How many times over the past decade (or longer) have you heard yourself say, “I’d love to do that someday,” or, “Once the kids are grown, I’ll finally get to…”? If you’re like me, your mental “someday” file is overflowing, and that imaginary finish line — where you can finally prioritize yourself — keeps getting pushed back.
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For example, my teen and I have talked about traveling to the Pacific Northwest for several years. I care for elderly parents (ages 98 and 84) and am self-employed (e.g., no paid time off). Earlier this spring, an editor friend reached out and asked if I (and my teenage son) would be interested in a cruise to Alaska, where we’d be the guests of the cruise line in exchange for evaluating all it has to offer for a magazine article.
Immediately, I thought of all the “what ifs” and “what abouts” — what if my parents need help and we’re 3,700+ miles away? What about the bathroom renovation and electrical rewiring, especially if I take 11 unpaid days’ vacation?
I broached the idea with my 15-year-old, whose first reaction was, “Heck, yeah!” and then I took a deep breath, called my friend back, and said, “Book the trip.” My parents were just fine. So were our four cats. And my kid and I had an incredible time exploring Seattle, Victoria Island, and multiple ports of call in Alaska. (Pro tip: If you travel to Alaska and have an option to visit a glacier or go dogsledding.)
What if your “someday” has arrived? You’ve done the heavy lifting and earned your stripes. Time for some fun. You’ve entered your next era and should reframe it not as a gentle slide into retirement but as your encore performance. You have the wisdom, resources, and delightful lack of giving a hoot about what others think.
If you’re nodding your head in agreement but stumped, keep reading. Use this list as inspiration to plan a trip, try a new hobby, stretch far outside (or stick a cautious toe) outside your comfort zone. As a former high school teacher, I give you this list as your official permission slip to be gloriously, unapologetically selfish with your time. Must you do everything on this list? Nope. But I bet reading them will spark a fire. Which adventure will you try first?
Adventure and exploration
- Become a solo traveler (start small): Take that first step by booking a trip where you’re the only decision-maker. Visit a quaint shore town for a long weekend or head to the mountains for a few days. Enjoy the solitude and having no responsibilities except for yourself. I love my overnight trips — alone — to Cape May.
- Hike a “big deal” trail: Love a challenge? Set one for yourself, like walking a few dozen miles (or all) of the Camino Del Santiago, trekking to the base camp of Mount Everest, or hiking the Appalachian or Kalalau trails.
- Find the Northern Lights: Chase the Aurora Borealis in Iceland, Norway, or Alaska. I’ve seen the sky dance with brilliant reds, greens, and blues. It’s incredibly humbling and a once-in-a-lifetime experience I’m so glad I had.
- Take a cross-country train trip: Try a vacation by rail, across the Canadian Rockies, through Sedona and the Grand Canyon, or over Australia’s Nullabor Plain or from Darwin to Alice Springs.
- Plan a wine or culinary tour: Doesn’t a week spent focused entirely on food and drink sound amazing? Head to the Finger Lakes in upstate New York or visit California’s Napa Valley, Sonoma or Santa Barbara Counties, or Paso Robles. Or venture abroad to France, Portugal, or Italy for superb wines and foods.
- Visit a far-flung place that epitomizes “remote”: If you really want to get off the grid, visit Patagonia, the Outer Hebrides, Indonesia’s Maluku Islands, or Uzbekistan’s Karakalpakstan.
- Take an epic road trip: Map out a route based on a theme, like historical landmarks, famous BBQ joints or diners, or quirky roadside attractions (see the world’s largest ball of twine is in Kansas or marvel at Carhenge in Nebraska and just go. Crank up your Spotify playlist and enjoy the open road.
- Spend a week completely unplugged: Find a cabin, yurt, or remote beach hut and commit to zero screen time (yes, including your phone) for a week. Rediscover the joy of reading, journaling, drifting through the days, and fully immersing yourself in nature.
- Sail or paddle a boat: Always wanted to learn to sail? Take a short course at a local marina or sailing school, or rent a kayak or paddleboard and get on the water. Depending on where you go, you’ll encounter all sorts of wildlife. We kayaked in Puget Sound, WA, and saw sea otters, harbor seals, and even a few far-off spouting whales.
- Explore your roots: Visit the town or country your grandparents or ancestors came from. Walk the streets they knew, visit the cemetery, and feel a deep connection to your own history. On my list? Traveling to Horsham, England, where my many-times great-grandfather grew up before moving to PA and becoming the state’s first treasurer and serving as the state’s deputy governor.
Creative, learning & legacy
- Master one unexpected, badass skill: Take up something that surprises people but is a great conversation starter at a party, like archery, welding, competitive ballroom dancing, or pole dancing. I started salsa lessons at 50.
- Write your own story: Put your decades of wisdom and experience on paper (or a Google doc). Not sure where to start? Many community colleges offer continuing education classes on memoir writing.
- Learn a new language: Pick a language that corresponds to one of your dream travel destinations and challenge yourself to become conversationally fluent. Buongiorno.
- Become a philanthropist of your talent: Volunteer your expertise, like pro-bono consulting, mentoring a young entrepreneur, or using your organizational skills to help a nonprofit.
- Take a university course for fun: Audit a college class for the intellectual stimulation, without the stress of exams (or cost of a credit). Or go back to school for a degree. One of my childhood friends’ mothers earned her doctorate at 66.
- Learn a musical instrument: Whether you pick up your high school clarinet, revisit your early piano lessons, or finally learn the guitar, making music stretches your brain and brings joy.
- Create something with your hands: Build a piece of furniture (many cities have maker spaces with equipment you can borrow), sculpt a work of art, or learn to reupholster a vintage chair. I’ve taken a ton of classes at the Banana Factory in ceramics, lampwork, glass blowing, and cartooning since I hit my 50s.
- Publish a recipe or craft book: Compile your best recipes, gardening tips, or DIY tricks in a book you can pass down as a family legacy.
- Start a successful side hustle: Turn a long-held hobby like baking, rock painting, crocheting, or jewelry making, into a small, profitable venture.
- Create a public piece of art: Get involved with a local community project, like painting a mural, or start a Little Free Library box in your yard.
Personal and physical challenges
- Run a marathon, half-marathon, or 10K: Whether you walk or run (or do a combination of both), set and work toward your goal.
- Get up close and personal with wildlife: Book a trip to see animals in their natural habitats, like an ecotour to the Galapagos Islands, Madagascar, or Tanzania.
- Conquer a major fear: If you’re not into public speaking, try joining Toastmasters. Not a fan of heights? Book a hot air balloon ride. Don’t like deep water? Try taking scuba lessons.
- Volunteer abroad: Spend time using your skills to help a community in another country.
- Master a signature dish: Find one complicated, show-stopping recipe, such as a beef wellington or a multilayered cake with multiple fillings, and practice it until you can nail it perfectly every time.
- Attend a massive cultural or sporting event live: Get swept up in the energy of a large crowd. Go to the Olympics, Wimbledon or U.S. Open, Coachella, or Glastonbury.
- Do something that requires a fancy outfit: Attend the opera, a gala, or a black-tie event.
- Host a themed dinner party where you go all out: Use the Met Gala or the Oscars for inspiration to create a magical, immersive event for your friends and family. I have friends who host a potluck on Oscar night, where everyone brings a themed dish capturing the essence of each movie nominated for Best Picture.
- Spend a day at a luxury spa: Indulge in a full day of massage, facials, and relaxation. Give yourself the gift of absolute peace — no phone allowed.
- Start a family tradition: Create a brand-new tradition for your friends, kids, or grandkids centered around connection, fun, and your personal interests. When my son was little, my dad started a tradition where the two of them would dress in their PJs, take a container of Christmas cookies, and drive around the neighborhood looking at the decorations and lights.
An important caveat
I love making lists and crossing things off as I finish them, but that’s not the intent of this list. I look at it more as a joyful nudge. Your life has hundreds of blank pages left to write on. You’ve navigated many of adulthood’s tricky parts, like parenthood and sleepless nights, career leaps, and that feeling of having to be everything to everyone. Now it’s your time to fill the bulk of those pages with things that make you feel alive and bring you pleasure and satisfaction.
Go! Find your happy!
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