The details of this week's letter may not 100-percent match your own sitch (maybe you've always worked for a large company, or it's your peers rather than your boss who make you resort to box-breathing relaxation techniques), but who among us hasn't felt a tad, well, freaked out when our career has started to look more like a zig-zag than a straight ladder?
In this week's Good@Work column, all-around boss babe Amy Odell—whom you may know as the former editor (AKA HBIC) of and founding blogger of New York magazine’s The Cut—helps lead a "lost" young woman back to her ambition.
Q: "Is work/life balance, a job you enjoy, coworkers you enjoy, and fair pay too much to ask? Is a job that’s all that a unicorn?"
This year has not been the year for my career. After working my way up from intern, I left my job as manager at a mid-sized company after three years. I LOVED my job and coworkers but ended up being one of many fellow employees to leave after being severely overworked. I went to a tech startup with a CEO that would say things like, "Let's hope this red dress works for investors.” I spoke up about the comments and got fired for “not wanting to work there.” Then, I freelanced briefly while job searching and LOVED it. It was great getting to choose projects I was passionate about and utilize my various skills.
I am now at another startup. The technology works nothing like they advertised, sales are stale, and my boss delegates 100 percent of her work to me but swears she works until midnight multiple times a week. She reaches out to me late nights and weekends with unimportant questions that I have already sent her answers to or that she could easily figure out herself. She is not nearly as smart or strategic as I had thought. I'm talking poor grammar in client emails. She has more than a decade’s worth more experience than me.
Wanting to be a girl boss has always been a part of my identity, but suddenly it isn't. The thought of climbing the ladder doesn't excite me anymore.
I was very thorough throughout both interview processes. I met with both bosses three times, each in person, and had multiple calls with each. I asked dozens of questions, but things just were not as they described in both scenarios.
I feel lost. I can't seem to find somewhere that feels right. I’ve lost my *boss babe* spark throughout this experience and I oddly feel like I should be ashamed. Wanting to be a girl boss has always been a part of my identity, but suddenly it isn't. The thought of climbing the ladder doesn't excite me anymore. I'm not even sure exactly what I want to do! I'm worried this has something to do with me being a millennial, but I really feel I can't catch a break when it comes to finding the right job that will bring me back that spark. Is work/life balance, a job you enjoy, coworkers you enjoy, and fair pay too much to ask? Is a job that’s all that a unicorn?
Do you have any advice you can offer me in this situation? Do you have a POV on job jumping, even if it can be justified? I'm having a hard time figuring out my next step.
A: "Whatever you do next, just take a breath."
OK first of all, working at dysfunctional offices filled with crazy people is nothing to be ashamed of. We ALL have to work at dysfunctional offices filled with crazy people, and their insanity and inability to appreciate us has nothing to do with us and everything to do with them being crazy and miserable inside. You were absolutely right to speak up about those inappropriate comments, even if it didn’t pan out the way you’d hoped, because it was the right thing to do (if you were made to feel uncomfortable by them, you certainly can’t have been the only one). And it doesn’t sound like you were loving it there anyway. No one gets fired from a job they love.
Whatever you do next, just take a breath. Try to take a couple of weeks off between your current job and your next one. Go to the beach. Have an aperol spritz. Catch up on Vanderpump Rules. Take a spin class at 10 a.m. Once you’re not feeling so dead inside, you’ll start to realize what actually matters to you about life and work. Maybe what you need is to do less for a while—and that’s nothing to feel bad about. Women face an inordinate amount of pressure to advance at work, have kids, take perfect bikini Instagrams, and care for themselves and their loved ones. It’s exhausting and you’re entitled to admit that you feel exhausted and kick your feet up for a few weeks or more if that’s what you need.
Once you’re not feeling so dead inside, you’ll start to realize what actually matters to you about life and work. Maybe what you need is to do less for a while—and that’s nothing to feel bad about.
That said, taking lots of time off is much easier said than done given that we have to eat and pay rent. So let’s say you save up so that you can spend a few Tuesdays at the beach with a can of rosé, but then have to find a job again like the rest of the world. What then? One thing that stands out to me about your work history is that you’ve only worked full-time at small companies and startups. Startups often come with less stability than big, established companies. This is not to say that a large company is better than a small one because they both have their upsides and downsides and (as I've said) everywhere you work is going to have some dysfunction. But if you’ve had three jobs at small companies and haven’t been happy, you might want to try looking for a job at a big company.
Startups are more likely to—buzzword alert—“pivot.” They start off doing one thing, and then realize that in order to make or raise money they need to do a different thing. For some people, this might be exciting and fun because they get bored quickly. But for others, it might just be frustrating to learn that the job you were hired to do isn’t what the company wants you to keep doing. Startups and small companies also tend to have less rigid policies in place surrounding really important things like how managers should manage people. They might not have had the time, foresight, or money to send bosses to management seminars or sexual harassment training. These things may sound dumb and worthless but they have the benefit of at least impressing upon managers that the company cares about those things.
There are a lot of disadvantages to big companies, though, which you might notice having spent so much time at small ones. Big companies are more likely to employ a lot of dodos who don’t do anything discernibly useful for the organization. Where bureaucracy exists, so do bureaucrats. These people might not have any skills whatsoever but navigating the bureaucracy. If you’re a creative, productive, and bright individual who finds herself reporting to such a person, you might find that to be extremely frustrating. It’s also harder to get a lot done quickly at a big company. Even things like getting a new laptop from IT when yours breaks or getting a contractor’s invoice paid on time might make you lose your mind. You might go work at a big corporation and realize that all those things you didn’t appreciate about your previous jobs you now appreciate. You might go to a big company and decide the stability and hardwired policies and 401(k) matching feel like a nice bean bag you could settle into for a while.
You won’t have horrible bosses or a tedious commute or be subjected to a toxic office environment or career bureaucrats—and the emotional uplift you get from this may be worth the extra work and the invoicing and the higher healthcare costs.
You also express anxiety about your role in the hiring process—it seems like you think you missed a crucial step in the conversations you had with the people you ended up working for. I’m not surprised you couldn’t tell they were crazy because I’m sure they were making every effort to seem competent and not crazy! One of the best ways to find out what it’s really like to work somewhere is to ask someone other than the boss what it’s like to work there. You can always ask the people you’re interviewing with to set you up with another employee for an informational interview, although then you’re at the mercy of their selection bias. They’re not likely to set you up with someone who will say they hate their job. But you can ask around and try to find someone on your own who has worked there or who has left. You can even search for people on LinkedIn who worked there and ask if they’ll talk to you about their experience. If they’ve left, they have nothing to lose by talking to you.
You may be surprised to learn that a lot of people are happy to talk to you about this sort of thing because people generally love talking about themselves. When you talk to these people, ask them what the person you’ll be reporting to is like. Ask what they liked and didn’t like about the job. And decide if the downsides outweigh the upsides or vice versa.
All of that said, you say that you were happiest when you freelanced. Is it an option for you to commit to doing that for a year? That would save you from jumping to another job that you might not like. Working for oneself is absolutely glorious, but as with any job, there are downsides: You have to hustle for work, your taxes are more complicated, you have to take care of your own health insurance if you’re not married or under 26, you have to open an IRA, and you will probably work by yourself at home without coworkers, which over time can start to feel isolating. That said! You won’t have horrible bosses or a tedious commute or be subjected to a toxic office environment or career bureaucrats—and the emotional uplift you get from this may be worth the extra work and the invoicing and the higher healthcare costs.
Finally, you and a lot of people have asked about job jumping. Staying at a job for less than a year isn’t ideal for your resumé, but it’s also not the biggest deal in the world. People will still hire you if you’re good because talent is so very hard to find. But your sanity and emotional well-being are more important than any job, so you shouldn’t stay when you’re miserable if you have the option to leave. I don’t know anyone who’s quit a job that made them miserable and then regretted it.
Amy Odell is a journalist and author living in New York. She is the former editor of, which became one of the most popular and award-winning sites for millennial women during her tenure. She is passionate about mentoring people starting off in their careers. She is from Austin, Texas.
Have a career question for Amy? Write her at email@example.com.
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