Dadvice Weekly #51 / Buy Once, Cry Once
Dadvice Weekly - #51
A few weeks ago my wife said, “Buy once, cry once,” about a purchase we were considering.
I thought it was the greatest way to describe what we were wrestling with. I genuinely thought she had made it up. Since then I’ve learned it’s actually a pretty common phrase, but the idea has stuck with me.
Your thirties feel like the first decade where you can start asking a different question: What is actually worth paying more for?
Think about your twenties. You’re probably living in a dorm, an apartment, or your first rental with roommates or a spouse. Everything feels temporary. You don’t buy the expensive light fixture because you don’t own the house. You don’t buy the forever couch because you’ll probably move in a year. Then you finally buy a house and every dollar goes toward the down payment, so you’re filling rooms with Facebook Marketplace finds, hand-me-down furniture, and whatever family is willing to give you.
That’s exactly what you should do.
But eventually something changes.
You realize this might actually be the house you’ll stay in for a while. You get promoted a time or two. Your income grows. Your kids arrive. Suddenly you’re not asking, “What’s the cheapest option?” You’re asking, “What’s the thing I’ll be happy I bought ten years from now?”
That’s where “buy once, cry once” starts to make sense.
I’m not talking about buying luxury for the sake of buying luxury. I’m talking about intentionally paying more for things that earn it. Things you’ll use every day. Things that make life easier. Things that won’t need to be replaced every couple of years.
When I’m trying to decide whether something is worth spending more on, these are the questions I ask myself:
Does one brand consistently hold its value on Facebook Marketplace? If so, that’s usually a good sign. Enjoy it while you own it, then sell it when you’re done.
How many times will I use this before it “pays for itself”? If it’s an espresso machine, how many lattes would I have to make before I break even? If it’s clothing, how many wears before I feel like I got my money’s worth?
How often will I actually use it? If it’s every day, spending more often makes sense. If it’s only a few weekends a year, calculate the cost per use before pulling the trigger.
Will it realistically last me ten years? Longevity changes the math. A purchase that lasts a decade feels very different than one that lasts a year or two.
Will it make my life noticeably easier or more enjoyable? Sometimes convenience is worth paying for, especially if you’ll experience that convenience every single day.
I’ve found that the best purchases usually aren’t the cheapest or the most expensive. They’re the ones that quietly make life better every time you use them.
Here are the things we’ve bought that were absolutely worth crying once. -SW
Espresso Machine
With small appliances like an espresso machine, quality means more than running without hiccups. It also comes down to how easy the machine is to maintain and how replaceable the parts are. For an intro-level machine, the Gaggia Brera fits the bill on all fronts. It’s an automatic espresso machine with a built-in burr grinder, milk frother, and hot water dispenser. We’ve used our refurbished one nearly every day for 2.5 years, and it’s saved us hundreds of coffee purchases in that time.
Here’s the interesting part about the Brera and other entry-level espresso machines: the newer models (generally those with manufacture dates before 2020) tend to have more issues with parts failure, so the best places to find them are used markets like Whole Latte Love or FB Marketplace. Refurbished machines typically run about $300 at Whole Latte Love, and they have a ton of troubleshooting resources and instructional videos for maintaining them. I’ve also bought machines on Marketplace for anywhere from $50 to $150. We take one camping, and I keep one in our office space. I love these things. –KC
Durable Outdoor Furniture
When we moved into our house, we bought a patio set that landed somewhere in the middle. It wasn’t the cheapest option, but it definitely wasn’t the nicest either.
Eight years later, it’s still here.
I’ve sanded and stained it once, replaced the cushions, and it’s due for another round. Looking back, I wish I had spent a little more on something that was designed to sit outside year round without needing much attention.
Our next patio furniture purchase will probably be something like this. It’s not cheap, but it’s also not dramatically more expensive than the set that requires you to sand, stain, and wonder how many more seasons the set has left. -SW
Dyson Vacuum
When we got married Brooke wanted to buy our first Dyson, I remember looking at the price and thinking, “There’s no way a vacuum should cost that much.”
I’m glad I kept that opinion to myself.
Nine years later, we still use that cordless stick vacuum almost every single day. It lives in our kitchen and is probably the most frequently used appliance in our house. It has easily justified its price.
When we bought our house and got Sadie, our golden retriever, we added a second Dyson with a larger canister because the original filled up too quickly. We’ve had that one for six years now and it’s been just as reliable.
If either one dies tomorrow, I’ll buy another Dyson without hesitation. -SW
TVs & Sound Bars
I’ve always enjoyed watching sports and movies, but having a child has completely changed how we use our living room. We spend a lot more evenings at home, and our TV gets used far more than it did a few years ago.
That’s why I don’t mind spending more for a great viewing experience.
Our current TV works perfectly, so I’m not rushing to replace it. But when the day comes, I’ll happily pay more for something that’s noticeably better because I know we’ll enjoy it for years.
The same goes for sound bars. We bought this one on a recommendation, and I didn’t realize how much it improved the experience until we had it. Dialogue is clearer, sports sound better, and movies are far more immersive.
When it’s time to upgrade, I’ll probably move up another tier. It’s something we use almost every day, and for us, that’s exactly what “buy once, cry once” is all about. -SW
Premium Cooler
We have a RTIC 65 Quart Cooler, and I can confidently say every homeowner should own a premium cooler.
We’ve taken it camping, loaded it up for road trips, and lent it to friends for parties, birthdays, and whatever they need. It has become one of those items that quietly gets used more than I ever expected. It pretty much always has drinks in it so even when its not being used for a party it has some utility to it.
There are certainly cheaper coolers out there, but this is the definition of “buy once, cry once.” Once you own it, you’ll never think about buying another cooler again. -SW
Golf Clubs
If you’re playing with your grandfather’s clubs, your dad’s old set, or the clubs you bought in high school, it’s probably time for an upgrade.
Golf clubs aren’t cheap, but they are one of the few hobbies where modern technology actually makes a noticeable difference. Moving from clubs that are 20 years old to something that’s only a generation or two old can make the game easier almost overnight. Mishits are more forgiving, drivers are more stable, and you’ll probably pick up a little distance without changing your swing. -SW
Just as important is you’ll have more fun.
One piece of advice I’d give to someone getting into golf is this: don’t feel like you need to buy the newest clubs on the market or spend hundreds of dollars on a fitting right away.
Your biggest goal early on is consistency, not optimization.
Buying a quality used set that’s one or two generations old gives you 90% of the performance at a fraction of the cost. As your swing becomes more repeatable, then it makes sense to invest in a fitting or upgrade piece by piece.
Golf is hard enough. Playing with outdated equipment just makes it harder than it needs to be. -SW
Dadvice Weekly is Kyle and Skyler—two friends in their thirties, living in Colorado, settling into fatherhood and trying to stay sane. Every Tuesday we share what’s working in our homes: gear we use, routines we’ve tested, ideas we’re trying. It could be a recipe, a product that solved a problem, or just what we’re thinking about as dads.
If you have a tip, tried something we mentioned, or just want to say hi, reply to this email or message us on Substack. We read everything, and we’re always looking for what works. Glad you’re here.