Falling Leaves: A Checklist for Life’s Autumn Season

Gnarly tree in early autumn

Even if I could ignore the red and gold leaves, the critters let me know when autumn has arrived. Every year, an epic battle ensues beneath the pecan trees outside my living room window. The crows squawk an awful complaint as they dive bomb the squirrels, who dash in to collect a nut almost before it hits the ground. It’s fierce. And loud. And comical. But it’s no game for the squirrels and crows. In response to their innate programming, they are all business as they prepare for the oncoming winter.

We humans should take note, but we tend to eschew checklists in our autumn season. After all, isn’t that what we most look forward to in retirement? No deadlines. No schedules. Ahhhh. But winter is coming, and being a planner, I approach my autumn years with a checklist to keep me focused. Here are the six items I’ve been clicking through for awhile now.

1. Get your financial house in order

One of the biggest stressors of retirement is wondering if your nest egg is sufficient to provide for your needs. But even if you have a hefty portfolio, you will still face many decisions. Now is the time to engage a qualified financial planner who can assess the quality of your planning and help you answer these critical questions:

  • How do we know if we’ve saved enough?
  • Given the size of our nest egg, what does our cash flow picture look like?
  • We have dreams….can we afford them?
  • How does our financial picture change with the death or terminal illness of a spouse?
  • Are we caring for parents, children, or grandchildren?
  • What’s the best time to take social security?
  • Are we invested appropriately for our time horizon and risk tolerance?
  • Should we manage our own investments or engage a professional?
  • Do we need long-term care insurance?
  • Do we need life insurance?
  • What do we want to happen to our assets after we die?
  • Is a will sufficient to carry out our desires, or do we need a trust?
  • Do we desire to leave a bequest to our favorite charity?
  • Should we move to be closer to our children?

So. Many. Questions. We engaged a financial planner two years ago, and it’s one of the best decisions we ever made. Even the first step of explaining your financial picture to someone else forces discipline and conversation around a topic we often relegate to the back burner. It takes time to flesh out your financial plan and clarify your investment strategy, not to mention the work involved in estate planning. Pace yourself, but definitely get started.

Of course, choosing the right advisor makes all the difference. Do some online research to get an idea of the industry, and decide what matters to you. Be prepared to interview a few before choosing one. We knew we wanted:

  • a CFP (Certified Financial Planner)
  • someone with no financial stake in our decisions, other than their fee (in other words, we don’t engage our financial planner to manage our investments)
  • a personal recommendation from someone we know and trust
  • a fee schedule we could afford
  • someone we liked and felt comfortable with

After two years, we feel like we can put a check mark by this item. We have completed our will and trust, we have clarified our investment strategy, we know our net worth and cash flow, and best of all, we have an independent third party to advise us on the purchase of a Wyoming cabin! Financial planning is ongoing, of course, but we’ve completed the heavy lifting. Woo hoo!

2. Time for some Swedish death cleaning

If you’re unfamiliar with the term “Swedish death cleaning,” I can best explain it as the thing you wish your deceased parents would have done, as you’re sorting through 80 years of their accumulated stuff! The phrase comes from Margareta Magnusson, who wrote a book called “The Gentle Art of Swedish Death Cleaning.” I may post more extensively about her technique later, but the gist is to clear your life of clutter as a kindness to your loved ones, to reduce their burden when you’re gone. In her own words,

Do not ever imagine that anyone will wish — or be able — to schedule time off to take care of what you didn’t bother to take care of yourself. No matter how much they love you, don’t leave this burden to them.

Magnusson, Margareta. The Gentle Art of Swedish Death Cleaning, page 7.

Unlike Marie Kondo’s litmus test — “does it spark joy? — Margareta’s litmus test is “Will anyone want this when I’m gone?” Now, Lord willing, we’re not leaving the planet this week, so of course we consider the present usefulness and personal enjoyment of our stuff, too. For that reason, Swedish death cleaning is not a “one and done” task. Rather, it’s a repeated culling, a response to our changing life circumstances as we age.

Life’s autumn season is the perfect time to start our Swedish death cleaning. Where do we begin? Decluttering involves sorting, eliminating and organizing by category. You may wish to start in the garage, basement or attic with those things you use less frequently. Then move to the house and work by category, not room: clothing, books, household items, linens, decor, collectibles, etc. Start with utilitarian categories, and save the sentimental items like photos, keepsakes and personal papers for last.

Give yourself plenty of time, but also set some goals to keep yourself focused. Let your family know you’re engaging in this project, and then as you come across items you think might be of particular interest to one of them, they won’t panic when you ask them if they would like to have it when you’re gone!

Here are a few questions I ask when I’m trying to decide whether to keep or discard an item:

  • Do I still like it?
  • Do I still use it?
  • Would I want to pack it for a cross-country move?
  • Would someone else derive more pleasure or use from it than I?
  • Am I supposed to like it because it’s attached to a memory of someone I love, but I really don’t? (Time to be honest!)
  • Will it have sentimental value to someone else in the family, even if it doesn’t to me?

If you have adult children, you likely still have some of their special keepsakes in your home. You know, high school yearbooks, packets of prom photos, letter jackets and athletic medals, school papers, favorite stuffed animals, etc. At one time, these items were too precious to part with but not so precious your little darling wanted to move them to her Seattle apartment. Okay. We’re reasonable, loving parents. But my Swedish death cleaning led to a new family rule, “By the time you turn 40, you take all your crap with you!” Just sayin’. Six more years…..

3. Preserve your family legacy

As the span of time ahead of us gets smaller, we naturally turn our attention to the span of time behind us. Memories grow sweeter. We grow reflective. We can now see the narrative arc of our own stories. And we wonder if anyone will care 20, 30, 50 years from now.

As one by one we lose family members, we start to value the stories that shaped us. Have you ever gone digging through a box of cool old photos, only to find you had no earthly idea the identities of the smiling faces? You know these are your people, your tribe, your history, but the story is lost forever because anyone who could have told you the story has died. What a tragedy! Suddenly it’s urgent that our children and grandchildren know their family history.

Here are just a few projects to consider:

  • Organize and label your photos. This is a DAUNTING task, since most of us don’t have hard copies any more, and the digital files live on multiple devices. You can find any number of tools to help you, but the biggest challenge is getting started. Choose a cloud storage option for your digital files (Google, iCloud, Dropbox) and started sorting, deleting and organizing. Make a plan and pace yourself. Full disclosure: I have started this project several times….
  • Digitize the best of your hard copy photos. My mother has elaborate scrapbooks of our family photos, but there’s only one copy and four children. So I intend to scan the best of the photos for easy distribution. Photo books of family history make great gifts for grandchildren, when they are old enough to have an interest in the family tree. These don’t have to be works of art! If you set the bar too high, you’ll never do it. Keep it simple.
  • Write your memoir. How better to ensure your story gets told than to tell it yourself! This can be as simple as a Walgreen’s photo book or as detailed as a published volume.
  • Write a personal letter to those dearest to you, and leave it with your will and important papers. Too many times, we leave our deepest thoughts unsaid. Your tender words of love and remembrances will be a treasure to those you hold close.

4. Get that bucket list in writing

How many times have you referenced an item on your bucket list? Does that bucket list exist on paper, or is it only in your head? For me, it’s only in my head. And while I think my husband and I share several bucket list dreams, I’m not really sure. Shouldn’t we talk about that? Yes!

As time becomes increasingly precious, the need to be intentional becomes more urgent. Have the conversation with your spouse or significant other, and write down your dreams and aspirations. When you see them in writing, you’ll more easily be able to prioritize them. And if you find your dreams going in different directions, you can decide how to negotiate or compromise to validate each person’s dreams.

It helps to look at your dreams in increments of time, maybe 7 years or 10 years. Because let’s face it, your health and energy will preempt some of those dreams as time marches on. So figure out which bucket list items have a shorter shelf life, and pursue those first. This also helps with your financial planning. If your bucket list includes extensive travel or buying a vacation home, your cash needs will likely be more heavily weighted to the early years of retirement.

5. Prioritize friendships

A curious thing happens in the autumn season — you grow a second family. They are called “friends.” No matter how close your relationships with your adult children, you still need a close circle of friends. Let’s face it, your kids will be in their busiest season of life when you start needing them more. Whether they live a thousand miles away or are geographically close, they will be weighed down with responsibilities and not entirely attuned to their parents. Don’t take it personally. It’s life.

Many of us neglected friendship during our working years. Too busy. Pulled too many directions. But now? Now you have time. Friendships can’t be forced, but they can be cultivated. If you’re a little rusty, start with this Friend Inventory.

  • If you had an emergency, what non-family member would you call?
  • If you had extra tickets to a ball game, concert or other entertainment event, who would you invite first?
  • Who are the people with whom you have significant shared history?
  • Who are the people who love you enough to tell you the truth when you need to hear it?
  • Who knows your secrets, has seen you at your lowest points, and still likes you?
  • Who makes you laugh?
  • Who makes you feel seen?

Start with these friends, and be honest about which ones truly enrich your life. Friendships grow and change over a lifetime. It’s okay (and maybe necessary) to let go of a friendship that just isn’t working anymore. Sometimes new friendships add an unexpected spark of joy in this season, so keep your heart open. But above all, be intentional about cultivating the relationships that matter most.

Autumn in the Big Horn Mountains, Wyoming

6. Write your eulogy

Of course, I don’t mean ACTUALLY write your own eulogy….that would be so vain! But in daily decisions about how to spend your time, focus on building your eulogy with the same energy and passion you previously devoted to building your resume.

The act of choosing includes saying both “yes” and “no” to requests for your time. Don’t let yourself get sucked into doing something out of obligation just because your work week looks like six Saturdays and a Sunday. Choose instead to devote your time to the people, projects and causes that give you the most joy. For all the years you worked 60-hour weeks and had to always say “no” to charitable opportunities, now you get to say “yes.” Choose wisely.

And while you’re thinking about how to best use your time, consider what mundane life maintenance jobs you might be able to eliminate. Do you love mowing your 2-acre yard? Do you get your jollies maintaining a 3,500-sq-ft home? No? Then why not scale down and free up both money and time for something more satisfying.

The heart of your eulogy will reflect your relationships. What do you want people to say about you at your funeral? Stated another way, whose life will be diminished by your death? If you can’t think of anyone, maybe your time investments weigh too heavily on wood, hay and stubble. Your best legacy won’t be found in your will; it will live in the hearts of the people in whom you invested.

Just like the last months of the calendar, life’s autumn season can be rich and vibrant, comforting and cozy. Address these winter preparations, and then relax and enjoy!


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  1. I enjoyed this article very much. I have ordered the book “The Gentle Art of Swedish Death by Margareta Magnusson. Also, I ordered 2 workbooks that go with the book. We started decluttering in February this year. The leak in the garage behind a water heater was a blessing in disguise. We still have a lot of clutter on the back porch that came out of the greenhouse. We also have a lot of clutter in the extra bedroom that came from the garage. We will eventually get everything srrasightned out and I’m sure the book & workbooks will be a help. We plan to deal with our tremendous number of picture albums this winter. Today, I’m going to the back yard & plant 14 new daylilies that I ordered from a catalog. I’ve ordered some ferns & I hope they come in soon. I’ve always liked ferns. Thanks for taking the time to write articles that will help a lot of people. I wish the best for you.

    1. Joanne,
      This is awesome! I had no idea there are workbooks, so I will definitely check that out. Sounds like you have a solid plan in place! Would love to hear how it goes, so feel free to comment later with an update.

      Take care,

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