This April, I was collecting stories and questions for the personal finance podcast I host for Real Simple magazine when I got this message from a listener I’m calling “Angela”:
“I’d love to retire comfortably. To be able to have a home someday, I have two step-kids and I would like them to have opportunities.
It’s unclear to me whether I’m actually ever going to make enough to be able to achieve all of these goals that I have for myself.
When I grew up I thought those were going to be easily achievable. None of that seems possible anymore and I’m not really sure what to do.”
I wound up interviewing Angela for the podcast (you can listen to the full episode here), and found she was struggling with career frustrations that are familiar to many of us: not making enough money, not getting enough meaning, and not sure what to do next about either.
Angela was working in retail, work she’d taken to cover the bills after graduating from college three years earlier with a degree in the arts. “I would love to dive back into that artistic world, but I worry about that financial security not being there,” she said in our interview.
“I feel like I’d have to go back to school to be able to really pursue a higher level of income, but then I feel like I’d be starting at ground zero.”
“I’ve looked into some of those jobs and I feel like I don’t have that resume to back it up. I guess I worry about getting my hopes up, it not working out, and then starting from square one. Then the other worry is, I don’t want to burn any bridges leaving this more secure job now.”
After talking Angela through some suggested next steps and interviewing author of “Unfollow Your Passion”, Terri Trespicio, about these common career questions, (again, you can listen to both conversations in full here), the episode aired, and a few weeks later, I got the following follow up email from Angela:
“I listened to our episode the day it came out, and I had such an epiphany. Listening to myself talk about how I might not be qualified, why should someone hire me, I won’t make any money, etc, was eye-opening.”
“I had no idea the amount of fear I had and how much I wasn’t giving myself credit for how hard I work.”
So I started applying to new jobs and lo and behold I just accepted an offer [to work in the arts]. I am making more money and living my dreams because of your help.”
So I reached back out to Angela to see if she’d be up for a follow up interview here at “Too Ambitious” about her job search, negotiating a base salary of $10,000/year more than what she was earning at her last job, and how she’s feeling now, a few months into the new gig.
Here’s our conversation (edited for length and clarity):
Stefanie: When we talked, it felt like you were going through this cycle of doubting yourself and I’m wondering if there was a moment for you that felt like something changed or shifted?
Angela: It was listening to the episode. I lied in bed mortified, just hearing myself – the way I was talking about my work and my job prospects.
I was like, “Wow, I have no faith that I went to school for this and I’ve spent a lot of time and money learning how to do this.” And I just realized I wasn’t giving myself enough credit. And hearing it from myself with that distance from when we recorded helped a lot, because I just realized that there was no proof to anything I was saying.
I think it’s important to put in perspective those moments in the past where you didn’t think you could do something and then you did, regardless of whether you thought you could or not.
Like I thought back to all of the other managerial positions that I’ve had, or jobs that I’ve taken that I had zero training or experience in that I did anyway. They were all just stepping stones. They were all learning blocks. I realized that I had done enough to deserve what I wanted in the next step. Like I was more than capable of reaching for that.
Stefanie: And then what was the tangible ‘next step’ for you?
Angela: The next step was just applying to as many things as possible regardless of whether I thought I was qualified. I was trying to apply to exactly what I wanted to do next because I didn’t wanna give myself the cop out of, “Oh, well, if I want to stay in retail, I could just apply to a store manager position.” I was like, “No, you’re not applying to a single retail position.”
So at the same time I expanded what I would normally apply to, I also kept that fine line of it is only going to be in the field you want to see yourself in.
And like 90% of the jobs I applied to, I did not qualify for. I did not have the experience they had listed on there.
I was like, I definitely don’t know how to do that, but I figured, I don’t know how many other people are applying, so who knows? Why wouldn’t they just take the chance to try to train me? Or I could figure it out on my own.
Stefanie: What you were running into before is that common roadblock, like, “Why would it be me? I’m not qualified. I’d have to go back to school to even think that.” How did you start to push past that?
Angela: I realized that I had time to find the job that I wanted. When I listened back to the episode, I had reached a point at work where I definitely knew I wanted to find something new, but I also felt very secure in my position.
I knew, “This isn’t going anywhere. It is still currently paying the bills. So if it takes me six months, a year, however long, to find the next job, I can stay here that long.”
It was also having that support group of my fiancé and close friends of mine who knew that work was really a sore spot for me at the time. Who knew that there are gonna be some nights where I’m gonna vent about this job for a couple of hours and I just need to get it all out and then I’ll be able to go back tomorrow, until I find something that makes me a little bit happier, a little bit more fulfilled.
Stefanie: And so after you submitted all these applications, were you getting responses immediately?
Angela: Some jobs I was getting responses relatively fast, like a week or so. Some I still haven’t heard from. And that’s just the name of the game.
Stefanie: Did you wind up combating any of those doubts that you had had before?
Angela: I was fine with the first two rejections, and then when the third and fourth ones were coming in, that’s when I felt a little bit more concerned that I was applying to things that I didn’t have experience in.
At the same time I would think, “I have time on my side” I would also think, “Yes, but you’re also very young and inexperienced” and that might hurt my chances. So I would feel the hope of, “Maybe somebody will just let me figure it out”. And then the fear of, “Maybe they want somebody who already knows how to do it”.
I was very lucky. It only took about a month, month and a half to find a new position.
Stefanie: So how’s it been at your new job?
Angela: It’s been amazing. It’s almost exactly what I had wanted. And some parts of the job I have zero training in, but I’m just figuring it out day-by-day. This job feels like a huge stepping stone for me for a future in this field. From this job, I’m confident I can easily transition into other positions similarly aligned that are going to be so exciting and teaching me so much.
So far it’s just been a great opportunity and I’ve been so much happier to go to work every day.
Stefanie: I was listening back through the episode and the thing I kept coming back to was the idea of this “choice” between money and meaning. And it almost felt like you weren’t sure that either was possible for you. And it sounds like you’re finding that both are possible for you.
I even negotiated my salary for this job, knowing that I wasn’t totally qualified.
I just took the chance in the interview process to go for it and ended up getting what I asked for, so that was a huge boost of confidence of like, “Oh, okay. Yeah, I can do both.”
And I feel like I get to show up to work a hundred percent ready and willing to do the work. And then I get to go home and 100% get to be my normal self and live that balance comfortably.
Stefanie: It’s interesting you’re having this experience at a time where it feels like everyone is having the opposite experience. Like “quiet quitting” and trying to figure out a way to “hate work less.” Having been through this reckoning with your own views on work and money and what’s possible, how do you sort through that?
Angela: Yeah. There are some places where you can work your butt off all the time for years for them and there’s no payback. And so for myself, I’ve just come into my own a little bit more: understanding my worth, what I bring to the table, and game planning for the future, exactly how I’m going to break down, “This is my worth. This is what you owe me to continue to maintain this relationship. And if you can’t fulfill that, I will start looking for other work.” And setting those boundaries early. Cause I’m a doormat. It is so easy to walk all over me. That is every job I’ve ever had. And the second I started this new job, I was like, “Nope, not gonna happen anymore. I’m tired of it. It doesn’t get me anywhere.”
Stefanie: How has this experience changed what you project for yourself for the future?
Angela: Oh my God, so much. Like one of my biggest dreams is having a house someday. I recently sat down and did the math and was breaking down exactly what payments I would need to make for the next 20 years to be able to achieve it. And I didn’t even have a second of doubt that I couldn’t do that because I’m currently making the money that I could achieve that. I’m going to be able to make that dream happen.
It’s kind of like what we talked about in that first conversation, that I was afraid, I felt like I couldn’t dream bigger. I’m finally feeling like I can. It still takes time and it takes patience, but it’s doable.