Dolly Parton has passed.
We all get two major transitions in life: birth and death. In between, life is made up of countless smaller transitions, some unfolding in sequence and others overlapping. Some announce themselves loudly; others are so gradual we barely notice them. Often, it is only with time that we understand how significant a transition really was.
In a culture that often portrays post-midlife as a slow roll downhill, I contest that idea. What is a stay-at-home mother supposed to do when her three kids have flown the coop? For so many of us, this is not simply an ending. It is a next act. With one ending comes the possibility of another beginning.
In What to Make of a Life: Cliffs, Fog, Fire and the Self-Knowledge Imperative, Jim Collins draws on his study and analysis of lives to examine how people navigate change, setbacks, and reinvention. There are many takeaways, but one of the most hopeful is essentially this: it ain’t over till it’s over.
Dolly is a wonderful illustration of that. She did a remarkable amount after 50, and not simply by continuing to sing and perform. She built businesses, expanded her philanthropy, wrote a novel, and kept finding new ways to create and contribute. Her later life was not a winding down.
Collins writes about the different encodings we carry, capacities that reveal themselves throughout our lives and can find expression in very different ways. Benjamin Franklin was a printer, publisher, author, scientist, inventor, postmaster general, politician, and diplomat, and he contributed until his death at age 84. Those examples aren’t rare. Over a lifetime, most of us do many different things, often even within a single career.
And now the work itself is changing.
As AI reshapes how products are built, teams are getting smaller and roles are becoming broader and less specialized. A product designer can now code, and a product engineer can design better than before. Boundaries that once seemed fairly fixed are getting blurry. With such a shuffle and rate of change, one of the most important skills may be a person’s ability to transition easily.
It’s like the song title Here You Come Again. Just when we get ourselves together and feel back on track, another transition waltzes through the door and changes things again. Sometimes the change is enticing and we move toward it willingly. Other times, we resist it. Either way, transitions keep coming, and part of life is learning how to meet them.
And so, here I stand in an almost empty house.
Our last kid was dropped off for her freshman year at college, and I dove right into the transition by purging our house to prepare for some home updates. I have found time capsules while cleaning out this house. When the bonus room couch was removed, there was clear evidence of seven years of teenage living: AirPods, probably 50 batteries, chips, fake fingernails, a retainer, and thankfully no vapes, bongs, or Trulys.
But the evidence was there, and now it has been cleaned away, ready for the next transition: my new home office. My she-cave, where I’ll work 9 to 5 (maybe not those hours exactly), pour myself a “cup of ambition,” and use tools that are changing quickly.
We’re transitioning together.
The way I see it, as long as I am breathing, transitions are a gift. They are another opportunity to keep carving one’s life. To use all that one has learned to shape the next era, while also finding some peace and excitement in the fact that circumstances and luck are factors too.
So what will happen tomorrow?
I don’t know.
AI superforecasting may have a better guess, though.
Preseen is an artificial intelligence forecasting platform that uses AI agents to operate something like a panel of expert human analysts. The company says its forecasting system helped turn $35 into $1.94 million on Kalshi.
Are you closing out this article to sign up for Preseen right now? I already tried. It currently appears geared toward high-stakes institutional decision-makers rather than everyday consumers.
But what interests me more than whether I can use Preseen today is what it represents. Even the tools we use to think about what comes next are changing. There are open-source codebases and communities experimenting with forecasting agents, and it seems only a matter of time before powerful prediction tools become accessible to ordinary people.
That is another transition.
Transitions in life stages. Transitions in skills and work contributions. Transitions in the tools available to us. Transitions in the intelligence available to us and how we use it. Even transitions in our ability to make sense of what may be coming next.
The confluence of it all, and how we move through those transitions, shapes our path ahead.
And through all of these transitions, one very human capacity endures.
Dolly said it best: “I never tried quitting, and I never quit trying.”
Amen.
Dolly After 50
1996 to 1999: The Rebranding and Traditional Roots
1996: She turned 50 and shifted her focus to new business models, releasing the album Treasures under a fresh record label.
1997: She dissolved her old, traditional pop-era fan club to completely remodel how she connected with the public.
1999: She launched a stark artistic shift by recording her first pure bluegrass album, The Grass Is Blue, intentionally walking away from radio-pop to preserve Appalachian acoustic music. [1, 2]
2000 to 2009: Going Global and Creative Control
2000: She officially took her Imagination Library national, scaling it up from just her hometown in Tennessee to a nationwide program. [1]
2003: Her literacy charity reached its first massive milestone, mailing out its 1 millionth free book to children. [1]
2006: She took her charity global, launching the Imagination Library in Canada to provide free books to kids across North America. [1]
2007: She established her own independent record label, Dolly Records, ensuring she retained total ownership and absolute creative control over all her future music. []
2007: She expanded her global charity footprint again by officially launching her free book program in the United Kingdom. [1]
2009: She brought her songwriting talents to the theater world, composing the entire original score and lyrics for the 9 to 5 Broadway musical production. []
2010 to 2019: Huge Expansions and Disasters
2010: She celebrated the 25th anniversary of her Dollywood theme park by heavily expanding the property, transforming it into the largest employer in her native Sevier County to keep thousands of local people employed.
2013: She launched her literacy program in Australia, bringing her free book charity to its fourth continent.
2016: When a massive wildfire tore through Gatlinburg, Tennessee, she instantly set up the “My People Fund,” giving $1,000 a month to hundreds of local families who lost their homes.
2018: Her charity achieved a historic milestone by gifting its 100 millionth book, which was personally donated to the Library of Congress.
2019: She continued her European charity growth by successfully launching the Imagination Library in the Republic of Ireland. [1, 2, 3]
2020 to 2026: Modern Innovations and Final Projects
2020: She donated $1 million to the Vanderbilt University Medical Center, which directly helped fund the early, critical research for the Moderna COVID-19 vaccine.
2020: She partnered with Netflix to write 14 original songs and executive-produce the holiday musical film Christmas on the Square.
2022: At age 76, she expanded into fiction writing by co-authoring the bestselling thriller novel Run, Rose, Run with author James Patterson, simultaneously releasing a companion album for it.
2023: She fulfilled a personal promise to record a rock-and-roll record, releasing Rockstar—a massive 30-track project featuring collaborations with classic rock legends like Paul McCartney and Elton John.
2025: She debuted Dolly: A True Original Musical in Nashville, a brand new stage production detailing her life and legacy.
2026: Even in her 80th year, she continued building her business empire by opening Dolly’s Tennessean Travel Stop in Tennessee and officially opening her brand new SongTeller Hotel on the Nashville skyline. [1, 2, 3, 4, 5]
(the above excerpt is from a Gemini search)