Letting Go of Expectations in Midlife: Whose “Shoulds” Are You Still Carrying?

What if living more authentically begins not with knowing exactly what you want, but questioning what you’ve been taught to want?

There are so many ways we’re told our lives should look.

We should have accomplished certain things by a certain age.

We should look and feel a particular way.

We should be happy with the lives we’ve built, grateful for what we have, and confident about where we’re going.

Somewhere along the way, we may begin treating these expectations as though they’re our own.

I should look different.

I should feel better about myself.

I should be further along by now.

I should be happier.

Sometimes the most difficult expectations to question aren’t the ones other people openly place on us. They’re the ones we’ve absorbed so thoroughly that they sound like our own thoughts.

But what happens when the life we’re actually living doesn’t match the life we’ve been taught we’re supposed to have?

And what if the expectations themselves deserve a closer look?

When Expectations Become the Stories We Tell Ourselves

Many of the expectations we carry develop gradually.

They come from family, culture, relationships, communities, and the countless messages we encounter about what makes a life successful, meaningful, or worthwhile.

We may absorb beliefs about what it means to be a good parent, partner, friend, or professional. Or ideas about how our bodies should look, how much we should accomplish, and what happiness is supposed to feel like.

Over time, these expectations can become standards we use to evaluate ourselves.

And when our experiences don’t match those standards, we may assume we’re falling short rather than questioning the standards themselves.

What if the problem isn’t that we’re living our lives incorrectly, but that we’re measuring them against expectations we never consciously chose?

The Expectations We Carry About Our Bodies

I’ve been thinking about this particularly in relation to aging and body image.

Our bodies change throughout our lives, but midlife can bring changes that feel especially noticeable.

We may experience shifts in energy, health, appearance, strength, or how our bodies respond to familiar routines.

These changes can be genuinely challenging.

But sometimes there’s another layer of difficulty: the judgment we place on ourselves for experiencing them.

We might notice a change in our appearance and think we should look younger.

We might have less energy and believe we should still be able to do everything we used to.

Or we may feel frustrated with our bodies and then criticize ourselves for not being more accepting of them.

We’re surrounded by contradictory messages.

We’re encouraged to embrace aging while also being offered endless ways to resist its visible signs. We’re told to love our bodies, but often within a culture that continues to judge them.

Even the idea that we should embrace every aspect of aging can become another expectation to meet.

I don’t believe we need to love every change in order to develop a more compassionate relationship with ourselves.

We can acknowledge disappointment, frustration, or grief without turning those experiences into evidence that something is wrong with us.

And we can begin questioning whether the standards we’re using to judge ourselves are ones we actually want to keep.

When the Conventional Path Feels Safe but Doesn’t Quite Fit

For much of my life, I’ve felt that conventional expectations about how we’re supposed to live didn’t entirely fit me.

And yet, there was also something reassuring about following a familiar path.

When the people around us are making similar choices, those choices can feel safer, even when they don’t completely reflect what we want.

I’ve been thinking more about that tension as I navigate midlife.

What does it mean to live authentically when we’re still discovering what that looks like for ourselves?

How do we begin questioning expectations we’ve carried for decades when some of those expectations have also provided a sense of security or belonging?

And what happens when we’re not quite ready to let go of the familiar, even as we feel drawn toward something different?

I don’t have tidy answers to these questions.

I’m still exploring what success, happiness, and a meaningful life look like for me now.

But I’m beginning to appreciate that questioning a familiar narrative doesn’t mean we need to have a new one ready to take its place.

Sometimes we can simply acknowledge that something no longer feels quite right and give ourselves permission to be curious about what might fit better.

You Don’t Have to Replace One Set of “Shoulds” With Another

There’s something worth noticing about the way personal growth is often presented.

We’re encouraged to let go of expectations, embrace authenticity, prioritize ourselves, and create lives that reflect who we truly are.

Those can be meaningful invitations.

But they can also become another set of instructions about how we’re supposed to live.

I should be more confident.

I should stop caring what other people think.

I should know what I want by now.

I should be making the most of midlife.

Suddenly, even questioning expectations becomes something we feel pressured to do correctly.

What if we approached it with curiosity instead?

We might begin by noticing when the word should appears in our thoughts.

Not every should is unhelpful. Sometimes it reflects a responsibility or commitment we genuinely value.

But sometimes it signals an expectation worth examining.

Whose voice does this sound like?

Is this something I believe, or something I’ve learned to expect of myself?

Does this expectation reflect what matters to me now?

What might I want if I weren’t measuring myself against it?

These questions don’t necessarily lead to immediate answers.

Some expectations may reflect values we genuinely hold. Others may have helped us navigate earlier stages of life but no longer fit in quite the same way.

And some may take time to understand before we’re ready to reconsider them.

We don’t have to sort everything out at once.

A Few Questions to Sit With

If you’re beginning to question some of the expectations shaping your life, consider:

• What are some of the “shoulds” I notice most often in my thoughts?

• Where did I learn these expectations, and how have they influenced my choices?

• Which expectations still reflect my values, and which feel less aligned with who I am now?

• What feels reassuring about following a familiar path?

• What might I become curious about if I didn’t need to have everything figured out?

You don’t need to answer these questions perfectly.

You may discover that some expectations still matter to you. Others may feel more complicated than you realized.

And perhaps some are ready to be questioned.

Making Room for a Life That Feels Like Yours

This is part of what inspired me to create Rooted & Becoming.

I wanted to offer a space where we can question the narratives we’ve inherited about aging, success, relationships, our bodies, and what a meaningful life is supposed to look like.

Not so we can replace them with another prescribed version of how to live.

But so we can begin discovering what feels authentic and meaningful to us.

For me, that process is still unfolding.

I’m continuing to question old expectations, notice where judgment shows up, and explore what I want this stage of life to look and feel like.

Some days that feels exciting. Other days, it’s uncomfortable or uncertain.

And I’m learning that both experiences can belong.

We don’t have to know exactly who we’re becoming to begin questioning the expectations that may no longer fit.

Sometimes the invitation is simply to become curious about the life we’re living—and whether we’re giving ourselves permission to experience it in a way that feels like our own.

A Place to Begin

If you’re questioning familiar expectations or wondering what a more authentic next chapter might look like, the free Rooted & Becoming Reflection Guide offers a gentle place to begin.

Through thoughtful prompts, you’ll have an opportunity to explore what matters to you, what you may be outgrowing, and what you’d like to make more room for.

No pressure to have the answers. Just space to begin asking your own questions.