The Weight of Leadership: Invisible Struggles Behind a VP's Rapid Rise

First, apologies to those who wanted to read my Business Insider piece last time but couldn’t access the link — here is an updated alternate link! I talk about a recent “setback” experience of my own — experiencing a cardiac issue at 29 that limited my ability to walk and totally changed the way I see the world. I hope you enjoy :)

Today, I’m thrilled to introduce you to Ashley Rudolph - a leadership coach for high-performers based in New York City. While she had a staggeringly fast rise in tech — rising from an individual contributor to managing large teams as a VP in 5 years — she is open about the difficulties it took to get there, including layoffs, imposter syndrome and being taken seriously as a young Black leader, and soul-searching to find the right career path when her old one no longer felt aligned. Today, she works with all sorts of leaders at places like Disney, Citi, A24, and Harvard Business School, and is regularly featured for her insights in outlets like Teen Vogue, U.S. News, and Inc.

In today’s conversation, we cover all sorts of practical tips for boosting confidence in your career, how to strengthen your identity outside of work, and ways to network and make connections in an authentic and non-cringe worthy way.

In the early days of your career, what kind of person were you?

The way that I am now, I was the complete opposite early on in my career. I still had all these high performer traits — I've always been a high achiever, straight A student. But early on in my career, I struggled so much with carving out what my identity was and who I wanted to be.

The other thing that was hard for me was I went to Babson, which is a business school, and I felt like all of my friends or classmates were going into very traditional paths when I graduated. They were going into finance, accounting, consulting, all these paths that just were not interesting to me.

I took the path of getting into marketing and working at an agency and I hated it. I'm thinking, oh my God, my classmates are doing well. I'm underpaid, doing work that I don't like and I don't know what's next for me.

In the beginning of my career I struggled for the first five or six years trying to figure out exactly what I wanted to do.

That’s comforting to hear.

I graduated in 2008, so it was at the beginning of the startup scene outside of San Francisco. I knew I didn't want to be in a corporate space, but I also had no idea what a non-traditional or non-corporate path could look like for me.

I did find it eventually and I ended up in tech. There was a burgeoning startup scene in New York at the time. That was the unlock for me in my career, especially getting into a company that was growing.

I went from an individual contributor to a vice president in five years. I negotiated nine raises for myself over the course of eight years. There was just something about the move that was the right professional choice for me. Because I was doing work that was really exciting and engaging, I became more confident and that empowered me to go after the things that I wanted.

That’s amazing you found the intersection of something you liked and the right organization.

Right. The organization was doing well, which I know, the tech industry is a completely different place now. It's not like you can jump into any startup and it'll be growing. But I happened to be lucky.

I also happened to be willing to lean into the challenge of going after what I wanted. Being a young Black woman in tech was just hard. I think something that does come naturally to me is that I kind of don't care what people think. If I want something, then I'm gonna go after it. It takes a lot for people to rattle me.

But once I moved from the manager level into the director level and started experiencing things at work that were completely new to me, it was rattling. I can't say all of it or any of it was mean-spirited, but it still has an impact. I could be in the kitchen at the office and someone would walk by and assume that I was cleaning staff. And I'm a director in the company. So it's like, ascending to a level where you are visible because you're a leader, but also at the same time feeling invisible because people don't see you as a leader.

How did you deal with that feeling?

I'm lucky. I had a very strong community. I have really great friends. I did not have a coach at the time. I wish I had a coach. But I leaned a lot on friends and family during that time, and I think that's what got me through some of those moments.

It’s interesting you to say to lean on connections outside of work specifically. I've learned from so many different people on this newsletter that connection is so important to get through tough times— but I think it's important to distinguish what kinds of connection.

Outside of work created a nice barrier for me because another thing I learned over the years was how leaning too heavily on colleagues could create this toxic echo chamber.

I would definitely say to lean on some connections that aren't at work, and maybe that feels hard because you're like, my friends and my family don't understand what's happening at work. But I think it's equally as important to get an outsider's perspective, because that takes the temperature down.

What are some of the other meaningful challenges you’ve faced in your career?

My first layoff was my first job. I don't even know if I knew what a layoff was. I just remember calling my dad and calling my mom and just crying. That was at a time too, where you were given a box with all your possessions and escorted out. How humiliating!

What I learned from that was, this isn't what I want to do, and I need to figure out what I want to do. At the time, I chose to go back to grad school. I went to grad school and I studied abroad in France and in China. During that time, we had the opportunity to consult for startups in each of those countries. That was when I realized there's a part of me that really likes business strategy.

I came back and I did the thing that was easy instead of the thing that was brave. I went back into marketing, even though I knew I didn't like it. I feel like many people feel that way now. You feel kind of stuck in whatever path you've chosen. It feels hard to break out of that.

What was the transition like out of marketing?

Getting out of marketing was interesting. This was when I had just had enough. I thought maybe I could make marketing work if I went into a purpose-driven type of company. So I tried working at a nonprofit and I tried working in traditional education for a charter school network. And it didn't matter. I felt good about the mission, but the work still wasn't exciting to me.

I had heard about the fact that if you message someone on LinkedIn, a stranger, or if you find their email, you can set up all these coffee chats. So that's exactly what I did.

I leaned into networking a ton and I networked specifically with people in tech. I chose all of the companies in New York that I was interested in working for and set up a bunch of coffee meetings. I ended up connecting with a woman who worked at General Assembly (a tech education provider). I talked to her about a role on her team and I actually didn't end up wanting the role because it just felt way too close to marketing. And I was trying to get out of it.

But I knew that I liked General Assembly. So I told her that I was no longer interested in the role on her team, but asked her if she would be willing to refer me to another role in the company, which was a risk. But she did. That's how I ended up getting the job that I did.

How did you actually present yourself to potential employers? Because you mentioned up until that point your experience had been marketing.

The interesting thing was that since GA was in EdTech and I was working in traditional education, they loved the fact that I had an education background. At GA at that time, there were a lot of smart young people who came from finance or consulting, but they didn't have anyone who was close to education and could say, "Oh, this may be how we need to train our instructors."

I had enough proximity to teacher training at my charter school network where I could say, "Here are the basics." Because I had about six years of work experience and managed projects, I think they were open to the fact that I could manage contract instructors. They needed someone who could recruit the instructors that would deliver GA programming and care about having a really positive student experience.

It was understanding what their pain points were throughout the interview process and then marketing myself as the solution to those pain points. That helped a lot.

Tell me about the layoff you experienced in your last role.

The last year at my last company was hard. I was a VP and I reported directly into the C-suite. When the decision was made, my boss told me immediately that I was going to get laid off and so would almost my entire department. I had that information two months before the layoff was going to happen.

Going through it the first time, it was about how it impacted me. Going through it the second time, it was about how it impacted me, but also how it impacted the entire department that I built. I very much felt like I was responsible for their careers as the leader.

I wrestled a lot with the ask of keeping the news confidential, which was also my responsibility as a leader. But I also knew that I absolutely was not going to mislead my team into thinking that everything was okay and surprise them when the layoffs happened, or disappear and hide until the news was dropped.

So what I did was I did not tell my team that I knew they were getting laid off. I did not tell my team the date. But I very indirectly said, "Hey, I've worked at startups before and the business isn't growing. So do what you will with that information. If you are someone who is comfortable with a certain level of risk, maybe your action is to wait and see. If you're someone who's risk averse, you work at a company that isn't growing, revenue isn't growing, you might want to start your job search." So I let people make a decision based on the information that I had.

What I ended up doing was repurposing some of our team meetings into meetings where I let the team talk about their work. I gave them pointed feedback about how they were talking about their work. They got a chance to present about the projects they were most proud of. And what I was really doing was preparing them for interviews.

We did those project review meetings every single week for about six weeks. And then the layoffs ended up happening earlier. And no one on my team was surprised when they happened. On other teams, people were surprised.

When it was clear to me that my team was okay, I breathed a sigh of relief. Then I think the reality hit me, and I cried a lot. I felt like a failure. I felt like I established this team, and I took all of these people under my wing, and I failed. And because I failed, everyone lost their job. I blamed myself for that happening.

I went through this whole cycle of emotions, and what I ended up doing was going to Mexico City for three weeks, and that's where I did a full reset. That's when I decided to go into coaching. It didn't feel right to me to start a job search all over again. I wasn't drawn to doing the work that I had done for 10 years anymore. I had coached my team, without knowing that I was coaching them, and that felt like work that I really enjoyed doing. So I just decided to do it.

How did you acquire your first clients?

I put up my website and then I sent it to two friends, and then those friends sent it to some of their friends. And the next day I got my first client.

Then my other clients came from reaching out to my former coworkers at General Assembly. Either they hired me directly for various reasons or they referred me to people. I think the single most important thing that I did was talking to my network and telling them what I was doing. And it just picked up steam from there.

What tips would you have for people who want to network in an authentic way?

It was so hard for me in the beginning because it feels transactional. I think the biggest shift that I made was the mindset shift of being someone who people wanted to help.

So I went into conversations excited, instead of being apprehensive to ask for something. Not making it about "what can you do for me?" but more "I am so excited about this idea that I'm pursuing" or "I'm so excited about the prospect of getting into tech and I feel like I could learn from you." Bringing that excited energy into the conversation just changed everything.

I think the other thing is playing to your strengths. I am such an introvert. I do not love events. I think there's this idea that you have to talk to as many people as possible at events. I hate that. That will never work for me.

If you are someone that enjoys being in those spaces, do it, lean into it. But if you're not, and let's say you really like one-on-one interactions, then do that. Find a way to connect with people who maybe share your same values one-on-one. Just finding the right connections or the right forums for yourself and not believing that networking has to look a single way for you.

Another way to network is content creation. By putting content out there — whether it's TikToks, long form content, or posting on LinkedIn - people have just randomly DMed me because they liked something that I put out there. Make sure that the content that you create is in your authentic voice so people feel like they know what you're about.

For anyone who might be going through a tough time in their career, what advice would you give them?

It's so hard to be at a point in your career where either you feel stuck or you're legitimately struggling. It feels incredibly lonely.

One piece of advice is, if you're struggling in your career, try to find other areas in life where you can be successful first. Because we kind of treat our career as if it is our identity. And then when things go wrong in your career, it feels like your world is falling apart.

But I think when you invest in other areas of life and feel like you have things going on there, whether it's personal life, romantic life, passions, hobbies —— starting there has a major impact on your professional life.

Thank you so much for reading! What insights did you take away from Ashley’s story? Comment below!