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The Challenge

20 years of diverse, cross-industry experience that Carolina couldn't position, told repeatedly that being a jack of all trades meant she fit nowhere.

The Shift

Stopped asking 'who wants me' and started asking 'what problem can I solve for you,' changing the dynamic of every interview and conversation.

The Outcome

A role created specifically for her, built out of a conversation that started about a completely different position.

Olivia Gamber

A Note From The Founder

Olivia Gamber, CEO

Carolina came to me after seeing a video I made about being a jack of all trades. She messaged me because it named something she'd been carrying for years: the belief that her diverse, 20-year background across multiple industries was a problem to explain away rather than an asset to lead with.

She'd tried the conventional route before. She once handed a recruiter her resume and asked for help making sense of it. What she needed wasn't someone to organize her history. It was a different question to ask entirely.

The work with Carolina wasn't about finding the right title for her to chase. It was about shifting her out of pitch mode and into problem-solving mode, so the market could see what she actually brought instead of trying to fit her into a box that never existed.

THE WRONG QUESTIONS

Carolina

So I think before we met, I had a couple of issues that I was grappling with. One, I have a very diverse work history across a number of industries, about 20 years. And sometimes that diverse history can be problematic as you're looking to pivot or look for new roles. You're trying to figure out where you stand in the market, who you are, what you want, that sort of thing.

We're often told that if you are one of these people, you don't fit in anywhere, or it's hard for employers to see where you fit and know that they want you.

Carolina

I went to a recruiter once a long time ago and I just like dumped my resume. And I was like, I have a little bit help me. What do I do with all of this?

“You put it in such a way where this is not a detriment to your future. Being a jack of all trades can be a benefit.”

THE SHIFT IN THE QUESTION

Olivia Gamber

I know when you have all this broad experience, it's overwhelming when you don't know where you fit in the market. So what were some of the biggest shifts that you made to be able to break through that?

Carolina

I think the biggest shift was that I was asking the wrong questions. It was like, I was in the wrong meeting, right? I was looking for roles saying, where do I fit square peg and round hole? Like who wants me? And those were the wrong questions to be asking.

The huge shift came as I was having more conversations with folks and saying, my diverse history means I have a diverse array of perspectives across a number of industries. How can I help you? What do you need? That's keeping you up at night that I can help you solve. And that shifted and changed the dynamic in all of my conversations, in all of my interviews... you could see folks shift their thinking of like, let me ask this person these questions and get to know them too. Like, oh, wow, you could actually help me. Let's really chat now.

“The shift came in that journey when I started asking myself, not where I wanted to work and what job I wanted to have, but what problems I wanted to solve.”

A ROLE THAT DIDN'T EXIST YET

Olivia Gamber

This role wouldn't have, you wouldn't have gotten it if you went through a conventional job search, needing to know what the title was. The role was creative for you, right?

Carolina

That's correct. I was having conversations about a totally different role. And by changing the dynamic of those conversations and asking more questions about what their needs were and how I could possibly help, that escalated quickly to a role that was created for me.

I started asking myself, not where I wanted to work and what job I wanted to have, but what problems I wanted to solve. Who were the people I wanted to work with? Who are the people I wanted to help?

Carolina

I think I'm celebrating finally the validation that all of those years weren't job hopping. They were preparing me for a role where I could pull from so many different experiences. I finally feel that I can just be myself. It feels like I can just show up as me.

Carolina

There was a lot of work in the backend of self-reflection of what my value was, exploration of the problems that I wanted to solve. I wasn't going to ask myself those questions. It took you on the outside to challenge me to ask those questions. So I think the biggest advice is to look for folks like you and start building that little village of support for yourself, the people that are going to boost you, lift you, challenge you to reach for that next role.

Ready to Stop Applying?

Carolina stopped pitching her background and started diagnosing problems, and a role was built around her. If your experience feels scattered instead of marketable, this is the work that changes that.

Read the full transcript

Olivia: share her story with you. So Carolina, go ahead and share kind of where you were at, you know, when we first met and what your biggest challenges were.

Carolina: I have a very diverse work history across a number of industries, about 20 years. And sometimes that diverse history can be problematic as you're looking to pivot or look for new roles.

Carolina: how I found you actually was you did a video on, you know, are you a jack of all trades? And I was like, yes. Oh, and you put it in such a way where like, this is not a detriment to your future. Being a jack of all trades can be a benefit.

Olivia: where I feel like you started really breaking through because this role wouldn't have, you wouldn't have gotten it if you went through a conventional job search, needing to know what the title was. The role was creative for you, right?

Carolina: I was having conversations about a totally different role. Um, and by changing the dynamic of those conversations and asking more questions about what their needs were and how I could possibly help, um, that escalated quickly to a role that was created for me. I

Olivia: was kind of a journey, right? And so what were some of, as you think about the journey, what were some of the biggest shifts that you made to be able to break through that?

Carolina: I think the biggest shift was that I was asking the wrong questions. It was like, I was in the wrong meeting, right? I was looking for roles saying, you know, where do I fit square peg and round hole? Like who wants me? And I, those were the wrong questions to be asking.

Carolina: my diverse history means I have a diverse array of perspectives across a number of industries. How can I help you? What, what do you need? That's keeping you up at night that I, that I can help you solve that I

[Question shown on screen]: And so I'm curious for you, like, how did you actually just let go and flow at the market?

Carolina: the shift came in that journey when I started asking myself, not where I wanted to work and what job I wanted to have, but what problems I wanted to solve. Who were the people I wanted to work with? Who are the people I wanted to help? And what were those problems that I wanted to solve?

Olivia: what is the biggest thing you're celebrating? Obviously you just created a role in the market, which is amazing. Those are the best roles. They're so in alignment, but what are you most proud of that you're celebrating?

Carolina: I

Carolina: I think I'm celebrating finally the, the, the validation that all of those years weren't job hopping. They were preparing me for, for a role where I could, you know, pull from so many different experiences. Like

Olivia: I love it. That is amazing. So if you're talking to anyone that was where you were at and they're just like, man, I've done all this stuff. What do I do with it? I'm overwhelmed. What would you tell them?

Carolina: me a lot of homework that was necessary. I had to do, there was a lot of work in the backend of self-reflection of what my value was, exploration of the problems that I wanted to solve.

Carolina: that shifted and changed the dynamic in all of my conversations, in all of my interviews, you could see interviewers. And as I would network and make connections, you could see folks shift their thinking of like, let me ask this person, this questions and get to know them too. Like,