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Things I want to do differently in the second half of my 20s
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Things I want to do differently in the second half of my 20s

How to not regret, part 2

Ryan Barry
May 28, 2025
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Things I want to do differently in the second half of my 20s
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Before I get on with the second part of this list (read part one here), I’d like to share something.

In reflecting upon this feeling I have—this yearning, as I talked about in part 1—to be a part of something, I’ve realized, because it’s felt recently a bit like life is slipping through my fingers for all the time I’ve spent alone, how important it is to lead a life surrounded by and in service of people I love.

And while I know that’s not necessarily easy, per se (see Sahil Bloom’s How We Spend Our Time), since everyone’s got their own lives to live,

it’s what matters.

Even though I need my alone time, especially when I’m writing—and even though I still want, as noted in part 1, to travel a whole bunch—it’s become pretty clear that a life not shared is generally inconducive to a life well-lived.

The problem, as you can see, is that it’s kind of hard to be with people nowadays (especially, in my case, if I’m living halfway across the country, away from my home 9+ months of the year).


On one hand, this struggle seems typical to life in one’s 20s (indeed, I’ve heard this sense of “tribelessness is inherent to the 18-28 decade), when everyone is uber-busy, on their own journey to figure their life out.

Trying to get in contact, by phone or in person, with some of my friends can often feel like a vain attempt to reach the president of the United States.

Everyone lives farther away than ever before in their own apartment, doing their own workouts, cooking their own dinners, watching their own TV’s . . . And I’m not so sure it’s gonna get any easier (you know, once everyone’s got families and stuff).

On the other hand, I don’t think the graphs above must come to reflect everyone’s realities.

Of course, we all must work . . .

But I don’t think, just because it’s the case for the majority, that individuals have no choice but to spend increasingly less time with loved ones as we age.

I believe we do—I do—have a choice, however small, to orient our lives such that we grant ourselves the ability to be with (and serve) the people we love, if only a little more than we are now.


As those who’ve kept up with my recent work may know, I am in the midst of taking my next step. Where should I live? Should I stay out here in Charleston, or should I move home to Chicago?

And as articulated many times already, I’ve been struggling deeply . . . because I’m conflicted, pulled two separate ways by seemingly opposing forces.

Part of me wants to hold on to Charleston for its beauty, the few connections I have here, the memories I’ve cultivated, and the possibilities that await should I choose to stay. The other part of me is called home, to be with my friends and family, to root myself and forge the stability and community I so deeply need.

Several things have come to mind in reflection and prayer, things I want to share . . .

For one, I must acknowledge the fact that all I can do (again, as I said in previous posts) is put one foot in front of the other, giving those things out of my control (and even those things within my control) up to God. The fact is, you see, that I am not yet in a place to make this decision I’ve been thinking so much about as of late (that is, where I’ll sign my next lease); the only thing I know that lies ahead is my trip home this week.

I’ve heard multiple times now, by reading the Bible and listening to certain podcasts, that God often reveals our next step without revealing why, or what the subsequent step might be. I am, in other words, called home for a reason . . . but only when I get home will what I must do next be revealed to me.

And so, not only is there no reason for me to wonder what the step after my trip home might be, since it is out of my control, but it is clear that my faith is being tested, that this process I’m enduring is God’s way of molding my belief.

Second, I must acknowledge that—in addition to the fact that by trusting in God, what’s best for me will transpire—I am not leaving Charleston forever by not returning here next year.

It’s easy for individuals (I am certainly prone to this habit) to identify with and attach themselves to what steps they take, be it a job, a location, a school, etc . . . And while I don’t know exactly what leads to this way of thinking (most likely a lack of faith in the process), it’s become apparent that this state of mind will inevitably lead one down a path of despair, since most everything in life is transitory—since we have been set on a journey.

Indeed, our identity comes not from any of these worldly things, but from the divine.

I heard recently on a podcast I was listening to that we are not put in this world to be employed, but to be deployed, in service of a mission.

And so, my “ideal” location, you see, has nothing to do with what’s cool or beautiful or most in accordance with who I think I am, but with where I must be to fulfill my divinely-bestowed mission; any job I take is not so I may have some career to identify with, but because it is, at that time, what I must do to fulfill my divine journey.

While I was sent out to Charleston for a reason (to learn), whether or not I return to Charleston ought not to matter to me, because it’s not up to me. And my desire to hold on to this place has evidently held me back (I’m sure it was all a part of the plan) from taking my most proper next step—from moving into the next season of my life.

I admit, part of the reason I’m reluctant to leave is because I feel I’ve not done everything out here I could have or needed to do. But I think this feeling merely indicates my journey is not over . . . Whether I’m here or there, the fact that I feel I’m leaving behind something incomplete most likely indicates the fact that something more lies ahead.

And of course, I’ll never not have that urge to road trip it through the Appalachians down into the Lowcountry, as it’s become for me a near-spiritual trek. But right now, I must trek my way back up to the Midwest.

A C.S. Lewis quote I’ve been thinking about.

What matters most, you can see, is not these “outward things,” these labels, but whether I’m walking the path I’m designed for. And what I need right now is not another year in paradise, away from my family, working random jobs just so I can be near the ocean I rarely visit, but to be with my people.

Which leads me to my third revelation—that I say I’m struggling to feel like I’m a part of something while simultaneously not doing everything in my power to focus on meaningful relationships . . . An expectation no different from wanting to lose weight without adjusting my diet or exercise regimen!

I say it’s difficult to get in touch with my friends, and that everyone lives on their own, so far away, but this is only because I moved away from home. I say I’m struggling with some of my friendships, but I could not honestly say I’ve done everything in my power to be a good friend!

I have, in other words, voiced “complaints” about the world when in reality these complaints have reflected my own actions (not the objective state of the world).


While this point is a tangent, I feel I must share it: people—I say this because I obviously have been this person—especially when they’re young, get so caught up in appearances. “It would be so cool to live there, because, like, look at how beautiful it is! Look at the weather! The women! The ocean!”

And though I would never discourage people from taking these steps, as it’s often a necessary step in one’s “self-discovery” journey, the fact is that (at least for me) home is not where you make it.

You don’t get to pick where you’re from. For most people, the fact is that they are born and raised somewhere, and that’s where their people are.

I recall reading a post by

Ryan B. Anderson
, whose work I’ve been referencing a lot recently, a while back in regards to this matter.

In “How to Ruin Your Small Town in One Easy Step,” Ryan states,

“The interstate highway system didn’t create the rural diaspora of young people, but it certainly compounded it. We often praise this vast network of concrete veins as a marvel of modern ingenuity, of freedom, and it is, but it’s also a subtle destroyer of roots. The speed and ease with which we can now flee our hometowns is a historically strange phenomenon; for most of human history, the distance between where you were born and where you died could be measured in miles, sometimes even steps. Now, you can leave behind the fields, the factories, and the people you know, hop in any old car, drive halfway across the country, and never look back . . .”

“What mattered was getting that degree—any degree—and leaving town to do it. For Millennials, the message was clear: staying meant stagnation, failure, and wasted potential. Never mind that many of those degrees led to crippling debt or careers that could just as easily have been built without them. By the time those young adults graduated, they were so disconnected from their roots that returning home felt like moving backward. What started as an admirable effort to democratize education has unintentionally caused a mass exodus from our small towns. The result? A generation untethered from place . . .”

“So, how do you undo the damage? You start by coming home. Not just for holidays or long weekends, but for good. Return to the place that raised you, to the people who poured their lives into giving you a better future. It may not be easy. The jobs might not be there, the schools might be struggling, the streets might feel smaller than you remember. But your presence matters. Your children matter. Your parents matter. To leave them to age and die in obscurity is to contribute to the decline you once mourned. Your hometown doesn’t need a savior; it needs its people. It needs you. Because in the end, the only way to ruin your hometown is to leave it—and the only way to save it is to return.”

Echoes from an Old Hollow Tree
How to Ruin Your Small Town in One Easy Step
Read more
6 months ago · 764 likes · 14 comments · Ryan B. Anderson

Now, my hometown isn’t dying by any means, but that’s beside the point.

At the time I read this post, though it made perfect sense to me logically, I objected to it emotionally. Because, well, I didn’t want to leave Charleston! How could I leave behind this southeastern oceanic paradise for the Midwest??

But through reflection and prayer, it’s become clear: anchoring myself at least closer to where I was raised quite simply makes a heck of a lot more sense. Because what matters most is what’s meaningful. Not what’s most beautiful on the surface.

Yes, homes are meant to be left behind. But they are, for many, also meant to be returned to.

All I know right now is that I’ve got to keep moving forward, one step at a time. And this next, most sensical step, is (counterintuitively) starting to look like a return home. Though it’s been a profound journey, I cannot keep blowing around like a leaf in the wind. I must take root somewhere. I must serve my people, my family.


So, with that being said, what other things do I want to do differently in the second half of my 20s?

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