Former Facebook exec. Paul Ollinger left his job with a pile of money and no plans. But retirement wasn’t all that and he decided to use his financial freedom to pivot to his true love, making people smile as a standup comedian and host of the podcast "Crazy Money". 

“The experience of being retired early was far far less satisfying than I ever anticipated that it would be.”

Paul's money story:

Yeah, I did quit at 42 and I left Facebook without a plan. I just thought, "Hey, I have enough money. I don't want to work and be stressed out all the time. I don't want to be away from my family. I want to be close to my mom who's sick," and I bailed on work and I didn't have a plan, so I thought, "Well, I'll just go be kind of rich for a while." After you take a few trips after you start getting back in shape and work on your golf handicap, one day I came home after dropping my kids at school and I turned on my computer and there was nothing there. It was like, you have no mail. I was like, huh. I was like, I missed work. I missed having a goal. I missed my friends. I missed my colleagues. I missed the challenge of being a part of a team and I was like, well, what now? The experience of being retired early was far, far less satisfying than I ever anticipated that it would be.

Bobbi Rebell:
Yeah, because we talk a lot now, there's this growing enthusiasm for this acronym FIRE, as I mentioned, Financial Independence Retire Early. You have some very strong opinions about that.

Paul Ollinger:
Yeah, I think FI is great, financial independence. I think it's hugely neglected in our country and that we should all work very, very hard to buy ourselves back from the bank and to give ourselves a buffer so that we have the independence to leave a job if it's unhealthy for us, but I think the fascination, the fetishizing of RE, retire early, is hugely misdirected. You don't want to not work. You want to work on your terms and if that's how you interpret RE, then we're on the same page. but you want to be able to do work that's sustainable, that feeds your soul, and that is done in a way that leaves time in your life for things like family and staying healthy. The goal of retiring early and having nothing to do, that's not something any of us should aspire to.

Bobbi Rebell:
Okay, so back to the blank computer screen. You're sitting there, you got no mail, you got nowhere to go. What happens next?

Paul Ollinger:
Well, I had done comedy before I worked at Facebook. I worked at Yahoo. I paid off my student loans and I went and I did comedy for two years before I went to Facebook. Then I got engaged and I just happened to end up getting a job selling advertising in Facebook, but when I left Facebook, I didn't have a plan. I was just walking away from something; I wasn't walking toward anything. After a year and a half, two years, of kind of goofing off and not finding what I wanted to do, I sucked it up and I decided I'm going to write every day, I'm going to get back in the open mics, I'm going to figure out how to reinvent myself as a stand-up comedian at, I guess it was 45 or 46 years old by that time.

Bobbi Rebell:
Wow. What was the first thing you did? What was the conversation like with your family because you are now married and you now have children? If you're comfortable, tell us. You're welcome to tell us all your financial details, but give us some context for what this would involve financially.

Paul Ollinger:
On my very first date with my wife 14 years ago, I told her that I was going to quit my job and be a stand-up comedian and she was in from day one. You might also say she was warned on day one, so we've gone through periods of me doing very, very well in the corporate world and me making very little money as an artist. Four and a half, five years ago, when I really started back after Facebook, I said, "I'm going to commit to doing this, to getting after being a full-time comedian." She was fully onboard. Now, full disclosure, working at Facebook as one of the first 250 employees and getting stock options provided us with a size-able nest egg from which we have enough money to live indefinitely if we don't overspend. That certainly puts salve on the wounds of financial... the questions around finances if you don't have to make a living to feed your kids and pay your mortgage,

Bobbi Rebell:
What is it that you think people misunderstand then about the whole FIRE concept?

Paul Ollinger:
What people don't understand is how much they get from work that they're not computing on the positive side of the ledger. They think about work, they think about, okay, I get a paycheck and then it comes with all these costs of stress and hours and travel, but they're not saying, oh, what I get from work isn't just a paycheck. It's camaraderie, it's an identity, it's respect from colleagues, it's the satisfaction I get from learning and solving problems. All that stuff is really, really important. I mean, look at Maslow's Hierarchy. Belongingness is something that takes us one step above where we would be without work.

“I missed work. I missed having a goal. I missed my friends. I missed my colleagues. I missed the challenge of being part of a team.”

Paul’s money lesson:

Find work that you want to do for as long as you can. Find work that doesn't just pay the most, but that you want to do for as long a period as you can. If you have a dream, by the way, it's a lot easier to chase if you've paid your bills first. Putting a little nest egg away before you chase your dream is a far safer way to do it than just saying screw this when you're 32 and then when you're 55 not having anything to show financially for your efforts of the previous two decades.

Bobbi Rebell:
Do you think there is a danger that some of the young retirees are putting themselves in by, especially, we're recording this at a time when the stock market is extremely volatile, so people may have historic calculations in their savings, but they may not necessarily play out as they expect?

Paul Ollinger:
Well, I think there's two things there absolutely. One is, if you think having a million dollars when you're 32 in the market is going to last you forever, then you haven't lived through too many economic cycles and that million dollars can easily be $600,000 after a couple of bad quarters, so there's that. The second thing is that it's human nature that our wants continue to expand and it's not that we can't manage that as people, and I think we should be very aware of how we spend our money so that we're making sure we're spending it on what we value and provides us with more happiness, but however much you have and think you can live on when you're 32, it's not going to be the same number when you're 42 as perhaps your family expands or your parents get sick. There's all kinds of stuff that's going to happen in life that million bucks that could turn into $600,000 probably won't be able to pay for.

“If you have a dream, it is a lot easier to chase if you have paid your bills first.”

Paul's everyday money tip:

Paul Ollinger:
Be on the same page as your spouse. As difficult as it may be, go sit down and talk about where you're spending your money with your partner because there's nothing more expensive than not being on the same page with the person who shares, not just your life and your household, but the money that you all spend together.

Bobbi Rebell:
Yeah, and I'm just going to add, have that conversation ASAP if you're not already and don't be afraid to actually bring documents and go over what you're actually spending. Right?

Paul Ollinger:
Well, that's the first part is to find out where it's actually going and to say, "Hey, do you know that we're actually spending X on this? Do you feel like, are you getting what you want out of it? Because it doesn't feel like that's bringing us as much happiness as the top line number would indicate it should be."

Bobbi’s Financial Grownup tips:

Financial Grownup tip number one:

My favorite line of Paul's in this entire episode was quote, "If you have a dream, it is easier to chase it if you have your bills paid." The truth is that is not so easy, but it is often the harsh truth. We get so caught up in the romance of going for it that we forget the role of financial stability in getting to our goals. No one wants a comedian who is stressed out about his bills, although actually in Paul's case, that could probably work into his act, but you get what I'm saying here.

Financial Grownup tip number two:

After our interview, I asked Paul how we could score discount or even free comedy tickets. He gave me the inside scoop. He said a lot of the shows don't actually sell out and the clubs make a lot of their money on the drinks and then the other stuff that you buy there, like souvenirs, so they really want to fill those seats and they often do this by sending out last minute email blasts offering free, free, free seats. You need to find out where the comedy shows are in your area or where you're going to visit. Get on those email lists, follow them on social media, so you can be on the list or get the social media tweets or posts and find out when those free tickets are happening.

Episode Links:

• Blinkist - The app I’m loving right now. Please use our link to support the show and get a free trial.

• Paul’s website - www.PaulOllinger.com/

• Paul’s podcast Crazy Money
  
  
  
  

Follow Paul!

• Instagram - Paul_Ollinger

• Facebook - @PaulOllinger

• Twitter - @Paul_Ollinger

• LinkedIn - @PaulOllinger

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Tanja Hester explains why she had to call it quits on the side hustle she loved in order to create new opportunities at her primary job. Plus her big money tip on how to save big on medical expenses while traveling the world. 

In Tanja's money story you will learn:

• The flip side of the side hustle

• When to call it quits

• Why she decides to leave her side hustle as a yoga instructor

In Tanja’s money lesson you will learn:

• Being aware of your options

• If you're side hustle is going to hold you back

• Realizing that a side hustle may not be forever and that's okay

In Tanja's everyday money tip you will learn:

• The surprising places you can schedule your dental and eye exams to save you money

In My Take you will learn:

• Why it’s important to be clear about your purpose if you have a side hustle

• The importance of knowing if your healthcare is valid overseas
  

Episode Links:

• Tanja's book Work Optional

• The Fairer Cents podcast

Check out Tanja's website -

• Our Next Life

Follow Tanja!

• Instagram - @our_nextlife

• Pinterest - @our_nextlife

• Twitter - @our_nextlife

• Facebook - @ournextlife

Tanja Hester explains why she had to call it quits on the side hustle she loved in order to create new opportunities at her primary job. Plus her big money tip on how to save big on medical expenses while traveling the world. In this Financial Grownup podcast episode you’ll learn how you can retire early without having to pinch pennies doing so. #Author #RetireEarly #FIRE

Tanja Hester explains why she had to call it quits on the side hustle she loved in order to create new opportunities at her primary job. Plus her big money tip on how to save big on medical expenses while traveling the world. In this Financial Grownup podcast episode you’ll learn how you can retire early without having to pinch pennies doing so. #Author #RetireEarly #FIRE

Some of the links in this post are affiliate links. This means if you click on the link and purchase the item, I will receive an affiliate commission at no extra cost to you. All opinions remain my own.

Transcription

Tanja Hester:
Within that year of quitting, I got promoted. I was able to take on a lot more interesting assignments at work. I was able to start traveling more, which I did really enjoy. Ultimately for me, it's crazy, but yeah. As much as the side hustle served me earlier, it was giving it up that really let me get ahead.

Bobbi Rebell:
You're listening to Financial Grownup with me, certified financial planner Bobbi Rebell, author of How to be a Financial Grownup. You know what? Being a grownup is really hard, especially when it comes to money, but it's okay. We're going to get there together. I'm going to bring you one money story from a financial grownup, one lesson, and then my take on how you can make it your own. We got this.

Bobbi Rebell:
Do you guys have side hustles, multiple income streams? It's kind of becoming the normal thing to do these days, but they are also, if we're being honest, second jobs, and sometimes it just becomes too much. Welcome everyone. The show is growing and we have a lot of new listeners. Thank you for checking us out. I would love to learn how you heard about the show, so special ask here. Let me know how you heard of the podcast. DM me on Instagram at BobbiRebell1, or on Twitter at BobbiRebell, and you can always email at hello@financialgrownup.com and feel free to give other feedback as well.

Bobbi Rebell:
All right. Let's get to our guest. She is Tanja Hester. First of all, she has one of my favorite podcasts, The Fairer Cents, with Kara Perez. She also is an award winning blogger. Her blog is called Our Next Life, and we were able to get her on the show because of her new book. It is called Work Optional, and based on the story she shared, it also could be called "And Side Hustles Optional," because it seems like everyone expects you to have a side hustle these days and sometimes you just don't or you just can't anymore. And learning when it is okay to say no is definitely a very Financial Grownup thing. Here is Tanja Hester. Hey, Tanja Hester. You're a financial grownup. Welcome to the podcast.

Tanja Hester:
Hey Bobbi. I'm so happy to be here.

Bobbi Rebell:
And I am happy to be talking to you about your new book: Work Optional, Retire Early. A lot of people already know you though because you're an overachiever, Tanja. You have, first of all, your blog. Beyond the fact that you're a part of the FIRE movement and you are financially independent, you are retired. This is some busy retirement by the way, just saying. Your blog, Our Next Life, was Blog of the Year for the Plutus Awards, which is huge. I am not a Plutus Awards winner. I was nominated though. This podcast was nominated, I should say. You're also the cohost of really one of, if not my very favorite podcast, Fairer Cents, so love all of them. So happy to have you.

Tanja Hester:
Thank you. Wow, that was the best intro ever, I think.

Bobbi Rebell:
But it is all sincere and all true. I really loved your book. I actually have asked you to talk about a money story from your book that really hit home with me and I think is really relevant to so many listeners, and something we're going to be talking more about, and that is the flip side to the side hustle and when to know when to call it quits basically, because in the book you talk about leaving your side hustle as a yoga instructor, and I really wanted to hear more. So tell us your money story, Tanya.

Tanja Hester:
Yeah. I started my career in DC and then LA, and at the time I was making not no money, but close to no money, especially considering how expensive those places are to live. And so I started teaching yoga when I think I was 23 or so. I loved yoga. I needed a side hustle. It was relatively low startup cost. I really do recommend actually teaching fitness for folks who want a side hustle, because you get paid to work out, and the overhead, you don't have to invest a whole lot to get certified, and it also makes you really comfortable on your feet and makes you a better public speaker, which are all my side effects. I did that for a long time. I also then started teaching spinning to supplement that, so I was doing both yoga and spinning. Yeah. About eight or nine years in I started realizing, for my main job, which was as a political consultant, I was having to travel a lot and I was starting to sub out more classes, or I was occasionally having to say no to things at my main job because of my class schedule, or I felt like I was subbing out too much stuff.

Bobbi Rebell:
Because you had to have a commitment to that people. You were on the schedule.

Tanja Hester:
Yeah. Yeah, and I had students who were my regulars who expected me to be there. It just got to a point where my main career and my side hustle were really in direct conflict with each other and I realized that continuing to teach yoga on the side was actually holding me back in my career, and was preventing me from being able to be a full team player, being able to say yes to things, so I made the really hard choice to give it up, which was hard because I love teaching yoga. I loved that community that I built, but within that year of quitting I got promoted. I was able to take on a lot more interesting assignments at work. I was able to start traveling more, which I did really enjoy. Ultimately for me, it's crazy, but yeah. As much as the side hustle served me earlier, it was giving it up that really let me get ahead.

Bobbi Rebell:
How did you prepare to lose that income stream? Because that is something a lot of people worry about.

Tanja Hester:
The truth is, I want to be clear that I'm in a financial unit, so my husband Mark was also working really hard through all of this and he had earned more. I think that this, I'm not remembering exactly, but I think he may have gotten a little bit of a promotion that year that I quit, so that kind of smoothed it out a little bit. But the truth is, by that point, we were both earning significantly above what we were spending, and so it was just a question of maybe taking a tiny temporary hit in what we were saving, but we were living so far below our means that it wasn't a question of constraining any spending because of it.

Bobbi Rebell:
What is your lesson for our listeners who are getting such a very strong message, many of us, about having those multiple income streams, having those side hustles? There's downsides to it.

Tanja Hester:
Yeah. There potentially are, and I think it's just being aware and intentional about what all of your options are. So if you're in a low level job right now and you want to stick that out, I think it's just paying attention to, is there a point at which having a side hustle is going to be too big a distraction? Is there a point at which it's going to start to hold you back? You know, I really am very pro side hustle, but I think it's just noticing that this may not be forever, or there might be stages in my life when I need to focus on one thing. So that's really I think what I'd advise, is just be smart about it. Just keep your eyes open.

Bobbi Rebell:
And side hustles don't have to be forever.

Tanja Hester:
Absolutely not. They can be a great chapter of your life. I think of the decade when I taught yoga as a really special thing, but that doesn't mean I still have to be teaching it now.

Bobbi Rebell:
All right. Let's move on to your everyday money tip. This has to do with health care, actually.

Tanja Hester:
It's a better time to be early retired with healthcare than it used to be. Before the Affordable Care Act, people who didn't have a traditional job, and that could be freelancers and side hustlers and gig economy folks too, but we didn't necessarily have good ways to get it. Now with the Affordable Care Act, you can buy insurance, but for most of us that is not going to include dental or vision, and so a great way to save some money if you especially love international travel anyway, is when you're traveling, to schedule a dental cleaning, or schedule an eye exam, or do some of the predictable medical stuff that you know you can schedule when you're abroad.

Tanja Hester:
I think as Americans we tend to think of the rest of the world as not having high quality care, but that's just really not true. You can do a lot of the stuff for pennies on the dollar compared to what we pay here when you're already taking a trip, and if you're older and you need something like a hip replacement, it's worth pricing out what it would cost in a place like Thailand or India versus at home. Often, even if you have insurance, the total cost out of pocket in another country will be less than what you'd pay after copays and everything here.

Bobbi Rebell:
What's been your experience? Have you done it?

Tanja Hester:
You know what? I have not yet. We just haven't had the opportunity because we're only a year into early retirement, but for the book I interviewed a bunch of people who had and really heard nothing but positive experiences.

Bobbi Rebell:
We'll have to look into that. Alright. I want to talk more about your book Work Optional: Retire Early the Non-Penny Pinching Way, because it really draws from your experience. You mentioned FIRE, which stands for "financial independence, retire early." Is that correct?

Tanja Hester:
That is correct.

Bobbi Rebell:
By the way, your blog also won best FIRE blog I think the previous year, so you're an all star on all levels, but there's a lot of things that I like about the book, and one of them was, as a parent myself, that you also address the challenges that parents face when they have this goal of FIRE.

Tanja Hester:
Yeah. I did not want the book to be, "Here is the story of how Mark and I did this." I think that's pretty boring. We also recognize that a lot of our circumstances are not applicable to everyone or easy to replicate. We got really lucky in some key ways. We didn't have huge student debt. As you just said, we don't have kids, so I wanted to make this a book that was accessible to just about anybody, so I included a lot of case studies with parents. In fact, most of the people featured in the book have children, because I just felt that was so important to cover. Some people are couples who are earning under six figures combined, some single folks, so it's really trying to cover the bases.

Tanja Hester:
But yeah, I'm a huge believer that you can build a plan that works for you and you can, even if full retirement isn't an option, you can at least create a life where work is more optional, whether that's being able to cut back or take a year off or just work in a job that's fun for you as a part-time thing. I really do believe that it's accessible and so that's really what I set out to do with the book.

Bobbi Rebell:
Another thing that really stood out to me in the book is a data point that you bring up, and that is that most people, we talk about the idea of choosing to retire early, but the truth is, data shows that most people don't actually even retire when they plan, so we think this is a choice, but really a lot of us just have to be ready whether we like it or not.

Tanja Hester:
Oh, it's so true. I feel really strongly about this because I get frustrated when there are new stories about early retirement that sort of go like, "Hey, look at these young weirdos." Because I think the discussion about early retirement should be inclusive of everyone, because as you said, that's just reality. We know that most Americans intend to work to 66 or 67, but end up having to retire at 62 or 63 on average. Although for many workers it's a lot younger, because companies are generally pretty cruel to those over 50. They lay people off without really much regard for how it's going to affect them, and so a ton of us, two-thirds are not retiring when we plan, and we also know that more than half of Americans are wholly reliant on Social Security as their only retirement income, which the very highest social security checks only give people about $30,000 a year.

Tanja Hester:
So we're talking about a real crisis and a real problem that just being able to put yourself in a position where you can retire securely is already enormous, and if you can put yourself in a position to be able to retire even sooner, all the better, because we just don't know what the future holds for all of us.

Bobbi Rebell:
Wow. All right. Everyone needs to check out Work Optional. Tanja, before I let you go, please tell us more about where people can follow you, your blogs, your podcasts, your books, all of you. There's so much happening in your retirement, Tanja.

Tanja Hester:
I know, I know and I know there are those who will say I'm not retired, but this is all stuff that I'm choosing to do that feels like play, and I feel lucky every day. My main site is ournextlife.com. From there you can find everything else. The podcast is The Fairer Cents, C-E-N-T-S on iTunes and all the podcast places. On social, I'm @Our_NextLife, mostly Twitter and Instagram, but from Our Next Life, you can kind of find all the different tentacles I have out there, get info on the book. The book is in all the normal book places, so yeah. It's a fun, fun thing to do.

Bobbi Rebell:
Amazing. Thank you so much Tanja.

Tanja Hester:
Thanks Bobbi.

Bobbi Rebell:
All right, my friends. Let's do this. Financial Grownup tip number one. If you have a side hustle, be clear about its purpose. For Tanja, it no longer was a needed income source. It was fun. She liked it, but it was holding her back. If the point of your side hustle is to build a business so you could leave your job and things are on track, of course you should stick with it, but as we move up in our primary jobs, side hustles can be a distraction, and you could be missing opportunities even just by not being as focused on the main job as you could be.

Bobbi Rebell:
Financial Grownup Tip number two. Tanja talked about medical procedures overseas that are planned. Even if you don't plan to have something done, it's a good idea to note if your health care insurance is valid overseas, especially in the case of an emergency. In many cases, insurance will cover an emergency but will only reimburse you once you get home, so you have to pay out of pocket while there, keep the receipts and file afterwards. This actually happened to my family. We were vacationing in Jamaica and my son cut his head after falling getting out of the shower. We had to go to an emergency clinic and pay 100% out of pocket. The insurance company would not promise whether or not they would pay, and in the end they did pay as an out of network expense, but there you have it. By the way, Harry was completely fine. If you are traveling internationally, know what your health care coverage is and make a plan just in case you have to see a doctor while you are traveling.

Bobbi Rebell:
And thanks to all of you, my Financial Grownup friends, for joining us. If you like the podcast, please help us grow, please, by sharing with your friends, and take a moment to leave a review as well. We read every one and they really mean the world to us, and they help us get discovered. Big thanks to Work Optional author Tanja Hester for helping us all get one step closer to being Financial Grownups.

Bobbi Rebell:
Financial Grownups with Bobbi Rebell is edited and produced by Steve Stewart and is a BRK Media production.