Downtown Oakland, CA // Structure your life to avoid overspending money and boost your savings // by Tanja Hester at // early retirement, work optional, financial independence, saving, investingwe've learned

Structure Your Life to Avoid Overspending

In early March, Mark was out of town on a ski trip with his family, and I decided to escape the cold and house sit for a friend in Reno for a week. That week was illuminating.

Did you know that there are apps you can use to order all kinds of delicious food that people will BRING TO YOU and that let you pay on the app so YOU DON’T HAVE TO PAY THE DELIVERY PERSON?!  

Yes, of course you know this, because you live in a normal place in the world.

I knew this theoretically, but there are zero people or places who will deliver food to our house in Tahoe that I can eat (there’s maybe one pizza place, but it’s not celiac-friendly), so I’ve never given it any real thought. Until, that is, I happened to see an ad for GrubHub, and thought, Huh, I know that won’t work in Tahoe, but I wonder if it would work down here?

The answer is: Why yes, yes it does. And they offer so many tempting discount offers just about every day that I found myself ordering through them multiple times that week. Despite being less than a quarter mile from a perfectly well stocked supermarket. And despite their ridiculous delivery fees (mostly the “discount” just makes delivery free or nearly free).

Other things I did that week that I can’t do at home:

  • Dine in or order takeout at other restaurants
  • Pay to visit the art museum
  • See the symphony (comped, a small budgetary mercy)
  • Get takeout coffee at Starbucks multiple times (funded by Christmas gift cards)
  • See Captain Marvel in the theater… three times
  • Get a massage at a spa (locals discount… but still)

It was an expensive week. And while I know that a good deal of that spending was thanks to the novelty factor of being in a place where I could do all these things I can’t do at home (as well as a post-book release de-stress fest), I also know this to be true:

Despite saving a large amount of money and successfully achieving early retirement, I’m still not an especially frugal or disciplined person.

It’s true: I’m still a spender. I never stopped knowing that about myself, but that week put it into stark relief. We’ve known for a long time that our saving success was entirely built around taking the willpower and decision-making out of the process, via an extensive set of “pay ourselves first” systems, what we call “hiding money from ourselves.” And it’s a strategy we still use in early retirement, keeping only the money we’re allowed to spend in the short term in our checking account and making sure we don’t overspend that.

And it works! Even if you’re a natural spender, it’s possible to create structures to help yourself act frugal and disciplined, even if you don’t feel frugal and disciplined. We did, and you see what happens when I’m left to my own devices in an unstructured environment. (But I still stuck to my money mission statement and didn’t set foot in Target! ;-) Chapter 3 of Work Optional is all about creating a money mission statement to guide your spending — and not spending — and is a great resource if you want to go deeper on this stuff.)

So let’s talk about what that looks like: how you can structure your life to avoid overspending.


I know that if I lived in a city that offered the full range of spending options that I wouldn’t spend money every week like I did that one week, but I’d certainly spend more than we do now. The fact that I don’t usually spend like that (and Mark doesn’t either) is what let us retire early six years after getting serious about the goal instead of double that or even longer. And that not spending was thanks entirely to living a life structured around not overspending.

Structure Your Life to Boost Your Saving and Avoid Overspending

Here are some ways you can structure your life similarly:

If you can… Live somewhere that forces frugality

Obviously not everyone can do something similar to what we did when we left LA and moved to Lake Tahoe, but if it’s an option for you, it can be a powerful force for saving. In addition to the fact that no one will bring us food, there’s also nowhere we can even eat after 9 at night, and forget about attempting to dine out on the weekend or anytime near a holiday period thanks to the region’s many visitors. There’s also a culture here of potlucks, game nights and meeting for hikes, unlike our old life in LA, when seeing friends meant spending $100 on dinner (more if we had to valet park). Living in a ski region also saves us a ton of money because we are no longer traveling to ski, and we can spend $650 a year for a ski pass rather than $100+ for every day we ski if we were buying regular lift tickets. In our day-to-day life, we happily live pretty cheaply and getting an $8 rotisserie chicken at the grocery store feels like a splurge. The combination of factors that make us spend less here, despite it being an expensive place to live (#mountaintax), are probably unique to small ski towns, but the point still remains: it’s easier to spend more money in some places than in others, and if you can live somewhere that makes it harder to spend, you’ll be able to save faster and live on less.

Make frugal friends

We’ve spent a decent portion of our adult lives around friends who, like us at the time, were caught up in lifestyle inflation. And since we moved to Tahoe, we’ve been around the opposite: people who don’t spend money thoughtlessly. And I can absolutely say that having frugal friends makes it a whole lot easier to hang onto our money than does having only spendy friends. We may not be naturally frugal ourselves, but when we hang out with frugal people, we act frugal. Because we’re not going to be the jerks to suggest an expensive restaurant to friends who we know would prefer a potluck dinner. The more you surround yourself with frugal friends, the better for your account balances.

Keep apps off your phone

When we visit friends in LA and New York, I’m always amazed to see the range of apps they have that are useless here: GrubHub, Seamless, UberEats and I’m sure plenty of others. And when I had that GrubHub app on my phone for one week in March, I know that I gave in to spending I’d normally scoff at. It was just so easy to part with those dollars. While I’m far from a digital minimalist, I’ve made an effort the last several years to keep any apps that let you spend money off of my phone, and it’s made a positive difference. And that’s my rule now: no apps are allowed on the phone that are primarily about spending, with that one-week exception. I even deleted Lyft and only download it if I’m truly in a bind, and then I delete it again after that. It’s that much harder to convince yourself to use public transit while traveling, for example, if a few taps on your phone will magically bring a car to your door. Why put yourself through that? Give yourself the gift instead of less temptation.

Delete your credit cards from sites you frequent

If you find it a little too easy to spend money online — that’s by design, of course — then put some structural barriers into place to make it harder to keep doing that. For the sites you buy from, delete your credit card information from them (and don’t let your browser or password manager save them either), and bonus points if you also don’t let the sites save your billing and/or shipping address. That makes buying something online a bit more annoying, because you have to type all that stuff in every time, and that annoyance factor can be a helpful deterrent.

Unsubscribe from tempting emails

You know sales are a sham, right? On any given day, you can find coupon codes for virtually any site online, and there are rarely times when things truly get a lot cheaper than normal. So don’t let marketing emails advertising “sales” manipulate you. Go on an unsubscribing spree and get rid of all of them. If you’re tracking prices for a big planned purchase to get the very best deal, that’s one thing, but companies cook up fake sales and email us about them because that approach works and people buy more as a result. Remove the temptation from your life. Every sale or deal you never heard about is that much more money you didn’t spend.

Learn to recognize and avoid your spending triggers

Maybe ordering food and online shopping aren’t your issues, but you have another spending trigger. Do you know what it is? Chapter 3 of Work Optional has an exercise to identify your spending triggers, and once you know what they are, you can structure your life to avoid them. It’s why I no longer set foot in a certain Minnesota-based big box retailer with a bullseye logo, because I always overspent when I used to go in there. And so I structured my life to avoid it: that store is no longer a part of my rotation when running errands. Whatever your triggers are, consider how you can avoid them and do what you can to build that avoidance into the actual structure of your life.

Your Turn!

What are some tricks you’ve learned to avoid spending money without it feeling like a willpower-based decision? Please share with all of us in the comments!

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30 replies »

  1. San Francisco is ground zero for all these apps and I do use Uber eats and Grub hub very frequently. The convinence of healthy food and time saved in grocery shopping, cooking, cleaning is totally worth it.

    I don’t shop for “stuff” though so I guess it balances out.

    • I began to fight my consumerist tendencies by coming to terms with the fact that Amazon is a great big monster of useless convenience shopping. I haven’t bought anything from Amazon in 8 months, and I am now embarrassed at how much I averaged each month before I gave them up. Admittedly, I still spend more than I should on things like vinyl records, bike stuff, and board games, but all that money goes to locally owned businesses (and it’s much less spending because it’s much less convenient!)

  2. Good advice all around!

    I would also recommend to periodically downsize and optimize your recurring payments – and even consider whether you need them at all. I’m talking about stuff like your phone bill, internet, utilities, etc. Take advantage of special deals and don’t hesitate to change contract when you find better conditions.

    Just to give one example, I am currently on a $10 a month, 50GB data phone bill. This is a special offer that lasts 12 months before the real pricing kicks in. So my strategy is to change contract every year, taking advantage of the best available offer.

    I also figured that I could exclusively use my phone’s internet for my computer as well, so I don’t have Internet at home. I estimate I’m saving around $550 a year on internet and phone alone.

    Thanks for the post :-)

  3. I buy most of my clothing online & I don’t want to unsubscribe from emails that offer coupon codes. I’ve set up a filter that sends these emails directly to the trash. My inbox doesn’t have emails that encourage browsing and I can search for coupon codes in the deleted folder if I need them!

  4. Oh I wish I could find more frugal friends! That truly does make a difference. It would also be easier if I lived in a home that offered space to host social gatherings, but alas I live in a shoebox, so I can’t just invite some friends over for cheaper wine and appetizers, we have to go out and pay extra just for being in a restaurant, ugh.

    I agree with the one above about looking at monthly services. I have two VPN accounts (because one works better, but only some of the time) and I just never get around to cancelling the one I could cancel because it’s going to be a big hassle (and the price is really cheap, but still. Every bit counts.)

  5. We are not frugal at all. The way we manage this is also the pay ourselves first method. Every month money is moved into 401k, HSA, 529, and other accounts. Therefore, whatever is left in our checking account is fair game. The most difficult part is managing cash flow within the checking account — with 2 kids we have several recurring big ticket expenses.

  6. This makes a huge difference for me as well. I also find that I need to unsubscribe from some travel blogs, it bring on some major FOMO and doesn’t really align with my money mission. I need to save a little more now, so I can have the free time to do all of those travels with friends and family.

  7. This one is specific to clothes and other home goods but I’ve been trying to make a point of checking local secondhand stores before just buying something vintage online. Sure, it takes more work to physically go to the store and look through the takes, but everything is so much cheaper in person (especially when you don’t have to pay shipping).

    Also, I’ve come to terms with the fact that I’m also naturally a spender and I loved reading your book because of it! Thanks for keeping an eye out for us spenders and not making us feel like crap because of it.

  8. When I take a walk during mid-day at work, I don’t bring my wallet. If I did, I’d probably buy a coffee EVERY day. :)

  9. Making frugal plans in advance really helps me turn down the spending. No, sorry I can’t join you for after work drinks at the trendy bar because I’ve already made plans to attend a nearby free concert. Yes that restaurant sounds amazing but so is the stew waiting for me in my crockpot when I get home. Waiting till dinner time each night to figure out what to eat was a dumpster fire for my wallet and waistline.

    • You are 100% correct on the dinner planning- ever since we focused on planning on dinners made at home and brown bagging it at lunch, we’ve saved a huge amount that we used to blow on restaurants.

  10. My big focus for this is to be really dialed on any recurring monthly expenses. Avoid them whenever possible, and minimize what’s left. I’m talking rent, cell phones, internet, and subscriptions of any type. The time you spend getting rid of these or getting the best deal you can on these comes back to you every month.

  11. Deleting food delivery apps (and Groupon) has been HUGE for me. Post baby having food delivered felt like magic, but then it just became normal and it took way too much effort to wean ourselves away from it.

  12. Moving from the Bay Area to “Sierra Foothills Adjacent” as part of our FIRE transition has helped us limit the temptation to eat out or order in. But even more than that, my wife has improved her cooking skills so much that our home meals are often tastier than our restaurant meals. We typically eat out as a family once a week, but we don’t miss it terribly when we skip a week.

  13. Grocery shopping is the most challenging item in our budget to keep under control. It takes willpower to stick with the budget. A couple of strategies I use is 1) use a grocery pickup service so I’m not tempted to buy something I see that is not on my list 2) stay on the perimeter of the grocery store as much as possible – also helps us eat healthier 3) shop less fancy grocery stores with less tempting items.

    We live in a small town with few dining out and spending opportunities in general. We are considering a couple of towns to retire to, but they have more spending opportunities and I’m not sure if we would be able to resist the temptation…we are natural spenders too. The fear of slipping into our old ways is real.

  14. Having frugal friends and keep apps off your phone will do a lot when it comes to curb overspending IMO.

  15. We also pay #smalltowntax and insourcing our dining out and entertainment has helped somewhat. The kids knew when we moved here that we would have to be our own coffeeshop/movie theater/fast food place (our most frequent indulgences). So we stocked up on hot cocoa and a bottle of flavored syrup, bought an older model LCD projector, and cooked our own treats. Sometimes that means grabbing boxes of frozen clam strips or chicken nuggets in bulk when we’re in the city, but it’s still cheaper than regular takeout.

    When I travel to big cities though, I totally fall into the same habits as you. Love coffeeshops and takeout!

  16. Have chronic fatigue and an old phone. This limits the amount you can go out AND the apps that your phone will actually accept due to an outdated iOS. But seriously, I don’t know if GrubHub/Postmates would even work on my phone — and I’m not eager to find out (just in case they do). Though the one time I did use it (when we had Tim’s newer phone) the delivery fees rankled enough that I doubt I’d use it regularly. Why tempt fate (or myself) by downloading the app?

  17. OMG – I used to go to Target every Sunday before my grocery run, then I discovered FI and it’s the first place I cut. Crazy how I survived that phase – what was I thinking??? I do go when I need something, but not ‘just because’.

    We stopped eating out regularly a while ago and I was shocked to learn recently that Olive Garden dishes are about $20+ each, I don’t know that I can jump back into the routine of eating out again – it’s not worth it – at least not OG…

  18. So we are neighbors! not as close as I thought though. I’m in Tahoe Donner, or at least I’m here part of the year, still keeping primary home in SF.

    Anyway I am resonating with what you are writing. I want to congratulate you and Mark on your market timing for buying a house in Tahoe. Wow! and you locked in the lower property taxes too. So happy for you on that.

    That manipulative sale thing really P’d me off when I first realized. I had my cart all ready for the “sale” and that was the first time I realized this website jacked up the price of everything that was in my cart before putting it on “sale.” I wised up after that and use internet for comparison shopping. It is so often much less expensive to buy basic supplies like laundry detergent online than it is in the stores in SF and Tahoe. Example – laundry detergent at Safeway the other day was $17 or $18 with tax, whereas the same product online $11 with tax. And it’s delivered to the doorstep. Sometimes Amazon has the best prices and other times they don’t so I try to remember to run a quick search before clicking the buy button.

  19. Just discovered your blog! I didn’t retire early, but knew when I was laid off from my journalism job at age 61 that I needed to leave high cost of living New York, and not replicate my free-spending habits elsewhere

    So I sold my apartment and got rid of everything that didn’t fit into five suitcases, and six months ago I moved to Mexico. I rent a lovely house with a swimming pool that costs a fraction of my NY mortgage and monthly co-op maintenance. I eat out regularly, and rarely spend more than $10 or $15 for a meal at a good restaurant with friends. My last Saturday night out was hearing a great live band at our local cantina for the price of a $3 glass of wine. I walk almost everywhere but can Uber across town for $3 or take a luxury bus to a nearby beach town for less than $10. I already spoke Spanish when I moved here, but I learn new words every day, and that’s very satisfying.

    Having just gotten rid of almost all of my possessions has killed at least temporarily my desire to shop. And Mexicans are naturally pretty frugal, especially because salaries are quite low here, so I’m not trying to keep up with anyone. (NY was very different!)

    We’ll see how this goes long term, but just waking up every day in a place where it’s 85 degrees or so and sunny, and I can live mostly outdoors (I’m typing this from my outdoor living room) is pretty priceless.

  20. I love the idea of having frugal friends. Going out can get very expensive, so it’s certainly nice to have friends who don’t mind a night in!

  21. Sort your mail while standing next to the trash can, before you even get in your house/apartment. Catalogs go straight into the trash. Other Junk Mail, too. No temptation to spend and less clutter, too!! Yes, Ive tried to get off catalog mailing lists and some still arrive. I am not a beekeeper, do not buy shoes for tall men, etc. Yet I still got those odd solicitations…

  22. I went on a make it yourself binge when I was forced into retirement. I DIY search nearly everything on Google and You Tube, and designed my hobbies around making better items, ie) soapmaking and ice cream making. You CAN have BETTER than you’re used to. Equipment for both projects has been purchased at our local thrift stores. See if your library has a used bookstore. I picked up 2 cookbooks recently, including a brand new William’s Sonoma Ice Cream hardcover book for $1. I’m using it, and now I’m the family ice cream guru! If you were really good at your job, you can be really good at whatever you do in retirement. Yes, frugal friends are MUST!