673: Navigating Misalignment, Burnout & a Big Career Pivot: When Your Career Path Stops Making Sense

(00:00) Hayley Lowe: We often sort of rationalize our way into roles that look great on paper, but feel wrong in practice.

(00:05) Scott Anthony Barlow: That's Hayley, and she's far from the only person to make this career pivot mistake. Haley'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.

(00:22) Hayley Lowe: I was really clear on that career path until I wasn't.

(00:26) Scott Anthony Barlow: So she did something most people only fantasize about. She stepped away without another job waiting.

(00:31) Hayley Lowe: How could it feel like a failure when I had only gained from that process?

(00:35) Scott Anthony Barlow: But then she took a role at a Fortune 500 organization and almost immediately knew it was wrong.

(00:41) Hayley Lowe: I think, if I had 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.

(00:54) Scott Anthony Barlow: Through coaching and reflection, Hayley stopped chasing what everybody else was telling her to do and started chasing alignment.

(01:01) Hayley Lowe: There's real power in recognizing early when something doesn't fit and being really honest about that.

(01:08) Scott Anthony Barlow: 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.

(01:22) Hayley Lowe: I'm wired to solve problems and move things forward.

(01:25) Scott 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. Let's dive in.

(01:52) Hayley Lowe: 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. I guess I probably subconsciously thought that careers were linear.

(02:14) Scott Anthony Barlow: We've now learned differently.

(02:16) Hayley Lowe: Yes, exactly. I started off in PR agencies. And I think those roles really played to my strengths because there's a lot of diversity in agencies, there's a lot of problem-solving. You have the opportunity to operate very strategically. 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. There were lots of things. I had become a mother after a really difficult, infertility journey, undiagnosed postnatal depression, 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.

(02:59) Scott Anthony Barlow: Can you tell me a little bit about that when you were so burnt out that you needed to, as you said, 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.

(03:25) Hayley Lowe: 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's not gonna be an option that's available to everybody.

And so I do recognize that, and I recognized that at the time. 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.

I did their sustainability business management program, getting up at 4:00, 5:00 AM to study and going to bed at midnight, which is crazy, but 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 without having another job to go to.

I think there were two reasons for that. One was that I had an amazing team, and I felt like they needed someone to be leading them properly, and I couldn't do that if I didn't have my head in the game, and I was looking for another job.

Looking for a job is, at this level, it's like a full-time job in itself. And so I felt like I would be much better served doing that outside of a role than in a role.

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, 3 or 4 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. A lot of it was high-end because we'd spent a lot of money on things for our miracle baby. A lot of it was brand new and hardly used, right?

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 there were a few businesses in this market that were more focused on clothing; they were more focused on things that you can kind of box up and ship.

And my focus was more on things like buggies, bikes, scooters, and toys. 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. But there was something in it that just, again, it's difficult to sort of explain or kind of pinpoint one particular thing, but there's lots of difficulties there. Right?

So I'm a Female founder. It's a lot harder for female founders. They only get like, I don't know, back then it was sort of 2% of VC funding, which is crazy. I was also a solo founder, and it's a lot harder for solo founders to build and exit successful products. And I was building a B2C proposition in Europe where there's a lot more skepticism around B2C versus, say, B2B SaaS.

Europe's a lot more risk-averse than the US. And I was also building a marketplace, which I knew would require huge amounts of investment. And I had some amazing advice from a mentor at that time. He was a former Chief Product Officer that I had worked with at Expedia, and he said to me, “Maybe you're not a number one. Maybe you are a number 10.” And so, yeah, there was something in that that just didn't feel 100% to me, and I felt like before I took on external investment, I had to be 100% committed, and I wasn't. I wound down the startup, and I think what was really interesting about that process, which again, kind of led to me all of these paths sort of joined to get to this point. 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? And I think we have to normalize people starting and closing businesses because that's a really important trait to have.

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. Everybody in startup land talks about resilience. But I think there's a big difference between knowing that you could survive something and then actually wanting to survive it. And I guess, yeah, I don't know. 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.

(08:39) Scott Anthony Barlow: What made this feel different? What made this feel like a clear mistake?

(08:42) Hayley Lowe: 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 quite emotionally draining. Kind of extricating myself from that process.

(09:14) Scott Anthony Barlow: How did you go about it? What were some of the conversations or what was going on sort of behind the scenes for you to get to the point where you were able to remove yourself from that situation?

(09:28) Hayley Lowe: We often sort of rationalize our way into roles that look great on paper, but feel wrong in practice. And I think 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?” Like, I'd also sort of I was reaching my mid-forties, and there's the whole midlife crisis thing. So it felt like a real midlife crisis, although both Roberta and Laura did encourage me to reframe that into, I don’t know, a period of reflection or—

(10:16) Scott Anthony Barlow: Something other than crisis.

(10:19) Hayley Lowe: Yeah, something other than crisis.

(10:20) 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 and not just reframing, but really trying to pursue as much as possible with that growth mindset.

There is no point in time where we as humans are a hundred percent in growth mindset versus outta growth mindset. It's a combination of fluctuation, right? That's just where you were at that period of time. And then as you shifted, it was less about crisis and more about trying to take those opportunities and recognize where it creates that benefit.

(11:05) Hayley Lowe: Yeah. I think that's exactly right. So I am talking about growth mindset a lot with my 7-year-old because there's a lot of narrative around, “Mommy, I can't do it. Mommy, I don’t know 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 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 where it would lead yet.

So yeah, I think doing some of that sort of reframe work was really important to help me get to the next step.

(12:03) Scott Anthony Barlow: I think that's such a hard place to be. It's one thing for us to sit here and talk about growth mindset. It's an entirely different thing to be going through that experience and continuing to try to find ways to remind yourself that it's okay, I just don't know where it's going yet. What did you find worked for you as you were literally in the midst of all of that to allow yourself to jump back to that growth mindset more frequently and remind yourself that, "Hey, this is going in a direction that I can't entirely see and I don't have full visibility to yet.” What did you find worked for you?

(12:40) Hayley Lowe: I think it was a particularly tough place to be because, as I mentioned earlier, I was super keen to kind of get back into earning and sort of kickstart my career. And there's always that again, it's like the way your rational and irrational brain work against each other, oh my gosh, honestly, the irrational part of my brain was sort of saying to me, “You are running out of time. You will be wiped out of the workforce; you have become irrelevant.” I was sort of hearing that on the one side, and then obviously, very rationally knew that that was not the case.

And also wanted to really find peace in having the patience to get to the point where I was clear on what I wanted to do because I've always been really ambitious, and I'm a really motivated person, so I knew that I would find the right path. It actually just reminded me when I left high school, I actually made the decision, as I said, I'm from New Zealand. I made the decision to come to the UK on a working holiday, and I remember this teacher in my final year of high school saying to me, “You are throwing away your life. You will never come back here and go to university.”

And I told a lot of people that at the time, who a lot of people like—so another amazing teacher I had said to me, “I know you. I've known you for five years. You are extremely driven and motivated. If you wanna come back to university, you will.”

And I went off, and I had a few years out, and I did go back to university, but I think I always knew that I would find a path and be quite driven and motivated to kind of get back on it. But when you are in that situation where you are kind of really desperate or eager to get the ball rolling or to get things moving, it's quite—you have to be quite disciplined about finding the peace in the process, and that can be quite difficult.

(14:38) Scott Anthony Barlow: What have you found allows you to sort of come back to a place of being able to operate and move forward?

(14:45) Hayley Lowe: We live by the sea. We're sort of 5, 10 minutes walk to the beach where we are. So I'm in the south coast of England, near Brighton.

And I would say just getting out for walks and feeling the breeze on my face or the sun on my skin and hearing the sea was incredibly helpful and kind of finding the peace. And then I would say more active, things that I did were like meditating, surrounding myself with the right kind of people, was really important. So I got out and tried to broaden my network quite a lot.

(15:18) 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?

(15:30) Hayley Lowe: Flexibility was gonna be the number one thing for me, and actually, what I came out with was growth and learning. I mean, flexibility I think, is important. And I think it's something that's become a lot more important to most people in the workforce now than maybe kind of 5, 10 years ago. But growth and learning was number one for me. So, really being able to be surrounded by 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 yeah, being able to work with people that I genuinely like and that I have a lot of respect for. And yeah, that's something that I feel like I have in my current role. It was helpful to have someone else who could kind of challenge me on that, I think. 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. So I've been freelancing with someone, who I used to work with at Expedia, since, well, 10 years ago. But 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. It is sort of the only part of the travel mix that hasn't been automated in the same way that business and leisure travel has, and the company's on this amazing growth trajectory.

And this is a guy who, as I say, 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.

(18:23) 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.

(18:34) Hayley Lowe: I'd been freelancing for this company since earlier in the year, and I had a really close relationship with the CEO, so I could see that there were things that he was involved in and that some of the other co-founders were involved in where, perhaps we had moved to a point where, because of the company scaling really quickly due to its growth.

I mean, you know what it's like in the sort of early days of a startup, everybody wears multiple hats, and then you get to a sort of inflection point where you need to move people into—you move away from sort of those generalist roles into more of a specialist skillset. And some of that was already happening in other parts of the business, and that kind of left some gaps of stuff that needed to get done, but it didn't necessarily have a natural home.

And 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 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 I could just see that there was a role there to operationalize a lot of the systems and processes that the company has had up until this point. And we actually talked a bit about this in a team call yesterday where we talked a bit about process and kind of the shift that we are making as a company, clearly from that startup to scale up phase where you know when you've only got five people, you can pop a note on Slack to tell someone that you're gonna be off for the afternoon 'cause your kid's sick or that you need a Wednesday off in two months time.

But when you've got 25, 30 employees, where we are sort of heading to, those processes, they don't work in the same way that they used to. 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. And as I say, Felix, the CEO, had also identified that gap. And so it felt quite serendipitous when we kind of got into those conversations.

And I think part of what works is that we are really different people. Obviously, I work really closely with him, but I come back to that point that my former mentor said about maybe you're not a number one, maybe you're a number 10. And if I think about Felix and a lot of other founders that I know, he's got that real visionary kind of futuristic ability, which I just don't have, like my skill is I get shit done.

And so we are quite complimentary in that aspect. And I think, yeah, 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.

(21:31) Scott Anthony Barlow: When you started laying that at out, did you literally put that on a Google document? Or how did that actually look as you started scoping it out so that you could exchange ideas back and forth?

(21:44) Hayley Lowe: It was writing a sort of a list of where I could see there being opportunity, and I mean, Felix was quite clear that coming into this role, I would retain comms and marketing, which at first I was a bit like, “Oh, I don't know if I want to do that.” But actually, I think just by the nature of where we are as a company, that carrying that through has actually been really interesting in itself. But yeah, I mean, he had sort of come up with a—I mean, I guess for want of a better word, it was a roll spec, and I had sort of come up with a roll spec, and then we almost did a, “I'll show you mine, if you show me yours” kind of exercise.

(22:23) Scott Anthony Barlow: The unveiling of roll specs.

(22:26) Hayley Lowe: Yeah, we sort of shared those documents, and I think we were pretty broadly in alignment, so it actually felt quite easy from there in. 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, and I think what can be really difficult about that is you are often going through a talent team or a recruiter in a company, and that can make it a bit more difficult because it feels a bit more one-sided. I guess the benefit of this situation is, I was dealing directly with the CEO, and he's obviously it's a great position to be someone that you've known for a long time as well.

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 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, 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, so I really knew it had been a live test, so I knew what I was kind of getting myself into, mostly.

(24:22) 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?

(24:33) Hayley Lowe: 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 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, so 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 what I'm doing now.

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.

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