Buy Once, Cry Once: 8 Rules for Investing in Quality > Quantity

March 12, 2025

A few years ago, my brother bought me a Patagonia jacket for my birthday. I was shocked, because if you know me, you know I’m the king of cheap clothes. 😅 I’m a $20 hoodie type of guy, not a fancy name brand fella.

But daaaaang, this jacket was different. The moment I put it on, I knew I’d be rocking it for decades (unlike my usual bargain sweaters from Ross that fall apart after 6 months) That Patagonia jacket completely changed my perspective on choosing quality clothing over quantity.

The idea behind “Buy Once, Cry Once” is paying more upfront for a higher-quality item, to avoid spending more and having more headaches in the long run.

That being said, not everything you buy needs to be top-tier. Some things are overpriced, trendy, or just unnecessary.

So how do you know when to spend big and when to save? Here are some simple rules of thumb to help make the right call.

1. The “Daily Use” Rule

If you use something every single day, it’s usually worth investing in quality.

Think of items like your coffee maker, your shoes, your mattress or even your office chair. These things get a lot of wear because of every-day use, so quality is super important.

Yes, it stings to pay $1,500 for a mattress. But good sleep is priceless. It bleeds into every other area of your life, affecting your health and daily productivity.

Cheaply made items wear out faster, and kind of make your life worse.

So if you’re replacing something you use every single day, don’t skimp!

2. The “Will This Last 5+ Years?” Test

Before buying anything new, ask yourself: Will this still be functional and useful five years from now?

If the answer is Yes, consider paying a bit extra if there are more durable options.

Think things like luggage, winter clothing, kitchen knives, etc. Cheaper, low quality items not only need to be replaced much sooner, but they are more of a joy to use.

If the answer is No to the five year question, then budget-friendly options might be a smarter move.

Items like trendy gadgets, fast fashion items, and accessories rarely matter after 5 years. It’s probably ok to be thrifty here and save money.

3. The “Break Even” Rule

For some purchases, it might help doing some quick math.

The goal is to see how long it would take for something expensive to pay for itself.

For example, consider a $1,200 espresso machine vs. a $5 daily coffee shop habit. The coffee machine would pretty much pay for itself within ~1 year, including the cost of beans.

If fancy coffee is your thing, paying more and getting a high quality machine is well worth it. A high-end espresso machine will bring you joy (and save you money) for decades.

Just make sure you actually USE it. If you buy something expensive and then just revert to old habits anyway, that’s money down the drain.

4. The “Resale Value” Test

Many high-quality items hold their value over time.

Even if you have no intention of selling something, it’s worth looking into likely resale values to get a sense of future quality.

Toyota vehicles are a great example. The reason second-hand Toyotas are way more expensive than other cars of similar age is because they have proven high quality.

If you’re deciding between a $40,000 Toyota and a $40,000 BMW, many people think the BMW is the smarter option because it’s a flashier brand.

But in 10 years time, I bet the Toyota actually has a higher resale value than the BMW!

If there’s a strong resale market, the upfront cost stings a little less. You can usually bet there’s more quality and higher resale value later on.

5. The “DIY First” Rule

If you’re the type of person who jumps head first into new hobbies and ideas, this rule will help.

Instead of buying the most expensive high quality item available, see if a budget-friendly or DIY alternative will do the trick to start with.

For example, Joel Larsgaard recently got a pop-up sauna from Costco for only $120. It’s nothing fancy. But it works just as good as a $3,000 custom sauna. Genius.

If you find yourself consistently using and loving it, then consider upgrading.

6. The “Repair or Replace” Test

Ask yourself this question: If the cheaper version breaks, will you be stuck buying another one?

Good quality products that can be repaired over and over again (leather boots, high-end appliances) often are better investments than disposable ones.

You don’t want to replace your fridge every 5 years. You want your fridge to last you 20+ years!

That being said, it’s also important to think: How much are those repairs and maintenance going to cost?

I recently bought a Viking oven and stove top (I got a good deal, it was secondhand). Anyway, little did I know that calling a maintenance guy out to work on a Viking is $600+!  Ouch.  Even though this stove should last me decades, it’s going to be pricey to maintain.

Always think about repairs and maintenance. High-end luxury brands often end up costing you way more just because of higher service costs.

7. The “Can I Rent or Borrow?” Rule

There are a lot of “kooks” at my local surf break… These young and enthusiastic beginners are funny to watch.

One common mistake they all make about surfing is to go all-in too soon with this new hobby. They drop $800 on a wetsuit and $1000 on a fancy surfboard before they even learn to paddle correctly.

A month later, they’re frustrated and selling their boards on Craigslist for next to nothing because they have moved onto another hobby.

It happens in every sport. Folks end up wasting money on gear that they don’t really need yet, because they want to skip the learning curve.

A better (and cheaper!) approach is to rent gear when you’re starting out. It’s the perfect way to test all different types of equipment without making a huge commitment.

As your experience grows and commitment to something is proven, then it’s time to invest in high quality gear.

For other items you’ll only likely use once or twice – like a pressure washer once a year or a fancy camera for one trip) why drop hundreds on something that will collect dust afterwards.

Try before you buy. Rent when needed.

8. The “If It’s Just for Status, Skip It” Rule

If the only reason you’re considering the expensive version is to impress other people, you’re probably about to make a big, expensive mistake.

Trust me. Nobody cares how much money you spend on things. Spending money to impress others will only lead you to broke-ville.

Plus, your life isn’t materially better when you accrue fancier things. A $10,000 gold-plated phone won’t make your calls sound any better. 

Quality should be about function and longevity, not flexing.

The Bottom Line

Buying high-quality items can sting when you first pay for them. But in the long run they can save you money, time, and frustration.

Of course, not every purchase needs to be of the highest quality. Sometimes going the budget-route is smart, especially if you’re unsure of how long you’ll use something.

Hopefully these rules of thumb can help guide you. Buy once, cry once!

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