Dear Molly, How Do I Get Past Imposter Syndrome?

Lately, I’ve been feeling more and more like a fake at my job. I just got hired last month and I constantly feel like I’m am behind everyone else. There’s so much I don’t know! I feel like I spend every meeting trying to hide my confusion. What should I do? Should I go to my boss about it? Have you ever felt like this? How do I get over imposter syndrome?


I’m a woman in my mid-20s writing an advice column for women in their mid-20s. Trust me, I’m well versed in all things imposter syndrome. Interestingly enough it’s something I’ve discussed numerous times in an academic setting as well. Within the world of Philosophy, you are often building a thesis to defend your own argument and interpreting other’s works to support your claims (just writing that gave me flashbacks to defending my 100-page senior thesis). Philosophy is dense, and misinterpreting classic texts is something every Philosopher is guilty of at some point — you often can have an out of body experience of feeling like everyone in the room is watching you dig yourself into a philosophical and metaphorical hole.

The takeaway of that digression is this: we have all felt that feeling. Especially in a professional setting. Here’s the good news, if you feel a little behind or outside of your comfort zone you are exactly where you need to be. That ‘uncomfortability’ is how we grow. The Educo Community has a great graphic to illustrate this:



In their model “Complexity” is where you currently are. Trust the people who put you in this position. When I was in middle school I had this idea (after taking five years off) to join my high school’s soccer team. I went to my dad about it and asked him if he thought it was possible and he told me one of those parental drops of wisdom “Just want it more than anyone else out there. They can teach you how to play, they can’t teach you to care.” I made sure I was the most aggressive person on the field and was offered a place on Varsity (and ended up running XC instead 😂). You were hired not only because you are capable, but because the person hiring you saw that you cared. That being said, there is a growth and adjustment period for every new position you are in.

Think about it like merging onto the highway, just because everyone else is coasting along and you are catching pace doesn’t mean that you are behind. You are finding your pace, your rhythm, and learning along the way. A good leader/boss/supervisor will anticipate a one to three month adjustment phase when they onboard someone.

Personally I would not suggest going to your boss about this, unless you are drowning. Playing on a previous metaphor, if it feels like you are merging onto the highway, stay the course. If it feels like you are merging onto an F1 race track, ask for a lifeline. Going to your boss and saying something along the lines of “I’ve really enjoyed the past few weeks, but would really like to dive in X deeper. I’d like to take next Wednesday to really learn all the nitty-gritty of the system.” You want to be sure to approach them with a solution/plan, not just a problem. Avoid words/phrases like “feel behind” or “confused” and speak in a more proactive and positive tone.

And to get you through meetings remember this, no one knows what’s going on in your head unless it’s on your face. Keep a neutral expression, take a lot of notes, and follow up one-on-one, after the meeting, with any questions you have.

Best of luck with the new job and I’m sure you earned it 🙂



Dear Molly, How Do I Tell My Boss ‘No’?

So this is a little different than some of the questions I’ve seen you get, but I think I remember you work in business or marketing? I was hoping you could help me with something. My boss is always asking me to do things on off hours and I don’t get paid overtime. Like I’ll have to come in on Saturdays or weeknights. I don’t want to seem ungrateful for the job or lazy, but I also need my weekend. How can I tell her “no” without coming off the wrong way?


First, what your boss is doing could be illegal in your state. I highly suggest investigating further.

Second, this is definitely the right place to ask those kinds of questions! Context, in my 9-5 I’m a Director of Business Development and Marketing for a digital back shop. I always advise my friends on how to negotiate a contract or raise, how to advocate for yourself in the workplace, and how to say ‘no’.

If you consider yourself a millennial or Gen-Z then you’ve likely been told for the majority of your professional career that you are “too entitled”. We all know that the boomer generation thinks that we take everything for granted, but the truth is that we (and clearly you) do not. Instead, in an effort to prove that we aren’t entitled we allow ourselves to be overworked. In my first year as a salaried employee I used less than five (of my 15) PTO days. It took a little time for me to realize that you don’t need to justify not constantly being at work. You don’t need to check your work email before you brush your teeth in the morning and after you’ve had dinner each night. You don’t need to spend your weekend’s tethered to your inbox. You are allowed and free to take time away, and you should.

Next time your boss comes to you with an off-hours request that you don’t feel comfortable taking simply say:

“I won’t be available.”

It’s that simple. You don’t need an excuse, a fake doctor’s appointment, you don’t need to say you’d “rather not give up your off-day”. You don’t need to give a why.

Simply stating that you “won’t be available” is a clean way of expressing that you are not an option. Be polite, be sympathetic, you can even phrase it as “I’m sorry, but I won’t be available”, but don’t make an excuse. If your boss is professional they will respect this as a “no” and move on. However, they might not be professional. Here are a few follow-ups that you may get and how to handle:

/ “Why?” “I have a prior commitment.” Even if that commitment is just to you and refreshing yourself for another week of work. You matter and are allowed to take time for yourself.

/ “Can you reschedule? We really need you.” “I’m afraid not. Maybe someone else can come in?”

/ “Are you sure you’re not available?” “Sorry, but yes I am sure.”

/ “What is your prior commitment? What will you be doing?” “Sorry, but that’s personal.”

If you don’t provide a why you distance yourself from any pressure that an unprofessional boss is going to attempt to lay on you.

You need to learn how to say ‘no’ in a professional space just as much as in a personal space.