Tell Me What You Want (What You Really Really Want)

Tell Me What You Want (What You Really Really Want)

A while back, I was out for a friend’s birthday; having drinks and sitting around a table talking with some incredible women and we got to discussing our careers. It began with me stating that I didn’t know where I wanted to work once I completed my MBA, since I didn’t want to wait out the retirement of an executive at my company but did want to be an executive or at least in a more prominent role after graduation.

The incredibly interesting thing that then happened was we all began sharing stories of why we were waiting to take that next step in our careers.

Most of it boiled down to not being, or rather not feeling, ready.

The second thing that happened, was we all marveled at how our less capable co-workers or former co-workers were seizing up those very opportunities within our organizations or were rising through the ranks in other organizations. They did this while we were toiling away; working on the big projects, gaining the extensive experience and racking up the credentials we thought we needed but that they don’t even have.

It seems we all shared the same innate feeling that we weren’t ready or we weren’t qualified even though lesser individuals were racing passed us, grabbing the very things we wanted for ourselves.

Why was this happening? The theory amongst the table was those people were selling themselves better, and it makes sense, but it also opens up a bigger question – why couldn’t we overcome selling ourselves in the same fashion?

We were echoing the countless voices I’d read in books and magazines, or heard at talks or on podcasts lately, but I had never encountered the thought vocalized in life. Elizabeth Gilbert’s “Big Magic”, all the powerhouse women at the GirlBoss rally, Shonda Rhimes’ Year of Yes, and so many other embodiment of this sentiment were ringing through my thoughts but all I could think was, “but how do we fix this problem?” And to that I drew a blank.

I, along with the women I was with, grew up in the 90s - the age of The Spice Girls and “Girl Power!” but where was our power now?

Unfortunately it seems this problem is not generational and affects large swathes of women – as evidenced by the behemoth of material that exists on the subject and, more poignantly, by a discussion I had the next morning with my mother.

My mother is talented in an array of ways; one of them is her creativity. While I was out at the birthday celebration she too had been out and she wore a bracelet she had made herself. Multiple people asked her where she had bought it! I told her she should open an Etsy shop; she already had all the supplies and it was something she enjoyed doing – there was no downside. She said, “yeah, maybe”, and I could sense her hesitation -- I was thrown right back into my thoughts from the previous night.

Why does this happen? How can we fix it?

I went back and poured over the words of some of those who’ve already addressed the topic:

Elizabeth Gilbert’s book Big Magic is infinitely exquisite and, on this topic, she has a lot to say!

  • In the chapter called “Courage” she says, “fear is a desolate boneyard where our dreams go to desiccate in the hot sun.” Isn’t that the truth? She goes on to list the vast and varied ways in which you may be afraid - all laughably accurate! Facing your fear is a big theme throughout the book and I highly recommend it for anyone facing that particular obstacle.
  • In a chapter called “Permission”, she gets at the heart of dealing with what my friends and I were feeling that night. It begins with defending what you want by defining yourself as that thing (ex. I am a writer) and convincing yourself, every day if need be, to have the conviction to face down your “negative interior thoughts.”

Her book is meant for those who want to live a creative life; however, I think anyone chasing a dream or battling an obstacle can appreciate her words of wisdom.


Sallie Krawcheck, the founder of Ellevest and an incredible advocate for women in the realms of finance and investing, is a huge champion for women achieving what they want. In March’s Money magazine, she discusses closing the gender pay gap and advice on handling this problem of asking for what we want is sprinkled throughout the piece. Some of the best insights include, “schedule a talk with your boss…to define what success looks like” and “don’t give up if you get a no”. She quotes Venus Williams saying, “there’s nothing more impressive than a woman who knows her power.”


A recent read, Hiding in the Bathroom: An Introvert’s Roadmap to Getting Out There (When You’d Rather Stay Home) by Morra Aarons-Mele, also addressed this problem of selling ourselves and her perspective was that what puts off many is the idea we have of the salesman, that “like the patriarchy, the image of the salesman as an alpha male asshole is internalized into our work culture.” However, she argues, this method is not the only way and that “what matters most is selling like yourself.” In order to do that, she says, “owning your passion is essential.”

This was a great read for anyone looking to navigate their career without guerrilla marketing tactics, certainly for introverts (like me); however, the bits about selling and pitching are awesome resources for anyone needing to pitch or sell (in this case themselves) who needs help mustering the gumption and tactics in order to do it.


It seems to boil down to the oft cited quote, “If you don’t ask the question, the answer is always no” or “you miss 100% of the shots you don’t take.”

I know it goes deeper than that. I also know one blog post is not going to change a predominant mentality. But maybe it will be a start. Maybe it will open the door and allow us to start brushing away the cobwebs so we can get out there!

Tell people what you want – ask for it – you just might get it.

The Light at the Beginning of the Tunnel

The Light at the Beginning of the Tunnel

The Morning After

The Morning After