It’s Lonely at the Top

It’s lonely at the top.

I found myself saying this to an EA yesterday who is currently realizing that there’s no one she can trust at work anymore.

The EA role changes you the “higher” you go in terms of the person and title you support. Your title may stay the same: Executive Assistant. But how you operate inevitably has to change.

When you become an EA to the CEO or other C-suite execs at a hyper growth, startup company, it’s exhilarating (or at least I think so), until you find yourself in the corner with no one but yourself.

Being in this role, especially after it has grown so quickly, you now know too much. You are exposed to secrets and tactics. You know which executive is going to get fired or layered before they even know it. You know who is about to quit. You know where the company strategy is headed. You know what your executive is doing during Do Not Schedule (DNS) time. You know who is disappointed in whom. You know all the things.

And considering the number one quality you need to have as an EA is “trust”, you have to keep your mouth shut about it all. And if you’re anything like me, and your reactions show all over your face, even if in micro movements, you now have to avoid everyone.

You can’t say anything to anyone. You can’t confide in your best friend at work. If you confide in your partner, they won’t really understand. You can’t discuss strategy with anyone not involved in what’s about to happen. You can’t have 1:1s with other EAs or coworkers anymore just in case you reveal something in your body language or a muffled reaction or a hesitation.

I remember at Dropbox, when I cancelled all my 1:1s with EAs for these very reasons, someone said to another EA that they felt like I did that because I thought I was too good for everyone else. And even then, I couldn’t defend myself, because how could I? “Sorry, it’s actually not because I think I’m too good for you that I cancelled my 1:1s with you, but rather I know that your executive is going to get fired in the next 2 months, and I cannot show any inkling of evidence of knowing anything”.

That, and I had recently come back from maternity leave, and I had to incorporate two pumping sessions throughout the day and also leave work by 3pm to make it home by 5pm, so I guess I also just genuinely did not have any time.

Regardless, the point is, it does get lonely at the top. I’ve experienced it, and I’ve talked to countless EAs who are going through it now or have been through it or will be going through it soon.

Your relationship with your executive is different from everyone else’s relationship with them. Your association with the executive also makes people treat you differently. I’ve had so many experiences where people have befriended me at work, taken me out for lunch or coffee, checked in on me regularly, bought me presents on Admin Appreciation Day, all of which I thought were genuine acts of friendship, only to realize that those were their ways of getting close to me in order to get information, which they did not get.

Oh, but Janet, you’re such a pessimist, maybe they really were being genuine and wanted to get to know you!

Sure, except as soon as I stopped supporting that executive or left the company, all of that stopped. Even when I reached out to ask for a favor post-Dropbox, suddenly, they were radio silent. I supported over 45 individuals of all levels and titles at Dropbox. This happened regularly.

One of the greatest assets an Executive Assistant can have is being observant and noticing patterns and behaviors. And oh, I noticed.

Anyway, I digress.

The point is, if you’re going through this now, you’re not alone. If you feel siloed, like you can’t talk to anyone about anything work related, like you have to distance yourself from others, like you have to be a little more cold or brief in your answers to prevent over communication, you’re not alone.

Understand that it’s lonely at the top. Accept it. And know that this time and feeling will pass. You will get better at changing yourself a little to operate in a new way. You will become stronger and wiser. And as you progress in your career and you notice it continues to happen in your different roles at different companies, you’ll become better at managing the feelings and actions.

In the meantime, stay humble. Don’t be sad about it. Continue to be discreet. And know that these are the steps and growth you need in your career to become a better and better EA.

You’ll be fine.