Pragmatic shopping

I resented shopping until I got good at it. I got good at it by overthinking it. This is the story of how that happened and what I learned from it.

Starting from the beginning: Erik and I recently moved back to San Francisco from Berlin. We left almost everything in Germany — all of our big furniture, certainly, but also a lot of regular, day-to-day objects. (Knives, scissors, brooms.) In most cases, the cost of shipping an object back to the U.S. was equivalent to or greater than its depreciated value, so we only brought things we’d need right away or couldn’t bear to part with. It was sort of the ultimate Lifechanging Magic of Tidying Up cleanse.

All of our earthly belongings

All of our earthly belongings

Here on the other side, we had to restock an entire life, which in practice meant doing A LOT of shopping. I define shopping as seeking and securing a transactional solution to an identified need. And, like most things in life, shopping can be turned into an optimization problem. My objective function for shopping looks something like this:

Time + Money + Conflict − Anticipation  Solution + Feeling − Problem

If shopping’s inputs are time, money, conflict, and anticipation, and its outputs are solutions, feelings, and more problems, my goal is to get more out of the experience than I put in.


  • Shopping takes time. Identifying a need requires reflection; researching the best way to address that need requires gathering information; procuring the solution sometimes requires running a meatspace errand, which takes more time yet.
  • Shopping takes money. And, insofar as time is money, the opportunity cost of time spent shopping can be looked at through this lens, too.
  • Shopping can involve conflict—between ideals and reality, in the general case, or between your opinion and your partner’s opinion if you’re making a shared purchasing decision.
  • Depending on the timeline, shopping can involve anticipation. I experience anticipation positively, which is why its sign is reversed in my objective function. But, of course, anticipation of negative outcomes is not so nice.


  • Shopping can lead to solutions and feelings. If the need being addressed was large, or small but frequently-experienced, or tightly bound to identity, a solution can be immensely satisfying.
  • But shopping can also lead to more problems: bringing a new object or service into your life means you might eventually need to get it out of your life—by returning the object, if it turns out not to really solve the problem; by recycling or otherwise getting rid of the object, eventually; or by canceling a recurring payment, in the event of subscription services.


Broadly speaking, there were two ways to cut shopping’s optimization function: shrink the inputs and/or improve the outputs. For me, that meant minimizing time, money, and conflict where the ceiling on the solution was low, and focusing on maximizing solution and feeling value (and preempting looming problems) when the ceiling was unknown.

I also took advantage of a few things I’ve learned about myself to manage the inputs and outputs:

  • I dislike errands. Some people enjoy the discovery aspect of in-person shopping, or the immediate gratification aspect of securing a solution on the same day they identify a need or a want. Conversely, I prefer the endless rabbit holes and slice-and-dice-ability of online shopping, and I hugely enjoy the anticipation that accompanies delayed gratification.
  • Reducing dread helps a lot. I experience anticipation vividly; that’s equally true of positive anticipation (hope) and negative anticipation (dread). If I can convince myself that I have a solution at hand to “the worst that might happen,” or break the dread cycle by deliberately articulating to myself “let’s just see,” I can shrink the input side of the function significantly.
  • I need to know what I’m solving for. In debating how to furnish our apartment, Erik and I kept arriving at incompatible conclusions until we stepped back and expressed our personal optimization functions. It turned out that I was focused on minimizing our time investment and the waiting game and he was focused on finding the best solutions regardless of timeline. Once I heard his argument and reflected on my own relationship to delayed gratification, I realized that an exhaustive search for the right couch or bed frame (even if it would take 8–12 weeks to ship) was compatible with my priorities, too. I was rushing to find solutions because I love closing loops. But in reality, negative anticipation of suboptimal outcomes is a major factor for me, and in practice, I enjoy the waiting-for-delivery game once a decision is made.

Scenarios and solutions

Shopping scenarios fall into a few different buckets:

Functional basics. These are one-time purchases that consistently solve a problem over a long time horizon. Recent examples from my life: kitchen scissors, a broom, and a paper towel holder.

For functional basics, my first move is always to search for the generic object name on The Wirecutter or The Sweethome—sister sites that, together, serve as the modern version of Consumer Reports. The Wirecutter covers electronics; The Sweethome covers domestic goods. The SEO between the two sites is pretty good, so you can generally type a search term like “scissors wirecutter” into Google and it will still return “The Best Scissors and Kitchen Shears” on The Sweethome as a top result.

The great thing about reading write-ups on The Wirecutter and The Sweethome is that, in the process of identifying a topic pick, they always outline a thorough framework for all the factors that could influence your decision. They interview experts, explain jargon, and explicitly articulate the optimization function they’re using to make their recommendation. Even if I don’t go with their pick, I always learn something.

If the object I’m after doesn’t have a write-up on The Wirecutter or The Sweethome, my next step is typically to search on Amazon. If the top result meets my needs, I’ll just go with it.

For objects that are always in view, like a paper towel holder destined for a countertop, aesthetics become more of a factor. If the ceiling on how functional an object could possibly be is pretty low (which is true for paper towel holders, in my experience), and the aesthetic impact on my day-to-day life is high, it can be worth seeking out a non-Amazon, non-Wirecutter/Sweethome solution. This is a case, too, where the cost ceiling is generally reasonable—if the optimally functional but ugly version costs $10, the beautiful version probably only costs $20—so it can be a place to play. Three steps to finding a beautiful version of a functional basic:

  • Enter the generic name of the object in question into Pinterest to get a sense of “the range of solutions to this problem that people consider appealing enough to pin.” The trouble with Pinterest is that pinned items are often long gone from the shops they were pinned from, but you’ll still come away with some keywords and a sense for the spectrum of possibilities.
  • Using keywords collected from browsing Pinterest, run a fresh version of the search on Etsy to see whether your problem is one that people have solved through handmade goods. There are often lots of great options there—ones you never would have found by running a generic search.
  • If there’s a general aesthetic theme going, try plugging in those keywords as search terms alongside the name of your functional basic on Pinterest, Etsy, and Google.

In the case of the paper towel holder, I searched Pinterest to get a sense for the possibilities; searched Etsy and found a few that I thought were fine and interesting, but wasn’t that excited about; then, tried searching “paper towel holder marble” on Google for kicks (since we have a lot of marble and walnut going on in our apartment), and found this one at Crate and Barrel, which Erik and I both liked a lot.

Consumable basics. These are things like tissues, soaps, and groceries—things that get used daily and run out quickly. The ceiling on solution value is low and the downsides of a suboptimal solution are minimal (we’ll just run through consuming the product and buy a different one next time), so the key here for me is minimizing time by reducing decision friction.

For paper products and soap, that means Amazon Prime / Amazon Prime Pantry all the way. For groceries, that means using Instacart—which, on top of same-day delivery, has the extreme benefit of saving items you’ve purchased before and making it easy to purchase them again. For anything that you consume at a predictable rate, subscribing to it on Amazon can make sense, since prices are often lower. For instance, we subscribe to sparkling water.

Major shared purchases—mainly, furniture and household electronics. Erik and I made a lot of these purchases recently, and got into a groove. Since the cost is high and the risk of conflict is high, too, investing the time in identifying and reconciling our individual optimization functions for each object proved to be worth it. Here’s the groove we found for furniture shopping:

  1. Go on an exhaustive tour of San Francisco furniture shops. Despite my general dislike of errands, this ended up feeling more like museum-hopping. In a single day, Erik and I made it to something like ten different shops. This helped us each discover and articulate our individual optimization functions, and ensured that we dedicated solid, synchronized time to that discovery process.
  2. Use the optimization functions identified during the tour to fuel an online window-shopping spree; stash strong candidates on a shared Pinterest board or, if on Etsy, using Etsy “likes.”
  3. Review strong candidate items together side by side on the couch.(This only became practical once we had a couch.) If we both agree on an item, sit on the decision for a few more days, then pull the trigger on the purchase after discussing one more time. If we disagree, try to articulate the friction in a way that generates keywords to fuel a second round of searching.

In the end, we bought our couch and ottoman from Joybird, our mattress, sheets, and pillows from Casper, two mirrors from Room & Board, and everything else from Etsy. Inspired by a tip from Lisa, Erik and I discovered that Etsy is the ultimate furniture store. Who knew! Once you have some search parameters in mind, you can find almost anything you can dream of. And since everything is handmade or manufactured in small batches, it’s generally possible to get things customized according to what you have in mind.

Identity investments—mainly, clothing and accessories. Once a baseline wardrobe is in place, the purpose of buying additional clothing and accessories changes a lot. For most of my life, I’ve stuck with a minimal baseline wardrobe because developing personal style sounded costly and high-risk. (It’s hard not to take it personally when something doesn’t look good on you.) Identity investments are, for me, the natural enemy of the shopping optimization function:

  • Shopping for clothes takes a lot of time, particularly because trying on clothes produces a lot of valuable information. (Especially when focused on protecting against the downside risk of having to manage return logistics.)
  • The conflict between ideals and reality can be high, since the clothing has to fit my style, which forces the question: what is my style?
  • Clothes cost a lot of money, especially considering that they can wear out quickly and, in most cases, the same item can’t be worn daily.
  • Anticipation of any sensible item is a neutral factor; it’s hard to look forward to yet another blue sweater. Positive anticipation of bolder items can be higher, but the negative anticipation of problematic outcomes—what if I have to manage the logistics of returning it? What if I wear it once and then never again, and it becomes a waste of money?—tends to cancel out the positive anticipation.

Deciding to invest in solving for this scenario is one of the better choices I’ve made this year. Here’s what I figured out:

  • In resetting my baseline wardrobe, I aimed for quality and chose a few brands to figure out my size in once and for all, enabling effective online shopping. In practice, this meant: figuring out my size at J.Crew and Everlane, then buying items I liked in lots of colors.
  • To cancel out dread of the negative outcome of having to return an online purchase that didn’t fit, I used Shyp—a courier service that picks up, packages, and ships items here in San Francisco and other major U.S. cities for about $10 per return. (Less, if shipping multiple items at once.) That’s far from nothing, but by applying probabilistic thinking, I found that the idea of Shyp resolved a lot of conundrums. If I believed the likelihood of me keeping an item was 80%, the expected cost of protecting against downside risk was $2, which in most cases seemed totally reasonable.
  • Beyond the basics, the upside potential of identity investments derives from the promise of developing a bolder personal style and injecting novelty into everyday life. The first requires trial and error; the second requires a steady inflow of items. Both spark negative anticipation. I figured out my solution to this conundrum with help from Lisa, too: Rent the Runway Unlimited, all the way. For a set fee per month, you get access to an old-style Netflix for clothing and accessories. Rent three items at a time; return them; order three more. This enables lots of trial and error without generating a graveyard of failures, and ensures a steady inflow of items that’s matched by a steady outflow on the other side.
  • Orthotically, I prefer sensible shoes. But there’s no reason those shoes can’t come in interesting colors and designs. For this, I love Ten Points—a Swedish shoe brand I got hooked on while living in Berlin.

Experiential goods—things like movies, music, and books. My solution here is simple: subscriptions all the way. I subscribe to a few different services for video on demand, plus Spotify for music. For books, I keep a few different to-read lists, download a Kindle sample when I’m ready to give a book a try, and then buy it for real only once I reach the end of the sample. Because I’ve put so many checks in place to enforce real commitment to a book before making a purchase, I have zero resistance to spending money on anything that makes it to the bottom of the funnel.

What it all means

At this point, you may be wondering: do I really optimize a mathematical function every time I’m gearing up to make a purchase? Consciously, no. In fact, I hadn’t even articulated the variables until I sat down to write this piece. But I do think a lot about everything I do often, and I find frameworks helpful—especially when they’re built from first principles.

I learned to like shopping by:

  • Turning shopping into a research project (I love research projects)
  • Paying attention to interpersonal dynamics in shared purchasing decisions
  • Neutralizing logistical downside by combining online shopping with a willingness to invest in easy returns through Shyp
  • Starting to see delayed gratification as a positive
  • Being explicit about inputs and outputs and realizing that optimization can mean tuning either or both sides of the function at hand (Time + Money + Conflict − Anticipation  Solution + Feeling − Problem)
  • Solving my desire for novelty and discovery independently from my need for functional basics
  • Getting lots of practice

As simple as that!

For more adventures in lighthearted life optimization, check out Should We, the podcast Lisa Sanchez and I make together. We recorded a whole episode about online shopping. (Unsurprisingly, we’re both for it).

Originally published on Medium

Diana Berlin