San Diego is one of my favorite places on the planet. Getting the opportunity to live there and embrace America’s Finest City as our own for over seven years made us feel all kinds of lucky.
We were living in a vacation destination with the most enviable weather in the country.
The news that we were leaving San Diego, then, was a shock to some.
I got a lot of the, “I thought you’d never leave!”
“Wait…you’re leaving California??”
“You’ll miss it too much to stay away for too long.”
Well, it’s all a little more complicated than that.
Planning a Trip Anyway?
Your Flight: Seek out deals to San Diego using Skyscanner. Love deals? Subscribe to Going.
Your Accommodations: We lived in San Diego, but browse Booking.com or Hotels.com for some options. Vrbo is my Airbnb alternative.
Your Ride: You’ll need a car to explore San Diego. Book a rental car ahead of time.
Top Spots: Hike at Torrey Pines State Natural Reserve, museum-hop in Balboa Park, and enjoy a scenic happy hour at Fathom Bistro Bait & Tackle.
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Leaving San Diego: The Why Behind It All
San Diego is hella expensive. Moving to San Diego without a job is ill-advised.
I don’t blame taxes, property or otherwise. That last bit was actually an improvement over our time in Chicago. I don’t blame Gavin Newsom, either, as much as some folks in the state would like me to.
I blame San Diego…just not in the way you might think.
People will always want to live in San Diego. It’s pretty ideal. Many of the things people complain about when they’re thinking about leaving one of the country’s most vibrant cities can get quite silly.
Note: This is all opinion and should be treated as such. Obviously there are real issues like the cost of living and affordable housing. Those real issues just don’t include things like missing seasons. Go visit ’em.
Despite the cost of living in the California city, we were fortunate enough to buy property before it got even more expensive over the course of the pandemic.
It seems inexplicable, but it happened. (Prices haven’t magically come down since, either. I look once in a while just to evaluate my prospects.)
Again, we were and are very lucky, and I always say so. Not everyone can buy a home in San Diego County, even back when we did.
We bought a home that we enjoyed very much on a very random street in North Park, one of our favorite San Diego neighborhoods near the just-as-charming South Park.
It was the place that worked for the time being, a phrase I’d repeat over the years we’d live there as it was located on Works Place, said random street.
Would we be able to afford a similar home there today?
Nope.
We also told ourselves that if sale prices in our neighborhood reached a certain number, we’d put our own home up and figure things out from there.
The Beginnings of a “Plan”
Now, it may sound crazy to some, the not-knowing-bit after you sell your house. The pandemic broke our brains, though, giving us a renewed sense of YOLO and FOMO and whatever other acronyms related to using your time on Earth wisely.
The numbers on a potential home sale kept ticking up, hitting what seemed like their peak (at the time) in the summer of the big decision.
So we did it.
We put our house up for sale.
The plan was to see what we could get for our house. We knew it wouldn’t be instantaneous, despite everyone filling our heads with well-wishes and promises we’d have bidding wars within the first hours of listing that’d result in offers over-asking.
It didn’t quite work out that way, but it worked out very well for us nonetheless.
You don’t walk away from the kinds of numbers we’re talking about here, even if that means you don’t have a plan on the other side.
I realize some of this sounds ridiculous and know how fortunate we are to have even been in that kind of position to begin with.
We never intended to leave San Diego, but we always knew the house itself wasn’t our forever home.
When you’re essentially priced out of your neighborhood (and really, any San Diego neighborhood) after selling your house, weird ideas start to form.
Could we be nomadic?
What if we didn’t buy another house right away?
Buying a new home in San Diego right after our own home sale would certainly leave us less comfortable financially. Prices there right now are a force to be reckoned with, and continue to be.
We decided we didn’t need a new, stable home right away at all. It was the beginning of a plan, or in this case the lack of a set plan, that was very out of character for me.
Fun fact: Some people describe impulsive people as adventurous risk-takers. Let’s go with that!
When You’re Navigating the World With No Real Plan
There are a few things we knew.
We knew we’d missed travel immensely over the course of the pandemic.
We knew that we were fairly resilient, with a strong relationship that has managed to survive all kinds of travel fails.
Finally, we knew we loved San Diego. Leaving the city didn’t make that any less true. It just meant we’d appreciate it more in the time we had left, ticking things off our San Diego bucket list.
We’d also leave it on the list as somewhere to return to one day if we could, even if just temporarily. (I already mentioned that fun thing about how we’re priced out of affording property there now.)
Instead, we decided it’d be fun and a little uncomfy and life-changing to hit the road with not much of a plan. We’d never done something like this before and even enjoyed returning back to San Diego after long trips abroad or stateside.
Fun fact: San Diego’s airport is consistently ranked as one of the least frustrating airports in North America. It’s also one of the busiest single runway commercial airports in the country, so kudos all around, San Diego.
First, Next, Last
As we hadn’t been back to Chicago, my place of birth and home to the other love of my life, Pequod’s Pizza, for a while, we decided to start there after the big sale.
We sold a bunch of our stuff, rented a storage unit for the really good stuff, and came up with car-packing strategies that’d allow us to bring along winter gear.
The strategy was to downsize and identify the essentials.
Brian installed a hitch on the car to get said essentials out to Chicago, as large dogs take up quite a bit of space in the car.
Obviously, Kimmy was coming, too.
As an anxious dog who didn’t love car rides, we tried to make her as comfortable as possible in the car, which meant losing out on valuable space for other stuff.
With that, a car full of suitcases and bins pulled in a small trailer that we learned scraped against the ground if it had to go over potholes, sharp angles, and speed bumps, we were on our way.
Note: That trailer didn’t make it much beyond the Midwest. The scraping was just too much, so we downsized further.
We drove across Arizona and New Mexico, Kansas and Missouri. We stopped where we had to, with a few additions where we wanted to, like Santa Fe.
The objective on this leg was just to get to Chicago, take a few breaths, visit with friends and family we hadn’t seen in years, and plot the next move.
That move continued to extend itself. It was driving through New England for the first time to see its spectacular fall foliage. It was a slower pace through cities like New Orleans and Tulsa, a pleasant surprise.
Kimmy appreciates more time spent from place to place, too, especially if there are goats involved.
The End Game
This is where things get a little fuzzy.
After nearly two years of nomadic travel, a different kind of vibe overtook us. It was an urge to find a base to call home, even for just a few years.
As a continued aggressive response to years of hitting pause on travel altogether, we started investigating a temporary move abroad.
We started seeing some things domestically we didn’t love, and needed a break from the political climate.
I realize how spoiled I sound, but I’m not here to address the perils of toxic positivity, either.
We chose France for starters, but we’ll see where things go from here.
Will be ever return to San Diego?
San Diego is also the most scenic place I’ve ever lived, with an underrated food scene and a not at all overrated beer scene. It’s very much worth your time in an extended way if you have the resources.
READ MORE: Here for the beer? Check out my guide to the best of San Diego’s craft breweries.
People come to San Diego for a reason. We moved there in the first place for a reason.
People come and go when it comes to San Diego. It’s quite transient. Recent Census Bureau numbers suggest there has been a population decrease in the last few years, but the idea of a mass exodus is overblown.
Before the pandemic, our guest room was booked on the regular for a reason.
It’s pretty near perfect.
And yet, here we are.
Yes, it’s scary not to have a long-term plan, and a little anxiety-producing.
All I know for sure is that we’ll figure it out together, wherever that “it” is.
Love San Diego and want to read more? Start here:
- San Diego’s 9 Best Waterfalls
- Love Spooky Stops? Visit the Whaley House
- Hit the Road for Delicious Julian
- San Diego Has Polish Food! How to Find It
- A Guide to the Best Southern California Wine Region
Explore more of my favorite San Diego areas:
- Ready for Underrated? Visit University Heights
- Visit Delicious, Harborside Little Italy
- What to See & Eat in Ocean Beach
- Your Guide to the Best of Historic Old Town
- A Guide to the Best of PB, Party Central
Want to see more?
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