign tumor. A life-ending and life-altering medical events before the age of 50.

As I dealt with the shock and sadness of what had happened to my friends, I committed to taking care of my “life & death” business. Our neighbor shared some of the difficult decisions he had to make for his wife, and I didn’t want to put my loved ones in that position should something tragic happen to me.

Protected, but in the Minority

If you already have an estate plan that’s up to date – congratulations! But unlike you and me, recent surveys show that most Americans don’t have any estate planning documents prepared. 

While it makes sense that Boomers have them in greater numbers, Gen Xers, Millennials, and even some in Gen Z need a few of these crucial forms too.

No matter your age or net worth – if you’ve put “life & death” planning on the back burner or failed to realize that you need to get started, it’s time to pull your head out of the sand. 

You know that “nothing is certain but death and taxes” – right? You don’t skip paying Uncle Sam each year, and you shouldn’t put off planning for your death. Even if it is an emotional topic.

Remember, your lack of planning shouldn’t create a burden for others – especially the people you love – during a crisis or time of mourning.

Learning From the Mistakes of Others  

It’s hard to argue with the old saying that “we learn best from our own mistakes.” But I think there’s plenty to learn from the missteps of others too.

In the introduction to The Simple Path to Wealth, JL talks about why he started writing letters to his daughter. The goal was to help smooth out and accelerate her path to financial freedom by sharing what took him decades to learn.

If you haven’t been involved in or heard details about the settling of an estate gone bad, pay close attention. There’s plenty to learn from these situations too. 

And many of the issues stem from a person becoming incapacitated or dying without having completed estate planning forms.

Neither Karen Ann Quinlan nor Terri Schiavo had advance directives when they were deemed incapacitated as young women in their 20’s. The legal battles that ensued over continuing various life-sustaining measures took years to conclude.

And Prince, Sonny Bono, Amy Winehouse, Bob Marley, Aretha Franklin, and oh so many more celebrities died from serious illnesses or injuries without having a will in place. 

Think about who gets a massive cut of complicated estates when someone fails to act. It’s the lawyers who rake in cash! 

Their grieving loved ones are left behind to face the burden of reliving the death over and over while dealing with attorneys and the probate court system for years.

The lessons you should take from their mistakes are clear. You don’t want to want to become incapacitated without advance directives and power of attorney documents. And you don’t want to die intestate – without having a will.

Instead of just saying that your family always comes first, back up your words by making an estate plan. 

The (Fairly) Simple Path to an Estate Plan

You probably know Warren Buffett’s quote about investing. The one about it being simple, but not easy. It shouldn’t be that difficult to stick to your investing plan to reach your financial goals. But your emotions can often get in the way – especially during significant market swings. 

JL addressed that in The Simple Path to Wealth. He taught you how to get there and manage your feelings and reactions along the way.

We recently wrote a book for Adams Media (an imprint of Simon & Schuster) called Estate Planning 101 and took a similar approach. Estate planning is a fairly simple process to understand, but it may not be easy to deal with the feelings involved.

Our goal was to explain not just what to do but also address the emotional aspects involved in estate planning.

The book is a comprehensive guide to help people start estate planning. It explains each of the following forms in detail and what you need to consider as you complete them. 

Add these three documents to your must-do list:  

    1. Advance Healthcare Directive (aka Living Will and Medical Power of Attorney). A living will is a free document you complete that describes your wishes concerning the types of treatments you agree to and the end-of-life care decisions, including life support measures, pain management, and organ donation. If you’re deemed unable to make decisions (incapacitated), your medical power of attorney takes over to make healthcare choices for you.
    2. Financial Power of Attorney. If you’re unable to manage your finances at some point, this legal form lists who you authorize to take over managing your money and under what circumstances. 
    3. Last Will and Testament. You need a will unless you are single, childless, have very few assets to distribute to heirs, and have an uncomplicated family life. Your will directs how to distribute your assets and names a guardian for your minor children.

As your assets grow and your life situation becomes more complex, you may also want to consider starting a trust. These aren’t just for uber-wealthy people! 

A living trust is a legal tool allowing you to keep control of your assets while you’re alive and direct how heirs receive an inheritance after you’re gone. Trusts also keep your matters private, unlike the results of probate proceedings.

Examples of when drafting a trust makes sense include protecting a special needs dependent or children from a previous relationship. You can also set up a trust to prevent your young adult child from inheriting a large lump sum of money all at once when they might not be ready to handle it responsibly.

You might be wondering if you can DIY any of these documents. You can definitely fill out your own living will. But use caution when it comes to the other legal documents. 

While plenty of online services offer various options to help you with estate planning, we can’t suggest that unless you have few probatable assets and uber-simple family life. You don’t want your documents to be deemed invalid or fail to meet legal challenges because you chose the most frugal option.

There are plenty of ways to save money by DIY’ing, but for many people – this shouldn’t be one of them.

Also, be sure to review the beneficiaries you’ve listed on various policies and accounts. An ex-spouse will inherit assets if they’re listed as a beneficiary. Don’t make the mistake of assuming your will has your wishes covered. Beneficiary designations trump what’s in a will. 

Spend Some Time and Money on What You Value Most

While I much prefer to write about more uplifting topics, I feel strongly about this one. I wish it didn’t take the scare from witnessing what happened to my friends to get me to act. But I’m proud of my husband and me for getting our plan done.

It took less time and energy than I predicted and cost about half of what I had budgeted. If you do your homework (and use resources like Estate Planning 101!), you’ll have drafted much of your plan before you even meet with an attorney. Then you can use the time with an attorney to answer questions and craft the plan that best meets your unique financial and family circumstances.

If you still think it’s too soon to tackle this project, what’s the worst that can happen? You might need to spend a little time and money updating it. But that’s a small expense to relieve what could be a considerable burden on your family.

I shared some examples above about some of the worst things that can happen if you become incapacitated or pass away before you get these forms done. If your assets and family circumstances are uncomplicated, it might not be a big deal. But as you get older, there’s more urgency to finalize your plan.

Don’t skip over these essential steps as you walk The Simple Path to Wealth. When you finish your estate plan, you can relax and follow the words of the flip-flop-wearing Jimmy Buffett and breathe in, breathe out, and move on.

You’ll find several more estate planning articles here, and you can grab free planning checklists here.

For more information on “life & death planning” and getting started with estate planning, check out our new book Estate Planning 101:


Estate Planning 101 happened to hit my desk at exactly the right time. We’ve had the documents Vicki and Amy describe for about 10 years now — yes, we should have had them sooner — and they are due for an update. We’ll be meeting with our attorney this fall, and I had been reviewing what we had and creating a list of questions and things we need to add and/or subtract.

This book is simple, to the point, very well organized and clearly written. It is exactly the guide I needed. That’s coming from a guy whose eyes glaze over on this subject.  You probably need it too. 

JL Collins



For more from Vicki and Amy, check out:  Women Who Money


Some other books I’ve been reading…


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Important Resources

  • Talent Stacker is a resource that I learned about through my work with Jonathan and Brad at ChooseFI, and first heard about Salesforce as a career option in an episode where they featured Bradley Rice on the Podcast. In that episode, Bradley shared how he reached FI quickly thanks to his huge paychecks and discipline in keeping his expenses low. Jonathan teamed up with Bradley to build Talent Stacker, and they have helped more than 1,000 students from all walks of life complete the program and land jobs like clockwork, earning double or even triple their old salaries using a Salesforce certification to break into a no-code tech career.
  • Credit Cards are like chain saws. Incredibly useful. Incredibly dangerous. Resolve to pay in full each month and never carry a balance. Do that and they can be great tools. Here are some of the very best for travel hacking, cash back and small business rewards.
  • Empower is a free tool to manage and evaluate your investments. With great visuals you can track your net worth, asset allocation, and portfolio performance, including costs. At a glance you'll see what's working and what you might want to change. Here's my full review.
  • Betterment is my recommendation for hands-off investors who prefer a DIFM (Do It For Me) approach. It is also a great tool for reaching short-term savings goals. Here is my Betterment Review
  • NewRetirement offers cool tools to help guide you in answering the question: Do I have enough money to retire? And getting started is free. Sign up and you will be offered two paths into their retirement planner. I was also on their podcast and you can check that out here:Video version, Podcast version.
  • Tuft & Needle (T&N) helps me sleep at night. They are a very cool company with a great product. Here’s my review of what we are currently sleeping on: Our Walnut Frame and Mint Mattress.


  1. Alexis says

    A litte superficial but very necessary post. I, like millions of green card/ work visa holders living in the United States, face one of the worse nightmares regarding estate planning. If you leave the US the Exit tax kills your assets. If you stay, then if you have assets ex-US your screwed up really well as US and Eritreia are the only countries in the world who taxes worldwide income. I really would like to see a post about that kind of estate planning since audience doesn’t fall short.

    • Vicki from Women Who Money says

      Hi Alexis! We aren’t lawyers but maybe someone else can fill that gap. Our book is intended as an introductory resource to get people thinking about a topic they often put on the back burner. JL has quite a following – so maybe someone else can chime in on your concern.

      • Alexis says

        Thank you Vicki, yeah that wasn’t mean as a criticism, just an observation. I’m sure your book is great and will help most people. It’s just the category of investor I’m in makes things really complicated and as most FIREEs, I don’t like to pay for anything much less attorneys or estate planners since it falls in that thing WE ALL HATE “having to pay in order to pay” taxes.
        Congrats on the book and the post anyway! Cheers

        • Just me says

          Hi Alexis, I had exactly the same reaction to this article about estate planning. For non-citizens, or dual citizens, or if there is a non-citizen spouse, it is a nightmare.

          I’d go further than you and say that EVEN if one is willing to pay (a bit!) for estate planners, it’s still incredibly difficult to get information or know how to proceed if there is a major international component to your estate.

    • Abigail says

      Hi Eli

      We were green card holders back when we did our estate plan. We did hire an attorney and she built in quite a few extra provisions and explained that we needed them because we were not citizens.

      Our most important assets were and are our children. We needed extra wording and provisions to make sure that they could go straight to relatives off shore.

      Yes, we paid a bit more than US citizens would have needed to but our needs were greater.

      It was all set up so that if something happened to both of us, the kids and the money would both be able to leave the country.

      I do not know where you are, but Silicon Valley is teeming with ex pats and that is where our lawyer was, although we are elsewhere in CA. So I encourage you to look for the biggest concentration of ex pats in your state and call the estate attorneys there.

  2. patrick says

    Thanks you for this service you’re providing, Vicki and Amy! Is there a “201” in the works, by chance?

    I’m interested in a multi-generational death plan to avoid the trap of successive gerations that “sow, grow, and blow” wealth.

    • Vicki from Women Who Money says

      Hi Patrick! Thanks for your kind words. There isn’t a “201” in progress yet! The “101” books are a long series run by Adams Media. We are taking notes from the comments here about what people are looking for though! We’ll keep you updated 😉

  3. Mark says

    I’m an attorney by trade, and I spent the first year of my career drafting the three basic documents noted above. Since this is not really my area of expertise I’m not going to go real far out on a limb here. But here are a few thoughts.

    1) Wisconsin has a statutory form for the Medical Power of Attorney (or whatever name you want to use). It is designed so that any person can fill it out for themselves. Maybe your state has a similar form.

    2) I use a will with a trust built in for children. When we updated our wills last year (children are 20 and 25 now) we actually lengthened out the age at which the trust comes into play, as well as the age at which it can terminate. Our kids are smart and responsible, but we have a lot more money than we expected and anyone can be tempted. The basic requirements for wills are pretty universal (in writing, signed and witnessed). Check out the requirements of your state but you will probably find that most forms you might buy on-line are o.k. in your state. If you choose to use an attorney it probably will run $300-$500. I wouldn’t recommend giving your attorney any role other than drafter if you want to keep your costs at death down.

    3) Living trusts go in and out of style. I don’t understand them well enough to publicly comment on them except to say this: I don’t see the need in my case. I have heard all of the arguments against wills (cost, public records etc.). When I’m dead, I don’t really care what the public knows. The costs of creating, maintaining and updating a trust are not nothing, and the costs on the will side can be contained if a family member acts as executor. If your financial life is fairly simple, so will be administering your estate. As far as delay goes, if my heirs are in that much of a hurry to get their mitts on the money, then they are probably not practicing what we taught them. I will say this though: I should check into this topic more thoroughly.

    4) At a minimum, spouses should give each other an immediate financial power of attorney, even if you live in a marital property state. How property is titled does not match up to ownership. You can save your spouse a lot of headaches if temporarily or permanently unable to make financial decisions.

    5) Remember that the federal estate tax threshold is now very high. $11.7 M per individual, which is over $23M per couple. You can most definitely reach FIRE live a long retirement and never be impacted by the Federal Estate Tax. Only a minority of states (17) have an estate or inheritance tax. Treat anyone who tries to worry you about this issue with suspicion, unless you really are that wealthy.

  4. JLH says

    I would be interested in understanding recommendations for the many single adults out there with no dependants. I find that there is very little written with this audience in mind, which seems to be quite a gap considering the rising popularity of choosing this lifestyle especially among those aiming for FIRE. What recommendations do you have for the many single adults with sizable assets and no dependents?

    • Melissa says

      I have the same question. I am single with no kids. Also I don’t have the best relationship with my family and don’t necessarily want them making decisions for me. However, who would I want to make these decisions?

      • Amy @ Women Who Money says

        Hi Melissa, when you don’t have family members you’d like to serve in critical roles you’ll want to consider trusted friends, responsible adult children of dear friends, or turning to a professional fiduciary or trust firm. Please see our response to JLH for other points/recommendations.

    • Amy @ Women Who Money says

      Hi JLH, we actually devoted a small section in our book to solo individuals, as well as unmarried partners and other unique circumstances. We’d suggest considering family members and very close friends to serve in roles such as personal representative, and health care agent, and as heirs/beneficiaries of your assets. A living trust is something you might want to consider depending on the value of your estate and if you want more control over when and how any of your assets are distributed after your are gone. An alternative option to naming family or friends to important roles in your estate matters is hiring a professional trust firm or corporate fiduciary. If leaving all or a portion of your estate to charities and causes you care about is appealing to you, donor-advised funds and charitable remainder trusts are a few ways to do that. It’s challenging to provide extensive recommendations due to everyone’s personal circumstances but we hope that can spur some ideas for you.

  5. Jane says

    Ah, this has been on my list for a while now as something I really should get around to. Soon. Ish.
    Thank you for the reminder- I’ll check out your book and your website.

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