Reflection #10: The Challenges of Rising Quickly at Work, With Ashley Rudolph
Last time, I had the fun of speaking with Ashley Rudolph, a former VP in tech who rose the ranks quickly, becoming a leader in twenties. She discussed the hidden challenges we don’t see in high-performers, like struggling to find a role that energized her, dealing with discrimination and self doubt, and managing layoffs of her team while navigating her own career uncertainty. Today, she is a career and executive coach who works with leaders at companies like Disney, Citi, A24, and Harvard Business School. She is full of wise, practical career insights for ambitious people, both in our interview and also in her excellent newsletter “Reframed.”
You can check out our last conversation here — and I hope you enjoy these 5 takeaways from our conversation.
Once again, there is a community for literally everything.
I have seen time and time again in this newsletter series that despite the challenge one is facing, there is always a community for it. In my very first interview, I interviewed the wonderful Joel Hoekstra, who was laid off from his management role at Uber and also became a career coach. He discussed how he followed the playbook of another former colleague who made the leap from corporate to coaching. Even though it seemed niche at the time, he was inspired to take the risk by watching someone else he admired.
Similarly, when Ashley said in our chat that she struggled because she went to a school where most people ended up in traditional careers like banking and management consulting, but she didn’t gravitate toward those things — I could relate completely. I felt similarly confused as “high achiever” who didn’t feel drawn toward these jobs, and for a long time I wondered if I made the wrong choice by not pursuing those paths. I always thought my problem was a niche one that only I understood, but it was so validating to hear that there was another person just like me.
At the same time, it’s also important to lean on people outside of work.
Over and over again, I have also seen my guests on this newsletter stress “community” — that whether you’re dealing with layoffs, cancer, divorce, or grieving a loved one, the most powerful way to deal with it is by building true connection with the people around us.
You would think this means that if you’re struggling at work, we should lean on those in a similar situation — our colleagues. But Ashley brought up a great point that relying on people who are too similar can cause a negativity spiral that turns into venting and losing perspective. She said she got through her most difficult times by leaning on people outside of work. She said the perspective of her friends and family reinforced her other identities (which ironically, helped her do better in the workplace), by helping her remember the other areas of competence in her life.
Feeling invisible and hypervisible at the same time is a shared experience.
Ashley shared a devastating experience that even though she was a director at her company, as a young Black woman, sometimes people would pass her in the kitchen and assume she was cleaning staff. She said that she felt “invisible and hypervisible” at the same time — a concept that struck me deeply, since I’ve also felt the same way. As a fellow ambitious woman in tech (and in my case, being mixed Asian-Jewish) I’ve also felt awkward and out of place sometimes, often being the “only” (insert whatever category). Whether for ethnicity or any other characteristic, feeling like an outsider and different-yet-invisible is a truly isolating and odd experience. It makes me remember why it’s so important to create a welcoming environment for all types of people, because others may be dealing with all sorts of hidden baggage we might not even realize.
Get excited for people to help you.
In all of Ashley’s pursuits in her career — whether getting into tech, leaving marketing, or starting her own business — she made connections with people to land her next opportunity. She pointed out that most of us feel nervous about asking people to do things for us — whether it’s asking someone for an intro, or a coffee chat, or their help.
But there’s a better (and more fun) way of looking at it: get people amped to help you. Share that you’re excited for your next step, and that you’d be thrilled to get their involvement to do it. That energy shift, she said, and sharing the excitement changed everything for her.
Finally, play to your unique strengths.
I appreciate Ashley’s admission that despite her strong networking, she is actually an introvert! I feel the same — huge conferences without any deep connections are also exhausting to me. She reminded me that “networking” doesn’t have to be the stereotype of meeting hundreds of people at a conference— it can be customized to you. If you like having 1-1 conversations, then have those. If you like talking in quiet, you don’t have to force yourself to be in loud, unnatural environments.
Ashley also mentioned that content creation - whether on LinkedIn, Substack, TikTok, et cetera - can be a great way to stay in touch with people, too. I never thought about it in those terms, but there are so many people I wouldn’t have ordinarily stayed in touch with had I not started this newsletter.
It reminded me that growing our network is so powerful - and it doesn’t have to be boring, exhausting, or insincere.
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Thank you so much for reading - what did you take away from Ashley’s story? Comment below, and I’ll see you next time!