Talking to Alanna Okun About Spending, Saving, and What We’ve Learned From Asking People About Money

Alanna Okun is a Senior Editor at Racked and the author of the forthcoming memoir The Curse of the Boyfriend Sweater.

Hi, Alanna! Thanks for setting aside some time to talk with The Billfold!

Hi Nicole! Thanks so much for having me—I actually just got a Facebook notification about the fifth anniversary of the first freelance piece I ever published, which was for you guys! “In Search of a Place to Live.”

Oh wow, that was during our very first year of Billfolding! Are you still in that apartment?

Hahahah NOPE. It was a lovely place but eventually I decided I wanted to live alone. So I’ve had my own little studio in Brooklyn for the past three-and-change years now.

Very nice.

It’s funny how the places/things that once mattered SO MUCH can totally recede in the rearview mirror.

So it goes with many of the purchases we agonize over. But then there are the ones where we think “I am so glad I bought this [bed, car, pair of shoes]” and that’s why we spend so much time worrying about the rest of them!

Yeah, I’m sure you hear this all the time, but as I’ve gotten older and started to really take stock of my spending/finances, I’ve tried to be a lot better about buying the things I absolutely love, even if they’re a little more expensive, rather than a bunch of cheaper things I only half-love.

Which is easy(ish) to apply to shopping, and a little tricker when it comes to things like going out to eat or trips or living expenses.

YES. FOR SURE. I want to talk about the things you and I both hear all the time in a minute, but first: for Billfolders who aren’t familiar, tell us a bit about your How Do You Shop series.

Absolutely! So I’ve been a Senior Editor at Racked for close to a year now, and about six months ago we sat down to talk about ramping up our coverage of how normal people shop. A big part of that push has been this series, where I or a writer interviews someone all about their finances, purchases, and general relationship to shopping.

I totally love it because not only am I very nosy, but also super interested in hearing about people’s different strategies and philosophies; for example, we always ask about folks’ backgrounds as they relate to shopping, like whether they tend to spend more or less than their parents, which I love as a question because it gets to the heart of the fact that money (or maybe would be more accurate to say “personal finance” but that always sounds so sterile to me!) isn’t just this static, objective entity, but is emotional and social, and taught and learned and unlearned and relearned.

Absolutely. We spend based on our previous experiences with spending (and earning), and our decisions change as our experiences change.

So what is your background as it relates to shopping?

It’s funny, because I think my siblings and I have fairly different relationships to shopping even though we all grew up in the same house and are relatively close in age—my mom was the one who would take us to get clothes, and even though I always liked shopping (especially as a bonding experience with her) and felt grateful for the fact that we could afford what we wanted in addition to what we needed, I’ve always been fairly cautious about it, and that’s carried through into my adult life. Like I’ll agonize over whether I REALLY TRULY want something, to the point where I’ll often end up not doing so and then regretting it later or not taking some style risks.

I tend to buy the same type of thing over and over and over again—jumpsuits, striped crop tops, ugly but comfortable shoes—often because I KNOW I’ll wear them and therefore get value out of them.

That is fascinating, because my shopping background is so different. I grew up in a frugal house, which meant that although we could afford both wants and needs, there was this understanding that you wouldn’t get everything you wanted and that you might have to delay gratification for a while until you’d saved up your money.

My allowance in high school was $20/month, which meant that every month I was able to buy one CD. I would try to make the tracks last for a long as possible; I’d listen to the whole thing once, and then put off listening to the later tracks until I’d gotten everything I could out of the earlier ones.

I have a hard time buying non-essential stuff as an adult because of all that frugality both as a kid and as an adult who didn’t earn much money!

Yeah, it really gives me pause to pull the trigger on big / non-essential stuff—we ran a piece semi-recently on people’s different “retail flinch points,” a phrase that I love, and it made me think a lot about mine. When it comes to things like clothes or like, craft supplies (I buy an unholy amount of yarn), I think my flinch point kicks in around $40—more than that and I start to get anxious, like how could I possibly enjoy / use this thing to make up for the work it took to earn that money (or, more abstractly, some future emergency or need I might need it for).

I have a lot of that sort of anxiety—that one day (which feels a lot sooner now that everything that’s happening in the world is, you know, happening) the bottom is going to drop out of my life and I’ll need a lot of money to keep going, and the thought that Past Alanna could do harm to Future Alanna is enough to make even somewhat innocuous purchases feel fraught at times!

ME TOO! I have that exact thought about waiting for the bottom to drop out.

I think a lot about that incredible piece y’all did on the Fuck Off Fund.

Which basically comes down to “save money because you’ll need it someday.”

Totally, and of course that’s super reasonable! There’s just an edge of catastrophe/panic at times.

But it’s not all doom and gloom, lol; I’ve been forcing myself to stare it all in the face and really get control of my finances in the past six months or so (incidentally-ish tied to when I started editing the series) and the act of tracking every dollar, in categories as well as itemized, and creating several separate savings and checking accounts has made me feel more confident for sure.

I’m saving more than I was, and now that my rent and other big, fixed expenses, like therapy and utilities, are coming out of a separate account, I’m a lot more clear on how much I actually do have on hand at a given moment. Clarity and accountability are kind of unsexy but one of the best antidotes to my anxiety that I’ve found (financially and otherwise).

My life also changed when I set up separate savings accounts (one for savings and one for taxes) and started depositing percentages of each paycheck into both accounts. It doesn’t stop all of the anxiety, but at least I know I’m doing the best I can right now—and I’ve been able to save a lot of money!

I’m in my… third year of doing this?

Yes!!! It’s the single best boring decision I made this year for sure.

It’s weird because it feels like I’ve been able to save more than I would have anticipated over three years. (Plus pay down my debt.)

Absolutely, and it makes it clear where it all lives.


Before that I felt like my accounts were always swelling and contracting so dramatically that I never had a super clear picture.

In my case it was more like “I didn’t think I was earning enough money to have extra to save,” and then… surprise, I was. You make your life fit the money, for better or worse.

YES, absolutely!

I don’t want to keep you for too long, but I did want to ask what you’d learned from asking other people about their shopping. I’ll throw in what I’ve learned from interviewing people for our Doing Money series, and we can do this lightning-round style:

Everyone thinks they spend too much on groceries.

Many people have the same favorite clothes they wear constantly—a woman named Janine told us that she lives by the “we wear 20 percent of our clothing 80 percent of the time” rule, which has definitely been echoed a lot!

When I ask people to share their budgets, women often include clothing/hair as an expense and men rarely do.

Oooh interesting!

Also, this is so obvious but rent is way cheaper like, everywhere in the world but NYC and SF.

YES. Though housing is hard for just about everybody.

A lot of the people I interview are planning for the next five years: homeownership and parenting are the big two plans.

This could be self-selecting, given the group of people who would consent to being interviewed about their finances, but nearly everyone we’ve spoken to for the series thinks that they tend to spend less than their immediate friends and family (at least when it comes to shopping etc.)

OOOOH that is interesting.

Again, that’s a sample size of like, 20, and I don’t have everyone’s answers laid out in front of me, but it does make me wonder if a lot of people think that about themselves!

The people I interview often worry that they’re spending too much, but I haven’t asked them whether they think they’re spending more or less than their peers.

I imagine it depends on how you define it, too, like whether it’s “essential” or “non-essential.”

Which is obviously a varied (and often gendered / loaded) question, especially when it comes to things like clothing and grooming.

FOR SURE. It’s hard to have any kind of conversation about spending without having a bunch of separate conversations about family, peers, gender, work expectations, personal goals, etc. etc. etc.

Ahaha absolutely! When I do these interviews, there’s always a point at which the subject will apologize and say something like “ahhh so sorry to get us off track!” and I have to explain that no, this IS the track

Yes. I know you said you didn’t like the term “personal finance,” but that’s why I love it. It’s so personal.

Ahaha yes, I think my distaste for the term is pretty unfounded (I… no stranger to that kind of linguistic aversion) other than the fact that it just feels kind of dry? I don’t actually have a suggestion for a better one, though, so I think I should just zip it.

Here’s the last question I always ask during these interviews: do you have any financial advice for Billfold readers?

Tracking spending is so easy (to the point, I’m sure, where most of the people reading this will be like DUH ALANNA) and doesn’t have to be this big scary endeavor or even done with an app or anything—after tinkering around with a lot of methods, I found that just writing everything down in a phone note worked best for me. I start my weeks on Wednesdays, and track what I spend each day and how it breaks down into categories, and I also threw in alcohol and water tracking too (I just use emojis for those).

Your mileage may vary but I found that going out to drinks was by far the biggest spending category that I truly did not need, and just the sheer fact of becoming aware of how often I was going out, couple with how much it cost, was enough to help me scale back significantly.

I like this method too because it lets me be kinder to myself—it helped me set a budget that was realistic and somewhat flexible week to week, and means that if I overspend or don’t drink enough water one week, the whole month isn’t shot —I can just start again Thursday morning with a little more information.

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