What do you want now (not what you “should” want)?
Published about 2 months ago • 5 min read
August 19, 2025
Peeling Back the Shoulds...Living by values
Hello friends! 🌻
So much of midlife and beyond is about peeling back layers of 'shoulds' and rediscovering what truly matters to us now.
Earlier this summer, I caught myself saying, “I should’ve been more productive today.”
It was a Saturday, and I’d already had a full week of meetings, chores, and family responsibilities. But instead of feeling satisfied, I felt that familiar tug—that I didn’t accomplish something measurable, and that somehow, I wasted time.
That’s when I paused and asked myself the same question I often pose to clients: What do you want now?
And the honest answer wasn’t another checked-off list. It was quiet. Space. A slow cup of coffee on the deck with no agenda.
Wiilow Older and Deborah Huber
For years, I equated productivity with worth. But in this season of life, I’m slowly realizing that what I want now isn’t to do more, but to live more intentionally—to give myself permission to savor the things that don’t show up on a checklist, but matter just as much.
Pealing Back the Shoulds
The “shoulds” of midlife and beyond are often subtle, deeply ingrained, and tied to old stories about productivity, success, aging, gender roles, and what a “good life” is supposed to look like.
Internalized expectations often shape our choices with our family roles, career paths, and societal pressures.
Do any of these societal pressures resonate with you?
You should downsize and simplify.
You should stop working or start slowing down.
You should be focused on grandkids now.
You should have figured everything out by now.
You should act your age.
You should be grateful, not restless.
The Tug Between Shoulds and Desires
The “shoulds” are sneaky. They sound responsible, respectable, even admirable. But they can keep us chasing productivity, approval, or expectations that aren’t truly ours.
Our true desires, on the other hand, often whisper more quietly. They ask us to slow down, to risk doing things differently, to trust what feels meaningful rather than what looks impressive.
It’s completely normal to feel conflicted between the two. Most of us were raised to prioritize the shoulds, so learning to hear—and honor—our genuine desires can feel uncomfortable at first.
What This Looks Like in Real Life
Should: I should say yes to every invitation or opportunity. Desire: I want to choose the connections and activities that truly nourish me.
Should: I should stay busy and productive every day. Desire: I want moments of rest, unhurried mornings, and time that isn’t measured by output.
Should: I should always offer to take care of the grandkids whenever I’m asked. Desire: I want to enjoy time with them when it feels joyful and balanced—while also protecting space for myself.
That tension between should and desire is also the invitation: to pause, to listen, and to begin aligning our lives with what we truly want now. And, giving ourselves permission.
On the surface, both might look “good” or “reasonable.” That’s why it helps to bring our personal values into the conversation.
Finding Your Compass
Values act like a compass—they point us back to what matters most.
If a should doesn’t line up with your values, it’s usually a signal that it’s draining rather than nourishing.
If a desire aligns with your values—even if it feels risky or unfamiliar—it’s often pointing you toward greater meaning, freedom, and fulfillment.
For example: I deeply value connection, and I may genuinely want to say yes to invitations. But if the “should” of saying “yes” every time begins to crowd out my health or my integrity (also values), then the alignment is off. The decision isn’t about whether saying yes is good or bad—it’s about whether saying yes in that moment supports my core values or stretches me away from them - and what I need/want in that moment.
The more we practice asking, “Does this choice align with what I truly value?” the easier it becomes to distinguish between a life lived by shoulds and a life shaped by authentic desires. That’s what alignment looks like in real time.
Your Turn: Reflect & Realign
What are the “shoulds” that show up most often in your life right now?
What desires have been quietly whispering beneath them?
Which of your personal values are calling for more attention or action?
If you made a choice today based on alignment with those values, what would that look like?
Sometimes just noticing the tension between shoulds and desires—and checking in with our values—can open a door to living more intentionally.
A Tool to Support You
I’ve put together a worksheet to help you rediscover what you want – beyond the “shoulds,” expectations, and old scripts. You can download it here.
THIS & THAT
Exciting news!I had the joy of joining my friend Wendy Rimmelspacher on her inspiring podcast Dim to Daring. We went deep on “how stillness became a game-changer in my life.” The episode drops tomorrow—can’t wait for you to listen!
🍑 A Little Peach Inspiration
I’ve been really enjoying fruit this summer. It started with watermelon, then blueberries, and now I’m into peaches- the kind that drip down your chin and make you pause for a moment to just enjoy the sweetness of summer!
Did you know peaches are a symbol of longevity and vitality in many cultures? A single peach has only about 60 calories, is packed with vitamin C, and (fun surprise) belongs to the rose family! No wonder they’re so irresistible this time of year. 😋
What have you been savoring this summer?
👉 UPCOMING: Legacy Workshop
Back by Popular Demand ...
“A legacy isn’t what you leave behind; it’s what you live every day.”
Every choice, conversation, and moment of connection adds to the story you’ll be remembered for. But in midlife and beyond, something shifts — we begin to see our legacy not as a far-off destination, but as the way we’re living right now.
On Friday, September 12, I’ll be hosting Building Your Legacy in Midlife and Beyond — a hands-on workshop to help you clarify your evolving sense of purpose, reclaim your identity, and define the values and gifts you want to carry forward.
If you’ve been feeling the pull to live more intentionally, this is your space to reflect, connect, and create a plan for the legacy you want to live.
If you joined me for last year’s "Building Your Legacy in Midlife and Beyond," and I’d love to welcome you back this September for a revamped and refreshed experience.
This year, you’ll recognize some familiar inspiration paired with a deeper guided process for reflection, honoring your story, and sharing collective wisdom.
*Save $10 if you bring a friend, or if you’ve attended a previous workshop of mine.
📅 Reserve your spot today→Registration Link for more information and to register.
CLOSING THOUGHTS
As you move through the rest of this month, I invite you to notice where “shoulds” might be guiding your choices—and to pause long enough to ask, What do I want now? Aligning with your values isn’t always easy, but each small step toward honoring your true desires creates a life that feels more intentional, joyful, and deeply your own. ☺️
If this resonates, I’d love for you to join me in my upcoming Legacy Workshop, where we’ll explore what it means to live your legacy—not someday, but today. And if you’d like a dose of inspiration in the meantime, tune into my conversation on the Dim to Daring podcast this Wednesday.
Here’s to peeling back the “shoulds,” practicing reflection, and savoring the sweet, simple things that make this season meaningful—one choice, one moment at a time. 🍑
To living your legacy,
Judy
PS: If you know someone navigating their second half of life who would enjoy these reflections, feel free to forward this newsletter their way. They can join the email list to get future issues (and join us for upcoming Office Hours!).
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