4 bucket-list items you have to check off, first

Fellow traveler on his 21st-birthday trip — atop our river boat heading down the Nam Ou (“rice bowl river”, a tributary of the Mekong) through the karst landscape from Muang Khua to Muang Ngoi, Lao PDR. 2013

Digging into Your Bucket List

Almost everyone I know has a bucket list that cites their hopes and dreams, propels them to action, and covers wishes that to some may be tricky to bring up in conversation.

If items on your list may seem far, far away — in distance, time, and reach—know that it’s part of the allure and, consequently, becomes your personal challenge: To. Be. Met. Your bucket list can be your catalyst.

Sometimes you seek distant lands: Maybe it’s a peak experience in Tibet, or fathoming the depths of a deep dive in Indonesia, or a cross-country bike trip — all to help realize the expanse of our shared journey through life.

These days a friend may say, “Homeslice, go homestyle,” to spur you to explore your community and countryside, where the treasure is right under your feet, or closer. Bucket list items are not only about traveling far away, they also include delving deep within.

Long ago there was someone who likely didn’t have a bucket list. He lived like a prince; in fact, he was a prince. At age 29, he decided to explore the world, so he headed out from the pleasures of his protective palace grounds with his charioteer, Channa. Even then, it’s unlikely he had a bucket list — much less any kicking-the-bucket items on it. But, then, he experienced four events. The first three included his sight of an old person, a sick person, a dead body, and finally an ascetic who was dedicated to finding the cause of mankind’s suffering. These induced a profound transformation of Prince Siddhartha’s heart and psyche and set him on the path to becoming fully “awake” —becoming the Buddha—and enlightened.

Top Three

Informed by the pandemic, I switched out my bucket list to start with four goals—I’m still working on the fourth. It is transformative. I hope it is for you, too.

  1. Investment plan
  2. Healthcare directive
  3. Last will and testament
  4. Next step, so informed and inspired

Let’s go through them one-by-one.

Fellow traveler along the road—bamboo grove below the hills of Sa Pa, Vietnam. 2014

1. Investment Plan

The good news first: You are likely to live a lot longer than you thought. Since 1900, we have gained and been gifted an average of 30 years, added to our lives. Now the bad news: it’s likely you may have underestimated your longevity (and the time available for accomplishing everything on your bucket list).

To “spend” your life well, it will “pay” to invest in yourself and your life — and that includes your future self. In financial investing, being short in an asset means investing in a way that you profit if the value of the asset falls. Don’t short yourself; go long on longevity — couple life-long learning (in part, through bucket list achievements) with long-life learning. Save each day along the way. Now.

There are many biases that may hinder you from investing in and for yourself toward becoming self-actualized and financially self-sufficient, respectively. Carefully cultivated, your bucket list can actually help overcome some bad biases — for example, when you prioritize your present self and put more value into immediate events and outcomes than those in your future, especially those most distant. But remember, those bucket list goals most distant in time and space should serve as an impetus to add value to their, and your worth, far in to the future—your future.

Where does your money go? Budgeting.

Unlike the federal government, you need a balanced budget—and you can’t just print money. Budgeting is a balancing act between income and expenses, over a specific time — starting with your monthly “maintenance” costs.

Sound tedious? Then view this as an opportunity to really delve in to what you truly need, how not to overspend (especially on possessions), the best way to reduce or eliminate debt, the need to squirrel away an emergency fund (say three to six months’ expenses), and how to set-up savings for big items — your future, included.

Try a budgeting app

Where does your money grow? Financial investing.

Save, each day along the way. Just as paying bills should be automatic, so should saving. To pay it forward, pay yourself, today. Save at least 15% of your pre-tax income, to include employer contributions. Put your money aside before the rest makes it to your bank account. Spoiler: investing creates wealth, compounded by compounding.

Don’t try to “beat the market”-if you speculate, you may be lucky; more likely, you will be humbled. To help achieve economic equity, invest in equities (stocks). To illustrate my point, contrast the disparity between the last four decades’ stagnant wages with the rise in the stock market. Don’t be content with breadcrumbs; seek shared ownership of the bakery — knowing that corporate culture needs to change, too.

To hack wealth accumulation, invest early. Let’s say you just turned 18 and finished your health care proxy — bucket list item one, done! Next, take that $50 your grandmother gave you and make it a beginning. Set up an account, which takes less time than picking up that take-out dinner you just treated yourself to.

Try an investment app.

To start, invest in exchange traded funds (ETFs), which passively follow an index — the SPY 500, for example—and have low-cost fees. Do the same for fixed income, starting with bonds.

Invest for, and in, your future

Next, if you plan to live in a livable world, (1) consider companies whose strategy includes environmental, social and governance (ESG) standards and (2) intentionally investigates social impact investments, including bonds, that seek a financial return coupled with a measurable environmental or social impact. These will extend your “diversified” portfolio far beyond holding “just” (read: only) stocks and bonds, to just (read: fair and equitable) investments that invest in our shared future.

Actually, sustainable funds as a group performed better than funds overall in 2018. If you need help getting started with your sustainable responsible investments (SRI), these apps offer a good introduction: Swell, Motif, and Wealthsimple.

At first, you work for money; through strategic investment, your money works for you; it generates passive income (for use now, or for reinvestment) and wealth (for the future) to help meet your nearby needs, distant dreams, and philanthropy, (love of humanity).

To really demonstrate your love of humanity practice effective altruism, which is “about using evidence and reason to figure out how to benefit others as much as possible, and taking action on that basis.” Will MacAskill, founder of Effective Altruism, has — since his mid 20s.

Your increase in assets must be matched by risk reduction. Wealth (financial) advisors can help reduce the risk of your biases and emotions in stable (if ever!) and turbulent times with an eye toward professional advice and long-term investment in the market. They can also make sure taxes are not too taxing. Advisors can also help you invest in your future self, too — your long-term security with 20:20 vision (long beyond 2020) to help keep your boat afloat, set your sails, chart your course, and eye (“I”) the distant horizon. Advisors can also help assess how much debt you may wish to assume — or, better, how to eliminate your debt; how to plan for buying big items such as a house, or your first/next van; coping with transitions or abrupt change (before it hits); help meet your loved ones’ needs; inter-generational transfer of wealth, to or from you; and retirement, which is not a DIY project. Wealth, or wele (in Middle English), means well-being.

A great impetus for saving and investing is the power of compound interest, interest on interest that is reinvested; this results in a significant boost to your investment returns — especially when you start early.

Invest Starts with “I”

Don’t just take stock in stocks, take stock in yourself. Invest in your future self. Stock analysts are quick to say, “Past performance is no guarantee of future results.” Invest in yourself the same way. Forget past performance; it’s passed. Above all, it’s about your self worth, not your net worth.

Café companion, veteran traveler—Hanoi, Vietnam. 2014

2. Healthcare Directive

Prepare a healthcare directive. Do so now.

Two-thirds of adult Americans do *not* have a healthcare directive; here, there is no safety in numbers. The time to prepare a directive is not when you are 81, but the day you turn 18. All adults should have one — to help themselves, their loved ones, and others who care for and about them.

A healthcare directive is a legal document that allows you to appoint someone else (an “agent”) to express your wishes for medical care and treatment, if you are unable to make your own medical decisions.

A healthcare directive may include: a health care proxy (or durable power of attorney), which identifies who will make decisions on your behalf), or a living will (or advance healthcare directive), which provides specific instructions regarding your medical treatment. Your appointed agent (or a successor, as backup) must be trustworthy, at the ready, and rock steady.

A good healthcare directive is far more than just a legal form, it informs your loved ones and healthcare providers of your wishes and hopes, if you are incapacitated. Equally, in the process of its creation, it informs you of your wishes and hopes, as you co-create the rest of your life. To guide your conversation towards creating a directive, The Conversation Project can help.

There are many options. An intentional and inclusive one is Five Wishes, which combines a health care proxy and a living will. More than 25 million people and 40 thousand organizations have used Five Wishes, which was written with the helpof the American Bar Association Commission on Law and Aging and developed by Aging with Dignity, whose mission is to safeguard our human dignity as we age or face serious illness. Five Wishes, available for $5.00 per copy, meets the legal requirements for an advance directive in 42 U.S. states and D.C.; In the other states, it can be attached to the required form for each state (here, provided by AARP). Most states’ directives work nationwide, but not all. If you need more help, consult an attorney to address your specific needs, and provide oversight and accountability.

Your directive must be within easy reach, any time. It’s best to distribute hard copies to your agent, family, and healthcare providers — for starters. You can register your directive and related documents online where they are secure yet available when needed. Consider MyDirectives (free), Docubank ($175, five years), American Living Will Registry ($65, five years) , U.S. Advance Care Plan Registry ($60, five years), and others; all have varying features.

In keeping with its name, developing a directive is empowering. In the process of its creation, it informs you of your deepest beliefs and values, hopes and fears, and your trust in others, your future, and your self-determination — informed by your constitutional right to make your own healthcare decisions. In summary, there are many pathways and choices.

You might need a financial power of attorney (POA), too. But, a thinking about a POA is not as motivating a factor for what is to come with bucket-list item four.

Fellow travelers in Sri Lanka —at the royal ancient city of the Kingdom of Pollonnarua, heading to Lotus Pond and Thivanka Image House. 2019

3 . Last Will and Testament

“I am what survives of me.” - Erik Erikson

When your bucket list doesn’t plan for mortality, you’re not playing life smart enough-for those you love most, for yourself, and as a motivation to reassess your bucket list. That’s why you need a “last will and testament.” When there’s a will, there’s a way; but with no will, your legacy may well go astray — along with relationships among those who love you the most, as they attempt to guess your wishes, with closure compromised.

A will is a legal document that deals with distribution of your property after you die. You, as testator, designate an executor (or two) who you trust to manage the distribution of your estate to specific people or organizations (“beneficiaries”) based on your written instructions.

If you-or someone else you love-is reluctant to develop a will, start a conversation by asking, “How Do You Want to Be Remembered?

If you die without a will you are “intestate.” Then, your state’s inheritance laws (they vary), administered by probate court, will — on their own timetable — determine who inherits your assets. When an estate is probated your most private possessions are exposed to public scrutiny. (If you think social media exposes you to public view, try probate court, which will have review over your will — unless you set up and direct all your assets to a living trust or other trust (there are many kinds). Trusts keeps the contents of your will private and allow beneficiaries to have access to your assets. Probate “freezes” your assets, until settlement; this doesn’t help your bereaved partner to pay the mortgage.

If you don’t have a last will and testament, you are in good company joined by Aretha Franklin, Jimi Hendrix, Michael Jackson, Amy Winehouse, Pablo Picasso, Howard Hughes — and, most recently, Tony Hsieh. Yes, protracted estate battles usually ensue, sometimes for decades at the cost of millions of dollars. Over half of adult Americans do not have wills, either. And the percentages are increasing. There being no designated beneficiaries, it’s lawyers who will most benefit.

Planning for bucket list items is fun. Thinking of kicking the bucket, much less planning for it, is not something anyone wants to do. But, every senior should think about it, then act. Once again, “seniors” are 18, not only 81, as every adult should have a will. If that doesn’t spur you on, how about when you get married, have kids (and need to name a guardian, if your family has minors), start a business, buy a house — and then there’s giving to that village school in Peru you hiked through.

Let your executor know where you filed your original will. They don’t have to know its terms. To be safe, put the original in a safe; it’s easier than a bank safe-deposit box, unless your executor(s) hold permission (and a key) to access.

If you don’t have a will, a simple start is using a DIY online will-making service. Most can be filled out in less than an hour, then printed, signed by executors, and notarized. Bucket list item three, done!

You can change the terms of your will by making a new will or adding codicils (amendments). As your life becomes more enriched — through relationships, experiences, and wealth, it’s a good idea to bring in a lawyer (and estate planner). If you think lawyers are expensive, try devil-in-the-details mistakes or omissions, which can cost—a lot.

Crafting a will involves the intentional, reflective process to realize your will, to give — reflecting your will to live (forever) and leave a legacy. Live to give; give to live on and on.

Fellow traveler — Confluence Point, The Needles, Canyonlands, Utah. 2020.

Back to Your Bucket List — Then, Beyond

Prince Siddhartha’s first three sights mirror your three bucket-list items:

  • Old age — Going long on longevity and investing in, and for, yourself today will pay dividends far in to your future — for yourself, and for many others. Each of us ages, if we are so fortunate. Spurred at the starting gate, you can couple life-long learning with long-life learning. This learning is not for some spring semester course; This learning is for your life course.
  • Sickness — Delving in to the essence of a health-care directive is a reminder of the preciousness of your life, and each day along the way. As a member of the specie sapiens — which means “one who knows” — you are blessed in having the capacity to know you are blessed — and to know, too, you are subject to disease, pain, and impermanence. Dwelling on this, empowers you to never take for granted the health and wellbeing you have been granted. Cradled by consciousness, gratitude is strong medicine.
  • Death — You will die. Denying your death denies the vital, profound meaning of your life. Right. Now. And far beyond. Having a will allows you to couple your will to live, every moment, with your will to give far in to the future. You can live forever — throughout your life and though your legacy.

Prince Siddhartha came upon the fourth sight, an ascetic who had devoted himself to finding the cause of human suffering. So spurred, Siddhartha renounced his princely life — with its hedonistic distractions and deceptions — to delve deeply for six years on the root cause of and solution to suffering and inevitable impermanence. All the while he suffered severe austerities, deprivation, and near self-mortification. But, spoiler alert, on becoming enlightened, Siddhartha — now the Buddha, “the awakened one” — realized ways we can transcend suffering to realize calm, insight, and even enlightenment.

Remember Channa, Siddhartha’s charioteer? Channa was Siddhartha’s guide. Siddhartha’s trip beyond the palace grounds was not to sight-see, but to seek insight. Perhaps Channa intentionally helped choose the day’s route to point out old age, sickness, and death, in cumulation — as a counterpoint to the varnished appearance intended by his protective royal family. Along the way, Siddhartha’s public procession became his private, personal progression.

Had Siddhartha been less hindered by hedonism and had he conducted specific meditation practices, these three experiences, informed by Channa’s pointing-out instructions, may have elicited immediate glimpses of the goal along the path. Thanks in part to the Buddha, millennia later, there are ways to glimpse the goal along the path. This way, the goal can illuminate the path.

The pandemic provides a pragmatic impetus to do the three first items that, in turn, are a catalyst for the fourth: to recognize your goal, and then gain glimpses all along the path.

How has dwelling on your first three bucket-list items informed — or transformed — your goal? What is your goal? Who are your guides along the way?

Please post your remarks, below.


Dedicated to Lori Stiegel, Esq., who helped many people realize their personal bucket-list items­ — starting with two and three, but extending far beyond. Lori also made many shared experiences — meals out, for example — worthy of bucket-list inclusion. Lori’s secret sauce? She recognized the preciousness of life, every day, together.

It’s not how you make it to the end of the road; it’s the road you get to help make.

Small Print, Disclaimer

The information provided in this article does not, and is not intended to, constitute legal or financial advice. It is for informational purposes only. Please consult an attorney or financial specialist for professional advice.

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