Bullish on The Billfold: When To Quit Your Job

Bullish on

This post was an interview with Bullish founder Jen Dziura originally published on The Billfold, which stopped publishing in 2019, so we have archived the post here.

Jen Dziura is the writer behind Get Bullish, tagline “Aggressive Lady-Advice.” (We love it already.) She also wrote the Medium essay “When Life Hacking Is Really White Privilege,” which you might have read when we raved about it a few years ago.

I asked Jen to help us continue The Billfold’s discussion of building your career by saying no. Turns out “no” might not be enough; you also have to be ready to quit your job.

So let’s talk about when to say no, and when to quit. In your article “The True Secret to Success? Quit,” you wrote “winners get out early and often.” What does that mean?

I think that a lot of times, because of the way girls and women are socialized, there’s a sense that you’re supposed to be nice and helpful and loyal to your friends — and there’s a sense among a lot of women that the people you work with, and your boss, and the company you work for are all your friends.

None of that is true. Corporations are not your friends, they’re not loyal to you, and you don’t have to worry about hurt feelings if you leave for a better opportunity.

A lot of people who very quickly move up in their careers understand that intuitively. They have no problem leaving something that’s not working for them, or even leaving something that is working for them, and moving on to whatever the next best opportunity is.

I think when you get too caught up in those kind of social relationships that happen in the workplace, and apply feelings of loyalty or guilt where they’re not really appropriate, there can be a lot of resistance to leaving for a better opportunity — or even looking for one in the first place.

What if you’re not sure where that next opportunity will be? What if you know you’re in a situation that isn’t great for you, but you don’t know where to find what’s coming next?

I think it’s really important to take a step back here and say: you need to always be thinking about your career separate from your job.

I love that.

What I mean is that a career usually consists of many jobs, but it also consists of the education and the training that you get, and your network, and the intellectualism, skills, and new ideas you bring. These don’t necessarily belong to your boss, and don’t even happen within the context of your manager’s supervision.

Think of your career as an entity. We’re in an era where we think of corporations as entities, so think of your future success as an entity. In fact, I think it’s helpful for people to anthropomorphize it a little bit. Like: “That career is a really nice lady, and let’s help her out! Let’s give her what she needs to succeed!”

Whatever it is that you do, it’s not just that you have a job, it’s that you have a practice. You just happen to be doing that practice for this employer at this time, but you would be doing your practice regardless. You have intellectual contributions to make, you have a network, these things exist independently of whomever you are giving your services to in exchange for money at this time.

So before the point where your job gets bad, or you know that you’re stuck in place, start looking for new opportunities. Ideally you’re not starting from zero. Ideally you have some kind of practice that’s separate from your job, and you have some kind of network you can draw on.

How do you say no in a job you like? I know a lot of us are nervous about losing what we have, so how do we value ourselves enough to start that conversation?

The Mary Jane Collection


Here we’re talking about bosses putting more responsibilities on you without giving you a raise, that kind of thing?

Yeah! [laughs]

I think the best way to say no to those kinds of things is not to say no outright, but to present a kind of “or situation.” If you’re already working in this capacity and a manager says “I want to add this additional large task to your plate,” it’s time to feign a little bit of ignorance and say “Okay, what am I going to be replacing with this task?” Or: “Okay, I’m bringing up my schedule right now, and if I add this task, that other thing isn’t going to get done. Who can we delegate that to?”

You’re not doing anything wrong here. It’s literally that there is a calendar with this many hours in it, your boss has asked you to put this many things in, and some other things fell out. You’re asking your boss what she wants you to do about it. Leave that choice up to her. This work cannot get done with the things you’re currently doing, so ask your boss what she wants you to prioritize.

When people read advice like that, about half of them are going to say “That’s really nice, but that’s not going to work for me because my boss is an asshole.” If that’s true, there’s no advice that’s going to solve the problem of “My boss is an asshole.”

It’s nice to have a technique that’s a good way to say no, and to manage your workload, but it’s also really important to realize that at least half of the time, this technique is not going to work. And that’s when winners quit. You want to have other projects in progress and be able to move on.

So if you’re reading this and thinking “this technique will not work for me,” I totally believe you. That means I want to you to work on your career so you don’t have to work for that boss if you don’t want to.

I suspect that sometimes the boss is an asshole, but sometimes it’s that your boss doesn’t know how to say no to the bigger boss who’s telling them they have to get all that stuff done!

Sure. There are complicated situations. But in these situations, in order to have options and to be willing to quit when something becomes unsustainable, you need two things. First, you need a strong network. Ideally, there’s always another company waiting to snap you up as soon as you become available. Second, it’s important to have some other irons in the fire.


Entrepreneurship is now part of the modern career lifecycle. It seems unlikely that you will never have to be an entrepreneur. Even if you don’t want to, or it’s not your bag, you’re probably going to have to be an entrepreneur at some point. So start training for that now. Get the skills you need. If bookkeeping scares the shit out of you, learn about it.

Even if being an entrepreneur is not your goal, if you always have it in your back pocket as something you could do if you had to, it’s going to make you less afraid about quitting or about negotiating for a better situation.

If you are really, really dependent on one job, you have the worst possible negotiating position. There’s no technique that will help you with that. There’s no magic thing you can say when your boss knows you have no other options. So I think it’s really important to have that network, but also to know that you could give it a go as an entrepreneur if that was the best option at the time.

A few weeks ago we looked at some advice that said, essentially, “you have to pay your dues first.” You have to say yes to everything until you’ve earned the right to say no. Do you agree with that?

There are some professions that specifically work that way, and those tend to be the professions that everyone wants to do. That’s why they begin with unpaid internships where people treat you like shit.

There are ways around those situations. There are. Just because all of your competitors are staying in a role in which they are treated like that doesn’t mean there isn’t a way around it. In the entertainment industry, for example, you can crowdfund a project. There’s also the idea that, you know, if you’re doing something that’s on the same path that everyone else is, there’s got to be a way around. People find those ways.

One of the things I always say is: find the opportunities that do not have applications. If you’re applying to an opportunity that has an application form, or that’s already been posted to the internet, that means the opportunity has already been negotiated against you. There’s already going to be too much competition, driving down prices — and if somebody’s already written that “this is what the job is and this is what it pays,” the person who wrote that has set it up to be beneficial to themselves. You have no leverage.

You always want to make opportunities that you have made for yourself. Opportunities that are not written down, that are not advertised. It’s hard to see exactly how to do that in many professions, but look at Tavi Gevinson, the teenager who founded Rookie. She didn’t get treated like Anne Hathaway’s character in The Devil Wears Prada, because she completely circumvented the way most people get involved in fashion.

There are often ways to do something like that, even in businesses that seem really regimented.


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