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‘I’m Afraid I’m Terrible at My New Job’

Photo-Illustration: by The Cut; Photos: Getty Images

Dear Boss,

I was laid off from my sales job due to COVID and then scored my “dream job” at another start-up as an account manager. I was so proud and excited to start this newish career path, and felt qualified, but also that I was going to learn so much. And I am. 

The problem is, I just don’t feel like I’m great at the job, and I fear I won’t get to a point where I’ve mastered it, or at least to a point where I don’t need my manager’s support on every issue I encounter. I worry I’m sorely underqualified for this role with regards to strategic thinking and supporting accounts of this size.

I’ve been at the job for almost six months. When should I begin feeling comfortable? I started off with tons of enthusiasm, but it’s waning now. I’m pretty much just doing prep for upcoming meetings and have lost motivation to go the extra mile for strategic planning for my accounts. Part of it is that I simply don’t know what to do, and part of it is that my anxiety is paralyzing. I sit and stare at my screen and try to figure things out and can’t focus. My manager has told me it took him a year to feel comfortable, but at the same time, he still had an incredible amount of success in that year, and I’m not awesome at the “fake it ’til you make it” mind-set.

I’m concerned that the company loved me during the interview process but are now disappointed in me, although I have no real feedback indicating this. I’m not going to hit my upcoming goals, but the company also understands they created those targets based on unreliable data, and my entire team is in the same boat. I have yet to have my 90-day check-in, and we currently don’t have any actual metrics to assess performance, so honestly, I don’t know how anyone would know if I were doing well or not. 

At what point should I look for a new job if I feel like I’m not able to do the one for which I was hired? Do you have any tips on how to get my managers to tell me what would be an indicator of whether or not I was a good fit and if I had potential to really excel? I don’t want to sit around wondering when the other shoe will drop and they’ll discover I’m actually terrible at my job. It’s my first job where my performance is not 100 percent connected to attaining specific targets. Is this just impostor syndrome? Is it the company’s fault for not supporting me more? Am I just ducking responsibility for my performance?

I don’t have the energy to keep fighting for feedback or for something that helps me measure my performance. I should note, I am the only woman on my team, and the only one who seems to be worried about whether or not I’m doing okay. I know this is a more common thing for women to experience, but I don’t want to brush it off as just being that.

Oh my goodness, please talk to your manager! One conversation might set you completely at ease.

You’re used to jobs where you would know precisely how well you were doing because you had specific targets that you either hit or didn’t. That can be very reassuring — you have numbers that measure your performance at any given time, and you never need to wonder. But now you’ve gone from that to an environment where you don’t have those clear indicators, and that can be unsettling in the beginning! (In theory, it could remain unsettling for you in the long term too, in which case you might conclude that this kind of job isn’t for you — but I don’t think things are that dire yet.)

That said, is it possible that you’re not very good at the job? Sure, it’s possible. That happens. But it’s also possible that you’re doing absolutely fine and are exactly where your boss would expect you to be at this point. This job might be one that takes longer to master than other positions you’ve had. You haven’t been there quite six months yet, and a lot of jobs take right around six months to even start feeling comfortable. And that’s just feeling comfortable, not mastering the role! Some roles can take a year or two to become good at, and longer still to fully master. If this is the first time you’re experiencing that, it makes sense that you’re feeling uneasy.

Of course, that’s just guesswork from me since I can’t know from the outside. But there’s someone who can tell you for sure: your boss. In fact, it sounds like your boss might have been trying to reassure you about this already! If he told you it took him a year (twice as long as you’ve been there!) to feel comfortable, my guess is that he’s either noticing your anxiety and telling you there’s no cause for it or preemptively trying to prepare for you for a job that simply takes a while to learn.

But rather than speculating, please talk to your boss about this! Tell him that you don’t have a good sense of how things are going and ask if he can give you some feedback on your work. Ask specifically, “What’s your sense of how things are going overall?” and “Am I about where you’d expect me to be at this point in my training, or were you hoping I’d be further along?” Tell him that you hadn’t anticipated you’d still be needing his support on so many issues you encounter and are wondering if that’s par for the course or an indication that you need to do more to get yourself up to speed. You can also be transparent that you’re struggling with how to assess your progress and ask what indicators he’ll look at when he’s assessing your performance at the end of, say, a year.

If your manager seems like a reasonable and supportive person, you could also ask for more coaching on the pieces of the job that you’re struggling with most. There’s no reason you can’t say, for example, “I’m new to doing strategic planning for accounts of this size. Could we sit down and talk through how you’d approach some of them so I can work on building my skills in that area?” It might feel like a bad idea to call your boss’s attention to your weaker spots, but a good manager will appreciate that you’re identifying your own development areas and being forthright about trying to improve.

Now, separately: You mentioned that your anxiety is paralyzing you when you’re trying to work! If the anxiety is specific to this situation and not something you experience in the rest of your life, it might be addressed by taking the steps above. But if it’s something you’ve encountered at other times too, I urge you to consider talking with a therapist about it — both because it could be playing a role in how you’re assessing things at work (it can warp how you perceive things pretty badly) and also because it sucks to go through life feeling anxious!

As for your question about at what point you should look for a new job if you continue to feel you can’t do this one … If you have the above conversation with your boss (and really have it — don’t water down the questions that I recommended asking) and it turns out that he shares your concerns about your work so far, that could be a sign that, indeed, the job just might not be the strongest match. Or, if you talk to him and he’s not discouraging, but he’s also not that helpful — if he’s disengaged, vague, or otherwise unable to help you contextualize how you’re performing — I’d give it more time. Again, you’re not even at six months yet and he’s suggested it might take a year to feel like you know what you’re doing. But if the idea of giving it more time feels excruciating — and especially if your concerns are growing — it might be that this setup just isn’t a great one for you. That wouldn’t necessarily mean that you can’t do the job; it could mean that you’re not happy in roles with this much ambiguity and you’d rather move into one with clearer metrics and goalposts. If so, there’s nothing wrong with that — and that’s actually a good thing to know about yourself, because it can guide your future job searches! But if you can stick it out a while longer to see how things progress, it could be worth it.

Order Alison Green’s book Ask a Manager: Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work here. Got a question for her? Email Her advice column appears here every Tuesday.

‘I’m Afraid I’m Terrible at My New Job’