Audrey’s Winding Path

I met Audrey Stewart over a decade ago while I was serving as an advisor to the Point Foundation fellowship. We came to know each other while serving on a career advisory committee for the Foundation. Audrey, 37, is a resident of New York City and is currently the Global Program Manager for Google.   


In two-three sentences how would you describe what you do most days/weeks?

Most days I am doing a combination of the following:

  • Bringing people together to solve a problem
  • Acting on the course of action that my team decided on to solve the problem
  • Prioritizing what problems to solve next

What did you want to be when you were eight?


What did you learn about work that you learned from your family? 

“Just do it and do it and do it, until you get the job done”- Art Williams

My dad introduced me to this line of thinking when I was very young, and it has stuck with me since.

What professional experiences/employers had the greatest impact on you?

The Army- by far and large the Army had the greatest impact on me, not only did I work for the Army during my most formative working years, but every job I go to I constantly refer back to my frameworks from the military to plan, manage risk, and strategize.

What is something about your career journey that people might not expect?

After I graduated from my MBA program, I didn’t land a job for nearly a year. Virtually every person in my program that wanted a job, had already found one and most of the class behind me had already found one. I spent a lot of my time thinking about what I could do differently and reflecting on what made me a unique candidate. I then looked at how I could position myself to tap into those unique traits. It might seem like an easy enough task, but when you’re laser focused on a goal, introspection can be an elusive exercise.

Why did you pivot?

The Army was a great experience, but I felt that I had accomplished what I set out to accomplish, the trans ban was still the law of the land, and a little bit of feeling the grass was greener on the other side. Though I left the military for mostly inclusion reasons, I underestimated the things the military did well, and often find myself looking for employers and leaders that embed many of the positives the military had such as career development opportunities and a team first mentality. For me, why I pivot my career will continue to evolve as long as I have a career, but inclusion, development opportunities, and a team first mentality will be central to any of those decisions.

What skills were portable from what you had been doing previously and what was brand new to you? 

The skill to bring together a team and come up with a plan was a skill that has been extremely portable from my time in the Army. As for what was brand new to me … managing up. Though I was constantly managing up in the Army, I found myself almost having to teach my managers how to be managers outside of the Army.

What was the hardest part about making a career pivot?

The hardest part is the unknown and constantly reflecting on where I would’ve been if I had not made the pivot. I would constantly think, and still do from time to time, what it would feel like to be at the rank of my Army officer cohort, or what assignments I would’ve had and how interesting those assignments would’ve been. Or especially when I first made the pivot, how much more senior I was to the role I had pivoted to. Like many career pivots, I had to take a few steps back in level from where I was at, and at times I wasn’t sure if I made the right choice/could set my pride aside enough to remember why I made the pivot to begin with. However, I’ve gradually gained a huge appreciation for the career pivots I’ve made and continue to make. I think it also helps if you lean more towards a “I did it” mentality than a “what could’ve been” mentality.

What were the most important lessons you’ve picked up along the way?  

The most important lessons I’ve learned along the way…

1) Knowing what you don’t like/aren’t good at is just as important as knowing what you’re good at/do like.

2) The biggest setbacks you’ll face are going to be the biggest lessons that you’ll learn, especially on how you overcome those setbacks.

3) Comparing yourself against yourself will almost always lead to a better result than comparing yourself to someone else.

What would you say to others who are doubting their ability to make a change in their career/vocation?   

Show me the book where someone regretted making the career change, and I’ll show you the library of the people that championed theirs- you’ll be okay in the end ;-)

Where did you get the confidence and support to make such a change? 

I think for me it all comes to this feeling of being uncomfortable where I was at, and that uncomfortability was what continued to push me to break out from what was safe.

What was the hardest thing you had to overcome in your professional life? 

The hardest thing for me to overcome in my professional career is that things are usually not “fair”. There will almost always be a situation where I think something isn’t fair, and a lot of times it’s not. I think growing up we’re so used to answering something right and being rewarded with a good grade, that we get trapped in thinking the world is like that. This has taken me almost 20 years to really come to terms with, but yeah, in the end the professional world just isn’t fair all the time.

What, if anything, are you hoping happens next in your professional life?  

If I continue to work for someone that they’re a leader that I truly want to work for and learn from. And if it’s working for myself…that I have the courage to make that career pivot ;-)

What social media links, if any, might you like to share in the piece?

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