Field Notes on Starting Over: Note #6—5 Signs You’re Outgrowing Your Old Life (and entering a new one)

The demolition before the rebuild

1. You stop defending old versions of yourself.

You no longer feel the need to justify who you used to be or why you made certain choices. Those decisions belonged to an earlier chapter, and you’re simply not living in that chapter anymore.

From the partner I thought I could see forever with to the career path that once made sense to my 30-year-old self, these and other decisions served their purpose in their time and place but are no longer relevant as my desires change and priorities shift.

Entering midlife, I am more intentional now—more aware of the patterns I don’t want to repeat. Maya Angelou said, “When we know better, we do better.” I’m sure I will continue to make poor life choices, just not the same ones I made in the past.

If the people in your life criticize the choices a past version of yourself made, remind them you acted with the knowledge and experience you had at the time. Now that you have gained new knowledge and experience, you choose differently.

Or simply tell them to bugger off. It’s your life and you owe no one an explanation for outgrowing who you used to be.

2. Nostalgia feels like a detour, not a destination.

You visit the past only to understand it, appreciate it, or say goodbye—not to rebuild it. You can love and honor a past chapter—the places, the people, the version of yourself that thrived there—without wanting to return to it, and that clarity is its own kind of forward momentum.

I loved my life in Bali and think about it often, but whenever I am asked if I would move back, the answer is no. I had a rich, full life in Minneapolis for a decade and most of my friend base is there, but I have no desire to move back Minnesnowta. Returning to any of the places I have lived would feel like trying to squeeze myself into an old life that no longer fits.

I don’t like going backwards. When I do eventually move back to the US, it will be to a state I have never lived in and a city where I have no friends or family.

I’m not trying to recreate an old version of myself. Even though I loved the person I was in those places, that person doesn’t exist anymore. I seek to move toward growth, not repetition.

This is a new chapter, not a revival tour.

3. Your old dreams feel too tight.

The goals that once thrilled you now feel narrow or outdated. As your values shift, so do your desires. You didn’t fail your old dreams—you outgrew them. They were built for someone you no longer are.

When I got certified to teach English abroad, I had grand visions: traveling the world, teaching at universities, developing curriculum, working as an examiner, even becoming a teacher trainer.

And I succeeded in all of that.

Yet the dream never quite matched the reality. After more than a decade in the field, even the thought of grammar tables and lesson planning makes my eye twitch.

I used to come alive and be fully in my element in front of a classroom. But eventually I burned out—full on, dark-night-of-the-soul burnout.

As much as I want to continue living abroad, I recognize that due to my current professional skills and experience, my only option for doing so would be to go back to the classroom. And I just can’t justify sacrificing my mental health for the chance to keep living out a dream that no longer fits.

I’m still coming to terms with the idea that walking away from a dream isn’t failure—it’s growth.

4. You feel the grief of shedding identities.

Even when you’re ready for change, letting go of who you were still requires mourning. Reinvention always costs something, and acknowledging that loss is part of the process. It almost feels like you’ve shed a skin but haven’t stepped into the new one yet.

For a long time, people have told me how brave I am for traveling the world solo—riding a motorbike into the mountains of Laos with no map and a missing headlight, hitchhiking through the deserts of Israel, trekking through Sumatran jungles known for their assortment of vipers and cobras.

And I wore that medal of bravery like it was my entire identity. I was the adventurous, intrepid explorer!

But recently, I was thinking of an old colleague from my corporate days in the States. She was 34 at the time and had bought her first house all on her own. And she lived in it all on her own. And if something broke, she fixed it. All on her own.

To me, that was the epitome of bravery.

Meanwhile, I was (and still am) afraid of the dark! My domestic repair repertoire extends no further than changing a lightbulb. The very idea of living in a whole house all by myself—where no one would hear me scream for help—is terrifying.

But also, kind of exhilarating.

Perhaps, entering midlife, “homeowner” is an identity I’m now ready to try on.

As I move closer to a version of myself who wants roots, I am also grieving the woman who was once defined by her passport stamps.

5. You realize you “quiet quit” your current life a long time ago.

Long before the logistics shift, your heart does. You’ve been going through the motions—doing the tasks, showing up on cue, performing the version of yourself everyone expects——but emotionally, you’ve checked out. The realization is subtle but unmistakable: I’ve been done for a while.

You stop investing the way you used to. Your enthusiasm flattens, your tolerance shrinks, and the things you once cared about feel strangely distant.

Have you noticed an internal restlessness? Do things that used to merely drain you now feel intolerable? Is your quiet inner voice becoming harder to ignore? These changes don’t arrive suddenly; they accumulate over time, becoming impossible to overlook.

By the time you consciously admit you’re ready for a new life, you’ve already been living with one foot out the door. Sometimes we have to reach the end of our tether before we finally take action.

Before Elvis even puts on his blue suede shoes to leave the building, he’s already had enough of the crowd and is eyeing the nearest exit.

If any of these points resonate with you, know that you are not alone and your life isn’t falling apart—it’s coming together.