How You’ll Know When It’s Time to Let Go

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Ego, irritation and exhaustion are the watchwords of this story — the emotional and physical habits that work against us as we age. TLDR is the cheeky abbreviation for “too long, didn’t read” (yes, I learned that from a Millennial), so if you’re stopping here, try to guard against:

Self-importance (the conviction that only you know what’s best).
Sanctimoniousness (feeling thwarted when others counter what you believe to be right).
Overdoing it (because you believe you can control the outcome).

I want to tamp down these tendencies in the autumn of my life. Quitting work at age 68 may help me do that.

I have talked about retirement so often in this blog that my friends and family just dismiss me: You love being busy. You’ll never quit working. The first statement is true. The second has changed, which I never anticipated during my decades as a careerist.

At the end of August, after months of hand-wringing and internal debate, I finally left the last of my part-time jobs. I embraced the word “retirement,” even as I struggle still with what it means.

Getting there has been a journey:

Three years ago, in September 2022, I resigned from full-time employment after I turned 65 and archly declared that no one should view me as “retired,” given the two part-time positions I’d taken on.
Six months later, in March 2023, I described those jobs as a “glidepath” toward retirement and interviewed two peers who were taking similar approaches.
A year into the gig work, in September 2023, I described how part-time professional work pulls more on your intellect and energies than a job you leave behind once the shift is over.
In July 2024, more than a year before official retirement, I wrote about the decision to draw Social Security at age 67. It was another step closer to the inevitable. And toward acceptance.

Finally, this past February, I gave six months’ notice and developed systems that would make the transition easier for my successor. Here’s how I reconciled my instinctive desire to keep working — despite the privilege of financial security — with the reality that it was time to move on.

The first half of life is devoted to forming a healthy ego, the second half is going inward and letting go of it.
Swiss psychiatrist and psychologist Carl Jung

Once ego takes over

My final job was as managing editor of Streets.mn, an online publication that advocates for “people-centered communities”: bike and pedestrian infrastructure, public transportation, vibrant public spaces and more abundant housing throughout Minnesota. The quarter-time position was the only paid job within the volunteer-based organization. I worked with board members who had full-time responsibilities elsewhere, with unpaid contributors who had little professional writing experience, and with copy editors who were donating their time and had varying degrees of commitment to learning the fine points of AP Style.

The work was rewarding and challenging — a big stretch for a part-time gig, with the responsibility of publishing a new piece of well-reported content every weekday. The board would warn me from time to time that donations were down and cut my hours for several months at the end of 2024. And yet I remained motivated and immensely proud of the work, getting to my computer every workday before 6 a.m. to ensure we met the 7 a.m. publication deadline.

Dedication morphed into ownership as I passed the three-year mark. I thought less about what “we” were accomplishing, together, with this reputable publication and more about how “I” had transformed it into a well-oiled machine.

My successor approaches the role differently and is contributing her own strengths. In the four weeks since I left, I have ceased to check the website every morning and note the copy-editing changes I would have made. (A friend challenged me to stop; just stop.) Time to separate, to let go and, for my own peace of mind, to abandon the notion that my way is the only and obvious answer.

Endings are a little overrated. When the ending is here, it’s here, and you just move forward.
WNBA all-star Diana Taurasi, who retired in 2025 at age 42

Restless, irritable and discontent

My insider joke, more relevant a year ago, was that I didn’t want to become the Joe Biden of Streets.mn — the oldest person in the room at board meetings, writers’ gatherings and readers’ happy hours; the leader who couldn’t accept that she was aging out.

Collaborating with younger people helps keep me mentally fresh. I’ve recognized that since I turned 60. Still, as my quit date got closer, little irritants kept popping up that I could only attribute to a generational divide:

A Macalester College student who wrote for us occasionally texted me after our coffee meeting to suggest I use AI editing to reduce my workload — apparently unaware of all the years of experience and mentorship it required for me to get good at this.
A guest on a Streets.mn podcast episode declared that “all cops suck” in Minneapolis, and the host agreed, as though it’s a verified fact. I don’t believe that to be true, nor is it my experience with police. But maybe those are the uninformed musings of an older white woman.
Though I often told writers that an editor’s job is “to make you look good,” I grew weary of polishing stories that lacked focus or solid reporting. I wondered whether my obsession with word choice, fact-checking and well-crafted sentences was outdated in an era when fewer people read books — or read, period — and when TikTok users see “celebrities” and “influencers” as a legitimate source of news.

A former college professor, a woman whose work was her calling, told me she knew it was time to retire when she got tired of dealing with students. Exactly.

We do best when we learn how to have both work and rest in our lives.
Women Rowing North (2019), by Mary Pipher

The body’s wisdom

I kept notes during the first month of my retirement to track how this life change feels physically and emotionally. I was sick the first few days: stomach problems, little appetite, a newfound love of naps. After consulting WebMD and freaking out at the possibilities, I came to recognize that my malady was pure exhaustion.

I am grateful every day that I enjoy such good health at 68. I can’t imagine life without biking, walking, yoga classes, physical mobility. Yes, these are the “golden years.” But how long can they last?

Two weeks ago, my cousin had to cancel our plans to meet at the Minnesota Landscape Arboretum, and I had an entire day unscheduled. I cooked and listened to podcasts, took a bath and read, baked spoonbread in two pans and shared one with a neighbor who has suffered a broken collarbone. I never allow myself this luxury of time.

“When transitions happen and identities change, one of our great challenges is to find a new sense of meaning and purpose in our lives,” writes psychologist Mary Pipher in the 2019 book Women Rowing North, which is written for the phase of life I’m entering.

This is my chance, finally, to put family first. To cultivate and honor friendships, the intentional family that has stood by me. To spend time with my first grandchild and be present for my grown sons. To retire not only from a career but from achievement and doing, from broadcasting accomplishments on LinkedIn, from filling up my calendar because it helps me feel important.

Time is fleeting. That’s a reality for everyone, but only in old age do you know it to be true.

Senior Timeshares: Beware the Hard Sell

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I should have been suspicious from the start. Because the older I get — and I just turned 68 — the more I recognize that when I react rather than respond, or am impulsive rather than intentional, allowing my body to move more quickly than my brain, the situation rarely ends well.

The story begins last March. When I reserved a hotel room for a women’s conference in Des Moines, Iowa, this coming February, the booking agent asked at the end of the call if I could stay on the line to hear a marketing offer. Because the property where I had booked a room is part of a major hotel chain, my reward would be 500 points in the organization’s honors program. “Sure,” I told the agent, “I’m game.”

Apparently, I had joined the program for repeat customers back when I traveled to professional conferences once or twice a year. On my own time, I prefer to stay at AirBnB or VRBO short-term rentals because the properties are homey and private, provide a kitchen that helps save on meal costs and tend to be situated among the locals. In short, I feel less like a pampered tourist.

A VRBO in North Carolina that my sister rented for three of us last April for a family wedding.

But pampering is precisely what this hotel chain — and all of the hotel-affiliated timeshare programs — aims to do. The marketing pitch was an enticing offer to spend a few discount-rate nights at a swanky property in Las Vegas or Florida or, my choice, New York City in exchange for a two-hour meeting about the company’s “exclusive timeshare brand.”

The pitchman on the phone asked about my travel habits, employment history and marital status. (Red flag!) Then he offered a reasonably priced deal for three days and two nights at a hotel in midtown Manhattan, but he emphasized repeatedly (another red flag) that I had to pay the $285.75 charge on the spot — that day! I also had to promise that both my husband and I would be on time for the 8:30 a.m. timeshare meeting the morning after we arrived. Otherwise, our hotel room would revert to full price, about double the promotional rate.

Some weeks later, we forked over an extra 65 bucks to convert the trip to a slightly longer four days and three nights at a property in downtown Chicago, a scenic train ride away from our home in the Twin Cities. The tactics of the hard sell at the morning meeting (“don’t be late,” the desk clerk warned when she checked us in at the hotel) harkened back to the original phone call. Not duplicitous but canny, and well rehearsed.

Buy now, pay later

From the get-go, the whole tone and tenor put me on edge, employing sales techniques I had never experienced, even on a car lot. Once we arrived at a modern, amenities-laden property a 15-minute walk from where we were staying, I had to answer a list of the identical questions the telephone salesman had asked me weeks before (marital and employment status being key).

Hotel representatives also wanted to know our top “dream vacation” spots to get away. My choice of Canada and the Netherlands may have been a clue that we weren’t their highest budget catch.

Once the Keurig machine had brewed our coffee and we’d collected mini containers of yogurt and cellophane-wrapped pound cake (the promised breakfast), the meeting began, led by a jovial salesman named Pete.

Dressed in business casual (a jacket and necktie would show up later on the man who tried to close the sale), he ushered us into a brightly lit office with partial walls and no door, lending an air of immediacy and vibrancy given the noisy activity in the hallway.
The persistent beat of the piped-in Muzak, loud enough that I sometimes couldn’t hear what Pete was saying, seemed designed to distract us. When I asked if he could turn the music down, he said the volume kept others from overhearing Social Security and credit card numbers when deals were getting done.
Within minutes of sitting down, Pete asked us what type of properties we usually like to stay in. I explained our preference for short-term rentals — they accommodate my early-bird and my husband’s night-owl tendencies — and specifically mentioned Airbnb. Later, when Pete was showing us a typical timeshare suite on an upper floor of the hotel, he told us that he once discovered a video camera in the shower of an Airbnb and (“thank goodness!”) removed it before his wife used the bathroom.
Noting that a key card is required for entrance to the elevators, Pete stressed the safety of the hotel chain’s timeshares — a selling point for the graying target market — and said only other timeshare members would be on the floor of any property we rented. Like a gated suburban community, we’d be tucked in among our own.

Throughout the exciting, emotional, enticing presentation (and it was all three), Pete flipped through digital photos of hotel-chain properties, from resorts and cruises to “glamping” sites at national parks, on a horizontal monitor embedded beneath his glass-topped desk. He said we could join the timeshare program for $80,000 — more than 20 percent of which would be due that day.

Florida beach: Photo by Michael Monahan on Unsplash

“We can’t access that kind of money on the spot,” I told him. “It would have helped to know this coming into the meeting.” He assured us the company could provide a credit card on which to finance the $17,000 down payment; we would sign a contract for the rest, plus the annual HOA fee of $2,100.

My head was spinning. “Could you give us your last name and mobile number,” I asked, “so we can talk things over this afternoon?” Pete said he carried no business cards — an odd practice for a salesman — and stressed again the act-now nature of the offer. Just like the telephone sales pitch that had gotten us to Chicago in the first place, the deal had to be done immediately. On the spot.

Nearly 90 minutes into the two-hour presentation, I learned that our assigned timeshare location would be in Florida, with options to use other company properties around the world. I had already explained to Pete that I wouldn’t spend money in a state where my transgender cousin could be charged with a felony for using a women’s bathroom and where the ACLU describes the year-old abortion ban as “near total,” with “no real exceptions for rape or incest.”

He said no other property was available that day — these being act-now, one-time offers. Then he brought in a “closer,” a trim man in a tailored suit, who consulted his iPad and said he happened to have a different Florida property for only $53,000, a considerable savings from the original quote of $80,000.

But it was Florida again, which we neither wanted nor requested. I walked out, leaving my husband to extricate himself while I waited on the sidewalk, red flags flying everywhere I turned.

Exit strategy

A timeshare sounds like a great idea, a cooperative ownership agreement with like-minded people for a property you have toured and approved. Or, so I thought, based on the arrangement my late father’s law firm had at a ski resort in Colorado.

In this case, the hotel chain wasn’t selling us a property per se. We were purchasing points for the right to stay a certain number of nights per year at any company property — 30 nights, based on our $80,000 purchase price — but we’d still be attached to this place in Florida, sight unseen.

Red flags by J.S. B. on Flickr. Creative Commons (CC) 2.0

My husband and I hadn’t realized that timeshare agreements can be notoriously hard to get out of. I learned that after a Google search led me to warning articles from AARP, a source I trust because they target scams that target seniors. A few days later, searching for the replay of a WNBA game on YouTube, I was stopped cold by an ad from Wesley Financial Group about “timeshare lies.” Apparently, my browsing history had led them to me.

Dubbing itself “the most proven and reviewed timeshare exit company” — CEO Chuck McDowell used to be a timeshare salesman — Wesley employed an attractive young actress to ask whether any of these sales tactics had been used in our timeshare pitch:

1. “Your maintenance fees will never go up.” Yes, Pete had told us that. On average, said the Wesley spokeswoman, they go up 4 percent a year.

2. “This is a financial investment.” We’d heard that, too. But real estate investments pay off based on supply and demand, “and the supply [of timeshares] is always high because of the massive marketing machine that is the timeshare industry,” the Wesley woman said.

3. “Your obligations will die when you pass away.” Actually, Pete had suggested the opposite, saying we could transfer the Florida property and the timeshare points to our two grown sons once we became too infirm to travel. Regardless, according to Wesley Financial Group, “most agreements are in perpetuity.”

After sitting through the mandatory meeting in Chicago, I recognized that a hotel- or resort-based timeshare — offered by Marriott, Disney, Wyndham, Hilton and others — could be ideal for people who travel more often than I do, who want luxurious accommodations where they are separated and safe, and who don’t let political leanings or social issues dictate their destinations.

That isn’t me. In hindsight, I am grateful to have walked away a little wiser and a whole lot less naive, and didn’t fork over $80,000 to remind myself of who I really am.

Travel as a Practice for Retirement

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A version of this story appeared on June 10, 2025, in Next Avenue, a national publication for older adults published online by Twin Cities PBS.

When I left full-time work in September 2022, two months after turning 65, people naturally asked me how I liked retirement. Once I’d barked out my disdain for the R-word — chin lifted, spine stiffening — they learned not to inquire again.

In fact, the anxiety masked as rigidity was less about them than me: Retirement is a daunting prospect for us Baby Boomers who link our identity and sense of self with work.

I still don’t call myself “retired,” even though I work only a quarter-time job and a handful of contract gigs. But that’s about to change. I’ve given notice at my job, and my first grandchild is on the way, along with some shared responsibility for infant care.

Husband, David Studer, and our older son, Sam Studer, who is at London Film School

Since my husband and I had planned an overseas excursion this past April to visit our older son, who is studying at London Film School, I decided to approach the trip — only my second time in Europe — as practice for the less structured, more selfless life that is awaiting me.

Here’s what I learned.

Lesson 1: Lose Track of Time

We go-getter careerists live and breathe by our agendas. This holds true for me even 32 months after leaving full-time work. My quarter-time job, my freelance assignments, even fitness classes and coffee dates with friends: All fill my calendar at least a month or two out from where I stand today.

The decision to avoid sticking to a rigid schedule in London, aside from ticketed events and planned outings with our son, was an exercise in letting go — both a relief and a discipline all its own. As we planned the trip, I insisted on only one “anchor activity” a day, forcing a spontaneity I rarely allow myself to experience.

My favorite times were early mornings, while my husband was still asleep. With no deadlines to hit or dogs to be walked, I wrote in my journal. Sent postcards back home to friends. Read the library book I had downloaded on my iPad.

I refused to check work emails, relying on the out-of-office message that told people I was away, and tried to sit with the discomfort of being unproductive. The clock dictates my day, and it took effort to silence the pragmatic voice that drives me, even on weekends: “It’s 10 a.m., and you’ve accomplished nothing.”

So what? No one was monitoring my output or keeping score on how deeply I dug into London’s vast cultural scene. Free to let the days and evenings take their course, I felt how nourishing a less hectic life can be. No coincidence, I slept longer and more deeply in a stranger’s British flat than I ever do at home in my own bed.

Lesson 2: Get Out in the World

As luxurious as it was to hang out some mornings, I also had days when I left my night-owl husband sleeping at the Airbnb and struck out on my own. March and April are London’s least rainy months, and a stretch of sunny weather made it a joy to start the day walking the streets or seeing the view atop an iconic, red double-decker bus.

Pro-tip: Google Maps and the Transit app were my best sources of navigation, but I also felt more comfortable being out alone in the daytime once I’d been in town long enough to learn my way around.

One of my fears about full-on retirement is losing regular contact with younger colleagues and allowing my world to shrink. It’s become tempting as I age to stay home with a good book and a homecooked meal, or to settle in with my pets and watch Netflix or women’s basketball and tell myself that is enough. Or that it’s safer.

So, following the lead of a widowed friend who goes alone to movies and concerts and routinely travels on his own, I spent the better part of one morning at the Tate Britain — one bus ride away — browsing the museum store, strolling through galleries and relaxing outside the cafeteria with my book. Yes, I was alone, but I was also among people.

Given my career in journalism and communications, I can easily strike up conversations with strangers, even in a city with thick English accents. The trip showed me how to carry my professional skills into retirement, when I no longer can wrap myself in the security blanket of a title and role, with a ready answer to the question: What do you do?

Lesson 3: Dress to Please Yourself

During my decades as a business reporter and later a marketing-and-communications director, I dressed up every day. Looked and acted the part of a career woman. I enjoyed shopping and the creativity of assembling a wardrobe — mixing and matching outfits, coordinating earrings, scarves and shoes — but toward the end of my career, especially after COVID, “dressing for success” felt like donning a costume. It wasn’t me!

In London, I had no one to dress for but myself. My comfort, the weather and how far I would likely walk that day dictated what I wore. That meant:

Comfortable shoes with heel support and a roomy toe box for the 17,062 steps I averaged during my nine days abroad.
Little to no eye makeup, even for “Carmen” at the Royal Opera House, because it could smudge in the wind and cold.
Refreshing my short razor haircut the day before we left, so I could fluff it with my fingers after wearing a hat for warmth or sun protection.
Ditching the more fashionable purse for a sturdy backpack, both to free my arms while walking and to discourage bag snatchers.

Now that I operate from a home office, I rarely dress up anymore. “Athletic casual” is how my younger son defines my style. Retirement allows that freedom — to quit comparing myself with younger women and dress for the age and body type I am today. And for movement, the best antidote to low energy and stiff joints.

Lesson 4: Keep Learning

My gradual glidepath to retirement these past two and a half years has given me time to adjust, both financially and emotionally. Of course, I worry: Will we have enough money? Who will I be without work? Will volunteering and family life fulfill the sense of purpose that a career has given me for decades?

A trip to London is not exactly high adventure for a white American with English roots. Still, I find it fitting that a foreign country became my place to try out a different way to live. Retirement is a bold undertaking, a journey toward a different land. My passport — my practice in the coming months — will be to remember and refresh these lessons learned.

The Middle Stages: Between Midlife and Old Age

By Amy Gage