Do You Love What You Are Doing?

Over the past few months, I’ve been interviewing many candidates for open positions in my company Glassdoor in Sausalito. Our growth is exciting on so many levels. Each interview (even the bad ones) reinvigorate me and reinforce the decision I made ten months to leave Chicago and my former company – CareerBuilder.

Without fail, when I turn the interviews over to my candidates for questions, I am asked, “why did I come to work at Glassdoor?” For those that have done their due diligence (generally from my LinkedIn profile, which I always appreciate a little detective work), they’ll couch the question from the perspective that I lived in Chicago for a long time and worked at CareerBuilder for a long time. Why Glassdoor?

My answer is a little more direct (two minutes versus the following ten minute read) than what I’m about to share, but the theme remains.

Before the answer, a little subtext would be appropriate. I don’t know if I always have, but I feel like I have always been infused with youth. When I was a kid and then a teenager, that manifested itself in my insecurity that I was always behind and playing catch up to my friends. By my late 20s and later, it manifested itself in other ways. I found that I had (significantly) more energy than my peers, and significantly more vibrant with a youthful world view. Some people call it being a late bloomer. Some people say I came into my own. Some would say it was just a matter of time. What I would say, irrespective of why, and now despite physical impairments, I feel younger than ever. The vibrancy of life has never been more evident.

For the majority of my time in Chicago, I rented (many different apartments in many different neighborhoods, all uniquely charming, each with a charm all it’s own – Roscoe Village, Lakeview, Bucktown, East Village, Ukrainian Village, Wicker Park then finally buying a condo in the West Loop) – rented, mainly because Chicago was just to be a temporary stopping place onto bigger and better things in New York or (drumroll, please) San Francisco. That decision took twenty years to materialise.

I was laid off from my job over eleven years ago, and for the first time since I was 15, I was unemployed. Quite frankly, in just a blink of an eye, over 15 years had passed, yet I was no closer to doing what I had wanted. (Quite frankly, my dream of being a superhero never quite took off.) It would take me a month to tell my folks what happened, both ashamed and afraid to tell them. Of course, as they have so often done in my life, they rose to their parental callings giving me unending support and love during that time. I’ll never forget those first words I wrote in my journal over eleven years ago, sitting on a bench on my parents porch, seems like yesterday, “What do you want out of life?”

And so I spent that year looking for a job. I spent it partying.

I interviewed at a great many places, turning down offer after offer. The conclusion I came to was that I still didn’t know what I wanted to do. (Being a superhero by this time was no longer an option, though there was still the faint possibility that I would strike it rich and resume the mantle of The Dark Knight. Ah, but I digress.) More importantly, I also came to the conclusion that not knowing what I wanted to do for a living was ok. What I did know was that I wanted to help young people, mentor the generation after me. I wanted to be a part of a company that was helping the greater good, and be a part of something bigger than itself. I wanted to be part of a company that was number one (which ties into my competitive nature), or there was a clear path to being number one. And (it goes without saying, if you want to be number one) be around young, intelligent, vibrant, passionate people who cared about today and tomorrow, wanted to make a difference, where someone with my life experiences would only accelerate their growth personally and professionally.

And so it was when I walked into the CareerBuilder offices by O’Hare International in Chicago over ten years ago. I met with several managers, some of whom eventually became good friends, one of whom became one of my best. Though at the time, just a kid himself (but whose age masked an extremely high-level of emotional intelligence) I’ll never forget his last question to me, “You have way more experience than anyone in my group, and your resume looks great. What makes me think you’ll stick around for more than six months and take direction from managers half your age?” I immediately liked him; eighteen months later, I would be working for him as a manager. To further my perspective on the age gap, I ended up shadowing a sales rep who was the kid brother of one of my close friends growing up.

For over nine years, working at CareerBuilder was a dream come true. I worked with amazing people – young, intelligent, vibrant and passionate. I had amazing experiences. I went to Africa (to Malawi where we partnered with Millennium Promise to sponsor a village – Dindi – in their people’s quest to rise above poverty), experienced The Amazing Race (where we came into the office one morning, divided into groups and solved a puzzle that led us to plane tickets to Denver and GPS coordinates to a meeting place outside that led us on a trip over the following few days across Colorado into Arches, Moab and Zion in Utah and Lake Meade in Nevada settling in Vegas, in between ATVing, hiking, rappelling, tubing, jet skiing, and sky-diving), made Presidents’ Club almost every year (in Atlantis, Cabo twice, Puerto Vallarta, etc.), countless trips to New York, not to mention working in The Loop in downtown Chicago, etc. During that time, I was involved in a terrible accident that made me appreciate life and all that I had even more. More importantly, thru the leadership positions I’ve held, I’ve affected in a positive way many lives along the way; and in that way, they’ve positively affected mine. Most importantly, I met some of the best friends a person could hope for – people that will be in my life till the end of time, all of whom I’m proud of and now, for the most part, the age I was when I first met them. I’ve literally watched them grow up to be adults, many now married, some parents. It’s been incredibly wonderful and fulfilling to see and be a part of their growth.

Through it all, we were part of something bigger. Indirectly, we were helping millions of people find jobs. In my opinion, we were part of a noble endeavor. At a very basic level, we were helping people provide for themselves and their families.

Who could want more?

Over ten months ago, I asked myself that same question. Through a couple friends of mine, the leadership opportunity at Glassdoor was brought up to me. Till that point, I had no intention of leaving CareerBuilder, let alone Chicago. It was home. I had built an amazing life there, and I was destined to grow old(er) there. The more I spoke with the leadership team at Glassdoor about the opportunity, as scary as it was to leave everything I knew and loved behind, home came to mean something different and destiny it seemed had plans for me outside Chicago. I had been a 49ers fan ever since I was nine years old. It was destiny that I move to San Francisco.

Glassdoor  ( helps people find jobs and companies they love. It’s a simple yet profound statement. I’ve always wanted to be part of something bigger. Adding the element of “love” spoke to me. We do that by providing rich content that people can read to make informed decisions before applying to the jobs in which they are interested. It’s fascinating. And it helps millions upon millions of people. And companies love working with us cos we help them find the best talent.

What does that mean for me personally?

If I were to tell you that you get to relive the best (nine) years of your (professional) life, but with all the knowledge those (nine) years gave you, would you take it? Sign me up! And that’s what I felt – the exact same feeling I had walking into the CareerBuilder office over ten years ago, I felt when I walked into the Glassdoor office ten months ago. The feeling I had during the interview process was incredible, a sense of déjà vu that something great was happening all over again. The people here – from the topline to the front line – all cared. They care a lot. The energy is electric. Everyone knows and feels they are building something great, a part of the greater good – helping people find the jobs and companies they love. And we are growing to reflect that. I get to draw upon both the successes and (more importantly) the failures of my past experiences each and every day with the teams we have in place, a culture built on both competition and collaboration.

It’s a great time to be in The Bay Area. It’s a great time to be at Glassdoor.

Are you doing what you love to do?

If you liked this post, please follow me on and look at your world half-glass full. Thank you!


8 thoughts on “Do You Love What You Are Doing?

  1. Reblogged this on The Secret of My SucCecil and commented:

    Thought about this today, after a trip to Chicago and back in the Bay Area, visiting family, friends and clients, missing Chicago but loving San Francisco (and Sausalito) loving where I am and living what I do, helping people both directly and indirectly find the jobs and companies they love.


  2. It’s an amazing feeling when you help someone find their perfect fit. Many times I have had the privilege of being the sounding board and had the opportunity to work through strategies with colleagues and close friends to develop a solid game plan allowing them to achieve that perfect next step in their career/life. I don’t know that there are many feelings better than seeing someone accomplish a dream.


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