If you've followed me for any length of time, you've heard me talk about my career journey and the fact that I was stuck as a director for five years before stepping into a VP role. I often share the mistakes I've made, the things I was only able to see in retrospect, and all of the changes that allowed me to finally thrive as a VP and EVP.

And I teach those lessons to you, so you can learn from them!

What I don't always share is that right before I landed that VP role, I almost left my corporate career altogether. I was frustrated, deflated, and feeling as though maybe corporate leadership was not for me. I didn't see a lot of leaders who looked like me, and I wasn't feeling valued in my current role.

Basically, I had worked my ass off for 15 years and hadn't achieved the goal that I set so early in my career. No matter how hard I worked, it didn't move the needle.

Today's newsletter is a little bit different because, instead of giving you advice or walking you through a framework, I want to share a bit more from behind the scenes of my actual career journey. I want to pull back the curtain and tell you how I was feeling at that time, what changed everything and made me decide to stay in corporate, and what I learned through the process.

The reason I want to do this is that my guess is some of you are in that exact same spot right now. You've been working towards that next-level role (maybe for years), and you've either been told to continue waiting or that you're just not ready. You might be wondering if it's even worth it anymore.

In today's newsletter, I want to give you a pep talk: it probably is. Let's dive in.

What was it really like?

I've told the story so many times that I don't even have to think about the points anymore, but I rarely tap into what that actually looked like. So here we go…

In the summer of 2012, my company did a major reorg of the leadership team, and I was asked to join them. At the time, I was leading our sales and marketing team and reporting to the CEO, but was not in our management meetings or involved in any of the strategic direction. I had been wanting to get in that room for years. I was thrilled.

But as the years went on, I started to feel as though I should have the same title as my colleagues, who were all VP and C-suite except for one.

I was running the function, had full ownership over my team and the decisions that were made, and was contributing to the strategic direction of the company. I loved all of those things, but wanted the title to match.

I think it's important to note that I was never someone who was afraid to advocate for my salary or my title. The fact that I didn't get promoted was not because I was working hard and not asking for it. I brought this to my boss many times, recommending a title bump to VP, given the level of responsibility I had. And every time I got the same reply, which was that I wasn't quite ready yet and I just wasn't strategic enough to be a VP.

We had many, many conversations over years where I became increasingly frustrated because there was no clear direction for me to make up this gap. At one point, my CEO tried mentoring me and, in those sessions, would ask me questions that he felt strategic leaders should be able to answer. To be frank, if he asked me those same questions today, I still wouldn't know the answers. I felt so frustrated that I didn't know what he wanted me to say, and I kept getting it wrong. There was no progress happening.

I finally convinced him to hire an external executive coach for me, who I worked with for about six months. During that time, this person saw what I was focused on and the work that I was doing behind the scenes, and was very confused because, in his words, I was “being strategic”.

What changed?

After six months, my boss told me I would no longer be working with my coach because, according to my CEO, that coach just didn't believe he could get me to the next level. My boss essentially told me that this coach never thought I could be a VP. That felt like a knife through my heart. I felt like he had given me really positive feedback, and the idea that he didn't think I was cut out to be an executive was devastating.

This was the moment where I almost dialled it in. I started to think about what my other options were. What was I actually good at? I thought about creating a running app. I thought about other people-focused businesses that I might be able to get involved with. Basically, in my mind, if I wasn't going to get to that next level, I didn't want to do this anymore.

Then two things happened:

  1. I reached out to the coach to ask him for feedback in terms of what I should do next in my career, and to my surprise, he told me that he absolutely thought I could be a VP. Just not at the company I was at. He encouraged me not to give up on this goal.
  2. I had lunch with a former boss and told him I was thinking about leaving and trying to decide what to do next. To my surprise (again), he told me about a company he was advising that was looking for a VP of Sales and thought I was perfect for the role.

Hearing that these two people believed in me at a time I no longer believed in myself, and after years of being told I wasn't good enough and wasn't ready, was the key thing that convinced me to seriously try to land a VP role at another company.

As you know, I landed that VP role that my former boss had told me about and the rest is history…

So what's the learning here?

The biggest thing I want you to take from today's story is that ‘failing' at one job does not mean you can't succeed at another.

I put so much stock in my boss's opinion when I was in that director role. When he told me I wasn't ready and wasn't a strategic leader, I believed him. And that was such a shame, because I went from feeling confident as a leader to questioning whether I belonged at all.

I thought that if I couldn't be successful in my current role, it meant I probably couldn't succeed anywhere. And that was completely untrue! I was terrified when I landed the VP role because the goals were WAY bigger, the team was more complex, and my confidence was already shaken.

But as soon as I started at this new company, I felt a shift. The culture was so welcoming and energizing, and the company was already seeing success. I could tell in my first conversations that leadership valued my opinions. Not only that, when I dug in, I could immediately see areas where I could make things better. I was able to contribute meaningfully to their success and learn a ton along the way.

At the end of the day, your success is shaped by so much more than your knowledge or experience. The culture of the company has a big impact on your ability to take risks and show up with confidence. The company stage impacts the skill set you'll need. The team dynamic changes the way you show up.

All of these things matter! And if you're in an environment that isn't working for you, it absolutely does not mean you can't go crush it somewhere else.

From the outside, it looked like I didn't have it in me. And then I turned around and helped create 9-digit growth at the next company I joined. Even more, I loved being an executive and building an amazing team and culture. Imagine I had given up?

So that's my pep talk for today. If you're feeling like I was – frustrated, stuck, and confidence shot – it's not too late for you. It doesn't mean anything for your long-term career trajectory.

And now, when I look back at those frustrating years, I honestly think of them as a blessing. Had I not felt so frustrated and stuck for so long, and then figured out how to be a successful VP and EVP, I would not have become SO obsessed with understanding that transition. And then I wouldn't be able to teach it to so many of you!

You probably know that the next cohort of ​Own Your Seat at the Table​ – my program that gets you VP-ready and helps you thrive as an exec – kicks off in less than 2 weeks. If you want in, reply back and let me know.

And if you want to gain the key insights into what keeps women stuck or helps you get ahead, you can still catch the replay of my masterclass until tomorrow at midnight. Check it out here.

Until next time friends… ✌️💜

Katy