486: How To Use Pivots To Advance Your Career With Jesse Janelle

HTYC Coach Jesse Janelle talks about how she experimented with her career (and eventually found her ideal role!) by continually pivoting into industries and roles she enjoyed more and more.



Jesse Janelle
Jesse Janelle, HTYC Career Coach

ACC certified career and life coach who helps high-vibe, high-achievers design their work around their life. Mom of 3.

on this episode

Jesse Janelle has gotten really great at making career changes. In fact, she’s had over 32 jobs! She learned throughout her journey that by defining the areas she enjoyed in each of her past roles and carrying those into the next iteration of her career, she’s been able to pivot into roles that fit her better and better. 

All of this experimentation led her to become a career and life coach. Who better than someone who’s had almost 3 dozen jobs!? In this episode, Jesse discusses her career pivots and how she ignored what society would tell her she “should do” and paid attention to what she enjoyed doing and what came naturally to her.

What you’ll learn

  • How to find your ideal career by dissecting pieces of your past roles
  • How to say no when you need to uphold your boundaries
  • How to craft the best version of your career story when job hunting
  • The importance of finding common threads between your roles, especially when switching industries

Jesse Janelle 00:00

I think that has been a thread throughout my career. And I think it's probably a pretty common thread if I've identified something that I'm really good at, never really stopped to think "do I actually love doing this? Or do I just love that I'm really good at doing this?"

Introduction 00:27

This is the Happen 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 00:47

I talk to people all the time who have excelled in their career, and they're exceptional at what they do. But they've also come to the realization that they're not finding enjoyment in their work. And honestly, this is a very normal experience. Here's what it comes down to. Just because you're good at something, doesn't mean you'll automatically enjoy doing it. Often the enjoyment that you're feeling is associated with all the positive feedback that you initially received for being so good at whatever it was that you're doing. So, if you've come to this realization that you want to find more enjoyment in your work, then something absolutely has to change. And you probably are wondering, what else can I do? If this thing that I've excelled at for all these years isn't what I want to do anymore.

Jesse Janelle 01:39

So when you're, you know, thinking about making a career change and want to move on to the next thing, you can position yourself in whatever light you want to if you can find the right thread throughout your background.

Scott Anthony Barlow 01:56

That's Jesse Janelle. And she's awesome. Jesse is a mom of three, an animal lover, a coffee enthusiast, which obviously I'm a fan of. And she's had many, many different jobs in her lifetime, everything from grocery store bagger to digital marketing consultant. But today, Jesse is an ACC certified coach on the HTYC team and also happens to be our Director of Client Results. Jesse joins me today to talk about how she's been experimenting with her career since a very young age. Pay attention to how Jesse really focused on the areas she enjoyed and each of her roles and carry those learnings into the next iteration of her career, continually making improvements until she found her ideal role. Here's Jesse kicking off our conversation.

Jesse Janelle 02:44

I started working when I was 14. And most of my career, I was holding anywhere from two to four jobs at a time. I've had over 40 jobs where... and I'm talking where I was a W2 employee type of jobs. If we're talking contracts, or clients that would be well into the hundreds.

Scott Anthony Barlow 03:07

That might be more than I've had. You might be the only person that I've met that has had, what I would say is, significantly more than what I've had, at least W2 is for sure. That's crazy. So was that... How did that happen?

Jesse Janelle 03:23

Yeah, so as soon as I was old enough to be able to work, I was always looking for ways to make money. And then as I got older ways to make an impact, but it definitely started when I was younger, with how can I possibly make more money. I just liked doing things. So my very first job that I was paid for, I wrote an article for my local newspaper, and I wrote a weekly article about the happenings at my middle school. So that was sort of my first paid gig. I'd get $30 for every article that I wrote. And I did that for a year in seventh grade. And then I started moving on to the jobs that, you know, high school kids would typically have– I worked at a childcare facility, I was a bagger at a grocery store, I was a barista for about four years. So those types of jobs throughout high school and college until I graduated from college and sort of landed my first full time job.

Scott Anthony Barlow 04:24

Tell me how you went from all of the different types of, as you call them more typical, high school kid experiences to other types of opportunities and experiences. What happened there?

Jesse Janelle 04:41

Yeah. So when I was in college, I went to Boston college, I majored in psychology and sort of crafted a major for myself in positive psychology. That was kind of a new thing when I was going to school and that didn't exist as an academic discipline but BC had a lot of courses around that. So I started studying positive psychology, and realizing I didn't want to go any of the traditional psychology tracks professionally. So I didn't want to be a clinical psychologist, I didn't want to be a researcher, a professor, anything like that. I really liked learning about and studying how people flourish and how people thrive. So while I was in school, the Institute of Coaching, which is a nonprofit organization out of McLean in Harvard Medical School, was founded. And this was my first sort of introduction to the idea of what coaching was, but it could be I started reading all about it. And I just reached out cold to the program manager of the Institute of coaching and said, "Here's all the things I can do for you. Will you bring me on as an intern?" So she said, "Yes." So I interned with them for three years. And it's something, we'll I'm sure we're going to come back to later in this conversation because it's a very full circle experience here. But I got to meet some really big people in the coaching world by attending their first conference. I got to learn a lot about coaching. One of my responsibilities was sort of organizing their entire coaching research library. So I got to read all the latest research about coaching, which was really cool. So when I graduated from Boston College, my first job out of school was as a health coach. So I got to sort of step into coaching full time right out of school. My school, Boston College, was just launching an Office of Health Promotion. So I came in as a health coach and sort of their operations and marketing person. So everything to do with like, launching this new office on campus, and also delivering coaching to the BC community.

Scott Anthony Barlow 06:59

What did you love about that at that time?

Jesse Janelle 07:04

A few different things. One, I loved that it was a familiar environment. I was still at BC, I was working with a lot of the people that I had worked with when I was an undergrad. And I loved that I did a million different things, which I still love today, in jobs. I was coaching. I was recruiting coaches. I was training coaches. I was like the administrator for the Office. I was developing all the marketing plans, like, everything that had to do with the setup of the office, I was doing. So I liked that. Every day was something different. And nothing was sort of out of my range of responsibility, like, anything that I wanted to do was available for me to do.

Scott Anthony Barlow 07:54

All of the million different things that you get to do, is that about variety for you? Is it about the learning? What causes you to love that aspect of it? Because not everybody loves being responsible or doing a million different things.

Jesse Janelle 08:10

Yeah, I definitely love learning. So that was a good call out there, Scott. I definitely love learning. I love being a beginner. And I know a lot of people don't like that. But I really do. I love when I can... when I'm tasked with doing something that I've never done before, and I have to figure out how to do it. That really excites me. I also really like multitasking. I know that the research says that people cannot multitask well, right? That most people cannot do more than one thing well at the same time. And also that 98% of people think that they can do more than one thing while at the same time. But I've really liked having a lot of things on my plate. I like being able to task switch and go from one thing to another. And I feel like I'm saying all things that people usually hate about their work or their life. But these are all the things that I really like– switching between different tasks, being a beginner and getting to learn new things.

Scott Anthony Barlow 09:17

How do you think about when you're a beginner for something new these days versus you know, say 10 years ago, how do you think or structure that in your mind? Like, what's something that you're a beginner at or have been a beginner at recently?

Jesse Janelle 09:31

Yeah, I'm trying to think of something that I just started– picking up tennis again. So yeah, I used to play tennis. I used to play varsity tennis in high school. But it feels like being a beginner again, because I haven't played competitively since I was 17 years old. Right? So it feels like picking up something new again. I think because I'm a lifelong learner and because I love learning so much, that's how I step into it, as being a beginner to me as an opportunity to learn. And if I no longer feel like a beginner, it almost makes me not like it as much. Like, as soon as I'm not a beginner anymore, some of the excitement is gone from it. So I need to find new ways to be a beginner again, new things that I can learn, and continue to do that over and over again.

Scott Anthony Barlow 10:25

That last statement about as soon as you're not a beginner, some of the excitement wears off, to some degree, I have definitely experienced that. In fact, I would say, arguably, that's probably one of the biggest reasons for many of the career changes that I've made personally, over, I don't know, how many years... last 20 plus years, that excitement wears off, my interests would waive, I'd get bored, quite frankly. And then my performance would start to dip in the early years, this is what would happen, my performance would start to dip. And then to avoid starting to have really awkward conversations with my boss about my performance dipping, because I couldn't make myself be excited about it again, I would eventually career change and then go someplace else, negotiate a higher salary. And that's how I started career changing. But that leads us back to the question of, you were there, you were having fun, you're off with BC, and what caused you to be able to move on from that situation that you were telling us about?

Jesse Janelle 11:31

Yeah, I probably got bored. Like you're saying, I probably got bored, it felt like I wasn't a beginner anymore. I was actually there for about a year and a half to two years. And then I took a job at Harvard, as a research assistant, hated it. Stayed there for about three months, and then moved into a marketing job. And I stayed in marketing for the next about five years. And that's where I spent the majority of my career. And I had done a little bit... Marketing was one of my tasks when I worked at BC in the Office of Health Promotion alongside coaching, and it was something that I was really good at. And I think that has been a thread throughout my career. And I think it's probably a pretty common thread if I've identified something that I'm really good at, never really stopped to think, "Do I actually love doing this? Or do I just love that I'm really good at doing this?" So, you know, I fell into that marketing career and succeeded in it. I was very good at it. And I would sort of be at someplace for a while, decide I was kind of bored of that location, that job, that company, and then negotiate a higher salary someplace else, move on to a different hire marketing role someplace else. So I did that for about four years, until a major career change happened for me. So in 2015, this was a big year for me, I got married, bought my first house, got pregnant with my first son, Jacob. And I had made a career change. I had been working at a company for about a year and a half. And I started a job at a new company, a small nonprofit in Boston. And about three months into working there, I let my boss know that I was pregnant. I literally got pregnant the week that I accepted the job. So when I accepted the job, I didn't know I was pregnant. And I had been working there for about three months. And after I let my boss know that I was pregnant, a week later I was laid off. Yes. So I had to kind of decide at that point, do I want to go out and find another job? Or do I want to do something completely different? I had never had a kid before. I didn't know how I was going to feel after I had a baby. If I was going to want to stay home, if I was going to want to work, what I was going to want to do. I had a pretty good inclination that I was not going to want to commute an hour back and forth into Boston. I live in the suburbs of Boston. So I had a pretty good idea that that's something that I didn't want to do. But I sort of explored a couple of different paths at that time for about three months. I applied to a lot of jobs. I got a couple of job offers and turned them down. And I ultimately decided to start my own business. So I started doing contract marketing consulting. So I have had a long career in digital marketing or a successful career so far. I have a lot of clients who always asked me if I did stuff on the side, but I never had in the past. So I sort of decided to turn that into my full time thing. So within about a month, I had enough clients, I was working about less than 25 hours a week, and I was making about double what my salary was from the job that I got laid off. So I did that. That's sort of how I started on this self employment path that I've been on for the past seven years.

Scott Anthony Barlow 15:35

Well, let me ask you about that. So what was that point in time like for you? Let's go back there for just a moment. When you realized that you were making, what did you say, almost double at that point in time?

Jesse Janelle 15:49


Scott Anthony Barlow 15:50

What was that realization like for you?

Jesse Janelle 15:53

It was very reinforcing for me. It felt validating. It felt like I'm actually probably better at this than I thought, because people were willing to pay me a lot more than I was making as an employee. And I got to pick the people I wanted to work with. The client was a jerk, I didn't have to work with them, right? So I got to sort of start to specialize, I got to work with the type of clients that made me feel alive and that I enjoyed working with, I tend to lean towards people who are kind and caring. So I got to work with those type of clients. And yeah, I mean, it felt really reinforcing for me, and really validating.

Scott Anthony Barlow 16:41

That seems to be a theme here. Each change that you made, created further reinforcement in one way or another. And, it seems like one of the things that you've done really well throughout your career is paying attention to those areas that get reinforced. And then just carrying that through to the next step, the next iteration, the next, not necessarily bigger, better, but next improvement in terms of what you want. So here's the question I have for you. You had that initial change decided, I'm going to do my own thing, got relatively close to immediate validation that, hey, you're actually really, really very good at this even more so. What caused you to pivot from there?

Jesse Janelle 17:30

That came more organically. So I had my marketing consultancy, really actively, until about three years ago. I started to specialize in coaches. So I started doing a lot of marketing consulting, and then sort of business operations consulting, like, almost like a consulting COO type of thing, for a lot of coaches and thought leaders. So then, and this is where it comes full circle back to the Institute of coaching, a couple of my clients were big name people that I met through my internship at the Institute of coaching, and being able to work with them, really helped me start to pivot into providing more coaching services and less of the consulting slant on it. So it's sort of organically... my business sort of organically shifted to instead of just me coming into your business and helping you grow from a marketing perspective, I was helping thought leaders and coaches position themselves to be able to get more clients and to be able to make a greater impact by being heard.

Scott Anthony Barlow 18:56

One of the reasons I was really excited to have you here at HTYC was this very unique mix of understanding and experience around psychology, particularly positive psychology, and then bringing that into how you're able to teach and share and communicate information, and how you put everything together holistically. So actually, all the elements that we just covered that you have, that have even caused you to move from thing to thing to thing, are some of the reasons why I am most excited to have you on our team. So first of all, meant to be a compliment. Absolutely. And second of all, I think that's a really wonderful illustration, though, to how you can harness all of those past learnings and really pull them together in a way that is more useful than the individual experiences themselves. What I'm really curious about is, what advice would you have for someone who's listening to this, about making changes, because most people who are listening to this have not made 40 changes?

Jesse Janelle 20:12

Yeah. What has made the changes easier is when I could find the thread to the next thing. So there's a lot of different points to connect that thread, right? When you've had 40 plus experiences, plus all the contract work and everything that I've done, when you can find whatever that thread is looking backwards between what you've done and where you want to go, that's when you can craft whatever that story is that you want to tell. And you can control that story. So when you're, you know, thinking about making a career change and want to move on to the next thing, you can position yourself in whatever light you want to if you can find the right thread throughout your background. And this isn't, you know, this isn't lying or being deceptive. It's just a matter of choosing what experiences and what learnings in your background you want to highlight, which ones you want to bring to the surface, and which ones are relevant. And being able to connect those in a story format, I think that's the easiest way to make a career change. If you can't find that story, if that thread isn't there, to me, that's a sign to think about, if where you're trying to go is really where you want to go, and really something that's going to serve you? Because if you haven't had any type of experience or any type of learning, where you can give yourself any type of evidence that this is going to be a good change to make, then that would be a reason to sort of really evaluate that and decide if it's the right change.

Scott Anthony Barlow 22:09

I love that piece of advice. And here's why I think that that's so important, and why I agree with you, is that on the surface when someone's listening to this podcast, and they're hearing stories of career change, what's not obvious all the time, is that even though something sounds vastly different, there's always that thread there. I absolutely agree with you. And I would love to leverage your experience on a couple other topics, too. Let's talk about boundaries for a second. Okay. So one of the things I've heard you say is that when people are afraid to set boundaries, it's usually because they are afraid that somebody is going to believe they don't care enough. Tell me about this.

Jesse Janelle 22:53

Yeah, boundary is a hot topic for me. So that's a good one to bring up. I have three kids. And, you know, working for Happen To Your Career, owning my own business as well, boundaries need to be in place for me to thrive in my life. When people set up boundaries, a lot of times the fear around that or around putting up a boundary is that you will be perceived as not caring about the person, or the thing that you're putting the boundary up against. I don't believe that to be true. I believe that boundaries allow you to be the best version of yourself. Boundaries protect you and your family, they protect your most valuable resource– which is your time. And it gives you the ability to decide which things you'll say yes to and which things you'll say no to. And one of the things they always say about boundaries is when you say no, you're protecting every future. Yes. So when you say no to something, when you put up a boundary against it, it opens up your capacity and your availability to be able to say yes to the things that are really aligned in that matter to you. And if you don't have those boundaries up, if you are someone who just says yes to everything, then you're eventually going to be at max capacity, you're going to be tapped out and something's going to give, most often what does give is your own self care or your own prioritization. And for me, that's something that comes first, those blocks of time for myself, whether it's, you know, working out with my husband or taking my dog for a walk or taking a bath in the evening, those get put in my calendar first. So I almost think of it like the way you might budget money and you'd pay yourself first or you'd put money into your retirement before you start, you know, budgeting the rest of your money out to everywhere else that needs to go out to, I pay myself first in time and that means putting up boundaries.

Scott Anthony Barlow 25:14

What are your favorite ways to say no? Because here's a little bit of pretext for my question. I think that boundaries has become a more popular topic over the last, say, 7 to 10 years, and rightfully so, I think it's very timely. And it's going to become even more important as we continue to grow more and more connected through technology, even more so than what we can imagine right now. And also, at the same time, I have found that sometimes the people who struggle the most with setting boundaries are the same people who don't necessarily know how to or haven't had a role model in a way. And this is definitely the case for me. I struggled early on, and sometimes to this day still can struggle with boundaries. That said, what's made it easier for me is picking up a lot of tools along the way. And so I'm curious, what are some of your favorite ways to be able to say no, and hold your boundaries?

Jesse Janelle 26:18

Yeah, I would start by thanking the person for thinking of me. So I usually would say something along the lines of, "Thanks so much for thinking of me for this. I'm sorry, I don't have the capacity right now to be able to do that." I love using the word capacity. I feel like I've already used that, like 30 times in this podcast so far.

Scott Anthony Barlow 26:39

We're gonna go back and count it later, we're gonna have a capacity tally.

Jesse Janelle 26:43

Yeah. But that is one of my favorite words. By telling somebody that I don't have the capacity to do it, I'm not necessarily saying that I don't have the time, I could possibly have the time. But by saying I don't have the capacity, it is saying this is something that's going to reduce my energy or my ability to do the other things that I need to do. And it's not a matter of, literally, there's an opening at 5pm in my calendar, and I could do it or not do it, that I don't have the capacity to do it. So that's usually how I phrase it.

Scott Anthony Barlow 27:22

But I know that you and I share a, how shall we call it, let's say a mutual detest of busyness being equated with good. And here's what I mean by that. When someone says... when you ask someone, how are you doing? And they tell you, "Oh, I've been so busy." And like they're happy about it. And it's like that is their version of good in one way or another. I don't get to judge for what everybody considers to be good, but being busy for busy sake, and confusing that with wonderful, that's a whole different thing. So does that make you crazy when that situation happens? Tell me about that.

Jesse Janelle 28:04

It does make me crazy. And It especially makes me crazy when busyness is equated with productivity, because I value efficiency as one of my highest values probably. So... and busyness in general, is something that I try to avoid like the plague. So this is pretty atypical for, you know, I would consider myself a high achiever. And I think a lot of high achievers fill their schedules. I mean, it's pretty common for high achievers to be busy people. They're doing a lot of different things. They're achieving a lot of different things, right? Over the past, I would say, about a year and a half, I've made a big switch away from that of adopting a very strong anti-busyness mindset. I love to have whitespace in my calendar. I do not feel the need to over schedule myself. I like to have as few things to do as possible. And I say that while still being in alignment with what we talked about earlier, where in my professional life, I like to have a lot of responsibilities. But I like to do the pre-work to organize that in such a way that my life does not feel busy, doesn't feel chaotic, it doesn't feel like I'm needed from one thing to the next thing. There's spaciousness. To me, that's part of what living a good life is. So when I hear that somebody is afraid of that whitespace or that they're afraid that if they're not busy, they're not achieving, or they're not being productive, it honestly breaks my heart, and it makes me really want to just sit down and have a conversation with that person.

Scott Anthony Barlow 30:06

It's fascinating to me that socially, we have, like, when that whole conversation that we just described where you ask somebody how they're doing, and then they're like, "oh, it's been so busy." And we're so happy about it and everything. It is so very different to not be busy or socially, we might judge people, accidentally or unintentionally, that if you are not busy then you're not doing well, or not achieving or not successful, or you don't have things to do, or any number of other judgments that can occur. So what advice would you give to someone who wants to become, just begin becoming less busy, and instead fill their life with more intentional activities?

Jesse Janelle 30:58

The first thing that needs to happen is that you need to know what your values are. Everything else becomes a lot easier when you know what your values are. So if you do some type of activity, whether it's a value sorter or whatever, to be able to, you know, do some introspective activity to find out what your values are, then it's a lot easier to act in alignment with them. So it's a lot easier to say, "No", we're talking about boundaries, and protect those future yeses. When you can ask yourself the question, "Who do I want to be right now?" When you can pause just for a moment and ask that question and then act in alignment with your values, you can start to create more space, because you'll find that there's a lot of things you can say no to. And it becomes a lot easier to say no, comes easier to free up your time, to free yourself of the guilt of saying no to things because they're not in alignment with your values. And it's a snowball effect. As you start to take more actions and fill your day with things that help you become the person that you want to be that are in alignment with your values and with who you're trying to become, then it's easier to identify, and those actions start to build upon each other. And pretty soon you're, you know, living a life where everything that's in your calendar, everything that you're doing is in alignment with who you are now, with who you're trying to be, and it feels good.

Scott Anthony Barlow 32:34

You know, for somebody who is listening to this, and they're really starting to think, "Should I make a career change?" What advice would you give that person?

Jesse Janelle 32:46

My advice would be to remove "should" from your vocabulary. To me, when somebody is thinking about, "Should I do this? Should I take this job? Or, you know, I majored in engineering, so I probably should just stay in that field. Or this field would make me a lot more money, so I should probably think about going there." Take 'should' write out of your internal monologue and your conversations with people. Because when you remove that force, which to me, 'should' is an outside force, it's thinking about what has society told me that I should do or what have people in my family or friends or people in my life told me that I should do. When you remove that, and that line of thinking, you can connect into what you really want. Where are you trying to go? What do you want out of your life? What do you want your life to look like? And it's not what it should look like. Should I make a career change? Should I stay here? Or should I move on to this? You can really just consider what is true to you and the life that you want to live in.

Scott Anthony Barlow 34:10

Many of the stories that you've heard on the podcast are from listeners that have decided they want to take action, and taking the first step of having a conversation with our team to try and figure out how we can help. And if you want to implement what you have heard, and you want to completely change your life and your career, then let's figure out how we can help. So here's what I would suggest, just open your phone right now and open your email app. And I'm going to give you my personal email address, scott@happentoyourcareer.com just email me and put 'Conversation' in the subject line. And then when you do that, I'll introduce you to the right person on our team. And you can have a conversation with us, we'll try and understand your goals and what you want to accomplish in your career no matter where you're at. And we can figure out the very best way that we can help you and your situation. So open up right now and send me an email with 'Conversation' in the subject line; scott@happentoyourcareer.com.

Scott Anthony Barlow 35:14

Hey, I hope you loved this episode. Thanks so much for listening. And if this has been helpful, then please share this podcast with your friends, with your family, with your co-workers that badly need it. Here's a sneak peek into what we have coming up in store for you next week.

Victoria Lyon 35:33

I was one of several people that was let go. And there had been some talks about some uncertainty coming ahead. But I had been taught that adding value to the company and making myself indispensable and doing good work that I shouldn't be one of those people that will lose my job.

Scott Anthony Barlow 35:53

What happens if you've gone through the hard work of making a career change, and you've now ended up completely changing what you thought you'd be doing for the rest of your life? You finally land in this role that you're really excited about, you're enjoying it, it's checking all of your boxes, you're pumped, and you get unexpectedly laid off? Bummer, right? Well, that's what happened to Victoria Lyon. Victoria had been on the podcast before in Episode 467, where she talked about her career change from the frontlines of COVID research to landing her unicorn role as a project manager at a health tech startup. We brought her back on the podcast because her new organization, unfortunately, downsized and Victoria's role was cut. However, she didn't let that keep her down for long and she's here to share the next chapter of her career change story.

Scott Anthony Barlow 36:47

All that and plenty more next week right here on Happen To Your Career. Make sure that you don't miss it. And if you haven't already, click Subscribe on your podcast player so that you can download this podcast in your sleep, and you get it automatically, even the bonus episodes every single week, sometimes multiple times a week. Until next week. Adios. I'm out.

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