He texted me to offer his condolences. His message was short and authentic. Though, still, I chose not to respond. We hadn’t really spoken much in the last four years. But I’d just lost my uncle, and he – a friend. So, after a few rounds of liquid courage, he followed up with a phone call, and in my half-sleep, I obliged.

“Brown Bear [a nickname complete with its own little brown bear figurine], are you sleeping? I, uh, was just thinking about the night I met your family. Remember? We went to the Rays Game and I stopped outside to smoke a cigar with your uncle. Anyway, I wanted to tell you what he said.”


“He said, ‘That girl in there, she is the best thing in this whole world.'”

Enter a remarkably awkward pause, followed by the words I never thought I’d hear…

“I’m sorry. I didn’t – I just… I want you to know that I am sorry for not appreciating you that way.”

By now, you’re probably thinking: how does this exchange help me do my job or understand my boss? Where’s the weekly A-HA! moment that sums up just what it’s like to be an assistant?

Readers, I waited a very long time for that apology. No, to be honest, I’d waited a long time for that person to see my value. But no matter how much I kicked and screamed, he didn’t hear me and, so, for years, I just exhausted myself.

Eventually, something had to change, but the only person who could change it was me. Instead of hoping someone else would find the value in me, I had to find the value in myself.

And, four years later, that’s right where his apology finally found me; indifferent to it – in a midnight moment, on a Wednesday night, five days after I’d lost the most dear man in my life, but still strong in the empowered person I’d become.

So here it is – this week’s A-HA moment served up!

Your life is a sum of all your moving parts. Everything you learn – everything you experience – every person you love and meet and pass by – every single tiny external factor you choose or you don’t, they all shape your perspective and your perspective affects how you relate to every job – be it spouse, friend, boss or assistant.

And at its core, the assistant position is simply a relationship with another human being, right?

It’s often the case that a relationship just doesn’t work or it did work, but has since outlived its expiration date. And you’re pulling out your hair, pacing the halls, wondering: WHY DOESN’T MY BOSS JUST HEAR ME?!, swearing that you’ll just quit and everyone who has neglected or undermined your value will suffer exponentially. But, instead, you choose to stay and wait and hope that the other person will change.

Readers, you can wait forever and, still, those millions of little factors that make you – you, won’t align with a person with whom you desperately want to connect. When you find yourself here, torn between what could be and what actually is, it’s helpful to have a short list; the outline of a promise, if you will, of when it is appropriate to redefine your own value and to administer self-care.


Your time is precious. Your life is valuable. If the fit isn’t right, if the synergy isn’t there – perhaps it’s time to look elsewhere. We can choose to live in discontent or we can choose to brave the wide world of opportunity that awaits just beyond those swinging doors.

When the time comes, which will you choose?


If a relationship isn’t working, it’s time to reevaluate.

Life is a sum of the choices we make. There are difficult decisions where the right answer isn’t clear and there are unpleasant ones that simply require temporary discomfort (shout out to Phil Libin for that gem), so in the humble words of my late uncle:

If you truly doubt it, don’t do it; otherwise, what are you waiting for?

Interested in finding a good fit assistant or assistant position? Executives click here and Assistants click here to join the wait list for EM’s beta compatibility survey.

Because life is too short to wait too long.




Catherine Elyssa Brown,
Founder & CEO

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