657: How Laura Landed Her Dream Career After 66 Job Applications (Without Burning Out)

(00:00) Laura MacDonald: I didn’t know anyone in the department, but I reached out to the director on LinkedIn and he answered and said like, “I hope we get to meet in the second round.”

(00:10) Scott Anthony Barlow: That's Laura.

(00:11) Laura MacDonald: And now he's our boss.

(00:12) Scott Anthony Barlow: She's a customer support manager who got laid off.

(00:15) Laura MacDonald: That time, we've been searching for something different or more, or feeling like I'm not exactly in the right place.

(00:21) Scott Anthony Barlow: She wasn't just looking for another job, instead, she wanted an extraordinary fit. Laura didn't just get a new job. She made a full-on career change into talent development as an instructional designer. Now, the question was, how did she make this happen?

(00:36) Laura MacDonald: Every person I've talked to is someone who's like a connection for next time or someone who's rooting for me or can give me information that I need to get where I need to go.

(00:47) Scott Anthony Barlow: Laura learned to rapidly accelerate a career change process that would take most people three to five years. She did it in just months.

(00:55) Laura MacDonald: The job I have now is the 66th job that I applied for.

(01:00) Scott Anthony Barlow: In this episode, you'll hear how Laura made connections very quickly, so quickly that it led to other problems.

(01:07) Laura MacDonald: The biggest challenge was probably learning to reject a couple offers.

(01:12) Scott Anthony Barlow: You'll also learn how she used her ideal career profile and designed career experiments to find an extraordinary fit, making the hard decision to turn away perfectly good job offers. This is Happen to Your Career, the podcast that brings you real people, real transformations, and the courage to do work that truly fits. If you haven't already subscribed, click Follow right now so you don't miss any of our new episodes.

Here's Laura, describing what led to her career change journey.

(01:39) Laura MacDonald: I lost my job in April of last year, and my mom is a huge like Happen to Your Career podcast listener. So as soon as that happened, she really encouraged me, not just to find a job, but was like, “This is a great opportunity, I think, for you to take that step and make more of a career transition.” Been searching for something different or more, or feeling like I'm not exactly in the right place, but I'm doing well, so I'm happy, or I'm happy with certain parts of my job. I started my career as a flight attendant, and in that role, there were so many great parts, but I've never really felt completely like my strengths were used or I was doing something that I found rewarding.

So I kind of always had one foot out the door. And then after I left that role, I was in customer service and similar kind of thing where I was like, I'm doing well, so this must be the job for me. But I still kind of felt like I was never quite satisfied.

(02:40) Scott Anthony Barlow: Shout out to your mom.

(02:41) Laura MacDonald: Yeah. I'm sure she'll be excited to hear that. So yeah, it was a challenge, obviously. Like, being unemployed is not the funnest time, but it was a really cool opportunity to kind of look at my entire career trajectory and really make a plan of what I wanted, you know?

(03:00) Scott Anthony Barlow: Well, and I think that you make a really good point, like I've been not employed for an extensive period of time before.

And you're right, it's not fun. It can be, like, but I think the circumstances that caused that, whether it's of your own choosing or somebody else's choosing, can definitely influence it quite a bit. And I think that the challenge, and I think what you did really well, is taking that time and taking advantage of it, even though like, there's some not-fun aspects to it.

So what I'm really curious about is when you started on the beginning part of this journey, after you separated from your past employer and you were starting to figure out what was the right fit for you, what was challenging about that time period?

(03:52) Laura MacDonald: The biggest challenge was probably learning to reject a couple offers. Like that was something I don't think I would've been able to do on my own without knowing I had the support of like a coach. And probably a lot of people, but me for sure, I have a really hard time not convincing myself, 'cause you see a job description, you're like, “Yeah, I could do that.” And then you are working so hard on your application, you're kind of convincing yourself that that's what you want.

And then sometimes after I'd be rejected, or even if I was successful, I'd realize, like, “This isn't what I want at all.” And when I look back, how did I get so confused about what I'm really looking for? So that was one of my favorite parts of coaching, was writing down my strengths and writing down like my ideal career profile, so I could really compare things back and be like, what is this measuring up to what I see for myself and kind of taking away some of the emotional feelings of that time.

(04:55) Scott Anthony Barlow: Let's dig into that. I think that's such an important point. How did getting to know in depth your strengths and what was most important to you, how did that translate into making better decisions along the way when you have real opportunities in front of you?

(05:13) Laura MacDonald: I have one side of me that's very analytical. So it was nice and visual to be able to compare two documents. One of them that's, I want a remote job or I want a hybrid job. I want one that pays me this and gives me these opportunities. And then taking a job description and kind of highlighting and going through.

Okay, so it's in office, so it doesn't match up with that. And okay, there's a large part of it that's doing a task that I hate to do and it kind of just, over time, I was able to do that without looking at two documents and just off the cuff, reading through a job description or even the job title that I might be exploring and thinking critically about, is this gonna make me happy?

Does it align with what I said I wanted? Maybe what I wanted has changed, but just kind of thinking critically that way, I guess, was helpful to have kind of a framework to work off of.

(06:07) Scott Anthony Barlow: So you're saying having that basis for comparison, where you have what we tend to call an ideal career profile, which for everybody listening, they can think about it as just like this big list of all the parts and pieces that create a phenomenal opportunity for, in this case, you, Laura, and then it sounds like for you, having that there to be able to compare against whatever existing opportunity it was, whether we're in the stage of looking at a job posting or even job title or job description wise, and then later stage, I would imagine, you know, offers as well. But being able to have those side by side was the part that was most helpful in being able to get to the point where you called it, thinking critically.

(06:50) Laura MacDonald: Yeah, and I think too, looking back at my past career, it kind of started to help me like understand why I wasn't happy in some of those roles where I could say, you know what, like flight attending for example, allowed me flexibility and the ability to travel and so many things, but I was lacking like purpose in my work or finding something that really I felt rewarding.

Or being able to create something which I learned during this process is really important to me. Yeah. So kind of was able to even look back and be like, “Oh, that's why these things didn't quite feel right.” Instead of just it being a feeling, it was like it didn't measure up in these specific ways.

(07:32) Scott Anthony Barlow: Oh. So that's really interesting. So for you, then, it allowed you to take these feelings and start to be objective about what are the actual specific parts that are missing?

(07:44) Laura MacDonald: Yeah. I don't think every job you're gonna be happy every day, but if there's parts that, like I've taken roles where even when I'm applying for, or even when I'm signing the contract and starting my first day.

I am thinking like, “Oh, soon this will lead to a promotion.” Or soon I'll be able to like, I'm convincing myself, here's a future state where it'll wind up better with my values. I think it was a skill truly where it was like at the beginning I was, had to go slowly and then now I can. If I heard of the promotion at work or something, I could really know very quickly whether that's something I'm interested in or not based on whether it matches up with my values, and my strengths and interests.

(08:27) Scott Anthony Barlow: We all start not very good, not very great at being able to assess what we want and, you know, where do we find it in the real world and how existing opportunities measure up against what we want. So I'm curious in your experience, what made that more challenging at the beginning? And then also, I'm curious, what helped you become better at it?

(08:49) Laura MacDonald: Yeah, I guess at the beginning it really took some time for me to build an ICP that I was really confident in. 'Cause when I first approached, I was like, “Oh, I dunno,” it just seemed, it was a blank page, right? So it's like, I don't know, what is rewarding work to me, and what tasks do I wanna be doing at work or things like that.

Filling it out was a challenge. But taking the time to go back into my work history and really examine, talk it through with my coach too, like, I think that was really helpful for them to say like, “Oh, it really sounds like you find it rewarding to create something tangible you can look at and say, ‘I created this and it's making my work better.’”

Or you know, like, really be proud of it in that way. I also took a lot of time to like chat with friends and family and hear from them about what they've heard me say I like or don't like. And then building that over time as well. I really wasn't looking for anything specifically creative at the beginning.

So that was interesting to me over time, that it was what was getting me excited in the job descriptions that I was seeing. So I added that in, and then by the end, it felt like it was so a part of me that I could probably write it down pretty close to my ICP if I lost it one day, like I know it pretty well, 'cause it's just reflecting on who I am and what I want.

(10:15) Scott Anthony Barlow: I think that's a really good illustration of the process of becoming, not necessarily just more self-aware, but specificity, a higher degree of specificity for self-awareness and what you need too, and being able to go from, “Hey, here's what I think I need, maybe. I'm pretty sure,” to observing those patterns like you discovered along the way that I really have this need to be able to create in a different way than what you thought before, and then being able to get to the point where you are actively observing and recognizing in real time, like, “Yeah, this is totally not a fit.”

Or, “Yeah, this is absolutely a fit.” It's not an easy journey that, you know, quite frankly, it does take practice.

(11:01) Laura MacDonald: Yeah, and for me too, I remember talking to my coach about. It was hard to parse out what I'm good at or have been told I'm good at and got positive feedback about, and what I actually enjoy doing and look forward to when I see it on my calendar.

After each one, I just felt exhausted and drained. So, really like listening to myself and taking the time to be like, does this fill me up? Does this make me happy, or is it something I'm doing and I'm told I'm good at, but I don't really want the bulk of my time to be spent that way?

(11:38) Scott Anthony Barlow: And I think that is where a lot of people struggle with. So I'm curious what worked for you to be able to start to separate out, here's what I'm good at, versus here's where I want to spend my time?

(11:51) Laura MacDonald: I think for me, talking it through is the biggest thing. I feel like even hearing what other people have to say, but also hearing myself say things out loud and realizing, kind of being able to think critically about what I'm saying as well was helpful. I remember my coach, Roberta, also really encouraging me to pay attention to my body and my physical reaction to things. So yeah, one for me that always stands out is just like turning off, this sounds like, it's not about that specific person I'd be meeting with.

But I'd like turn off my one-on-one camera, I'd end that meeting and just be like, “Oh, I'm so tired.” Or like, “I'm so drained, I don't wanna jump into another one.” Even though I like chatting with this person and I like chatting with the next person, and I enjoy our conversations. My body was saying like, “This is not where you wanna be spending your day.”

I've examined my past, and I've thought about my ICP, and I really think what's perfect for me is like an executive assistant, or admin assistant, or office manager. That's really, I think, the perfect thing for me. And then I went down and applied for those roles. I got a role, like a short-term, three-week role, so this is perfect. I'll have the chance to really practice it, see how it is, add it to my resume, which was a great thing, and then get up there and really pursue this trajectory. And I absolutely…

(13:16) Scott Anthony Barlow: What did you hate about it? What are the parts that didn't fit on your ICP?

(13:20) Laura MacDonald: Yeah. It was interesting because I felt like so much of it on paper, I was interested in, like, I like being organized.

I like managing calendars and responding to emails. All that sounds interesting, but I feel like so much of that role is changing depending on the executive you have and how organized they are, and things are always moving and changing. And so even if you prepared perfectly for this meeting they have tomorrow, it could be bumped, and it would be changed.

And I just, yeah, I guess that what I discussed earlier, of like wanting something tangible to like, at the end of the day, be like, “Wow, I did that well and now tomorrow's gonna be better than yesterday,” or something like that. It's like it's just a moving train and you're just trying to keep up the whole time.

And I found that difficult. And yeah, again, just a very physical reaction, physical or like I felt anxious. I didn't feel excited about it, but yeah, it was because I had been having these conversations with my coach and been like going through that Happen to Your Career, like library or curriculum. I looked at it more of like, “Oh, that was a cool opportunity.”

I tried it, crossing it right off the list, and like I can kind of bring what I've learned into my next experiment, and like maybe I wanna pivot into something else. So yeah, there was quite a few different phases of my journey that were like that, but it always kind of felt like I was a little further along than I was in the beginning.

And yeah, just like thinking about how different I was. And how different my skillset was from the beginning to the end. Yeah, I think like each bit kind of taught me more and more until I had everything that I needed to land the role that I did. So yeah, it was a cool journey.

(15:12) Scott Anthony Barlow: Let me ask you about the part where you were going through your conducting experiments for the purposes of learning what is a fit, and then they didn't work out the way that you thought they might, the way that you hypothesized that they might, if you will. What do you think really allowed you to look at those as making progress, versus, I think it could be very easy in that situation to say, “Oh, this totally didn't work out the way that I thought I did. Ugh, I feel like I'm starting over.”

And I think those are two very different outlooks, but one tends to be very healthy and be very useful. The other tends to, you know, keep people stuck in the same place. What allowed you to be able to have that more positive outlook?

(15:59) Laura MacDonald: Leaving myself space to feel those feelings and then get to the optimism afterwards was also helpful. Like when I was working really hard to get a certain job and I went, first interview, second interview, on prepping all the time, and then getting that rejection email. Like, I think it was really valuable for me to also be like, “Okay, I'm not applying for anything else this week.” Nobody asked me how my work job search is going because I'll just feel like I can't talk about it right now.

And then kind of moving into that next transitional phase of like, “Okay, now I've kind of grieved that or processed that emotion of like, I thought it was gonna go one way and it didn't, and that does suck.” And then kind of starting from a new place of like, “Okay, what did I learn? What can I take from that experience that's gonna better prepare me for what comes next?”

And just thinking of it more as like a process, I guess. And just working it one step at a time. Or like, thank goodness that I'm learning these things, 'cause I would much rather learn that's not quite right and pivot, rather than learn by doing that job and hating it every day and coming home at the end of the day, knowing that it's not the right fit.

Like, I guess I just tried to kind of keep that north star of like the goal is to get somewhere where I know I'm in the right place,

(17:24) Scott Anthony Barlow: And you're right, both paths are learning, but one takes significantly more time versus the other allows you to pivot much more quickly.

(17:34) Laura MacDonald: I kind of came in it with the energy of I could do all of this myself. But having a coach maybe will help me stay accountable or give me a different like opinions that I might not have considered myself. And I feel like that was a huge part, too, of feeling like I had that safety net to come back to. It wasn't just me trying these experiments, and you know, I could really trust coming to the next session, we could brainstorm of like, “How did that go? What went well, what didn't, we're in it together.” And having that coach along the way helped me to kind of have faith, I think, in the long-term goals that we'd set together, and we'd communicated if I was having a day where I was more discouraged or if I was having a day where I was like ready to go, guns blazing.

Either way, they could like match me there and help kind of counter me or challenge me in ways that I definitely wouldn't have done myself.

(18:29) Scott Anthony Barlow: You started talking about, you know, when things work out versus don't work out. My understanding is that you actually went after over 60 different opportunities as a whole. Is that right?

(18:43) Laura MacDonald: Yeah. I'm a very, I love a spreadsheet, so–

(18:47) Scott Anthony Barlow: I've gathered this. This probably says something about your strengths, right? And the analytical side.

(18:51) Laura MacDonald: Yeah, analytical. But yeah, I created a master spreadsheet with every single job that I applied for, and I feel like that really helped me. I like copied the job descriptions off LinkedIn or off like the job career page, because sometimes they'd take them down, and then you'd be doing an interview, and he'd be like, “What did it even say in the job description?” So, capturing all of that writing down when I applied, and it was really cool for me too, along the way to see what's effective and what's not effective, and kind of capture learnings along the way of like getting a referral is a huge, is like so much more likely to lead to an interview.

Or things like that. But yeah, I like looking at that sheet 'cause it's like I really like, I put in the homework. It was a tough journey. I think this job, the job I have now, is the 66th job that I applied for and the sixth, the fifth or sixth for the company that I work for. So by the time I got there, like I had learned so much compared to the first job I applied for, I think

(19:57) Scott Anthony Barlow: Let's leverage this analytical side of you and this analytical strength of you for just a moment, and let's go through some of the numbers, because I think, if I understood, there were some paths that were significantly more effective compared to other paths for you. What were some of your learnings when looking at the data afterwards?

(20:19) Laura MacDonald: Yeah, it was great because I know that I think you had said in some of your videos where the information on Happen to Your Career was saying cold applying for things online is never gonna be more effective. Like it's only 2% or 5%, but I'm the kind of person, “I wanna test it. I wanna try it out.”

So it was cool to kind of see it for myself, and I think I needed to kind of tests the waters, and yeah, just to feel confident in that. But yeah, the referrals that led to interviews, like 69% of the jobs I applied for with the referral led to at least the first interview, versus my cold applications, where I was just applying through the career side or something like that, was 8%.

So you can see like very clearly just from the numbers that even just a foot in the door, and I did become very, a lot more comfortable reaching out on LinkedIn and trying to create those warm connections, even if I didn't know anyone, like at the airline I work at now, I didn't know anyone in the department.

But I reached out to the director on LinkedIn, and he answered and said like, “I hope we get to meet in the second round,” and now he's my boss. So sending a really nice message to the like talent acquisition specialist that I met with and keeping that door open was really helpful for later when I applied to that, my company for the second and third and fourth time, and every person I've talked to is someone who's like a connection for next time or someone who's rooting for me or can give me information that I need to get where I need to go.

Reframing networking as like just being social and connecting with people that you know, and not necessarily like it needs to lead to a certain thing or you're just in it to get a job off of them, but just kind of, yeah, exploring what people are up to and what they're passionate about, and that part of this experience was a lot more positive than I had anticipated in the beginning.

(22:27) Scott Anthony Barlow: I think generally people wanna help. I think that is a desire that most humans have, except for sociopaths. But most humans are generally caring about others and want to be helpful to others, other humans. I mean, every time I get to have this type of conversation, like what you're describing right now, where somebody has gone through that trajectory where it's like, “Hey, this feels kinda weird and odd,” and eventually get to the point where. It's like, “Hey, like so many people were so helpful and it was so fun and way different than what I anticipated.”

That always restores my faith and humanity because people just generally are very willing to help as long as you can figure out ways that are genuine to you to be able to ask and interact. I think that's the key part that's a little bit hard and weird and uncomfortable for so many of us.

(23:19) Laura MacDonald: Yeah. I think that was really helpful for me getting over that hump of like reaching out to people was trying to write out scripts that I could send to them like by email or on LinkedIn or however, just yeah, that felt natural and it wasn't some template that it pulled off Google, but really spoke to like, and sounded like me, where I was like, “Hey, I'm looking for a job. I know you have this job. If you're around, you wanna chat for half an hour. I would love to pick your brain about this.”

My role now it is hybrid, so that's really helpful in having some work-life space and balance. And the work that I do, yeah, I find it so rewarding. I feel like I put a lot of energy into it, but it always feels like I am getting a reward from it as well. So there's things I've created in the few months that I've been there that I'm super proud of that I can look back at.

And like I was saying before, like tangible things that I could look at and be like, “Wow, we taught people in the contact center how to do this thing that they didn't know how to do before, and now they're doing it.” When it came to like on an airplane, you're working with new people every day, and then they go home, and tomorrow you have to teach them all the same thing.

You have to show them a seatbelt again, you know, and like help them again and explain the same things. In this way, like I really feel like I'm building on things. I'm building relationships with coworkers. You’ve got training, and yeah, I'm just excited to go to work each day.

(24:50) Scott Anthony Barlow: What advice would you give to someone else who feels like you did when you came into this, where it's like, “Uh, networking. I don't know why I feel so weird about it. It's uncomfortable. It's, you know, it feels sort of transactional.” Like all of those things that you felt, you know, just 12 months ago.

(25:09) Laura MacDonald: I'd say for me, having a coach for that can't be overstated. Like, yeah, I had read articles that were saying you should network, and here's how you can do it.

I'd maybe practiced or done it once or twice, but I always kind of was cringey about it. But having a coach that I could practice with and write scripts with and even go through my LinkedIn and kind of take a dive and be like, which people might be interesting people to reach out to. It's like any coach, like I do Pilates, you know, I could do it at home, I could put on YouTube, but I'm not going to, or my form won't be as good or sure. I won't feel as confident.

Whereas when you go to someone who's a professional and can really like give you the encouragement and give you a push and say like, “I've done it before and here's someone I can connect you with,” or, “Here's like how other people have done it that I've worked with,” is, so, yeah, for me was huge.

(26:10) Scott Anthony Barlow: What I'm really curious about is we started this conversation saying, “Hey, I was a flight attendant, and there were some elements that were really wonderful, some of the flexibility and being able to travel”, and those pieces, and then there were other elements that were completely missing. So how would you compare, going way back to those situations that were less of a fit to life today, where it is more elements that are fitting?

(26:37) Laura MacDonald: When I look at my ideal career profile, when I look at that role, I think it had so many of the things that I wanted for my life, but it had so few of the ones that I wanted for my work. And really, that helped me kind of build being satisfied one way and not the other way.

It just doesn't work for me, and I know everybody's different. Some people want a job that just gets them everything that they need, and then they close their laptop and they step away, and that makes them happy. But for me, I feel like I needed one that I could be fulfilled in my work as well as outside of my work.

(27:19) Scott Anthony Barlow: When you think back, what would you say is the most life-changing aspect of the work that you did?

(27:26) Laura MacDonald: I honestly I keep coming back to the ICP. I feel like for me, that was so big, being able to really verbalize like what makes me happy, what's my hypothesis of where I wanna go? And even outside of job searching, like I think I'll come back to that and assess, because no job is exactly what the job description says. You know, really assessing at the six-month mark or the year mark, or if I want a promotion or to transition to a different role.

Coming back to that and being like, is it what it promised? Am I rethinking what matters to me? Which I'm sure will change over time, and just like really bringing thought to that instead of just like, “Oh, I hate my job,” just because I hate it. And not really having the words to say why it isn't resonating for you.

(28:16) Scott Anthony Barlow: Here's what's not fitting, versus here's what needs to be different.

(28:19) Laura MacDonald: Yeah. And I wonder too if that has made me more satisfied in the role that I have, 'cause I'm able to look back and be like, “Wow, look, I wanted this thing and then I found something that's so perfect,” so I can rest assured in my day-to-day life, like this is where I'm supposed to be.

I'm not kind of searching and analyzing like, am I…am I not happy? I know what matters. I've written it down and I know that this fits. And if it stops fitting, then I can, you know, analyze why. Again, analysis, analytical.

(28:51) Scott Anthony Barlow: Yeah. A hundred percent. It keeps coming up, right? Well, and to your point, it actually does create that additional feeling layered over the top of better fit because when you understand how regret works for humans, then it's often caused by things that you didn't do or things that feel like it's outside of your control that you didn't do. And this not only is putting you in a different feeling of control, like control is an illusion, but it still feels like you're more in control when you're the one who's deciding, “Hey, here's what I want.”

And then you're the one who's taking steps to find it in the real world. And then you're the one who's saying no to some of these opportunities and saying yes to these others. And all of that creates that additional feeling of control, which creates additional feeling of, “Hey, I'm emotionally invested in this in a very different way,” which ends up being a good thing.

(29:47) Laura MacDonald: Yeah, compared to the last role that I had before this one.

(29:51) Scott Anthony Barlow: Yeah.

(29:52) Laura MacDonald: I feel like when I signed my contract, I wasn't quite happy with the deal that, or like the salary or the vacation, like the contract that I signed, and then a lot of things changed very quickly. And so I was, I feel like I already started on the back foot of like, yeah, this isn't exactly what I want, but I'll take it.

Like I'll settle for it. It'll lead to better things. And then when more responsibilities happened or more change happened on the team, I was so frustrated. I feel like, 'cause I was already settling or felt as though I was settling. Whereas this role also, very soon after I signed, a lot of things changed on the team, and my job description is very different from what I thought it would be.

But there's something about, like, me really making a conscious choice, feeling like I chose a good deal for what I wanted, and feeling like I have a long-term plan that this fits into. I'm not as easily like flustered by changes, 'cause I have like my site set further forward, or I know that I'm here for the specific reasons that I decided on. So yeah, there's something satisfying about that. I suppose.

(31:06) Scott Anthony Barlow: It changes how you show up day to day. It changes the relationship that you have with, you know, the people that you said yes to. All of those pieces end up dramatically impacting how you are experiencing that portion of work.

(31:19) Laura MacDonald: Yeah, and like how I'm showing up for my team, how like, you know, how I'm rising to those challenges is completely different. So yeah, I'm glad to, yeah, it's big to be able to see those changes from one job to the next.

(31:33) Scott Anthony Barlow: If you're ready to stop believing the stories that are actually keeping you stuck and start creating the career in 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.