Climbing The Ladder/Relationships

Choosing The Less-Prestigious Job & Taking Over Your Boyfriend’s Money

By | Tuesday, May 24, 2016

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In this week’s Ask Chelsea Anything, we’re talking to two women with two very different dilemmas: the struggle between what is the most prestigious choice and what is the right choice, and the struggle between loving someone and deeply hating the way they handle money. In each case, the answer is obviously a personal one that varies hugely based on the individual situation, but in each case, the answer ultimately comes down to: what makes you happy and healthy in a sustainable way? It can often be difficult to really determine what are our non-negotiables in things like work and love, because it’s impossible to tune out the expectations and opinions of others. We can try to be totally unfazed by the chattering of the peanut gallery, but ultimately it’s only human to succumb to them to a certain extent. And when it comes to our relationship dealbreakers, there is a fine line between “preserving boundaries” and “expecting any one person to fill every one of your requirements.”

To answer those questions, and explore those tough choices, let’s get into this week’s two questions. And as always, don’t forget to send your most pressing questions about money and life to

Hi Chelsea,

I just turned in my two-weeks notice at a boring and unfulfilling office job. I was very optimistic about the opportunity when I took the job six months ago, but the day-to-day ended up drastically different than the job description I’d agreed to, and I realized that my side hustles made me infinitely happier than the 40 hours per week I’d spent watching the clock from my desk. I’ve decided to go full-time at the cafe-bar where I’ve been working weekends, and pick up some extra babysitting gigs for now, while considering getting another part-time job as a server in another month or two, if money gets tight or I find that I have more time on my hands than I really need.

Essentially, I’ve realized that I really love working in the service industry. A lot of people seem to view serving jobs as “starter” jobs, side hustles, or reserved for people who don’t have any ~higher aspirations~. I’m very lucky that the people I’ve told so far (my parents, my boyfriend, and a few close friends) have been supportive and agreed that service jobs fit my personality and lifestyle well, and that they can be a decent way to make a living. Inwardly, I’m confident in my decision, but I can’t help but feel nervous about explaining this choice to people in the future – whether it’s my extended family, older friends I don’t talk to as frequently, or new people I meet in the coming months/years who ask the inevitable question – “where do you work?”

Do you have any tips or advice for answering those kind of questions, especially if I’m working multiple side-hustles to make ends meet, rather than having one neatly-packaged title-and-employer to speak of?


Full-Time Hustler

Hey Hustler! I think your question is great, and first, I just want to commend you on having the bravery to take your professional life by the balls (pardon my French) and really do what you want with it, prestige be damned. You have experienced something that so many people do (being disappointed by the reality of the heavily-hyped and heavily-prestigious “career job”), but you have actually found the courage to do something about it, and admit that you are happier to be working in the service industry and, at least for the time, figuring things out with a few different side jobs. So many people would love to do what you’re doing, and admit the things that you’ve admitted to yourself, but will never be able to take the deep breath and jump off the societally-approved career track. So, kudos.

Now, onto the meat of the question, which is twofold: One, how to answer the prying questions of people who might judge you for your new job(s): honestly? Fuck them. Seriously, figure out the answer that feels the most true to you and to your current work situation, and just say that, regardless of the side-eye you fear they might give you. I think you’ll be surprised how a “non-prestigious” answer can be perceived if delivered with confidence, excitement, and clarity. I used to feel this exact same anxiety about telling people I was a community college student, until I started delivering my answer with the forthright excitement of someone who was going to Harvard. It was sincere to my experience — I loved CC! — and it took the shame completely out of the equation. If someone is going to judge you for something you love and own completely, they just end up looking like an insecure asshole.

And for the record, anyone who judges you for being in the service industry is an asshole, which is important to remember in general. Anyone with whom you fear having this conversation because you know they’re going to be a jerk about it is not someone whose opinion matters, at least not until they’ve grown up substantially.

That being said, the follow-up question many people might have is more to do with your long-term plans in your chosen field. Now, obviously you don’t have to have a perfectly-outlined career in the service industry as of today, but it’s good to start thinking in those terms. Part of the reason many people imagine these jobs as being uniquely the realm of starter positions is because few people really look at them as the long-term, fruitful, satisfying careers they can be. And ultimately, no matter what your job is, if the work is just as rote and un-challenging as it was when you first started, you are most likely going to get bored and frustrated. The quality of a job shouldn’t be measured in financial terms, but it should be measured in satisfaction, and part of that means growth: growth in scope, growth in creativity, growth in responsibility.

So start exploring your options within the field you love, and figuring out what makes sense to you, and how to get there. Do you want to be the GM of a boutique hotel? Do you want to own a restaurant? Run a BnB? Do logistics for a resort? Work with a big luxury restaurant group, or a small niche place somewhere in another country? There are so many options, and all require some planning to be laid. Maybe your next step is taking some hospitality classes, learning a language like Spanish, or doing an apprenticeship. There are tons of options, but what matters is that you start thinking in bigger terms. That will only add to your confidence in your new path, and make you even less concerned about that (not-insignificant) hit in prestige.

Your path is your own, and should be. But you have to create it.

Hi Chelsea,

I’ve been dating my (wonderful) boyfriend for about two months. It’s scary how compatible we are in almost every facet of life: we have similar interests and professional ambitions, and what we want out of life seems to be perfectly aligned (marriage, kids, etc.). I can see myself being with him for a long time and perhaps even marrying him and starting a family.

The red flags are few and far between, but I’m on high alert because of a financially abusive relationship I was previously in for far too long. My current boyfriend is absolutely TERRIBLE with money. AWFUL. A few examples: he never grocery shops and survives solely on restaurant food (ugh, d00ds). He sees no issue in paying his bills a few days late (!), and until recently, had a $500 car payment for no other reason than, “uh, the car was cool.” He also has a few expensive hobbies, which include playing some card game with his friends (don’t make me say it), and fixing up his recently purchased starter home (the latter actually being a completely normal and positive way to spend money). He also has some student loan debt, so that’s another chunk of his income.

I feel like I can’t pry at this point since it’s only been two months, but I’m seeing extreme cracks in our future if he can’t get on board with being more frugal. We both make decent money, but also both work at nonprofits, so we’re by no means rich. I’ve adopted a very fugal lifestyle (thanks to your site!) and work hard to budget and save as much as I can. I don’t want to be with someone who I’m constantly fighting over money with – someone who I have to yell at for buying a $12 salad at lunch every day, or who blows $500 on a carpet shampooer without even consulting me first.

Am I jumping the gun on this since it’s only been two months? Is there anything I can do to help him have better financial habits? Or is he just a lost cause?


First of all, two months is way too early to really know anything. You are far from the part of the relationship where you would be merging finances (I hope), and probably also far from the part where you have any real idea of how much you stand a chance long-term. This has nothing to do with the money, and everything to do with the fact that two months is ridiculously new for a relationship, and it’s likely that the two of you are very much still in the lavender haze. Enjoy it, but also realize that asking yourself this kind of question is a little premature. For now, you’re still figuring each other out. And while, yes, this money thing is definitely something to be addressed, you’re not yet at the point in getting to know each other where it would really be appropriate to sit him down with an Excel sheet and a scolding look and start laying down the law.

That being said, this guy sounds a lot like me when I first met Marc (albeit an extreme version), and we started really talking money stuff just shy of the year mark, when it became clear that we were really in this for the long-term and therefore gave a shit about what the other person was like with things like money. (This was post-us vacationing together, meeting parents, etc, so likely much further down the emotional line than you guys are today.)

But the conversation came, and it became clear that two things were essential: One, I knew that my relationship to money was pretty messed up and that I couldn’t continue like that as a functional adult, much less a functional adult in a serious relationship. And two, I wanted to change and was willing to do the difficult stuff to make that happen. This meant learning exactly what I was doing wrong, relinquishing some control to him about things to get my finances in order, letting him hold me accountable for things like rehabbing my credit score, and being watched like a hawk about all things money for the first few years. I was not to be left to my own devices, and that required some humbling on my part. But it was all for the better, and although I am definitely more self-sufficient now, it also taught me that, long-term, it’s better if he takes the lead on money stuff (as long as I stay informed and an active participant in my own future). He is more attuned to planning, organizing, and being meticulous, and that’s not a bad thing — but in order for someone like him to be serious about someone like me, I at least had to reach the bare minimum, which was “not being actively destructive to our shared financial life.”

I think a similar conversation can happen with this guy if it works out, but first I would recommend letting the relationship flower a bit more before you decide whether it’s worth it or not to have an Extreme Makeover: Checking Account Edition on his life. Because of the past you mentioned with this kind of stuff, you seem a bit hyper-attuned to the money aspects of relationships, and while that’s not a bad thing, it’s also jumping the gun a bit at the two month stage. If you guys decide you want to make it work for real, he has to own up to some serious shit, financially, and let you help him. That conversation will be a tough one, but speaking as someone who has come through the other side of it, nothing has been more valuable.

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