Build Family Wealth and Happiness.

Fill out this form to receive our free 39-page Family Wealth and Happiness guidebook. You'll also receive periodic updates from me to help you take your family to the next level.

June 18, 2019

Why We’re Quitting Our Jobs and Moving to Hawaii (And Why You Shouldn’t) – with Erica Gellerman


This post may contain affiliate links or links from our advertisers where we earn a commission, direct payment or products. Opinions are the author's alone, and this content has not been provided by, reviewed, approved or endorsed by any advertiser. Information shared on this site is for entertainment purposes only and should not be considered as professional advice.

There’s a movement taking place amongst our generation. A movement that says, “Don’t work at a job you hate just because it pays well.”.

Today, I interview someone who, after 14 years of working the corporate life, has decided to leave their full-time job in order to pursue a new life of purpose … in Hawaii.

Erica Gellerman is my guest today. She’s a marketing consultant and creator of The Worth Project, a personal finance newsletter, blog, and podcast. She writes and contributes to major publications like Forbes, Business Insider, and NerdWallet.

She’s also a mother to a 1-year-old boy named Henry.

Andy Hill: What type of work were you doing after you graduated college?

Erica Gellerman: Right after college, I graduated and decided I like money, but I don't really know what I want to do with my life. So I decided I would go get my CPA. And I ended up working at a big company, PricewaterhouseCoopers, and did that for a while. And while I enjoyed the people I worked with, I didn't enjoy the work. So I went back to school and wanted to do something a little bit more creative, and so I went and got my MBA at Duke, and decided to go into marketing.

And so coming out, I did a little consumer marketing, and then I was like, you know, I really want to go back into the money world, and so I started doing marketing consulting for the financial space. I was like, “Alright, this combines what I like about money and marketing. So there we go.”

How did you decide to become an entrepreneur instead of continuing with the corporate life?

It was a long process, actually.

I went into consumer marketing, and my husband has had one job for 14 years, which he is actually now leaving since we started this new journey. But he was transferred to London, and I was like, “Okay, I'll come with you.”

And so, I transferred to London with him and had to find a new job over here. Because as I mentioned, I went to business school, which was great, but also very expensive, and it landed me in 6-figures of debt. And so there was no way I was going to start anything on my own with that sort of elephant weighing me down.

Related Podcast: I owe $200,000 in student loans. Where do I start?

And so I ended up finding a job with a tech company here in London. And I said to Jordan, “I want to do something on my own, but I didn't know what. I either want to love this job or despise it. I want there to be no in-between. Like, I hope I love it, but I don't want something to be just fine, that I feel comfortable with and live like halfway excited about my career forever.”

And so, unfortunately, I didn't love it. I despised it. And I needed to find something else to help me get through it. And so I started writing, and the only thing I knew to write about was money.

And so after taking the CPA exam, and just my own personal journey with my student loans, that was the only thing I could really think or want to write about. And so I started writing for some blogs that cater to millennial women, like The Everymom, and a site called Cupcakes and Cashmere.

So I started writing and getting a little bit more comfortable. Then I started my own blog. And then from there, I realized I had people signing up for my newsletter with companies that were either CPA firms or big financial firms, and I was like, “oh, this is weird”. Why are they signing up for my personal blog about money? This is strange.

And then the first email came in, and somebody was like, “Hey, do you do this for companies? And I said, “I sure do”.

I actually left my job while I was just getting this writing career started. And Jordan was employed, and so he luckily was able to help a little bit financially through that, even though, you know, it's tough. We're living in London and it's a very expensive place. And so I had a short runway to get myself up and running, and earn some income, and get myself back to a place where I was contributing meaningfully to our family.

So really I just despised my job, started something as an outlet, and I let it grow organically from there.

What has it been like growing a small business as a young mother?

It's been much more challenging than I thought, to be completely honest. And I listen to all of these podcasts where people say, you know, I was able to grow my business in five hours a week while my child was napping, and that just wasn't my reality. First of all, Henry was a terrible napper, and so he would go down for 20 minutes, and I was like, “Okay, I have 20 minutes to shove food in my face and shower. There was no work happening.”

And so it was more challenging than I expected. But it taught me to be really intentional with my time and with what I prioritized.

And so I actually had some clients that were outside of the financial industry, because people would pass my name along, and I'd say, sure, I'll help a natural food chef too, and sure, I'll help this person who's an interior designer, or somebody who's opening a yoga studio. And at the end of the day, all of those additional jobs, while they were great because they brought in money, they were sucking time away from the core purpose of what I was trying to do. And the really scary thing was to kind of say “No, I'm not going to continue working on these jobs that, even though they pay well, are taking me in different directions and splitting my focus. Because ultimately, I want to make sure I'm as focused as I can while I work so that I can work as quickly as possible to spend as much time as I can with Henry.

Related Interview: How This Mom Makes Over $100,000 Working Part-Time From Home

Why is your husband looking to make a transition out of his job as well?

And this is probably like the scariest, but not scary at the same time, thing we've ever done.

So I had started my business before Henry was born. Obviously, I scaled back when Henry was very young. While I was seven months pregnant, Jordan's parents were going to come out here and live once Henry was born for the first few months to help us out, which was amazing.

So we were over here because he's a chemical engineer for an oil company, and he's done the same job for 14 years, and he's loved it because it's allowed him to move all over the world, and try new project, and he really works with people that he admires. He thinks his co-workers are phenomenal.

So we're in London for his job. We're expecting a baby. I'm seven months pregnant, and we go out looking for a little cottage for his parents to stay in, and you know, we're getting everything together for Henry to be born. And we call his parents when we get home, and we're like, “We found the best place!”

And his mom just goes right into it, and she's like, “I can't come, I have a very aggressive form of breast cancer, and sorry, everything is off.”

I don't think I appreciated it until recently how challenging it was for Jordan at that time. Because he's about to become a new Dad, and he's so excited to bring a child into this world, and then he has his mom, who is 5,000 miles away battling breast cancer, and he can't be in two places at once.

It was a challenging time for him, and I think that sometimes you need that little nudge of something to get you to really explore, like, “What am I doing?”

Even though he really enjoyed pieces of his job, he felt that there was something missing in his purpose. You know, it wasn't what he ultimately felt like he's here to do. It wasn't the impact that he wanted to make. Because deep down, Jordan loves the environment, which is shocking for somebody who works for an oil company.

Jordan and Erica Gellerman
Jordan and Erica Gellerman (2019)

You get sucked into a career path and then you keep going, and you blink and it's 14 years later and all of a sudden you are on this track doing something that doesn't align with your values. And so I knew he was struggling with this. I felt terrible because, you know, at this point Henry is a couple of months old, and I'm making pretty much nothing because I've scaled back as I'm giving myself a little mini-maternity leave. And he's becoming unhappy as he starts realizing, “This isn't what I wanted my life to be, and my mom is far away, and I don't have the freedom that I want.”

And so I actually found, George Kinder's “Three Questions”.

How did George Kinder's “Three Questions” affect your decision to move to Hawaii?

George Kinder was a financial planner, and he gave up that side of his practice. But he created these “Three Questions” that sparked this movement called Financial Life Planning.

And because I was writing for advisors, this kind of kept coming up in that space, in things that I would write about for them, because he's really well known in that space.  So I was like, “Well, what are these three questions?”

I looked it up and I was like, “Oh, this is so interesting. These three questions are supposed to help you figure out what your purpose is in life and what you want to do. There's no way three questions can do this.”

But I printed it out, I gave it to Jordan, we put Henry down for a nap, and I'm like, “Okay, we're each going to do this.”

We walked through the three questions and we each did it separately, and then we came together and we started talking about our answers. And these questions are like, “If you have five years left to live, what would you do with your time?”

And you're like, oh my goodness, I've never thought like that before. Especially with his mom going through this, it really put it in perspective to him. So we got done with these questions and Jordan just sat there, and he's like, “I care so deeply about the environment, my company is in direct conflict with that. I can't do this anymore. I need to quit my job.”

And that was it. And it just happened.

That was what so great about these three questions. It helped make everything so clear that decisions that would take a long time, or you would think about but never actually do for years, it just made everything crystal clear.

And he made a decision, and we're like, “Okay, well what can we do to support this? What can we do to change our lives to make sure that this can happen? Because if that's your goal in life, and if that's the vision that you have for the life that you want to live, what do we do to get there?”

That's really what inspired this whole change. That was now a year ago, and we've been working slowly towards it since then, and we have our one-way ticket back to the U.S., and back to Hawaii. We're leaving the U.K. in August, spending a month with his family, and then going to Hawaii in September.

Jordan, Henry and Erica Gellerman
Celebrating Henry's 1st Birthday

How are you going to be able to afford to make this move to Hawaii?

Yeah. So I'm not going to lie, at first when he was like, “I'm going to quit my job.” I was like, “Oh no, you're not. Hold on. We have a mortgage, we have all of this stuff.”

And then we sat down. It was a lot of time with spreadsheets. So some of the things we started doing …

We looked at all of our expenses, everything that we were spending money on that we thought was crucial to our life. So, for example, Jordan has a car here that he wanted to keep, but cars are expensive, right? And so what happens if we decide to go car-less? What does that look like? Selling the car, going car-less, well that's actually a huge help money-wise.

We had also purchased a piece of land in California with the dreams of building our dream home on that. And because that didn't line up with the vision for our life anymore, it was really easy to make the decision to sell it, and to say, “Okay, well what if we take that out of the equation? How much does that free up every month?” Because we had a mortgage on it. So how much does that free up every single month?

And then we started making small changes, just really being very intentional with our money. So I like to think of it as for every dollar that I'm spending, I want to get the most amount of happiness from it. So is everything that we're spending bringing us a lot of happiness? Is it bringing us the most joy that it possibly can? And there were so many areas where it just wasn't.

Related Article: Create Your Budget on Mint in 10 Simple Steps

So, for example, we were eating out because we're busy parents, right? Because we're both working, we have kind of a hectic, crazy household. But we were picking up takeout, and we were doing things that just maybe weren't healthy choices for our money and for ourselves. And so we said, “Well, what would it look like if we tried to give up eating out and go move towards a zero waste household?” That actually made a huge impact on our budget every single week.

And we did these things more of like an experiment. Like what happens if we start doing this? What happens if we make these small changes? What happens if we take these things out of our budget? How much more breathing room do we have?

And all of a sudden we were saving so much more money. And we've always tried to live very lean, right? We've never been big spenders. We've never lived above our means, aside from the fact that I landed myself in a lot of student debt. That was definitely living above my means.

But aside from that, we always tried to be good, and it was shocking once we went through, with maybe a little bit more intention, looking at our money how much we were able to live without.

The final piece of it was we were looking at moving costs, and we're like, “Oh my goodness, moving to Hawaii, moving all of our stuff, doing this is expensive!”

And so finally one day, we were like, “What happens if we just sell it all? What if we just sell everything we own, because honestly, I didn't really want to pack it up and take it with us.” So we're selling like 90% of everything we own, and you know, we don't expect to make a ton of money from selling things because the track record of how much we're making so far is not a lot. But it's more the idea that we're just really downsizing our life.

And to some of our friends who are in similar corporate jobs, we look insane right now. You know, getting rid of everything with our one-year-old, and booking one-way tickets to Hawaii, to do work that we're more passionate about. But when we were able to remove all the clutter from our lives, of the things we thought we should want, we ended up with a lot more breathing room in order to chase these goals.

How is your new business going so far? And what will Jordan do for work in Hawaii?

So I am building up my business quite a bit. And so that has been really good. Thank goodness I have the opportunity to do that, right? And so I've seen it grow significantly every single month, and I'm to a point where I can cover our basic monthly expenses in Hawaii just based on my income. And that was our goal. Like we want this goal of not having to dip into our savings when we go to Hawaii.

The second thing we did was as we've been reducing our expenses so much over this year, we've put all of that excess into a savings account which we call our “Freedom Fund”. And that's for Jordan. That's his account. So right now it's like a nice cushion, and it's to cover, you know, the things that happen in life because these things happen. Things are going to happen that I won't be able to cover with my income.

And so we said, “Jordan, you get 12 months to figure out where you're going to work in this green space. Figure out what you want to do, what type of business you want to start, and once those 12 months are done, hopefully, we haven't touched that safety net cushion banking account that we have, but if we do that's fine. But yeah, you have 12 months to figure this out.”

And this was really important for me because when I was in a job that I hated and I wanted to transition to working for myself, he said, “Okay, we can make this work. We have a little financial runway and a cushion, and I'm happy picking up the slack for a while.” And so now this is my chance to repay it to him.

And I just, I'm really actually surprisingly excited to do that and to give him that space. I know he's a little hesitant, and a little worried, and I think it's going to be weird for him to not have an income, but I'm so excited that he gets to spend more time thinking about what he wants to do and spend more time with his son.

The Gellerman Family
The Gellerman Family

You've been quite responsible with your adventure plan preparations. What are some irresponsible ways of going about your plan?

Some irresponsible ways of doing this are not walking through the scenarios. Because, you know, we have taken a year to get comfortable with this and to build ourselves up to this place where we can go. If I was to look back at what we were doing last spring, and the assumptions that we made money-wise last spring…

Like, first of all, healthcare. We had no idea. That was the biggest thing we had to go research. It would be irresponsible to do this without knowing how you are going to be able to protect your family with something like health insurance. So not doing that kind of research, it would make your journey really hard.

We don't want to fall on our face with this at the end of 12 months. Or we don't want to get six months in and be like, “Oh no, Jordan, you got to go beg for your job back because this isn't working.” And so you just want to set yourself up as much as possible.

Another thing is having really unrealistic expectations. So you have to go into it knowing what your goals are, and if your goal is to come out of it and have a business that you've created for yourself on the other side, which is what Jordan's real goal is, I think that you have to be really intentional with how you set up your time when you are out there, and how you kind of set up the systems that you have in place.

Related Article: 5 Smart Reasons to Have An Emergency Fund

The money systems that we have to make sure that we're not spending a ton of money. You know, how we're setting ourselves up for success by getting rid of things like a piece of land. You have to look at your whole entire picture and not have unrealistic expectations about what is going to happen in this next year.

And then also doing it with a kid. Things happen with kids, right? Like unexpected things happen with kids. And I would hate to have something happen and we need, let's say, emergency care for Henry or something like that, and to not feel like we can financially help him.

Or that we have to put it on a credit card, or that it's, you know, “Oh, you don't need to go to the doctor. You're probably fine.” And risking it because of money, you know? And so I think if you have kids that you're having to think about, going into it without a safety net is just not a good idea. It's just not.

How will healthcare work for you and your family?

This is actually a really good tip that I should suggest that people do if they are in a place with their employer, they have a good relationship, but they don't want to work for their employer anymore.

There's a lot of negotiation that can happen when you are leaving a company. And so Jordan told his boss he was thinking about putting in his notice two months ago. We're not leaving for another three months. So five months early. And so giving them that runway, saying, “Hey, I think I'm going to leave”, gave his boss to say, “Well, what can we do to have you stick around for a little bit longer and transition?”

And Jordan was able to say, “Okay, I'll stick around for these extra 5 months, but I'm going to want something at the end. At the end, I'm going to want healthcare, and we want healthcare for my family. “

Erica Gellerman

And so he was able to secure us healthcare for the next 10 months once he leaves his job. Which is huge, and which is something we were not planning on.

What is the most exciting part about your plan right now?

So we've actually lived in Hawaii before. So 9 years ago we lived in Hawaii, and we said, “We always want to come back here because we really like the lifestyle.”

For us, it's such a wonderful place to live, and we had always thought we would go back in retirement, and we never thought we would have the chance to go back before then. And so it's just making me so happy knowing that we have created this option for ourselves to go back in our mid-30s, not in our mid-60s, you know?

Knowing that being intentional, and taking the time, and really creating a plan, you can do it. You can go move to the place you want to move to. And so that's just making me so, so happy.

I'm also really excited for Jordan to finally get into the space that he's so, so passionate about, and so excited about. I feel like every since we've decided to do this, everything is easier. So we've started to stay up late to work on ideas. And now that he knows what he wants to do in general, like he wants to explore this space. He's up so late every single night, and I'm like, “Go to bed, Jordan!”

But it just makes me happy seeing the fire and enthusiasm that he has for this new life change that we're embarking on right now. It makes me so happy.

And then the idea of getting to spend so much more time with him and with our son, and together as a family, like, “Yes, we'll be working, but there's also a lot more flexibility.”

Right now he's gone for 11 to 12 hours per day like most working people are. And just the idea that he's going to get to be there a lot more and be a lot more present in Henry's life as he's a little guy, I'm really, really excited for this.


Marriage, Kids and Money, Andy Hill

Would you like to quit your job and move to Hawaii?

Please let us know in the comments below.

Andy Hill

Andy Hill, AFC® is the award-winning family finance coach behind Marriage Kids and Money - a platform dedicated to helping families build wealth and happiness. With millions of podcast downloads and video views, Andy’s message of family financial empowerment has resonated with listeners, readers and viewers across the world. When he's not "talking money", Andy enjoys being a Soccer Dad, singing karaoke with his wife and relaxing on his hammock.


  • Hi Andy, I really enjoyed this episode but felt compelled to share my thoughts on one particular item … Oil & Gas and the conflict with caring for the environment. I have to start by saying that I’ve worked in the oil and gas industry for 10+ years and I couldn’t be more proud of the value our natural resources bring to society. It is easy to generalize given our historical track record but I still can’t agree with that statement. It is my opinion that it goes back to one’s company’s culture and values. I care deeply about the environment and so does the company that I work for. Therefore, everything that we do is centered around the environment, people and above all safety. Still a great discussion with Erica which I found extremely inspiring and worth listening to. Thanks!

    • Thanks for checking out the episode and leaving some feedback!

      I appreciate your perspective that working in Oil & Gas doesn’t mean you don’t care about the environment. I know very little about the industry but it appears that the Energy industry as a whole is constantly changing to keep up consumer demands and economic trends. Like personal investing, companies like these are probably diversifying as well (wind, solar, etc).

      As a guy who’s worked in the same industry (corporate event marketing) for the last 15+ years, I understand Jordan’s interest in making a change. I wish them the best of luck. I hope he finds something that makes him happy.


Leave a Reply

Your email address will not be published. Required fields are marked *

Marriage Kids and Money Podcast

About Marriage Kids & Money

The Marriage Kids and Money Podcast is dedicated to helping young families build wealth and happiness.

With over 400 episodes and counting, we share interviews with wealthy families, award-winning authors, and personal finance experts to help you find your version of family financial independence.

Scroll to Top