Why “Should” Is a Trap

By the time we hit 40, many of us have built lives around “shoulds.”

• I should stay in this career—it’s stable.

• I should be grateful—I have more than most.

• I should act my age—whatever that means.

But here’s the truth: “Should” is often just fear dressed up as responsibility. And if you’re feeling boxed in, stuck, or restless—it might be time to ask: Whose life am I really living?

Freedom after 40 isn’t about rebellion. It’s about returning to yourself.

1. Recognize the Cost of Living by “Should”

We all grow up absorbing silent rules about how life should look. By 40, many women find themselves living in carefully constructed boxes—some of which they never meant to build. We stay in relationships because we should be grateful. We stick with jobs that drain us because we should be responsible. We bite our tongues, play it safe, and downplay our needs because we shouldn’t make waves.

But here’s the hidden cost: every time you say yes to a “should,” you’re often saying no to your own truth.

That “yes” might cost you your joy, your health, your creativity—even your sense of self. Over time, those quiet sacrifices pile up. You may find yourself feeling numb, resentful, or like a stranger in your own life. And yet, from the outside, it all looks fine.

The truth is, fine isn’t the same as fulfilled. And doing what you’re supposed to isn’t the same as living in alignment.

Freedom after 40 doesn’t require blowing up your life. It starts with one powerful question:
“Does this still feel right for me?”

If the answer is no—or even not sure—that’s worth exploring.

We’ve been taught that doubt is dangerous. But doubt is often just clarity trying to find its voice.

💡 Try This:

Grab a journal and write down five things in your life you feel like you “should” be doing right now.

Maybe it’s:

• “I should call my mother every Sunday.”

• “I should keep my corporate job until retirement.”

• “I should be more involved at my child’s school.”

• “I should want sex more.”

• “I should have figured this out by now.”

Now, take each “should” and ask yourself:

• Who says?

• What do I really want instead?

• What’s the worst that could happen if I didn’t?

• What’s the best that could happen if I didn’t?

This small exercise can crack open the door to deep transformation.

Because when you stop living by default and start living by design, you don’t just reclaim your time—you reclaim yourself.

2. Redefine Success on Your Own Terms

From a young age, most of us were handed a silent script for what a “successful” life looks like.
It usually goes something like this:

Go to college.
Get the job.
Find a partner.
Buy the house.
Raise the kids.
Work hard.
Retire eventually.

Check, check, check.

And while there’s nothing inherently wrong with those milestones, here’s the problem:
They were never meant to define your worth.

By the time we reach our 40s, many of us begin to feel the cracks in that script. We’ve achieved things we were told would make us happy—and yet… something still feels missing. Maybe it’s meaning. Maybe it’s energy. Maybe it’s you.

This is where freedom after 40 begins to whisper:

What if success isn’t about appearances—it’s about alignment?

What if you gave yourself permission to rewrite the rules?

Imagine a version of success that feels soft on your nervous system and bold in your soul. One where:

• Peace of mind matters more than prestige.

• You work in ways that energize you, not just drain you.

• Boundaries are a form of self-respect—not something to feel guilty about.

• Your life feels rich, not just full.

This kind of success doesn’t always show up on a resume or impress strangers at cocktail parties—but it deeply nourishes you.

And here’s the secret:
The more you define success on your own terms, the more resilient and sustainable your joy becomes.

No more hustling for external validation. No more shrinking to fit into old versions of yourself. No more measuring your life by outdated metrics.

You’ve evolved. Your definition of success should, too.

🔁 Ask Yourself:

• What have I been chasing that no longer lights me up?

• What truly makes me feel successful—not just seen as successful?

• If I removed everyone else’s opinions from the equation… what would I choose?

Redefining success isn’t giving up.
It’s growing up—into a version of yourself that feels whole, not just accomplished.

3. Embrace the Courage to Disappoint

Let’s be honest—many women have spent decades being the peacekeepers, the dependable ones, the “yes” women. We’ve been praised for being agreeable, admired for our ability to juggle it all, and expected to keep everyone else comfortable—even at the cost of our own well-being.

But there’s a quiet truth many women start to uncover after 40:
You can’t live fully and authentically without disappointing someone.

And sometimes, that someone might be your partner, your boss, your best friend… or even the version of yourself that once thought she had to be everything to everyone.

Here’s what no one tells you:
Trying to keep everyone else happy is a full-time job—and it pays in resentment.

Freedom after 40 asks you to lay that job down. It invites you to consider this:

What if disappointing someone else is the exact price of no longer disappointing yourself?

What if saying no to that family obligation gives you back an entire weekend of peace?
What if declining that extra project protects your health?
What if not returning that call gives you space to breathe?

You don’t owe anyone an explanation for living a life that honors your truth.

You were not born to be palatable, pleasing, or perfectly agreeable.
You were born to be powerful.

And power—real power—often requires letting go of other people’s expectations so you can hold onto your own integrity.

💬 Try This:

This week, say no to one small thing that feels even slightly out of alignment.
It could be:

• Skipping a group chat that drains you

• Declining a lunch invitation that feels obligatory

• Letting a call go to voicemail

• Choosing rest over productivity

Then notice:

• How does your body respond?

• How does your energy shift?

• How does your self-respect grow?

The more you practice tolerating the discomfort of disappointing others, the more you strengthen the muscle of honoring yourself.

And that, my friend, is where freedom after 40 truly begins.

4. Start Tuning Into Desire, Not Obligation

Somewhere along the way, many of us were taught that desire is selfish.
That it’s indulgent. Frivolous. Even dangerous.

Instead, we learned to prioritize obligation—doing what was right, expected, or necessary. We built lives around what others needed from us: children, partners, employers, communities. And for a time, that may have felt purposeful.

But eventually, the question creeps in:

What about me?

Freedom after 40 is the permission slip to ask—and answer—that question honestly.

Because desire isn’t a dirty word.
It’s a compass pointing you toward your most alive, authentic self.

What do you want—not just what’s expected of you?

• To travel alone for the first time?

• To change careers—even if it “doesn’t make sense”?

• To spend an entire weekend resting, guilt-free?

• To stop volunteering for things you secretly dread?

• To finally write that book, start that business, or dance again?

Desire doesn’t always show up as fireworks. Sometimes it’s a quiet nudge, a longing, a whisper that you’ve been ignoring for years.

Tuning into desire takes practice—especially if you’ve spent decades putting yourself last. But it’s never too late to listen.

Desire is where your intuition speaks. And following it doesn’t make you irresponsible—it makes you sovereign.

🔍 Start Here:

Ask yourself one simple question:
“If no one needed anything from me today, how would I spend my time?”

Then, go deeper:

• What would I wear?

• What kind of work would I do—or not do?

• What would I allow myself to feel, create, explore?

Let the answers surprise you. Let them feel tender, even inconvenient. That’s okay.
You don’t need to act on every desire right away—but you do need to hear them.

Because the more you honor your desire, the more you return to yourself.
And that is the heartbeat of freedom after 40.

5. Surround Yourself With Women Who’ve Also Broken the Rules

There’s something sacred that happens when women stop pretending and start telling the truth.
Especially in midlife.

It’s easy to feel isolated when you start questioning the rules you’ve lived by for decades. Whether you’re thinking about leaving a career, ending a relationship, reinventing your identity—or simply wanting more—it can feel like you’re the only one waking up.

But you’re not alone.

Freedom after 40 becomes far more real, tangible, and doable when you connect with other women who’ve dared to break the rules too.

These women might not be the loudest in the room, but they carry a quiet wisdom that comes from having walked through fire—and chosen themselves on the other side. They’ve:

• Walked away from titles that no longer defined them

• Left marriages that looked “perfect” on paper

• Chosen peace over perfection

• Stopped shrinking for other people’s comfort

• Started over—on purpose

When you surround yourself with these women, something magical happens:

• You stop doubting your instincts.

• You start trusting your vision.

• You realize that the “rules” were never meant to fit you in the first place.

These relationships become mirrors, showing you what’s possible. They remind you that your questions are valid, your desires are sacred, and your freedom is worth it.

You don’t have to blaze the trail alone.

👭 Try This:

• Reach out to a friend you admire for her courage and authenticity. Ask how she got there.

• Join a circle, group, or community of women who are navigating midlife with curiosity and boldness.

• Share your story. Even the messy parts. You never know who needs to hear it.

You’ll find courage in their stories.
And they’ll find validation in yours.

Because when women witness one another’s becoming—without judgment or comparison—we don’t just break the rules.
We rewrite them.

And that, more than anything, is the heartbeat of freedom after 40.

Final Thoughts: It’s Not Too Late to Be Fully You

You are not too old. It’s not too late. And you don’t need anyone else’s permission to change.

Freedom after 40 isn’t a luxury. It’s a calling.

You’ve spent years showing up for everyone else. Now, it’s time to show up for yourself.

Want support as you break free from the “shoulds”?
Let’s Talk →
Whether you’re interested in private coaching, a workshop for your group, or have a question about your own reinvention—I’m here to help you create the next chapter on your terms.