Returning to Austin in Midlife: A Letter to Who I Used to Be
Hey you, it's me!
Well, y'all, guess who's heading back to Austin, Texas?
ME!
And I have some explaining to do. ๐
For four years, Austin was home. When we moved to Destin, Florida, I made this big declaration that I would be back at least 50% of the time.
Fifty percent, y'all. I said it with my whole chest. And then life happened.
Weeks turned into months. Months into years. We moved again, this time to Orlando, and somehow, I never made it back.
Not once.
Which is actually pretty ridiculous, considering how much I love Austin.
As I've been getting ready for this trip, I've caught myself wondering why it took me so long to return.
Then I realized Austin holds more than memories.
Back Then, I Was Mom
Have you ever loved a place so much, yet felt a little unsure about going back?
That's Austin for me.
When I think about those four years, I remember so much happiness.
The cheer competitions, my older daughter graduating high school, family adventures, friends, festivals, dinners, and some really good times.
I remember one Friday when my older daughter and I decided to leave at 1 p.m. and drive all the way to the Grand Canyon to catch the sunrise.
Apparently, that's what you do when you have a wild idea and absolutely no concern for how much driving it takes. ๐
But we made it.
Those are the memories I wish I could bottle up and keep forever.
Back then, I was Mom.
That was my world.
I was raising my girls, creating a happy home, planning our next adventure, and doing what I thought I was supposed to be doing.
We went places, laughed together, made memories, and settled into our own little routines.
I loved that life.
I really did.
But Austin also holds some of the hardest years of my life.
It's where I lived right after my dad passed away.
It's where I watched my older daughter begin to find her independence, while I was still figuring out what that meant for our relationship.
It's where my spouse and I separated.
And it's where I started feeling something shifting inside me.
I wanted to make more of a difference and move beyond some familiar patterns. I could sense myself changing, even though I wasn't quite sure how to put it into words.
And goodness, did I feel guilty about that.
How do you explain wanting something more when you've spent years building a life you genuinely love?
I didn't have the communication skills I have today or understand boundaries as I do now. I was still learning that loving someone deeply doesn't automatically mean knowing what they need from you.
I became a mom at 21.
I was a kid raising a kid, trying to figure it all out along the way.
Looking back, there are things I wish I had handled differently.
Sometimes I wish I could go back and be the woman writing this letter today.
The one with a few more tools in her toolbox.
The one who knows how to ask better questions, listen a little longer, and meet people where they are in life.
But back then, I didn't know what I know now.
And maybe that's one of the hardest parts of growing older.
You finally understand things you desperately wish you'd understood sooner.
The Ordinary Moments
You know what I miss most?
The ordinary days.
Having my girls together and watching them grow up as sisters has been such a joy. I cherish the little routines, the conversations, the laughter, and all those moments that didn't seem particularly important at the time.
I would give just about anything to relive one of those ordinary days.
Just one.
We snap hundreds of photos at graduations, birthdays, and major celebrations. We plan the vacations, book the tickets, and make sure everyone smiles for the camera.
But sometimes the moments that matter most are the ones we never thought to photograph.
Just another Tuesday, another dinner, and another lovely day with everyone home. It's funny how the most ordinary moments end up holding the biggest pieces of our hearts.
I think about that a lot these days.
Especially now that my girls are grown, and life looks so different.
And I wonder how many of us are walking through ordinary days right now that we'll wish we could have back someday.
Maybe that's our little reminder to be present: to put the phone down now and then, linger at the dinner table a little longer, and remember that the life unfolding right in front of us is worth remembering.
Okay, y'all, before I get us all crying into our coffee, can we talk about how much FUN Austin is?
Austin has its own vibe!
This city knows how to have a good time.
And I am READY. ๐
If you've never been to Austin, especially in the fall, you are missing out.
The restaurants, patios, live music spilling into the streets, and festivals; the energy just hits differently.
There's just something about that city to fall in love with. Have you ever heard the phrase "Keep Austin weird"?
๐ค Keep Austin Weird!
There's even a mural with those famous words. You'll find it on T-shirts, bumper stickers, and just about everything else around town.
Austin has always been a melting pot of personalities, cultures, and styles. Maybe that's one of the things I loved most about living here.
Everyone had their own personality, style, and definition of what normal looked like. There was something refreshing about a city that encouraged people to show up exactly as they were, quirks and all.
And if you know me, you know I fit right in. ๐
๐ "Keep Austin Weird. Don't worry, I'm coming back to contribute."
And then there's downtown Austin.
๐ถ Life on Lady Bird Lake!
On any given Saturday, you'll find people kayaking and paddleboarding, sometimes tying their boards together just to float, socialize, and enjoy a few drinks. Because, well, it's Austin! ๐
The trails around the lake are buzzing with people walking, biking, running, and strolling with their dogs. Everyone is out soaking up the sunshine, enjoying the outdoors, and taking in a little of that Austin magic.
๐ฆ Austin After Dark!
As the sun sets, Austin takes on a whole different personality. Speaking of sunsets, we must talk about the bats!
Austin is famous for the thousands upon thousands of Mexican free-tailed bats that emerge from beneath the Congress Avenue Bridge at dusk. Yes, real bats! ๐ It's one of those things you must experience at least once. People gather along the bridge, line the shores of Lady Bird Lake, and even head out on boats to watch them take flight across the evening sky.
Once the bats have made their grand exit, the rest of Austin is just getting started!
๐ธ Austin's Dining Scene: Come Hungry!
Can't talk about Austin and not mention the food.
Because, honey, Austin knows how to eat! ๐
From legendary Texas barbecue and little hole-in-the-wall restaurants to fabulous sushi spots, caviar bars, and Michelin-starred dining, Austin's food scene is an experience all its own.
And one of my favorite things about the city is how creative the dining experiences can be.
I once went to this incredible little sushi restaurant where only a handful of guests could dine at a time. The entire evening had a theme, and naturally, we dressed for the occasion.
The theme? Grease! ๐ถ
And yours truly showed up as Sandy! ๐๐
Yes, we fully committed to the assignment!
We sat right in front of the chef as he prepared each course, explaining where the food came from, how it was sourced, and the techniques used in each dish.
It was such an intimate experience. Everyone was part of the evening, and you could tell how much thought went into every detail.
That's Austin for you.
You can grab some of the best barbecue you've ever tasted from a food truck, stumble upon a tiny restaurant that becomes your new favorite or get dressed up for a fabulous evening where dinner feels like an entire production.
And sometimes, those unexpected little experiences become your favorite memories.
But the fun doesn't stop when dinner is over!
๐ถ Austin After Dark: The Live Music Capital!
After dinner, the patios are buzzing, bands are playing, and the streets are filled with people enjoying the night.
There's always something happening around the next corner. A comedy show, a concert, a movie premiere, or a little bar with an incredible band you've never heard of.
You can spend the afternoon on Lady Bird Lake, watch the bats at dusk, find a fabulous dinner spot, and end up dancing to live music before calling it a night.
And one of my absolute favorite things about Austin in October?
Austin City Limits Music Festival! ๐ธ
Or ACL, as the locals call it.
Every October, Zilker Park transforms into a massive music festival, bringing together incredible artists, thousands of music lovers, fabulous food, and people from every walk of life.
There's just something about being outside, listening to amazing music, soaking up the sunshine, and enjoying the energy of a city that knows how to have a good time.
Austin has always had this incredible ability to bring people together. Whether you're dressed to the nines for a fancy dinner or wearing cowboy boots and cutoffs at a music festival, there's a place for you.
And don't even get me started on Halloween! ๐
Y'ALL.
Halloween in Austin is practically an experience of its own.
Costume parties, haunted houses, festivals, decorated bars, live entertainment, and enough people-watching to keep you entertained for hours.
I still have pictures from our House of Torment adventures, and let me tell you, we knew how to have fun.
Some of those costumes deserve their own conversation. ๐
We've also made memories at Formula 1 and so many other events around the city.
Looking through those old pictures while planning this trip has reminded me how much we did when we lived there.
And how much I miss that energy.
And y'all, October in Austin is something special!
I'm putting together a full Austin Halloween guide with spooky festivities, fun things to do, and a few hidden gems. I'll share it soon, just in time for Halloween! ๐ป๐
And you better believe I have a few adventures planned while I'm there! ๐ค
I am fully intending to take Ike Jr. out on the trails! Our resort has MOD BIKES available, which just happens to be a brand I've been eyeing for Ike 2.0. So naturally, I consider this a little research trip. ๐๐ดโโ๏ธ
I've also booked horseback riding through the Texas countryside and a guided UTV adventure. With all the race festivities happening around Austin, I'm hoping to soak up some of that excitement, too!
We're staying at a beautiful resort just outside the city, somewhere I've never stayed before, so I'm especially excited to experience it for the first time.
And don't you worry, you know I'll tell you all about it when I get home!
My plan? Eat some incredible food, catch up with old friends, spend as much time outdoors as possible, and soak up every bit of that Texas atmosphere I've missed.
Of course, I'm also making room for a little spa treatment and some pool time. What's a getaway without a little pampering? ๐
Texas, I'm coming home for a visit, and I plan to enjoy every minute! ๐ค
Maybe We Have to Go Back to Move Forward
You know, there's something else about this trip that I've been thinking about. My husband and I haven't been back to Austin together since we reconciled. I hadn't really considered that until I started planning. Austin was home during one of the hardest chapters of our marriage, and we had some beautiful years there, too. A lot of life happened in that city. Now, years later, we're getting ready to return together.
Marriage, y'all. ๐ I wish I could tell you we've figured it all out, but we're still learning. We've had the hard conversations, made our share of mistakes, and had to take a good look at ourselves along the way. These days, we're learning how to be best friends again, and I think that's something worth celebrating. Nobody gives you an instruction manual for marriage. And even if they did, I'm pretty sure most of us would lose it somewhere between the laundry, the grocery store, and trying to figure out what the heck we're having for dinner. But seriously, I'm grateful for where we are today.
I wonder what it's going to feel like being back. I'm excited, of course! I've missed Austin. I also know I'll probably drive past places that bring up memories I haven't thought about in years.
Austin holds so many versions of me.
Some I miss. Some I've outgrown. Some I lost before I was ready, and some I'm only just beginning to understand. The mom who had both her girls by her side. The daughter finding her way through life after losing her dad. The wife who was working through struggles in her marriage. And the woman who sensed that something was changing, even though she couldn't quite put her finger on it.
Gosh, when I think about everything that happened during those years, it's a lot. Some of those memories make me smile. Others still sting a little. And there are probably a few I've tucked away somewhere in the back of my mind. Maybe that's part of why I haven't been back in so long. I mean, I love Austin. I've talked about going back more times than I can count. Yet somehow, the years kept passing. Was I avoiding some of those memories? Maybe. Did life get busy? Absolutely. Probably a little of both if I'm being fair.
But I've been thinking about something lately. Maybe sometimes we have to go back to move forward. There may be something good in revisiting a place that holds so much of our story and seeing it through the eyes of the person we've become. I wonder if I'll drive through our old neighborhood and remember things I'd forgotten, or sit somewhere familiar and think about how different life looks today. Maybe I'll simply enjoy a fabulous dinner, laugh with old friends, and wonder why it took me so long to come back. ๐ Who knows?
I do know that I'm looking forward to making some new memories with my husband in a city that means so much to both of us. And if a few old feelings show up along the way, that's okay, too. I think I've reached a place in life where I can appreciate the beautiful parts of my past while making peace with some of the harder ones. At least, that's what I'm learning. I'll let you know how it goes.
โ Before You Go, Can I Ask You Something?
Do you have a place like that? Maybe it's a city you once called home, the house where you raised your children, an old neighborhood, or even a restaurant you haven't visited in years. Somewhere that holds a whole chapter of your life. I wonder how many of us have places we haven't returned to because we're unsure what it might feel like.
One more thought I've been sitting with lately.
What if some of the ordinary moments we're living through right now are the very ones we'll wish we could go back to someday?
I think about that a lot, especially now that my girls are grown. All those everyday things I probably took for granted. The noise in the house, the conversations in the kitchen, the constant running around. Funny how the things that once exhausted us can become the memories we'd give anything to relive.
So maybe that's my little reminder for both of us this week. Enjoy where you are. Take the pictures. Have the conversations. Laugh at the ridiculous things. Hug your people a little longer. And give yourself some grace for the things you're still figuring out. Lord knows I'm still learning, too.
I'd love to hear from you. Is there a place that holds a special chapter of your life? Have you ever gone back after years away? What was that like?
Come along for the trip! I'll be sharing our Austin adventures, favorite spots, and probably a little chaos over on Instagram @justjennboard.
Until our next chat.
Just stay sweet out there.
I love you,
Jenn. ๐
"Keeping Austin Weird"
Don't quit in the quiet.
P.S. If you're heading to Austin for Halloween, I've got you! My Austin Halloween guide is coming soon, with ideas for where to go, what to do, and how to enjoy the city. Austin even made my 11 Best Places to Travel for Halloween in 2026 guide.
And if you are looking for a midlife companion, let me walk with you at lavishlifeliving.com. The deeper we dive, the sweeter it gets.
Write Me Back
Is there a place that holds a special chapter of your life?