Hayley: We often, sort of, rationalize our way into roles that, yeah, look great on paper, but feel wrong in practice.
Scott Anthony Barlow Anthony Barlow: That's Hayley, and she's far from the only person to make this career pivot mistake. Hayley's path looked textbook, communications degree, agency life, senior leadership roles. She was the definition of on track. And for a long time, that track felt clear, until life happened.
Hayley: I was really clear on that career path until I wasn't.
Scott Anthony Barlow Anthony Barlow: So she did something most people only fantasize about. She stepped away without another job waiting.
Hayley: How could it feel like a failure when I had only gained from that process?
Scott Anthony Barlow Anthony Barlow: But then she took a role at a Fortune 500 organization and almost immediately knew it was wrong.
Hayley: If I had an ideal career profile before, I would never have taken the last job that I took. It's so obvious to me when I look at that ideal career profile that would not have been the right fit.
Scott Anthony Barlow Anthony Barlow: Through coaching and reflection, Hayley stopped chasing what everybody else was telling her to do and started chasing alignment.
Hayley: There's real power in recognizing early when something doesn't fit and being really honest about that.
Scott Anthony Barlow Anthony Barlow: Okay, then the breakthrough came. She didn't find a posted job. She reverse-engineered the role she actually wanted. At a company she trusted, she co-created her own title, shaped the role around what the business needed, and what she does best.
Hayley: I'm wired to solve problems and move things forward.
Scott Anthony Barlow Anthony Barlow: Today, she's a chief of staff at a fast-scaling AI company, doing work designed to fit her strengths and her life. This is Happen To Your Career, the show that brings you real people, real transformations, and the courage to do work that truly fits. If you haven't subscribed yet, hit follow so you don't miss what's coming next. This episode is about listening sooner, trusting your gut, and building the role you actually want, even if it doesn't yet exist.
Hayley: I was always quite clear on what I wanted to do in my career. I studied communications. I went into communications agencies. I'm from New Zealand originally, so I moved to the UK at some point. And then, I went in-house, and that whole career path for me was super clear. But part of the reason for wanting to go in-house was just to build a bit more depth in one company.
And I did that for a period of time. And then I guess I was really clear on that career path until I wasn't. I had become a mother after a really difficult infertility journey, undiagnosed postnatal depression, and then COVID happened. And at the time I was at Expedia Group, the online travel tech agency, and obviously the business went through the floor in a matter of days.
Scott Anthony Barlow: Can you tell me a little bit about when you were so burnt out that you needed to drop out of the workforce for a period of time in order to work through it, for lack of a better phrase. What was that like for you? Because I think so many people in today's age get to the point where that is either a necessity or they're at that level of burnt out that it becomes very relevant in today's world.
Hayley: I recognize that I had a huge amount of privilege to be able to resign without having another job to go to. So I think there's that. That's not gonna be an option that's available to everybody. I'm not sure I knew at the time that I was burnt out.
The catalyst for that was I did some study at the Cambridge Institute for Sustainability Leadership. It really reignited a fire in my belly that I realized I just hadn't had for my job for quite some time.
And it almost felt like once I had that realization, everything else kind of came crashing down of the exhaustion, and I would say actually desperate need for something else, which was partly why I resigned.
Scott Anthony Barlow: What made this feel different? What made this feel like a clear mistake?
Hayley: I think it comes back to trusting your gut because I knew the role wasn't right. One thing that I've really learned over the years is that there's real power in recognizing early when something doesn't fit and being really honest about that.
So, I made the decision quite quickly to leave, which was tough because even though it was really amicable, yeah, it was still, it was quite emotionally draining, kind of, extricating myself from that process.
Sometimes it takes our intellect to catch up with our instinct, but I also think the more you ignore it, the louder it gets. Right? And I wish I had listened to those sort of early signals where I was questioning if this role would be the right fit.
I was in a bit of a moment of crisis, I think, where I just thought, "What the hell am I doing with my life?" Although both Roberta and Laura did encourage me to reframe that into a, I dunno, a period of reflection or something.
Scott Anthony Barlow: Something other than crisis.
Hayley: Yeah, something other than crisis.
Scott Anthony Barlow: Well, I think that that's important too, because one of the things you said to me before we actually got started earlier is that one of the biggest benefits to you in going through this more intentional type of career change was thinking about it from a growth mindset.
Hayley: Yeah. I think that's exactly right. So, I am talking about growth mindset a lot with my 7-year-old because he, you know, there's a lot of narrative around, "Mommy, I can't do it. Mommy, I dunno how to do it." And we have been working with him to sort of say, "Well, you can't do it yet." And that 'yet' is a really important piece.
And I think, I guess the reframe for me when I was in that moment of crisis was you just don't know yet where the path leads. So it made me feel a little bit less like I had come to a dead end in the road.
It was more that I had come to, I don't know, perhaps a fork in the road, and was kind of deciding which path to go down, and that I just didn't know that where it would lead yet. So yeah, I think doing some of that sort of re-framework was really important to help me get to the next step.
Scott Anthony Barlow: So then what happened from there? You left the organization and had that realization that this was something that you probably shouldn't have accepted in the first place. What took place next?
Hayley: After I worked my notice period, I expected I would spend a couple of months enjoying my time off and then go into another senior corporate affairs job in another tech company. And then probably about, I don't know, three or four weeks after finishing the role, I actually had an idea for a startup, which was slightly mad, but it felt quite serendipitous.
And, I guess like a lot of founders, it came from a problem in my own life where around that point my husband and I had come to the conclusion that we would be moving forward as a family of three with our beautiful son Jack, and we wouldn't be going on to have another child. But that left me with just a huge wealth of beautiful kids' stuff that I was struggling to move on.
And so, I struggled using kind of existing platforms, things like Facebook, and there's Gumtree in the UK, to move that stuff on. It felt like there was a big gap in the market for secondhand kids' resale. And my focus was more on things like buggies and bikes and scooters and toys, you know, the stuff that you can't just box up and pop down to the post office and ship.
So yeah, so I worked with someone to build an app. And we launched it in the app store and had a community of a few thousand users. We had early offers of investment. And it was really exciting, and I absolutely loved the journey. So I spent a couple of years doing that. I learned so much and met so many incredible people. I wound down the startup.
A lot of people asked me questions around things like "Are you grieving? You must be grieving. Going through a process of loss." And my honest feeling about that was how could I feel like I had lost, or how could it feel like a failure when I had only gained from that process? I just learned so much in the process that it felt quite clear to me that that was a step into whatever was kind of coming next.
Scott Anthony Barlow: How would you describe a couple of the pieces that you learned that are must-haves in future opportunities for you, including the one that you're currently in?
Hayley: Flexibility was gonna be the number one thing for me. And actually, what I came out with was growth and learning. But growth and learning was number one for me. So really being able to be surrounded by, yeah, super smart people and be able to learn every day was definitely something that, as I sort of made trade-offs on maybe other areas, it was pretty high for me.
It was good to kind of reinforce it as an absolute must was around relationships and people. And being able to work with people that I genuinely like and that I have a lot of respect for. And then, yeah, I guess I sort of came out the other side of those first three modules. I was really clear on my strengths and sort of where to take those. And I had a really solid ideal career profile, and I was about to move into the experimentation phase.
And what I had learned during those first three modules was that I was really looking for something that was more in the kind of strategy, transformation, change management type of space, or like a chief of staff type role. And I think it was even the same week that I had sort of had this realization.
The CEO of the company that I've been freelancing with his company since the start of the year, leading their comms and marketing, and the company's on an amazing growth trajectory. It is an AI automation platform that helps hotels manage their meetings and groups business.
And this is a guy who I worked with him at Expedia 10 years ago. We had a great working relationship, and I had always really admired him and had a lot of respect for him. And he came to me and said that they were keen to uplevel the comms and marketing work in the company.
And he sort of mooted the potential of a CMO role, chief marketing officer. I said to him, " I don't wanna be a chief marketing officer. But I can see that there's a gap in the company for this other role." And I started to sort of map out what that looked like.
And he had also, simultaneously, been having the same thought that there was this gap in the business. And so yeah, over time, we started scoping out what the role looked like. And yeah, I ended up taking a chief of staff role. So I'm a couple of weeks in.
Scott Anthony Barlow: That's amazing. And congratulations, by the way. It's not a small amount of work that you did to arrive at that result, so I don't wanna underscore that in any way 'cause you've done a phenomenal job.
Hayley: I guess as I had sort of started to think and understand a bit more about my strengths, I think I'm wired to solve problems and move things forward. And I organize fast, and I can focus deeply, and I have a good ability to kind of, sort of operate at this level where you can kind of connect dots, and see what's going on, but also really dive deep, when necessary.
And so yeah, really building the scalable foundations that are needed for our next stage of growth was something where I could just see this gap. Coming into the leadership team in this company at this time, I can definitely see that there was a role here to sort of support the company in that next stage of growth.
Scott Anthony Barlow: That is fantastic. What was the entire time from when you and I spoke to accepting the offer, and I know there's quite a bit of negotiation and everything in between, too, but how long was that? Do you recall?
Hayley: I think maybe three or four months. Four months, maybe.
Scott Anthony Barlow: Nicely done.
Hayley: I guess I sort of think of negotiating a role as being less about going in with, I don't know, like a hardball mindset of what you're getting out of it and more about... It's a two-way conversation, right? It's an opportunity for both parties to really gain clarity. So it was quite a free and easy conversation, but I think you've got to really understand what the company needs, right? And what they can realistically offer because a negotiation is about knowing your worth, but I also think it's about understanding the context that you're walking into.
So I was very clear of what a startup was going to be able to offer me versus a, you know, a multinational tech company. Those two things were gonna be quite different, and I was quite clear on that going into the process. So, yeah, I mean, I think as I say, "There is a degree of knowing your worth and sort of what you will and won't accept."
But for me, certainly it was; there were multiple aspects to that, and a big part of that was clarity about the role. And again, I think, coming at it from a position of privilege, right, where I had actually been working in this company on a freelance basis for a while, it had been a live test. So I knew what I was kind of getting myself into, mostly.
Scott Anthony Barlow: How would you describe what life and your work feels like now versus when you were at the most recent role that was a fit?
Hayley: If you were to say to me like, "Why this role? Or what is it that I'm sort of getting out of my current position?" I guess it's a really clear alignment with my signature strengths. That feels super clear to me.
And then I guess some of the other things, I think that are really crucial about this next stage of my career are having the ability to learn. So we're an AI automation platform. We are dealing with fast-evolving challenges that require a lot of strategic thinking, and I'm surrounded by really smart people, so I'm learning so much every day.
And then the people as well, so I've touched on having that great relationship with the CEO. There's a high degree of trust there and a lot of autonomy. And that is something really important to me because I always know where I stand with him. And that feels very genuine and authentic.
There's also several other people in the company who are ex-Expedia colleagues of mine and who I also have great relationships with. So yeah, that kind of trust dynamic with the people is really important. And then I touched on this a little bit earlier, but we're a remote-first company.
And although I didn't, at the start, sort of intentionally, look for a remote first role that does allow added flexibility. That means I can be committed to my job but also committed to my family. So yeah, those are some of the things that I think are really important about what I'm doing now.
Scott Anthony Barlow: If you're ready to stop believing the stories that are actually keeping you stuck and start creating the career and the life that you want, drop me an email directly, Scott@happentoyourcareer.com. Put 'Conversation' in the subject line. We'll connect you with the right person on our team, and we'll figure out the very best way that we can support you.