Three Important Career Questions

Three Important Career Questions

 Important career questions

Tomorrow I turn [REDACTED].

I know! I never thought I’d reach this wise old age of [REDACTED] either.

In fact, I can remember thinking when I was 16 how 30 seemed like an age so old I didn’t understand how people could reach it.

But anyway – birthdays always get me thinking.  They used to be a time to put a big stake in the ground: “I’m going to QUIT MY JOB AND FINALLY BECOME SOMETHING FUN LIKE A CIRCUS PERFORMER OR SOMEONE WHO WEARS TIARAS AS A PART OF THEIR DAY JOB.”

You know, completely normal stuff :)

Today I’m grateful that I view them differently. Birthdays give me cause to celebrate some of the little (or not-so-little) mistakes, big successes, and tough decisions that have led me to where I am today.

Today is a pretty cool  place to be.

So, next week I’ll go back to tackling your tough and really interesting questions, but – if you’ll forgive me a little indulgence- today I’d love to share with you some of the career questions that inspired me to get here, in the hopes that they help you too.


Question 1: Why are you doing what you are doing?

When I used to ask myself this as a consultant, the answer was usually: “Money” or “Ugh. I don’t know…money? *sigh*”  I HATED that sense of feeling like I was doing something for the wrong reasons, but I honestly didn’t know how to figure out what was right.

But asking that question again and again made me at least sit up and face some hard truths: Just doing something for the money would NEVER make me happy, no matter how much I was paid (even though I do like nice things).  And when I felt the most stuck, that question inspired me to keep looking.  I knew that there had to be something better out there.

Today, when I ask myself that question, often when something has just gone spectacularly wrong, my answer is this: “Because it makes me happy and I cannot imagine doing anything else.”  And that answer motivates me in an entirely different way to keep doing this work.  I LOVE this work.

Why are you doing what you are doing?


Question 2: What do you want to be doing?

Back in the consulting days my answer was often “I DON’T KNOW FOR THE LOVE PLEASE STOP ASKING YOURSELF THIS QUESTION!!”

It drove me nuts because I didn’t know, I felt like I should know, and not knowing made me feel like an idiot.

But, once the anger passed I kept coming back to certain ideas – I wanted a job with flexibility, I wanted a job with freedom of location so I could live anywhere, I wanted a job with creativity that I got to inspire, and I wanted a job that had a clear and definite impact that I could SEE and MEASURE.  And if you read my other blogs and materials you’ll know that I also wouldn’t have minded working on America’s Next Top Model, which gave me a whole other level of insight into what I actually really wanted.  Note: It wasn’t really to work on that show, but what the show represented to me.

And for me, when I stopped judging myself and started being open to the idea that while I didn’t know NOW, I would figure it out, that things really started to change for me.

Today,  I know the answer to that question, and I have SO MANY ideas for what more I can do.  It’s energizing to think about it most of the time (sometimes even I get tired :)), and whenever I feel lost or confused for a moment, I come back to: “What do you really want to do?” and I answer it.  Simple, but it works.

What do YOU want to be doing?


Question 3: Are you who you really want to be?

This question was a killer.  For me, the answer used to be no.  I wanted to be someone who felt like I was living up to my potential.  I wanted to be someone who had a real impact on people – not someone who was just a  bunch of powerpoint slides. I wanted to be someone who had something tangible to offer the world that was powerful.

Mostly, I felt like I was letting myself down by not being who I really wanted to be. 

But this question is also kind of genius, because this was the question that ultimately inspired me to leave my safe consulting job and strike out on my own. This was the question that inspired me to leave DC behind and move across the country to a city I’d only visited ONCE and basically knew nothing about, but seemed perfect for what I was looking for (and oh how I love you now, San Francisco, and also often overlooked but still amazing Oakland!).

Anytime I felt lost, scared, alone, nervous, or found myself finding excuses for “why not” I said: “Is this the person you want to be?” and found my courage to do what I really truly wanted.  I allowed myself to become who I always knew I could be.

So, my birthday wish for you is the same – I wish with every fiber in my being for you to do work you want to do, for you to be WHO you want to be.  You deserve it. 

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