If you’re an entrepreneur, you are trying new things and putting yourself out there in big, scary ways.

We need to learn as we go and figure things out. It’s the big joy and big challenge of the path we’ve chosen.

Oh yes, we entrepreneurs often have to build the plane as we fly it.

As an entrepreneur, I can personally guarantee that you will have more than a few crises of confidence and will feel like an impostor from time to time.

Maybe a lot of the time.

(If you are interested in this topic, Amber Naslund, a friend of the blog, has been writing terrific content about impostor syndrome here on LinkedIn.)

While I have had a few instances of impostor syndrome as an entrepreneur, most recently when I did a presentation on a new topic at an association event, I always see impostor syndrome flare up in my job search clients.

As soon as my client receives an offer letter, they spin out wondering if they actually can do the job they were certain was perfect for them just the day before.

Often, they go way out on the ledge, wondering if they have been faking it their entire career and fearing they’ll be found out. It’s so predictable that I have an intervention pep talk I give everyone after they sign their offer letter.

I have a lot of experience coaching professionals and entrepreneurs on how not to get derailed by bouts of impostor syndrome, but I have never seen anything that captures the crippling feeling of it like the video below.

Written by comedy writers as a fun bit for the Tony Awards, this short number captures the anxiety and angst of impostor syndrome perfectly. One of Sara Bareilles’s lines had me howling with laughter.

I think I have watched this 10 times. It is three minutes of pure genius that was undoubtedly inspired from some personal experiences with impostor syndrome.


James Corden, Sara Bareilles & Josh Groban in the Bathroom – ‘Be More Chill’ Parody – 2019 Tonys