266: Career Change Advice From Linnea Who Jumped 4 Titles In 6 Months


Picture this.

You’re a 14-year-old gymnast. Until now, you’ve lived a seemingly normal life. You’ve attended school, completed weekly chores, showed up at pizza parties… all the usual teenage stuff.

But now, you’re getting close to what could be the biggest moment of your life.

You’re training for the Olympics, and you have only two years until your life could change forever. You could make the leap from being an unknown girl in Virginia Beach to an international icon.


So you train. And you practice. And you envision victory. You immerse yourself in the process with a guide—your expert-level trainer—who will lead you through physical workouts, teach you calming meditations, show you practice film to compare your form to past Olympians, and make you listen to music options for your routines.

When you’re on your way to practice, grabbing a quick bite to eat, or reading before you go to bed at night, you’re still thinking about what having an Olympic medal placed around your neck will feel like. Maybe you even select books written by former olympic athletes and listen to interviews on their training regimens. Around the clock, you are fully immersed in your dream.

Eventually, you look around and realize you’re doing it… You’ve made it onto the Olympic team, and you’re representing the U.S. on the biggest platform in the world.

The big day comes. Before you begin your floor routine, you play back everything you’ve done over the last two years. You do a calming meditation, get a last-minute reminder from your coach, and wait for the music to begin.


You launch into your routine, and before you know it, you are standing in your final pose. You’ve stuck the landing, and you can’t help but smile from ear to ear.

Later, when the awards ceremony begins, a gold medal is placed around your neck. It feels better than you imagined. In a mere two years, you’ve launched yourself from an underdog to a national hero and international celebrity. You’ve accomplished your dreams.

This is the story of Olympic Gold Medalist Gabby Douglas. Gabby, now a three-time gold medalist, was the first African American to ever win the women’s individual all-around. In the span of two years, her immersive training experience took her from a 5’2” no name to a towering gymnastics superstar. Since winning, she’s been featured on countless magazine covers and talk shows. She even had a movie made after her and a Barbie made in her honor. There’s no question… she’s arrived.


Gabby’s story reminds me of my friend Linnea’s career leap.

Like Gabby, Linnea advanced from an average level—which most people are content with—to unparalleled success.

In the span of six months, Linnea jumped FOUR TITLES! Can you imagine that? Most people look forward to a promotion that advances them only one title. Four at once is unheard of.

After completing her MBA, Linnea knew she wanted something more, but she wasn’t sure what that was. Before long, she found our Happen To Your Career podcast.

Once she found us, she binge-listened to every episode. A couple months into listening, Linnea claims she experienced her EPIPHANY MOMENT.

While listening to our episode on How to Confidently Land Your Dream Job with Laura Morrison, Linnea realized Laura had the self-actualization she longed for. Immediately, she joined Career Change Bootcamp, and now, six months later, she’s a Senior Vice President of her company.


Linnea’s process involved full immersion, as she not only listened to the podcast, met with her career coach, and completed the Career Change Bootcamp modules, but she also scheduled unlimited meetings with potential employers, bought books written by our podcast guests (like “Wait, How Do I Write This Email?” by Daniel Rubin), and wrote follow-up letters to everyone she met along the way. (She did all of this while continuing to work her full-time job as a Marketing Manager.)

Linnea took advantage of every free moment, listening to podcast episodes while running on the treadmill, listening to audiobooks on her commute to work, setting up meetings while watching TV… She didn’t waste a second.

Today, Linnea is exactly where she wants to be. Only six months since joining Career Change Bootcamp, she’s moved from listening to the podcast to being featured on it! As she loves to say, “everything has come full circle.”

To hear all about Linnea’s inspiring story directly from her, click the play button below.

Linnea Calderon 00:00
I am a self proclaimed, you know, multipotentialite. I have many interests, many ideas, many things I want to do and there was so much going on in my head and I didn't know how to navigate, sort, or kind of figure out what I want to do next.

Introduction 00:20
This is what happened to your career podcast, with Scott Anthony Barlow. We help you stop doing work that doesn't fit. You figure out what does and make it happen. We help you define the work that's unapologetically you, and then go get it. If you're ready to make a change. Keep listening. Here's Scott. Here's Scott. Here's Scott.

Scott Anthony Barlow 00:44
What does it really take to make big moves when you're making a career change? Now we're talking like, three or four levels or job titles up from what you've done before. What do you think that takes?

Linnea Calderon 00:57
So I've been in financial services for over 13 years and thought, well, maybe I could try something and healthcare or maybe consumer packaged goods, but wasn't totally sure.

Scott Anthony Barlow 01:09
That's Linnea Calderon, and we got the opportunity to first meet her. Well, she was determined to make some pretty big moves, she wanted to be able to have the type of career fulfillment that she'd heard on our podcast many times before. And guess what? Not so many months later, she's now found that and we want to be able to break down how all of this happened.

Linnea Calderon 01:35
So my title now is Senior Vice President of emerging products. And what I get to do is develop product roadmaps and innovation strategies for retail partners across the US who ultimately provide payment services to their customers when they're in the store, in their app. And I'm part of developing what we do next with all of the top retailers in the United States.

Scott Anthony Barlow 02:04
That's awesome. Why was that something that is really exciting for you and your situation? Because we know that everybody's career looks a little bit different as far as what they need. But for you, why is this a great thing?

Linnea Calderon 02:15
For me, great, because it aligns with not only my personality, but what I wanted to do next. And so I'm someone who loves to think big picture and think into the future. I love to motivate people to do and think about what we want to do next, and how we can serve our customers, and then actually see it through launch and marketplace. And so all of those components align with myself and what I want to do, and I'm able to hit all of those key areas within this role.

Scott Anthony Barlow 02:48
That is awesome. And I said it before but congratulations again, because that's a big change. Nicely done. And what was for context, I know, but what was your role that you're coming out of, what type of situation? Fill people in on what's the previous role.

Linnea Calderon 03:06
Sure. So before then, I was Senior Strategy Consultant, or also Senior Marketing Manager for context. And I led a team of 10 managers across an organizational change management system, where we were deploying how we were working differently as an organization, and then also training executives on where they wanted to go within their business, developing their roadmaps and their goals and helping them get there. So.

Scott Anthony Barlow 03:37
So what is it that led you up this road then to want to make the change in the first place?

Linnea Calderon 03:45
So I love this question, because this is I put a slide together for Lisa, when I was actually consulting with her initially on whether I should do this or not. And...

Scott Anthony Barlow 03:54
Hold on. Can I just say that I love that you put a slide together for Lisa? That makes me so happy on so many levels.

Linnea Calderon 04:03

Scott Anthony Barlow 04:03
Sorry to interrupt, but just wanted to acknowledge that.

Linnea Calderon 04:05

Scott Anthony Barlow 04:06
So you put a slide together.

Linnea Calderon 04:07
Yeah, I actually put a whole PowerPoint deck for her. And then this is one slide from it. But this actually started back in August of 2017, when I completed my MBA program, and I knew I wanted to make a change but didn't know exactly what I wanted to do. And then in September of 2017, I started actually career coaching with another coach and went through that process. And at the end, I felt okay, but I wasn't fully prepared on what I should do next. And I wasn't 100% sure this what I should do next, and I just didn't feel comfortable and I was missing something and so January of 2018, I had found your podcast and I binge listen just like many of your listeners and even re-listened to many of the podcasts and in February of 2018, you know I went through and kind of picked my top two careers and I wasn't a hundred percent sure. And then, along with listening to the podcast, my epiphany moment was March 14th of 2018, when I had really listened to how to completely land your dream job with Laura Morrison, and...

Scott Anthony Barlow 05:24

Linnea Calderon 05:25
That was my moment when listening to her again, she had reached this self actualization and I wanted to feel that, and I didn't feel that after I've gone through my experience. So that was the moment where I was like, I need to make a change, and I need to invest more into myself and sign up for the program.

Scott Anthony Barlow 05:48
Well, I am one, so glad that you got to listen to Laura not once, but twice. And for context, Laura, we had her on past episode, she made a pretty large change of her own right. And clearly, you've been able to follow suit. So when you started and embarked on this change, and you recognize that you want some of those self actualization pieces, as you called it, that you hadn't felt that in the way that you wanted to, what caused you to keep going? What caused you to begin down that pathway? And was it just that podcast and you had listened to it and said, "Okay, I'm doing this, I'm making this type of change. And I'm figuring out," or was there some else along the way?

Linnea Calderon 06:34
Yeah, I would say another part of it along with the podcast was, I am a self proclaimed, you know, multi-potentialite, I have many interests, many ideas, many things I want to do. And there was so much going on in my head, and I didn't know how to navigate, sort, or kind of figure out what I want to do next. And so that was really the other part of my story, as I just had so much going on, and so much I wanted to do, but not a very clear way of getting to something and figuring out how best I should do that.

Scott Anthony Barlow 07:10
Hmm. So what were the areas that you were struggling with, in particular, what was making it hard for you to, as you said, figure out the way to best do that?

Linnea Calderon 07:20
One of the things is I was debating whether I want to switch over to different industry. So I've been in financial services for over 13 years and thought, well, maybe I could try something in healthcare or maybe consumer packaged goods, but wasn't totally sure. And the roles that I was looking at were a variety, they span from a marketing type of manager director role to consultant to someone in operations. And so the path I could have chose, there was just so many and I wasn't sure what industry or what type of role I'm really needed help with them.

Scott Anthony Barlow 07:59
So what did you do then to begin figuring that out? I mean, I know that you got the opportunity, and we got the opportunity to work with you on this. But what really made a difference for you in your situation in order to begin having some measure of assurance that you're heading in the right direction and in one direction.

Linnea Calderon 08:16
I think for me along, you know, was doing all of the homework and listening to the different modules, when we got to the point of kind of testing out different organizations and talking to people, that was really when I started to see the light or and understand that, "Okay, there's a lot to explore. This is a very succinct way to do it." And I think that really kind of jumped started, at least in my mind. And now I can really start to figure out where I want to go next.

Scott Anthony Barlow 08:49
That's really interesting. So why do you think that was such a not aha moment, that's not the word I'm looking for. But why do you think that was such a big deal that prompted you to be able to begin to see the light into that tunnel?

Linnea Calderon 09:02
I would say it's a big deal, because incorporated all the components and how you talk to people, how you understand organizations, how you understand different roles and get a sense and a sample of what the next role could be like, what the next company could be like, who can you work with and what the organization is like. And so being able to do that, and also have a way where there was a structured approach to do that, really helped me a lot.

Scott Anthony Barlow 09:32
What were some of the conversations that you got to have? You mentioned having a variety of conversations and getting to know different organizations and different opportunities. But what were some examples of those conversations and how did you go about that?

Linnea Calderon 09:45
Sure. So I actually started with my internal network first. And I put together a list of organizations that I was interested in and started tapping into my network and say, "Hey, I really want to meet XYZ person, would you be willing to introduce me?" and kind of went down that route. And a lot of those interactions, which I, my goal was to do about four to six, reaching out conversations a week, whether they were phone calls, or a lot of them were coffees or lunches, and just keeping those interactions in the pipeline, and always making sure I had someone next to talk to or reach out to.

Scott Anthony Barlow 10:28
With any of those conversations. Do you remember any in particular that were particularly useful for you in understanding, "Hey, I really should not head this direction," or, "Hey, this is great reinforcement that I'm heading in the right direction," anything stand out to you?

Linnea Calderon 10:44
Yeah. So there was one interaction, I talked with a recruiter, an internal recruiter for one of the banks in the Chicagoland area. And it was really an interview, phone interview where I was interviewing him. And a lot of the responses that I got back from him as he was describing the culture of the organization, but we just didn't fit, they were very reluctant to change and try new things. And some of the questions I asked, he didn't even have answers to. So that was a big red flag of this company wasn't for me. And I'm glad I knew that upfront. So.

Scott Anthony Barlow 11:22
So what did you do?

Linnea Calderon 11:23
Well, I thanked him for his time, and you know, did the follow up thank you, and wrote the thank you letter, as you're supposed to do, but then continue on my journey with other organizations or roles that really interested me. So it was kind of keep going through my list and figuring out where I want to go. And that was awesome that I didn't choose that place. And it was great that I knew that upfront, and I didn't have to spend a lot of time, if I had applied for a role and gone through the process, I would have wasted a lot of time if I had just reached out and did a 20 minute phone call. So.

Scott Anthony Barlow 11:59
That is amazing. And I just want to share how big of a deal that is. Because I think it's really easy, as you're listening to that, to underscore just how powerful that is. Because essentially, what I heard you saying that you were doing was, first of all, you had to have some measure of idea of what you wanted in the first place to be able to make those types of decisions. But then you were actively interviewing them, you were seeking out that information and rather than the normal traditional, I don't know what we want to call it, the normal traditional methods of the "I send my application in, and then I wait, and then maybe they interview me. And then I wait. And I'm sort of at their mercy," you took the exact opposite approach. And you were doing that exact same thing in reverse. And first of all, that's awesome. And second of all, what you said after that, I think is really, really powerful. Because that allowed you to not waste any time with that company. Who knows, maybe they would have given you a job offer, after you know, many months of interviewing and all kinds of stuff like that. And you didn't have to go through any of that instead could focus your time and energy on the other places that really did. So, awesome job. What was the hardest thing for you in making this type of transition? And going through the the process you went through overall in about six months, I think you said, right?

Linnea Calderon 13:28
Yeah, I would say the toughest part of all of this was the company that I was at, was going through a lot of different organization changes and restructures. And I was trying to ensure I had a job at that company while I was looking for my next role. And I know that I got burned out mentally, physically and even emotionally just kind of trying to switch my mindset between, okay, I'm trying to get a job internally just to have a job. And I would say, you know, survive to some extent, while I was trying to work on getting my dream job. So I think that was one of the most difficult parts of the journey was doing almost double work. But that was my own choice. And I just knew I had to get through it and take it day by day.

Scott Anthony Barlow 14:20
What did you do that made it easier on yourself or what did you do that caused it to work for you? Because I totally been there many times over with many career changes. That is not an easy thing where you have, for all intents and purposes, double work and searching for two jobs in two different ways at the same time, but what made it easier... what did you find that worked for you and your situation?

Linnea Calderon 14:43
Yeah, I tried to leverage the experience opportunities that I was going through with the internal search and use that in practice, for when I was interviewing or reaching out to people for the role that I really wanted to be at and so I tried to make it very purposeful, and utilize that journey, and to use it for my next one. And I think that really helped, because then from that perspective, I wasn't wasting any time. I was still practicing, I was still doing the same types of preparation and thought process to prepare. So that way, it wasn't as difficult as if I didn't purposely try to use you know what I've been going through for one search on to the next one.

Scott Anthony Barlow 15:32
So let me ask you another question about that, too. Because I know that I'm going to get a ton of emails about if we don't ask this question. But we sort of glossed over the fact that in terms of title, I don't know if it's necessarily as much in terms of day to day type jobs, but definitely in title, you made substantial jumps, like three or four jumps in terms of title. Is that fair to say?

Linnea Calderon 15:55

Scott Anthony Barlow 15:56
And a lot of people I know from experience in doing this for many years, a lot of people will automatically assume, "Oh, well, she could do that. But it's not... I could never do that," or a lot of cases, I get this question pretty much every day in one shape or another, "That's impossible. You can't do that. Like, that's just not feasible." And yet we see that happen again, and again, and again. And you're a great example of that. So I'm curious, from your perspective, after being there doing that, why do you think that was a real possibility for you? And what would you advise people that are having some of those impossible thoughts jumping into their head?

Linnea Calderon 16:38
I would say one of the keys to my success was very in depth preparation for every single interaction that I had, whether it was a informal coffee, whether it was an interview, whether it was following up in an email, or a handwritten letter, every interaction that I had, or knew I was going to have I prepared for to the nth degree. And so in that way, there is no question that I couldn't answer or anything that I couldn't be prepared for, because I genuinely prepared a lot, probably more than I've ever had, even for, like tests or anything. I mean, I genuinely prepared so much for every single interaction I had with someone.

Scott Anthony Barlow 17:19
I think that's great evidence, though, that when you do things that other people are not willing or unwilling to do, you get opportunities, and you get to do things that other people are not going to be able to do. So I think you're a testament to that. And I very much appreciate you sharing. So let me ask just a couple other questions here that I think are that people would want to know about your situation. One, for somebody else who is thinking about making this type of change. And somebody else who's maybe is back where you were back in December or January, and just really recognizing that something has to change in one way or another. And then just on the beginning part of making that decision. And actually for you it even started before that, right? It started with the end of your masters, right?

Linnea Calderon 17:20

Scott Anthony Barlow 17:22
When somebody is back there, what advice would you give them? Now that you've been through this journey, full circle, literally full circle. Listening to the podcast, as you said, and now on the show only so many months later.

Linnea Calderon 18:23

Scott Anthony Barlow 18:23
What do you think?

Linnea Calderon 18:24
I would say, use a variety of different avenues and educate yourself. So one of the things that I did was along with the podcast that I would listen to, in between driving to work or at the gym, I also from the podcast, took information and bought books and about specific topics that I was interested in. And so one of the books and I'll give a shout out is, "Wait, How Do I Write This Email" by Danny Rubin,

Scott Anthony Barlow 18:52

Linnea Calderon 18:53
Yeah, he had, I think it was on a couple times on your show. And he talked about his book. And he provided some really good content. And, you know, I was like, "Wow, this is a great sample. And so let me explore more." So I bought the book and read that and same thing with you know, negotiation, that wasn't my strongest point. So after listening to Josh Doody's podcast, I bought his book "Fearless Salary Negotiation", read it, did the exercises. And so my advice would be to use different avenues and educate yourself during the process. Because the more you know, the more power that you have behind yourself and the confidence that you will have when you get to the point of when you want to go after a role.

Scott Anthony Barlow 19:37
That's fantastic. One of the things that we don't talk a lot about on the podcast that maybe we should do a full episode on it at some point, but anytime you're making a change in your life, we found that anytime you can almost fully immerse yourself in a variety of different sources of, not just information, but things that are going to set you up to carry yourself forward. I know one of the things that we talked about inside career change bootcamp is building a plan for inevitable success, or building a plan for when it gets hard. But in some ways, a big part of that like completely surrounding yourself by all the things that you need to make yourself successful for whatever type of change that you're making, in your case, a pretty massive career change. And I appreciate you sharing, because I think that that gets glossed over in some of the other times that we talk about it and what it really actually takes.

Linnea Calderon 20:26
Yeah, I was gonna totally agree with you. Because I did immerse myself, it became almost my part time job where I would work on, you know, myself or prepare after work and up until like, one in the morning sometimes, because that was the time I had to work on this. And so fully immersing yourself and making it high priority is very important to getting where you want to go.

Scott Anthony Barlow 20:51
What was the hardest part for you in order to make it a really high priority? Because I think a lot of people really struggle to find the time or really to, I mean, it's even hard to acknowledge that it should be a high priority in the first place. And I think we find, I know, I certainly do from time to time and after yank myself out of it, and one way or another, but sometimes I'll revert back to the thinking of "There's only so much time in the day, and I just don't have the time for this," even though I am on the other side saying, "Look, this needs to be a really, really high priority." So what did you find really worked for you, in order to make this a high priority in actuality?

Linnea Calderon 21:27
Yeah, I scheduled time on my work calendar and personal calendar was one of the biggest ways and helpers to do that is to just carve out time and then put it on your calendar and stick to it. And I would say another thing is finding time in between when you're not doing something, or you could listen to something while you were driving. And, you know, whether it was on a plane or even on vacation, or wherever I was, I was listening to a module I was doing some of the homework I was drafting, I was always doing something all the time, or when I could. So that is another I think key to success is try to find all the little time in between where you can just know do something small, and doesn't have to be, you have to sit down for hours at a time, if you don't have that, but do something in between.

Scott Anthony Barlow 22:13
That's amazing. And I feel like when we're working with people, and working with our students inside career change bootcamp or in any place, a lot of what we find that we're doing is helping people tailor the work that they need to do that everybody needs to do to make this type of change into their world. And I think that's a bit about what you're talking about. If it really truly is a priority, you have to find the maybe not easy, but possible ways to embed it in your world. And you seem to have done a really, really nice job of that and Lisa mentioned that as well. So I feel like I keep saying really nice job and kudos. But I mean it.

Linnea Calderon 22:52
Well, thank you, thank you so much. I really appreciate it. And thank you, you know, for creating something so wonderful, helpful and meaningful to help people like me get to really where they want to go. I mean, that's such an incredible invention that you've created. That's just so helpful. So thank you.

Scott Anthony Barlow 23:11
My pleasure. As it turns out, it's what we love to do and is absolutely what we do. And thank you for giving us the opportunity to be able to help you too.

Linnea Calderon 23:21
Oh, really the pleasure's all mine, Scott, I mean, it's been great. And I would recommend this to anyone, at any point in time when they're trying to make a change. It's just so great.

Scott Anthony Barlow 23:33
The only other question that I have for you is, as you think back over this entire journey, if you kind of pick one thing that mattered more than anything else, what would that be? And I'm gonna force it to one thing here. Because a lot of time, you've probably even heard some of the podcasts where we talk about, let's choose the highest impact things, let's acknowledge that it could be different for everybody, but from your experience, what mattered most, overall, to really help you make this pretty gigantic change?

Linnea Calderon 24:05
I would say, to not let anyone or anything get in the way of achieving your goal. And that includes yourself, getting in the way in yourself, questioning yourself, or letting others question you just going and doing and figuring out a way to get what you want and working at every day, I think was his number one, you know, things can come up. And there can be experiences or things that may get in the way or take some time out of what you're trying to do. But ultimately, you know, don't let anyone or anything get in the way of your goal and your dreams.

Scott Anthony Barlow 24:41
Appreciate you sharing that. And thank you so much again for taking and making the time and coming on the show. And especially since you started out by finding us way back when at the beginning of this year. And it just means a lot to me that you'd come and share your story with everybody else and allow everybody else to benefit from it too.

Linnea Calderon 24:58
Oh, thank you for having me, and it's been a great experience. Thank you so much.

Scott Anthony Barlow 25:04
Hey, thanks so much for listening to the Happen To Your Career podcast. I really, really appreciate it. And I appreciate you. And guess what, we've got plenty more coming up next week, right here on Happen To Your Career. So take a listen to what we've got in store for you next week on the Happen To Your Career Podcast.

Linnea Calderon 25:26
And that's why I struggle in my current role because it's all very reactive, and it is draining. And the thing that's what I really enjoyed about the role I'm interview for, is I was so energized by it, you know, I'm planning something positive for the community to utilize in the future. And that was really the job.

Scott Anthony Barlow 25:46
That's right, all that and plenty more next week. It's here on Happen To Your Career. I will see you next week when the episode releases on Monday. All right. I am out. Adios.

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