284: Is Staying at a Job You Hate Holding You Back from Happiness?


Is staying at a job you hate holding you back from happiness? What if you’ve changed careers…and the new work wasn’t quite the fit you thought it would be?

That’s what happened to Audrey Romagnoulo. She was a talented Operations Manager working in the Events and Hospitality industry in New York City. She’d given much of herself to the job and had been rewarded with increasing responsibility, perpetual “thank yous” …and an increasing distaste for her work because what she valued most didn’t align with what the company valued.

When she came to us for help, it became apparent that the genuine, highly caring, no-holds-barred person that she was (and wanted to be more often) was being hampered because of the job she was working in.

This inability to be herself for 70 hours a week became so frustrating for her that it sparked an 11-month long journey to figure out what she really wanted and fight off the mental barriers that were keeping her stuck!

So how did she go from teary days staying at a job she hated to getting paid $20,000 more with a career that allowed her to be who she is?

Take a listen to Audrey’s story and find out!


After helping a couple thousand people make career changes, you notice a few commonalities.

We’ve realized that EVERYONE has barriers to making their change. Especially the busy, high achieving peeps that we’ve worked with. Audrey was no exception!

Audrey had 3 major barriers keeping her from making this change:

End-of-Day Energy Drain: She was working an absurd amount of hours and was drained by the time she was getting home from work and the hour commute each way.

Less Opportunities: She wanted to move to a smaller city many hours away that had less companies and less jobs.

No Job Title Experience: She had 10 years of professional experience but she had never worked in any of the professions that she was most interested in.

To get around these barriers we realized that we would have to do a few things.

  1. We set Audrey up on a schedule that allowed for her to do the work slowly with continuous effort every single week. This schedule allowed her to focus on doing the “work” for herself first thing in the day so that some of her best energy was going to herself.
  2. We realized that to be most effective she would have to avoid the “front door” (online applications) and go in the “back door” (relationships and connections) because she didn’t have the job title experience to be competitive AND because there were less opportunities in the area she want to relocate to.

We also knew that it would be critically important to make sure that Audrey’s next role was one that enabled her to be happy rather than detracted from her happiness.

This meant that she was going to have to do some experimenting to make sure that she got it right.


Audrey began by identifying what would make an ideal opportunity for her. Next, she created a list of companies that she thought might have the types of jobs and culture that she wanted. Then, she began test driving these companies to determine whether or not these were actually a fit.

What happened next is exactly why we always have our students test out their theories of who they actually want to work for and what environment will make them happy.

One of the companies on her short list was Google, partially because she wanted a more progressive environment than where she was already working and partially because they had office locations nearby where she wanted to live.

She worked to get introductions to people inside the company through a friend of her significant other (the weak ties are always there, most people just don’t realize it). She next scheduled some informal “no agenda” conversations to begin building relationships and learning more about the organizations.

These conversations led her to take a total 180 degree turn that may have saved her several years of another job and company that was the wrong fit!

She learned that she actually valued a much more traditional office environment rather than the open concept culture of places like Google.

There were a variety of reasons but Audrey put it this way.

“I learned that if I ever had to wait for someone to finish a game of ping pong so I could get what I needed for a project, I would probably go crazy”

Not at all what she expected! But boy was she glad she did the research as she could have easily ended up in one of those environments!

She also knew that she wanted to make more money in her next role but had no idea how much money she was losing by staying where she was!


I don’t think Audrey actually believed that she could make significantly more money while at the same time changing careers AND moving to a place with much lower cost of living (and lower pay).

…At least until we showed her the data for the types of roles she was exploring. I personally spent 10 minutes pulling together data from some of our favorite resources like Glassdoor.comSalary.com, and the Bureau of Labor and Statistics and we found that it was very likely Audrey could easily increase her salary by $10,000 – $30,000 annually!

This meant that for every month she was staying in her job she was losing $833 – $2500.

Here’s an example of how that works.

It doesn’t take a PhD in Applied Mathematics to figure out that not only is this amount what you’re losing every single month you’re in your current job, but that when when this begins to add up over years it adds to significant money for most people (especially if you are staying at a job you hate!).

For Audrey it meant $100,000 difference over the next 5 years. $300,000 over the next 30 years if Audrey never got another salary increase (highly unlikely).

So, in other words, changing jobs meant losing the equivalent of a large house where Audrey lives! (Or a reasonably nice apartment in Paris.)

What most people don’t take into account is that when you’re earning more in a job that you’re much more excited about, it gives you additional momentum because you’re more likely to get additional increases in the form of higher raises or promotions.

More important than all of the money, though, is that Audrey was able to get a job that allowed her to be herself and do what she was great at.


You know how you always hear those success stories of what other people have done? If you’re like me (or you’re human), sometimes they can make you a little jealous or depressed.

How come it always works out so well for those other people?

Well, here’s the hidden reality behind every single one of the success stories we’ve published:

Zero of them were easy, AND none of them went perfectly.

In fact, we find that much of the time we are helping our students make it easier to change to work they love by focusing on the right things, but focusing on the right things alone doesn’t automatically make you successful.

What happens when you get rejected from a company that you thought was going to give you an offer? Or when everybody is on vacation all at the same time and you feel like throwing in the towel on your career change because you don’t feel like you’re making progress? Or when things blow up at your current job and it sucks up all your time for 2 weeks straight?

All of these happened to Audrey.

It was hard to manage those things while working so much and working crazy hours commuting from state to state. I was crying on the bus ride to work and home sometimes. On those days my most fulfilling days were the days I finished a task. Rarely was it something I was doing on my own behalf.

The imbalance become more obvious as time went on. I was having hopeful conversations and I’d get really excited. I remember talking to this one company for three months and it was all positive but all of a sudden they closed the job because they acquired another office and had two people that could do the job. It was a huge slap in the face.

Even after all of this, she would still do it over again. When you make this type of change, it’s not just about making the change for more money, you end up taking back your life and your right to be yourself and live the life you want along the way.

It doesn’t happen all at once. For Audrey, it took over 11 months. It happens in small steps day after day.

Let me know what you’re going to do today to move yourself forward in the comments below (or congratulate Audrey on her recent change). Don’t let fear force you into staying at a job you hate!

Scott Barlow: Welcome back to the Happen To Your Career podcast. I am beyond excited to be here. I know I say that all the time but I’m especially excited for this episode. I’ve been waiting for it. Ever since I met our guest today I have had in the back of my mind that I want her on the podcast. Without further ado, welcome to Happen To Your Career Audrey. How are you feeling?

Audrey Romagnuolo: Hey Scott, I’m feeling great.

Scott Barlow: Good because this is going to be fun. You and I worked together. You found us, I don’t remember how though, but I got the pleasure to get to tag along for the ride as you made your career change. You allowed us the honor to help out with that. You’ve done amazing things. I’m super excited to dig into all that. We are going to get to all the things. Tell people what you do now, and you are just getting ready to start your new role.

Audrey Romagnuolo: I’m a Benefits Coordinator for a law firm in Boston.

Scott Barlow: You have not always worked as a Benefits Coordinator and in an HR capacity. You’ve done a lot of things I want to go way back and dive into how you got to the point where you saw a need to change. Where did your professional career begin?

Audrey Romagnuolo: Where it becomes relevant, I had a lot of experience in sales and marketing. I got a job in New York which is a mark on the to do list I had to do because that is what my mom did and people from New Jersey do. I got this job in a timeshare industry and hated it because it was boring. The work wasn’t engaging. I got to interact with traveling people and transient guests. I felt stupid and underutilized. I went back into the beauty and wellness industry where I began working straight out of college I missed the serenity and aromatherapy of the environment. I was an entry level guest service manager, got promoted after hosting a huge event and became an events manager, and then we lost three out of five people on our team and I was afforded the opportunity to dive into payroll and employee relations and investigations and benefits, open enrollment, all of that world. I absolutely loved it and fell in love with it because I could deal with things that mattered most to employees. It was difficult once those roles were filled to let go of the fulfilling tasks.

Scott Barlow: From working with you for a bit I know there were elements you were enamored with and had a ton of fun with but something changed and you stopped having as much fun. What happened?

Audrey Romagnuolo: In hindsight, I think this is a common coming of age for professionals. As a young person in any industry you feel like you need to take on as many new things and learning opportunities so you can apply the skills later. Adding tools to your toolbelt. You get to a point where taking on that extra stuff is wonderful but you aren't getting paid anymore for volunteering yourself into your grave. You feel undervalued and it's hard to develop the courage to having the conversations with your superiors especially when you enjoy the projects and it's now an expectation. If you are an overachiever, like probably many of your clients, saying no is difficult as much as saying hey I’ve increased my value and I need that to be reflected.

Scott Barlow: I know you had some of those challenging conversations and some were hard for you. What caused you to get to the point where you were struggling with thinking about those conversations and that they could be a reality and beginning to have them. What changed?

Audrey Romagnuolo: I think there were so many elements. One of the strongest was burnout. I was averaging 70 -80 hour work weeks. The breaking point was being offered a promotion but no raise to go with it. You’ve been so awesome with this portion of your job we’d love you to do it with this new department we’ve acquired but the salary is the same. This isn’t working. After declining the offer which was a hard conversation still being asked to assist with the project and not being compensated. I said yes to it because I didn’t want more awkward conversations. I knew I’d be relocating and had an awesome coach who recommended taking advantage of learning the new systems and we’ll work on getting you out of there. That’s what we did.

Scott Barlow: I remember having those conversations of that exact thing. At some point even before you brought us onboard you had decided you were going to leave. What was the sticking point for you? What was the final straw? There were things you did enjoy.

Audrey Romagnuolo: I had worked with another counselor on three appointments prior to contacting Happen To Your Career. She was in the city and a huge advocate of the Myers Briggs assessment. Assessments are a wonderful tool but there are some people of a certain mindset who are susceptible to use them as opposed to diving into their own desires and wants. You allow yourself to be placed in a box as opposed to making your own decisions. I think it was my third session with this counselor where I questioned that and she was almost defensive.

Scott Barlow: I can’t imagine you questioning anything.

Audrey Romagnuolo: I was like wait, I’m paying for this service to help me get clear. This is the Audrey show not I love Myers Briggs. I just stopped going and found Happen To Your Career. I heard you speak on another podcast. I reached out, and none of that answered your question. My breaking point was I was in a long distance relationship. It was a long time with a commute and I was the type of woman who was unwilling to move for love. Then finally the conversation, another uncomfortable one, was having someone who meant so much to me ask why was I choosing something that made me so unhappy over something that we could create together that would make us both really happy. I didn’t have an answer. Look I'm not comfortable moving without a job. I’m going to work with this guy Scott. He’s awesome and kind of looks like you and I think it's going to be great. That’s what we did and ultimately I ended up moving anyway.

Scott Barlow: Yeah, the twists and turns. I want to come back to that. You did end up moving but it wasn’t a small road to get to that. That is interesting that you were on the track where you were running as fast as you could and because it was what was happening in your life it was causing you to say no to things that were really important like considering the move.

Audrey Romagnuolo: Absolutely. I think that was the hardest thing to come to terms with finally coming to the decision to move without something lined up. For anyone contemplating the move if you have the means just go. I can’t stress that enough. It is the most rewarding risk you will take. You will be happier in your job search. You will enjoy the process more and be able to commit with more confidence.

Scott Barlow: That is super interesting. Not to take us off track but I’ve been reading every single book I can find that has a good set of research on what makes us happy as humans. I’m ten to fifteen books in. What is overwhelming in the research is that when we make decisions and take action we rarely regret it afterwards but if we don't take the action, like in this case it could have been not moving or waiting, that is the situation where it causes regret in the end. It’s absurd. Our brains tell us the opposite. The other way is more intuitive. You did it and clearly don’t regret it but I’m curious why you advise people to do it. Push the research aside. What was your personal reason?

Audrey Romagnuolo: If I may throw myself under the bus. Until Happen To Your Career I never once considered lifestyle for career path or a job. How much free time I had in a day was not something I included with my search. That break down in the eight day course has you break down your health, relationships and spiritual elements. None of those things ever came into my awareness of things to consider when looking for a job which is utterly ridiculous because your job is not what matters most. Everything else matters more. The job is just a means to support you living a life you enjoy and sharing with people you love. That was a huge mindset twist for me. I’m looking for a bigger picture than just a vocation during the week.

Scott Barlow: Interesting. How did that impact later that decision. It wasn’t just a one and done conversation, it was back and forth. You made a go of it trying to find a new job while you were at this job.

Audrey Romagnuolo: Yes. During my search and doing cold calling. If you hate cold calling don’t judge yourself or think about it, just get it done. It was hard to manage those things while working so much and working crazy hours commuting from state to state. I was crying on the bus ride to work and home sometimes. On those days my most fulfilling days were the days I finished a task. Rarely was it something I was doing on my own behalf. The imbalance become more obvious as time went on. I was having hopeful conversations and I’d get really excited. I remember talking to this one company for three months and it was all positive but all of a sudden they closed the job because they acquired another office and had two people that could do the job. It was a huge slap in the face. I was like I hate those people. But I moved here and got an interview with the same company for another position. What I would say and why I would suggest taking the risk sooner than later, and not that everyone will fall in the same timeline, but I spent six months in New jersey looking for work in Massachusetts then I moved to Massachusetts and decided to take the risk to be able to go to interviews to see people and it took me the same amount of time. Imagine if I would have moved here six months earlier.

Scott Barlow: Potentially could have saved some of those months.

Audrey Romagnuolo: Correct.

Scott Barlow: If you want a good outline for whether it's a good idea to quit and when it's okay to quit go to episode 203 with Mike Goodman our Community Success Manager who has also quit jobs, along with myself. We give you a good set of questions and outlines to decide whether it's right for you; it isn’t necessarily for everyone. We talked extensively about whether it would be a good decision in your case and correct me if I’m wrong but you had done a good job of saving money to make it possible and didn’t have significant amounts of debt or living expenses. For the type of person you are the other thing that was good for you was not having the stuff bringing you down and draining you keeping you from making the transition. How did you feel before and after the decision?

Audrey Romagnuolo: I remember the day I decided to move. It was during one of our Tuesday sessions. I thought I can’t do this anymore. I need to move. I said this is how much money I have in the bank Scott. This is what I’ve got to work with I need to buy a car. We wrote a budget. Just doing the math you were like you have thirteen months. You are losing money staying where you are. That was all I needed. To budget myself and realize it was real. That afternoon one of my friends reached out and said I just quit my job and I’m going to tour across the U.S. for three months. I’m like if this girl can quit her job and take a road trip I can quit my job and look for a job. And that was that.

Scott Barlow: That was a big mindset switch then. Tell HTYCers a bit more about losing money because that was a big mindset switch for you.

Audrey Romagnuolo: I’m a saver and like to put money away in the bank. It feels good to put money away and see the number increase. I didn’t want to move here and be dependent on anybody. I wanted to make sure when I moved in I was contributing 50/50 on everything. I’m a crazy person. My partner would have been happy to support me and relished in the opportunity but I’m a psychopath, not having it, I am woman I need to be 50/50 on everything. That was one thing. The other I was scared how I would feel watching my bank account dwindle every month as I paid my bills. I found an awesome deal on a used car. As soon as it was in my driveway everyday I thought I’m going to quit. I’m going to do this now. I just wanted to pack my car and leave.

Scott Barlow: If I remember one of the exercises we went through, we went step by step and figured out how much you were earning at your current job. We felt you were significantly underpaid for your experience level and what you could bring to the table. We came up with you being able to make around $20,000 more with a new company and job so what is the payback and time period in which you can go without running out of savings which was well over a year. And second for every month you stay you are actually losing that new potential salary by staying. Versus and we wrote it out on digital paper and figure out if it takes you six months to get a new role that is actually good payback because you are going to make it back in x number of months. If I recall what you said is now that you made the change you got like a $20,000 increase.

Audrey Romagnuolo: Yes I did. And I did it in six months.

Scott Barlow: Well look at that.

Audrey Romagnuolo: We forecasted it.

Scott Barlow: It's almost like we’ve done it before. What do you think was the hardest part for you in particular? The entire journey?

Audrey Romagnuolo: Coming to the point where I was ready to make the decision. Making the decision was easy. Putting the numbers on paper helped with that. Making the decision to transition out of the wellness industry with the understanding I could continue growing on this ladder and rapidly but I had no interest so making the decision to go entry level in a totally different direction. A lot of the rewiring was in terms of a resume, which I know they aren’t so huge, I had to take things out of the context of my current role and put them in transferable context which is way more valuable especially if doing applications online. No one cares about the specifics. You are the only person that knows the context of what you were doing where you were. If you aren’t taking the effort to translate that into the industry you want to be in you aren’t doing yourself any favors. I found myself removing accomplishments from my resume that were not relevant. It was hard because I felt great about those accomplishments they were awesome. It doesn’t matter if it's not relevant. Get it off.


Another part of rewiring that was interesting. I was so embarrassed to say to an interviewer when they asked why I moved to Massachusetts - I was embarrassed to say it was for love. I tried doing it on a phone interview for someone interviewing me for something I didn’t care about and I had other things going on and she was like oh my god me too. Blah blah blah. It’s a story. I started saying it more and more. I can guarantee that in every conversation I’ve had since someone has related to that story.

Scott Barlow: Because it's human, right? If I remember we had many conversations about that. And other details where you were afraid or unsure or uncomfortable with sharing those pieces of you. Which were authentically you. You are by far one of the most authentic people I know in general and I’ve told you that several times but it was hard in the context of I’m going to change up my world, talk to new people, and I want it to translate to something good for my career; But what should I share? It’s interesting that you found when you shared more of yourself you got a better response.

Audrey Romagnuolo: Yes, huge insight.

Scott Barlow: Were there other areas where you become more comfortable sharing more of yourself in the job search, interview or other process?

Audrey Romagnuolo: It took a long time and a lot of conversations to finally realize that if I didn't like something about a role, when you get further along in an interview process I’ve noticed most conversations I’ve had was with teams. Not just the standard interview with callbacks but six people one day in two hours. Somebody always asks is there anything about the job that you are concerned about or not interested in? Answer those honestly. I literally had a woman in Boston bring me in and say I brought you in because I liked you so much on our phone call but I really don’t think you are going to like this job. I need to know you are jazzed about it. Go home and think about it. I'm thinking to myself I’ve never been called to an interview for someone to say you aren’t going to like this. And two maybe you never know what someone on the other end of the phone intends for you. Who knows they could have you in mind for another role. If you aren’t being receptive to opportunities coming in front of you you can miss out on quite a bit. Don’t be afraid to put yourself out there even if you feel under qualified or not the right fit because you might sit down and they might say I know you applied for this but what do you think about this and it could be something you totally love.

Scott Barlow: That is amazing advice and counterintuitive but we’ve seen it with hundreds of people we’ve worked with. When you go into an interview and be frank with them about I love these parts but here are the parts I’m less excited about. Especially as you get along in the interview and you’ve built a relationship. Don’t just go in at the beginning and say your job sucks. That won’t be helpful. But as you get further along and are transparent more often than not that has created other opportunities. So few people are willing to be transparent. People connect with that.

Audrey Romagnuolo: I would also say if I could bullet one thing the more interviews you do that are outside of what you want the more exposure you get to other avenues where your skills may be applicable. I interviewed for an implementation specialist. In my role in New York I was doing a lot of training of older generations on technology platforms. I applied for a position called onboarding specialist. I anticipated more of a human resources onboarding function. On the phone interview they said it was more implementation teaching people how to use the technology. I never thought in a million years I’d get an interview with a technology company this is so cool. I applied for two other positions like that with other technology companies.


Be a little more receptive at the beginning. I struggled with having such a defined limited view of my ideal and wasn't seeing other opportunities out there. I was missing the mark. I picked this one company and said it's the dream company where I want to be and I would not see anything else. The hardest part was finding companies I was interested in based on a crazy standard I put on the blackboard. By the time I moved here working with you gave me more confidence. I was volunteering for events, working with the chamber of commerce, giving my resume to my friends, and shamelessly sharing my story. I can’t tell you how many tips and tricks and leads I got from making fun of myself.

Scott Barlow: Now I’m super curious what is an example?

Audrey Romagnuolo: Like I volunteered for this event called Chowder Fest, a really fun contest, I’m in the New England area, chowder is a big deal. I’d talk in my New York accent and make the judges laugh. They would remember she is so great we know this person. I was at the chamber of commerce. The events are a lot of people getting together to exchange leads. I have no leads just looking for connection. It's a blow to the pride. You feel stupid and it's okay. Going to networking events with nothing to offer is uncomfortable and hard. Do it anyway. You meet other people from New York or someone who knows somebody and it happened over and over again and I’m still in touch with those people. It's the gift that keeps giving.

Scott Barlow: Super cool. What happened then? I knew you set standards for yourself and weren’t going to take just anything. You were looking at it different than the average person to determine if the role is a fit. What happened at the role and company you accepted saying it could be a good thing? How did that happen?

Audrey Romagnuolo: I had quite a few conversations. I had three different companies that I interviewed with. A young spritely type culture with ping pong tables and catered lunches. A Google inspired type office space. In my head I thought that is where someone like me should pursue work but the truth of it is, knowing myself, if I were in a position where I had a question about a task I needed to complete and I had to wait for someone to finish a ping pong game I would lose my mind. It wasn’t until walking into this law firm. The formal respectful way of communicating that is straightforward, clear and concise that is way more my style. As opposed to getting something done in an office with a dog. You learn yourself. None of that made sense to me until I went to this interview at a more formal environment and felt more relieved that there wasn't Google-y type stuff going on. I think a part of me felt like because I was young I should want that but I don’t.

Scott Barlow: That is interesting, what you are talking about because I’m in this category so I should be___. Or this is what other people think good looks like that is more than likely the wrong place for you. I know many people that do enjoy that environment but it isn’t for everyone. I would get nothing done. Behind me I have nothing. Just floor space and workspace because I have ADD and get way distracted. Many people love that environment but you learned it wasn’t for you by paying attention to what felt right. Kudos because so many people ignore that.

Audrey Romagnuolo: I caught myself being disingenuous during interviews. One of my signature strengths is adaptability. I can make anything work but in terms of how I like to operate. There were several conversations where I had people ask me how do you feel about ambiguity?

You’ve had enough conversations with me to know I’m very clear, there is no guess work with what I’m saying and I prefer that environment. But I would tell people that is okay it’s nothing strange to me I’m accustomed to it. Which was true but not what I wanted. I’d leave and hoped they would call me back but then I’d think about it and be like I am going to get sick of that in like two months if I go through with this.

Scott Barlow: That is interesting because that is polar opposite of what you described in later interviews where you were saying all these areas fit well but there is this one area I’m less sure of. It takes courage to put yourself out there. Its awesome you did that because most people won’t. Instead of the way we think we have to interview like what you just described. Sure I’m okay with it but it’s not what I want. Asking for what you want. When you ask for what you want you are strangely more likely to get what you want.

Audrey Romagnuolo: Also being willing to say no that isn’t something I enjoy or am interested in. I think ambiguity has become the new hot word based on my interviews and my opinion. It's a word I’ve seen used frequently. To me it's a red flag of do you know what you are doing. Have you found yourself as a company? I love flexibility and innovation but in terms of working I want to know what it is I’m supposed to produce, who I’m working with, how we are going to get there. I’m a point B person. Once I know what point B is I don’t care about point A, I don't care about the past or anything in my peripheral I just want to get to B.

Scott Barlow: What advice would you give for people that are back where you were 6 -8 months ago in a role they aren’t excited about and want to make a change and on the cusp to move forward and find work to be themselves?

Audrey Romagnuolo: I think we all start at the same place of I don’t like this. I don’t want this. It's not I’ve been dreaming about this. You don’t get there being happy where you are. We start in the I don’t like this place. Happen To Your Career forces you to ask questions that didn’t occur for you to ask. You are working with professionals who have not only been in your shoes but are really good at helping other people get out of this place. Intuitively they know more than you do about this process especially if it's your first go around. Why not tap into that insight? What made it clear to me from the beginning was the 8 day email program.

Scott Barlow: We still have it around and had about 15,000 people through that at figureitout.co

Audrey Romagnuolo: That was more content than I have seen offered anywhere else. It was so easy and so much value added. It was crazy. That was just the tip of the iceberg compared to what is available.

Scott Barlow: That is super kind of you to say and it makes me happy that we get to chat after you've come full circle on this journey. I’m excited for you to get into your next role. I’m so proud of you for paying attention and putting what you thought you should be doing or had to be doing aside and paying attention to yourself because that isn’t easy. I can’t wait to talk again in another year because of how much progress you have made in that one area alone. I’m ecstatic for you and super happy. Congratulations again by the way.

Audrey Romagnuolo: Thank you and for everything, the whole team too.

Scott Barlow: Absolutely.

Are you ready to find work that fits you? Then sign up for our eight day “Figure It Out”  mini course to get clear on what you want in your new career. https://www.happentoyourcareer.com/8day

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