Two Writers With Control Issues Talk About Money

We are writers in our late twenties, we have control issues, and money is our psychological pawn.

Jessica: So we’re here to talk about how we feel about money.

Jillian: Yes, money. $$$$

Jessica: I guess we should start by saying, we are both writers in our late 20s. So $$$$ is really more like $$.

Jillian: Or maybe $.

Jessica: Right. So there are some practical concerns where money is concerned. BUT, I feel like we both have concerns that are sometimes disproportionate to how much money we literally need right now to live.

Jillian: Disproportionate or just unrelated?

Jessica: Ha. Maybe both. What do you think about when you think about money?

Jillian: Well, generally, when I think about money, I think of impossibility. The impossibility of ever having enough of it, in New York, to live comfortably and possibly have a family. But that impossibility also doesn’t actually register as real in my head.

Jessica: What do you mean?

Jillian: Like, I know theoretically that there’s a good chance I’ll have to leave New York one day in order to have certain things, but I don’t accept it. Sort of like knowing you’ll die but not accepting that as a real fact.

Jessica: Ah, yeah, I get you. Money, for me, is almost always tied up with this fantasy future that I have.

So I’ll start with, “Oh, man, this job fell through.” (As in, a freelance job.)

But then, almost immediately, that mushrooms into fantasyland, so instead of saying, “That sucks, I guess I can’t buy X,” I’ll go, “Oh my gosh, I can’t make it as a freelancer. I cannot support myself and will never be able to support my children.”

The reality is that I do not have children, and as a single woman, that concern is not actually on the horizon. So I feel like money quickly exits the realm of reality—a literal thing that I use—and becomes a symbol of ADULTHOOD and SELF-SUFFICIENCY and FUTURE HAPPINESS.

Jillian: I suppose that’s true. But it’s funny: In some ways, I feel like we’re opposite about this. I don’t immediately jump to that place, but I feel like I should more.

Because in reality, money is BOTH things, isn’t it? It’s both something we need tangibly in the here and now, but also something we’re going to need down the line when we want to be happy and self-sufficient adults in the future.

Jessica: Yeah, it’s true, but for me it’s hard to get to that middle ground of taking some steps to plan for the future—i.e. being prudent—without jumping to the “holy crap” stage. Why do you think you should do that more?!

Jillian: I don’t really save. I don’t think about the future in any concrete way. I never have. And this is what I get stuck on: We are in our late 20s. We might want to get married and have kids. Or just have kids. Or just not move every three years. Shouldn’t there be a way to approach this at least semi-rationally?

Jessica: There should. But for me, there often isn’t. Which I feel has to do with some kind of base-level enormous fear of failure. And the future, as an uncertain place, is ripe with possibilities for that. But I guess the other and maybe more answerable question is, why does money in particular hold such power as a pawn in these psychological games? Because I am pretty sure it’s not just us who use money as this kind of not-very-helpful symbol of our own potential demise.

Jillian: Good question. I wonder if money is, in some ways, the most tangible thing to latch onto when thinking about a future, because we can, in theory at least, control it. We can’t really control whether we meet someone wonderful, fall in love, get married, and have babies, right? (Well, we can control the babies part.)

Jessica: HA.

Jillian: But money is something that should be within our grasp—we can choose our careers, make it, save it, etc.

Jessica: Right!

Jillian: And since the other elements of the future are so uncontrollable, or seem that way, we revert to thinking about money.

Jessica: I think you are so, so right. But I guess that’s the catch, it should be within our control…but isn’t always. So that when a job falls through (out of control), it triggers all the other feelings of out-of-control-ness. I.e., if I can’t control whether I can support myself in this particular way at this particular second, all these other less-controllable things are hopeless.

Jillian: Totally. Also, we’re both, admittedly, control freaks of a kind, which probably make it even harder to accept. Which then of course begs the question: Why on earth did we choose such unstable careers?

Jessica: We admittedly are. And that is an excellent question (which I ask myself about every week). I think one reason—speaking strictly about the control aspect here, and not about the other things that drew me to writing—is that being a freelance writer does offer much more control than other professions in certain ways.

Jillian: I can see that.

Jessica: Like: I can choose when I work. I can turn down assignments. Which I think offers the illusion sometimes of total control…which, when shattered, is panic-inducing. Because no job offers total control, obviously.

Jillian: I have to say: Honestly, lately I’ve been fondly remembering the times when I had full-time jobs and regular biweekly paychecks. And my logic has turned upside-down: I went from thinking that I could control the projects I worked on by freelancing to now thinking that perhaps I can control them better by working full-time.

Jessica: Okay, wow, I’m having a kind of realization moment reading that, actually.
Because I feel like I do exactly what you described, in my head, all the time:
I flip between all the various possibilities (full-time freelancing, part-time job and part-time freelancing, full-time job, other “perfect” option that has yet to reveal itself to me) and compare them all on the basis of…the control they offer.

Jillian: Yes!!

Jessica: But again, coming back to what we said at the beginning, (a) total control isn’t actually available, and (b) is that actually the best yardstick by which to judge these possibilities?

Jillian: Sometimes I think this is what being in one’s late 20s is all about: figuring out what works for you and what doesn’t, which things matter (money, control, happiness) more than others.

Jessica: See, I want to say happiness, but then in my head I quickly say, “Yes, when I can control everything, I will achieve happiness!” Ugh. Yeah, I sincerely hope this is a late-20s phenomenon.

Jillian: Hahaha. Maybe you achieve happiness by letting go of the thought that you can control everything. That sounds zen-ish, I realize.

Jessica: Um, but exactly, totally, yes.

Jillian: So then what do we do about money?!

Jessica: I mean the question is really, how do we think about money in a sane, practical way (how much do I need to live right now, how much do I want to save, and how do I do that) without spinning off into the land of projection where money is a symbol and the thing we latch onto for the illusion of control?

Jillian: Right. Although one thing I think we haven’t said but is relevant:
We live in New York City. I think it’s so hard to extract money from its symbolism here, for a million and one reasons. It’s also a lot harder to literally live with less money: New Yorkers lose a huge chunk of our incomes to rent—more than in most other places. So obviously money is going to be a bigger burden.

Jessica: A bigger literal burden.

Jillian: Yes, but I think that literal burden seeps into our thinking, don’t you? The literal becomes part of the symbolic.

Jessica: Yeah, you’re right—it does make it easier to make the leap.

Jillian: I’ve also been thinking a lot recently about the difference between being broke and being poor. As in: I do not have a lot of money and am poor by poverty-line standards. But the conditions of my life are such that I will never be homeless (unless my family all dies in a freak accident).

Jessica: Yeah.

Jillian: So—not that I think my worries and fears about money are disingenuous, because I know they’re real. But I also sometimes wonder if the panic is overly inflated, given where I’m at, class-wise.

Jessica: Right. Yes, I think absolutely. Money feels like a dire, life-and-death concern, when in truth it is not.

Jillian: Exactly. And I think I don’t remember that often enough. I mean, how fortunate are we that that’s not actually the case? I wonder if remembering that would help with maintaining sanity in these situations.

Jessica: It’s extremely fortunate. But I feel like also, I don’t know how helpful it actually is. Because it seems to me the part of the mind that imbues money with all this symbolic significance is actually kind of divorced from the part of the mind that is in tune with reality/practicalities. At least in my mind.

Jillian: Hm, interesting point.

Jessica: It’s like saying to a fearful flyer, “You’re so much more likely to get hit by lightning than die in a plane crash.” I’m not sure the reality of that statistic can penetrate the irrationally fearful mind.

Jillian: Ha, yes, I definitely see your point. But I’m not sure I completely agree: In my case, I’ve been trying to do this lately, and occasionally it works. So maybe we agree to disagree? Slash, we have different minds that work in different ways, obviously.

Jessica: Yes, we do, it’s true.

Jillian: So, in the interest of people’s preference for neat endings: What are our takeaways, if any?

Jessica: We need money in a practical sense, but it is also a very convenient vehicle for projecting into the future, aka panicking. Oh, and money is very much tied up with control issues.

Jillian: And if you worry about money and control, freelancing will drive you nuts…but might still be worth it.

Jessica: Slash life will drive you nuts.

Jillian: #truth!


Jillian Steinhauer and Jessica Gross are writers in New York City. Photo Credit: Kate Hiscock


22 Comments / Post A Comment

OllyOlly (#669)

My money panic this weekend fit in so perfectly with all of this. I am fine on a month to month basis, but have these panic sessions about a hypothetical future – like no idea how I would ever afford children. How do I find a balance of being financially prudent but without a constant worry of my future hypothetical life. Probably a lot of my own issues wrapped up in this.

sherlock (#3,599)

Oh my god, this: “Yes, when I can control everything, I will achieve happiness!” This basically summarizes my inner monologue perfectly.

Really I related to a lot of what was said here in regards to worrying about money and the future, but that line in particular hit home.

therealjaygatsby (#4,053)

Why does it often seem that every writer lives in New York? If you’re writing for the internet and working from home, can’t that home be anywhere? Why prohibitively expensive New York? I’m not trying to criticize life choices, just trying to understand the rationale from a personal finance standpoint.

vanderlyn (#2,954)

@therealjaygatsby It’s a mixture of necessary professional networking and fear of missing out. Many writers originally came to New York for the excitement and action and fun, and money wasn’t as important because they shared a shitty apartment with two or three other people and had no expenses aside from rent, food, booze, and deferred student debt.

Once in New York, they made and maintained all their professional contacts. It wasn’t long ago that most of these contacts would have been editors at print publications with local distribution, like the Village Voice or NY Press, or national magazines headquartered in New York. Because getting well-paid freelance writing work is fundamentally about relationships, having drinks with these people and seeing them at birthday parties was—and still is—necessary networking.

Time passes, and suddenly sharing a fleabag apartment with a bunch of people doesn’t work as well. Apartments get more expensive, friends get married/go to graduate school/have children, and the creature comforts these writers were happy to forsake in favor of the city’s vibrancy are looking more like basic necessities.

But what can they do? Their friends are here. The eligible bachelors and bachelorettes are here. A lot of their assignment editors are here. Moving somewhere else to pay less rent would mean the dismantling of personal and professional networks that took years to build. It would also require substantial savings, and a total change in lifestyle. This might leave them with more money, but at what cost?

That’s the long answer. The short, less satisfying answer is that these trade-offs exist everywhere. The combined state and city income taxes in NY are close to 6% or 7%. That’s a huge amount of money, and it would make a lot more sense for everyone here to move to Florida. (Lots of rich people do this, at least technically.) Thing is, you’d have to live in Florida.

Also, a final note. While living in trendy precincts of New York (or other large cities) is indeed extremely expensive, there are plenty of neighborhoods with lower rent and affordable condominiums or cooperatives to purchase. Living in fancy Brooklyn versus utilitarian Queens is more about FOMO than anything else.

@therealjaygatsby I tried posting this already, but it didn’t go through, so apologies if it ends up showing up like 4 times. Anyway. What most everyone else said applies to me, too—my network is here, networking is real and actually helps beyond belief, grad school was here, New York is amazing and I’m obsessed with it, etc.—in addition to which, my family (parents, grandma, sibs) are also here. That’s a biggie. But yes, “why New York?” is the eternal question, and I will have to face it more substantially at some point. @vanderlyn “Condominiums or cooperatives to purchase”??! I wish. I don’t think the issue is choosing to live in a “trendy” neighborhood. I chose my neighborhood because it was cheap. But now it’s been 3.5 years, and it’s not so cheap anymore. And that’s a much, much bigger problem with New York that I don’t know who’s gonna solve it.

fennel (#2,494)

another thing people sometimes forget: real estate may be pricey in New York, but you don’t have to acquire, insure, maintain, or buy gas for a car, which definitely offsets apartment prices for me (even given the cost of monthly subway passes).

vanderlyn (#2,954)

@Jillian Steinhauer I spend a lot of my time in a lot of uncool neighborhoods for work, and I am frequently impressed at the relative affordability of buying (perhaps with FHA programs, which require very little down). I agree that housing affordability is a problem that won’t be solved overnight or with easy bromides, but purchasing something small in, say, Elmhurst for $140k (3.5% down is $4,900) is a time-tested way to keep one’s housing cheap in the face of rapidly rising rents. Not for everyone, but not as unobtainable as it can sometimes seem.

JessicaGross (#2,367)

@OllyOlly and @sherlock: delighted (but also sorry, for all of us) that you related!

@therealjaygatsby, great question — and fodder for a whole other discussion — but the short answer is that being able to meet editors and fellow writers in person (which is a whole lot easier in a place like New York) is an extraordinary boon to a freelancer, especially in the beginning phase of a career: you just get more work that way. But yes, technically, you’re right: the writing itself can happen anywhere.

JessicaGross (#2,367)

(Also, did I mention, I love New York? I do.)

aetataureate (#1,310)

I’d like to know how lack-of-benefits fits into the control feelings about this.

@aetataureate I have them, I just pay for them, which means…spending more money!!

hellonheels (#1,407)

This is really interesting to me. I have a degree in journalism like many of the writers and commenters on this site, but I got a corporate marketing job pretty much straight out of college and have never even for a second considered freelance writing in the seven years since. To me, the financial security is so much more important than any semblance of control I might get from being my own boss. The only situation in which I would be open to freelancing would be after having kids, and assuming my husband’s income would give us a solid safety net. But till then, I’d rather work for someone else, make a quite a bit more money than I’d be likely to make on my own, enjoy my awesome corporate benefits (preferably until after I have had any children I plan to have because $$$$ hospital bills!), and consider that possibility once I actually have some offspring who might benefit from me having a more flexible schedule.

Incidentally, this is why I have a really hard time relating to the New York writer community-focused content on this site and would love to see more from people who have made more diverse career choices. I know some people manage to do super well for themselves freelancing but I would just be so stressed out all the time, trying to hustle for the next job.

Mike Dang (#2)

@hellonheels Re: people who have made more diverse career choices. In the past few weeks in our “Doing Money” series, we have interviewed: an artist/non-profit worker, a tax accountant, a photographer, a matchmaker, and a comedian. We interviewed two small business owners who opened a brick and mortar store, as well as a young entrepreneur who left Pinterest to found his own startup. And there is more to come!

selenana (#673)

@Mike Dang Yup you did. It’s actually been awhile since you’ve put up a starving NY millenial freelancer piece and I’m grateful for it! I don’t mind them at all and find them interesting when they are indeed mixed in with a bunch of other perspectives.

And I am a freelancer-on-the-side who had a steady full time job at the moment and I don’t live in New York but oh yeah, contacts and meeting people is everything. Most of the (paid) jobs I’ve gotten have daisy chained off a previous connection. Editors are about ten times more likely (in my experience) to work with someone they already know or that one of their connections knows. It’s so much easier to get an assignment after you’ve had dinner with someone than from just cold calling (emailing (pitching)).

TARDIStime (#1,633)

@hellonheels I am really loving your “doing money” series since you started interviewing regular, non-millennial writers. I have nothing against millennial writers, but I just related to all of these other, more varied interviewees so much! Thanks, Mike!

asharpcookie (#3,478)

This is amazing, and it really reminds me of something I realized earlier this year when I actually had a (very tiny, short-lived) financial cushion: I am much smarter about money when I actually have money. As in, when I am completely broke, money stops seeming “real,” almost, and I make some really poor decisions. But when I have some money, I start budgeting, saving, asking myself if I really want something, etc…

liznieve (#37)

@asharpcookie completely agree. When I’m in a position to not be paycheck-to-paycheck, I am a way better saver, budgeter, etc, because I feel like I can actually save for something big (a trip, a new handbag, etc). When I’m squeaking by, I just say “eh, f it” and burn my checking account to the ground. because even though I know logically that $20 or whatever could one day add up, that knowledge somehow still doesn’t cross over into action.

@asharpcookie This is SUCH a good point. You are so right. I’m having a moment.

kelockhart (#4,762)

@asharpcookie That’s actually a scientifically proven thing! But even knowing that still leaves me in the same boat, too, unfortunately.

Really glad you guys mentioned class privilege and gratitude to put this conversation in context.
Otherwise, it was beginning to sound like an episode of Girls!

emmadee (#4,759)

@JessicaGross @Jillian Steinhauer I see you both did the cultural reporting and criticism program at NYU. Since we’re talking about money and futures and professional decisions here, can I ask for your thoughts? Was it worth it??

JessicaGross (#2,367)

@emmadee Yes, I absolutely think so. I owe much of my career to that program — not to mention I wouldn’t have met Jillian, whom I love dearly, otherwise.

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