Every Gain Includes Loss: The Hidden Grief of Growth, Success, Achievement, and New Beginnings

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We live in a culture obsessed with progress. We’re told to be better. Do more. Keep going.

There’s a loud, relentless push to grow “up and to the right”—like a perfect line on a graph. We’re encouraged to chase new jobs, new homes, better relationships, larger platforms, bigger wins, and brighter futures.

And sometimes we genuinely want to achieve success as society defines it. We aspire to build families or be the first in our lineage to get a college degree. We pursue dreams of opening businesses, finding romantic love, or winning metaphorical—or literal—gold medals for our talents or hard work.

Part of being human is our unique ability to envision a future for ourselves, and to ponder what specific achievements would mean the most to us.

It’s true that accomplishment of any of our goals is reason for joy, pride, and celebration. But what we’re not taught to expect—and almost never given permission to feel—is the very real grief that often hides just beneath these “positive” life milestones.

It’s a form of hidden grief, and it lives inside every gain.

A New Perspective: Every Beginning Also Includes an Ending

Let’s flip the script.

Instead of seeing milestones only as wins, what if we also recognized what’s being left behind?

What if every gain was understood as a both/and—a celebration and a quiet goodbye?

Because that’s what’s actually happening.

Is It Possible to Mourn Success and Other Happy Accomplishments? Introducing “Gain Grief”

What I call “gain grief” is the heartachey emotional residue that lives underneath a positive milestone or achievement, even when that success or achievement is considered generally good.

But because it doesn’t look like “typical” grief—a death, breakup, diagnosis, or other major loss event—gain grief flies under the radar.

You might feel irritable or overwhelmed or like something’s off, but then gaslight yourself into pretending everything’s fine. You may feel like there’s something about your happy milestone or event that it’s not being said—a deeper truth or a larger portrait of what’s really going on—but you’re not sure exactly what that might be.

The reality is, it’s the grief that comes with gain. And it’s okay to feel it.

It’s not brokenness. It’s not a flaw in your wiring. It’s just real, normal, everyday loss woven into growth.

Hidden Grief in Life’s “Wins”: The Loss in What We Leave Behind

If you're wondering what this looks like in real life, here are some of the most common “gains” that come with their own layers of hidden grief:

Graduation

You’re proud of your diploma—but you’re also grieving your campus, your classmates, and your identity as a student. You may feel disoriented about who you are now that you're not "in school." You may grieve shifting from the certainty of classes and routines to the uncertainty of the “real world.” And of course, you could also carry grief on behalf of your family or friends who didn’t—for whatever reason—have access to a college education.

Marriage

Love is real—and so is the loss of singlehood, independence, or living alone. In celebrating joining lives with another person, you’re saying goodbye to certain freedoms, rituals, and even ways of being perceived in the world. You might also grieve friend dynamics related to marriage, such as disconnection from friends who are still single, being the first in your friend group to marry, or being the last in your friend group to marry.

Parenthood

Welcoming a child into your world is extraordinary. But new parents often grieve the loss of their pre-parent identity (or lifestyle), autonomy, and even sleep. There’s grief in realizing life will never be “just yours” again. There can also be grief in being seen as a mother, father, caregiver, or parent before any of your other identities. For instance, you may be perceived as a “mom” when you absolutely have interests and desires outside of your child.

New Job or Promotion

You worked hard to land that new role—but now you’re grieving your old coworkers, rhythms, or professional comfort zone. Identity shifts happen here, too. And, if a change in pay is involved, you might grieve on a financial level too. There is grief that comes with a pay cut of course, but there can also be grief in having more money to manage, especially if others are dependent on you financially.

Moving to a New Home

Maybe your new home is your dream home. But it still means leaving behind familiar neighborhoods, routines, smells, and sounds. Even joyful moves come with grief. Whether you moved just down the block, across town, or to a whole new country, a change in your metaphorical “nest” can leave you feeling unsettled for much longer than the initial months of getting boxes unpacked.

Fame or Going Viral

It’s easy to glamorize attention and influence—but there is grief in losing privacy. The way people see you changes. You may mourn having endless free time to create or exist without eyeballs on your every move—or grieve not knowing whether connections with others are genuine or rooted in what they could gain from having proximity to you. You might also feel a pressure to constantly record or document your life and miss having the ability to have experiences away from a camera. If you have an agent, publicist, or manager, you may mourn a time when you were only accountable to yourself.

Personal Growth

Ironically, even healing can involve grief. You might feel a sort of “healing heartbreak” in saying goodbye to the old version of yourself—yes, even the version of yourself who was struggling. There’s loss in letting go of survival patterns, friends, rituals, and coping mechanisms that once kept you safe. There is absolutely grief in the process of outgrowing.

This Doesn’t Mean You Shouldn’t Celebrate

Recognizing hidden grief doesn't mean you need to stop wanting more or start fearing good things.

It simply means this: every gain includes a loss, and every loss deserves space to be felt.

You can throw the graduation party and cry in your car the next day.

You can feel deep love for your newborn and long for your pre-baby self.

You can toast to your promotion and miss your old coworkers.

This is what emotional honesty looks like.

Society Tells Us: "More Is Always Better"

The reason hidden grief hurts so much is that it’s invisible in a culture obsessed with growth.

We’re told that success is linear. That milestones are only ever good. That if you’ve “leveled up,” you should be grateful, not sad.

But that’s not how human emotions work.

Loss and gain are not opposites—they’re two sides of the same coin.

And when society only acknowledges the gain, the loss has nowhere to go. So it shows up in sneaky ways—fatigue, numbness, irritability, or even shame.

You might be grieving without even knowing it.

This Isn’t Meant to Add to Your Grief—It’s Meant to Free You

Now, if you’re already grieving something big—a death, divorce, diagnosis, or breakup—you might be thinking: Great, thanks for pointing out EVEN MORE LOSS I didn’t ask for.

But please hear this: This perspective isn’t meant to overwhelm you. It’s meant to empower you.

Because if you’ve made it through any major transition in your life—you’ve already survived grief.

• You grieved your childhood when you moved through adolescence.

• You grieved your school life when you graduated.

• You grieved your singleness when you got married.

• You grieved your relationship when you experienced a romantic or platonic breakup.

• You grieved your freedom when you became a caregiver—whether for children, parents, or pets.

• You grieved a role, a title, a home, a dream—possibly many times over.

Said another way, your past hidden losses served as experience for the losses you’re facing today.

Whatever you’re grieving now, you’ve been through loss before—even if you didn’t know to call it that at the time. That means you already know how to survive change, and you are not starting from square one. In some form or fashion, you have grieved before. This is not your first goodbye.

Noticing the Gain in Your Loss, Too

Just like every gain includes a loss… every loss also includes a gain.

And I want to be clear here: this isn’t a toxic positivity message glossing over your grief. It’s about widening your field of view.

It’s about asking yourself, “In the midst of what I’ve lost, what is the other side of the coin? What have I gained, even if it’s small or invisible to others?”

Yes, your person is gone. Your relationship ended. Your health changed. Your dream dissolved.

And still, some new things may now be possible.

• If you’re no longer caregiving, you might have time and energy to go back to school, rebuild friendships, or return home.

• If a relationship ended, you may be rediscovering your autonomy, or reconnecting to parts of yourself you lost while trying to keep the relationship together.

• If you received a diagnosis, you might now have clarity, or the validation to prioritize what really matters.

• If someone you love has died, you might find yourself living more honestly, more tenderly, or with greater urgency than before.

Again, these perspectives are not replacements for the pain of loss. They’re not successes that make the fact that you’re grieving magically okay. But they are real. And naming them can be a lifeline when everything else feels like it’s crumbling under your feet.

Closing Thoughts: Naming Hidden Gain Grief Matters

When we ignore the hidden grief under life’s successes and achievements, we deny ourselves the full picture of what’s going on.

When we rush past our emotions—or focus only on the positive parts of a milestone—we bypass reflection. And that reflection is one thing that helps us honor all the places grief shows up in our lives.

When we name hidden grief, we tell the whole truth about what’s happening. Yes, what we’ve gained, but also what we’ll miss about what we’re leaving behind.

Want to Explore This More Deeply?

If this blog stirred something in you—if you recognized yourself in the hidden grief of your own “gains” or began to see tiny glimmers of gain in your losses—I want to invite you to my free workshop: Grow Through Grief: 3 Ways to Stop Feeling Stuck and Start Moving Forward.

In it, you’ll learn how to:

• Stabilize yourself after devastating loss so you can explore your grief from solid ground

• Use two words to give yourself instant self-compassion on your hardest days

• Shift your perspective—from grief as an obstacle to “get over” to grief as a long-term relationship—so that you can build a life that feels meaningful to you

Life inevitably changes us.

Whether those changes are wanted or unwanted, celebrated or mourned, every transition carries the echoes of a goodbye—sometimes hundreds of goodbyes.

It doesn’t mean something’s wrong with you, or that you’re incapable of joy, happiness, or gratitude.

It just means that you’re aware of the full portrait of life—the gain and the loss, the growth and the grief. And that is a beautiful, human thing.

Want even more tools for navigating life with grief? Click here to get my free workshop sent to your email. (You can watch it whenever you’re ready.)