391. Stop Trying to Be So Happy | Achievable Contentment with Paul Ollinger

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Paul Ollinger:

Take the time to be grateful and be specific.

Dr. RIchard Shuster:

Hello and welcome to The Daily Helping with Dr. Richard Schuster. Food for the brain, knowledge from the experts, tools to win at life. I'm your host, Dr. Richard. Whoever you are, wherever you're from, and whatever you do, this is the show that is going to help you become the best version of yourself. Each episode you will hear from some of the most amazing, talented, and successful people on the planet who followed their passions and strive to help others. Join our movement to get a million people each day to commit acts of kindness for others. Together, we're going to make the world a better place. Are you ready? Because it's time for your Daily Helping.

Dr. Richard Shuster:

Thanks for tuning into this episode of the Daily Helping Podcast. I'm your host, Dr. Richard. And we are going to have so much fun today with our guest, Paul Ollinger. He's a nationally touring comedian and writer. He's done over a thousand shows and is open for the likes of Chelsea Handler, Davie Chappelle and Roseanne Barr. There's a huge piece of this bio I'm omitting because it's his story, and it's unbelievable and you need to hear it because it's important but he has launched the Crazy Money Podcast. Actually, do you want me to call that? 

Paul Ollinger:

It's Reasonably Happy. That's the original. We've rebranded. 

Dr. Richard Shuster:

Rebranded! So the Crazy Money Podcast is now the Reasonably Happy podcast. But his lifelong dream of being a comedian came true. On the show, he explores the connection between money, happiness, work, and meaning. And he's had guests such as Judd Apatow, LL Cool J, Dr. Drew and Guy Raz. We're here to talk about his book, Reasonably Happy. I can't wait to dig into this book. I can't wait to talk to you. Paul Ollinger, welcome to The Daily Helping. It is awesome to have you with us today. 

Paul Ollinger:

Thank you for having me, Dr. Richard. 

Dr. Richard Shuster: 

But we're gonna have fun. We're gonna try and keep it not too serious. Who knows what's gonna happen. But as I said, I purposefully omitted part of your story in the beginning because I think it's awesome to go back in time and jump into the time machine and find out, kind of, what people… how they get on the path they're on today. So take us through this is your life, Paul Ollinger, and talk to us about, you know, what put you on your path. 

Paul Ollinger:

Well, my career started scooping ice cream at the Haagen-Dazs in the food court at Perimeter Mall, which is not far from where you're sitting right now in Atlanta, Georgia. I wonder if… is that Atlanta or Dunwoody? That's probably Dunwoody where Perimeter Mall is.

Dr. Richard Shuster:

It kind of depends on your attitude. I think male comes to either one, but yeah. 

Paul Ollinger:

Yeah. So, I grew up in the burbs of Atlanta, Georgia, and a big Catholic family, one of six kids. My folks stayed together for 55 years. Very stable household, but it was crowded, and fun, and chaotic and had a great family with whom I'm still tight. We had everything we needed, but there was always this subtext of, like, financial stress, you know. And maybe that was because my parents were raised as depression-era parents and that was just sort of the way they saw the world. It was like everything could fall apart at any minute, you know. 

And so I was very oriented toward success and achievement and making money.  And long story short, eventually, I became an early employee at Facebook and I got everything I ever dreamed of. And then, I quit my job and then realized, "Huh, what do I do now? Where do I fit in the world? Who am I if I'm not working, if I'm not VP of this or that at XYZ corporation?" and started writing and reading about the sources of fulfillment and happiness in life.

And that's what eventually became the book that I just put out, which is a collection of essays called Reasonably Happy: the Skeptic's Guide to Achievable Contentment. And the subtitle comes from just being sort of somebody who's always been optimistic yet skeptical about people who are overwhelmingly positive in the world. But for those of us out there who are a little bit skeptical, there's still great ways for us to be happy on a day-to-day basis. We just have to remind ourselves to be grateful.  And the podcast came out of that writing. Crazy Money, six years ago, started with Dr. Drew, who was my second guest, and I had a great time doing it, and it's led me to conversations like this. So, it's been fun. 

Dr. RIchard Shuster:

So I want to go back to you said you quit your job, but did you quit that job at Facebook because you weren't happy? Like, what was the reason why you walked away from that? 

Paul Ollinger:

Yeah, I think this is sort of an example of how my quest for perfection. You know, I've always had this sort of tension of I've always wanted things to be perfect. Like in eighth grade, my classmates voted me both Most School Spirit but also Biggest Complainer. So, I've had this tension between being very optimistic, being very pro-organization where I am, being a leader, if you want to use that word, among my peers; and yet at the same time, being a total grump and always being dissatisfied with things that aren't perfect in life. And I think that has stuck with me. 

And at Facebook, I was working at this company that they had promoted me twice, and I was running the West Coast sales team in 2011, and they said, "Hey, we want you to take on more responsibility and move to headquarters." And I was just like, there's all these things that were frustrating me at work. Our ad products weren't developed yet because it was still a very young company back then. We had channel conflict in the company. My boss and I weren't seeing eye to eye. 

And you know, all these things about work, I was working really hard, tons of hours and all these things about work that weren't frustrating, what I thought was, "I just don't want to work right now. And just, I'm done working. And you know, I'd gotten to the point where Facebook stock had increased so much, nowhere close to where it actually got, but it increased so much. I looked at what my stock options were worth and I'm like, "Well, why would I need to work if I have this much money now?" which is a big error. It's a giant cognitive error that all of us were conditioned to think, "Well, you know, if you have a certain amount of money, well, what's the value of work?"

And that's something the answer to which you don't find until you quit, and walk away and you go, "Oh, I miss my friends at work. I miss having a place in the world. I miss being a part of this very interesting industry that's growing so fast and it's dynamic." And I've spent a decade here building up my credibility and my expertise. And I just walked away from that. And yeah, I have everything I need, and I belong to a nice country club, and I can play golf whenever I want but where do I fit in the world? And where do I get… you know, I'm sure you talk about Maslow's hierarchy once in a while on here. Obviously, your paycheck and your benefits are going to help you with your physiological and your safety needs but where do I find belongingness in the world? Where do I find self-esteem? And forget pursuing self actualization if you're sitting on the couch every day. 

And so, I started reading everything I could about money and happiness. And I realized that what I had gone through is a very typical thing when a family business, for example, sells their company or when an entrepreneur sells his company out or goes public, they have this big influx of cash, and then they have a massive identity crisis when they stop working. And it speaks to the value of work and purpose in life, and the role of money, which is, you know, you can have a bunch of it and still not feel safe because you don't know where you fit in life. And that's a big surprise for people who… the very small number of people relative to the population who get to have that experience but it's a very real thing. 

Dr. RIchard Shuster:

And as you said, a very small percentage of people who, actually, experience this. And yet what a gift for you that you were able to have that safety net and you could dig into the books and you could start spending time writing, and reading and really figuring things out. So, I absolutely want to take a deep dive into the book, but as you were going through book after book after book, what was kind of your Mount Rushmore of books that really helped you? Money, happiness, fulfillment, what were those things that stood out to you? 

Paul Ollinger:

Well, you know, I can't help but come back to Ryan Holiday and his writing about stoicism. I was fortunate to have Ryan on the podcast. I had met him coincidentally when he was working at American Apparel in Los Angeles. He was the interactive marketing manager or something like that back in 2008 or 2009. And it was bizarre because since he had left, he had become this, you know, the Daily Stoic guy and he had built this giant following, and I sent him an email out of the blue and he sent me a screenshot of my contact information in his contacts that he had gotten when I was calling on him from Facebook. 

And here we were eight years later, whatever it was, and both doing very different things. He's bringing the world a message about Stoicism, which is a very non-obvious platform on which to build a brand 2000 years after the height of that philosophical revolution; and yet, the lessons that you find in Stoicism are every bit as relevant today as they were in Epictetus' time, that the battle we're all fighting is a battle that happens right here in between our ears. And when we look in the mirror and the software, yes, our technology that we use every day,  the circumstances of our lives have changed, but this software hasn't changed one bit in those two millennia. And so, you know, the lessons that you find in Buddhism, in Stoicism, in the Bible, non-specific to religion but specific to humankind, are very worthy of reflecting on. 

Dr. RIchard Shuster:

I love this. And, you know, the title of your book, Reasonably Happy, called to my mind a couple of other books. One by Rabbi Kushner, How Good Do We Have To Be? Another by Bruno Bettelheim, The Good Enough Parent, right? And we don't usually think about happiness in terms of… you know, people think happy is like an on-off switch, right? You're happy or you're not happy, right? But I like that happiness in your book is contextualized as you could be happy enough, basically, is what you're saying. So, let's start talking about the book. And I like the stoicism piece. I think it is very relevant today. But as you started writing this book, when did the concept of being reasonably happy, being happy enough, when did that click for you? 

Paul Ollinger:

These essays were written over the last decade. So I was just writing them periodically, trying to my… you know, writing is a form of meditation where, you know, you take a kernel of an idea and you work it, and you rework it, and you deconstruct it, and you put it back together. And through the writing, you come to an understanding of how you really feel about something or how you really think about something or, you know, where it fits in the world from your perspective. 

And so, I find writing to be therapeutic in helping me grapple with some of these questions. So, I never really thought about it as a collection of essays. I was just writing because I wanted to make sense of the world. The Reasonably Happy part started - gosh, it's been a couple of years now. I realized that Crazy Money wasn't a great name for the podcast because it didn't describe what I was going after. Crazy Money sounds like a podcast about investing or making millions or clipping, you know, where to find the best cell phone plan or something like that. This is really about trying to understand what happiness means.

And as you start writing and thinking about happiness, one place to start is, well, what does it even mean? And you think about, well, happiness, if you look up, you know, go to the Thesaurus and plug in happiness, you're going to see a broad spectrum of synonyms, everything from exuberance to contentment. And those things are both synonyms for happy, but they don't mean the same thing. And so, you have to ask yourself, "Well, if I want to be happy, what does that mean? Does it mean I want to live a life of, you know, I want to go out to the clubs and drink Cristal with celebrities, and my idea of happiness is to be rich and famous, or do you want to wake up every day and feel good about who you are and who you're next to? 

And you know, certainly, when I was younger, I probably leaned a little bit more towards the former, but as you get older, you're like, "You know what I want in life? I want a lack of drama. I want to have … I want to wake up and know my kids are safe. I want to wake up and know that I can trust the person that I'm next to. I want to wake up and feel that I am healthy and that I'm in a good place." And you start to put a lot more value on the things that lead to that outcome. 

So, start by asking what does happiness mean? When we started rebranding the podcast, you know, it's funny is you look at podcasts and go, "I know what we should call it, we should call it "Now, What?" because I got to a certain point in life, and then I ask myself, "Now, what? What do I do now? But I've accomplished this thing that I always thought was my goal." Well, then, you search an Apple podcast for "Now, What?" or "What Now?" and there are 47 other podcasts that already have those words in the title. And you go, "Well, I guess that's not going to be the title."

And so we kept searching for terms that kind of captured the essence of what I wanted to talk about and both a little bit of the grumpy attitude that is on brand for me, because I'll go ahead and put myself out there and say, even though I have all this great stuff in my life. I am, by nature, discontent. That is who we are. We've evolved to have negative filtering, to see the world as full of danger and people who are competing against us. And that's okay. That keeps us alive. But if we let that be the driving force in our life, we will never be content. We will never be grateful. 

And so I wanted to say, "Okay, look, we're all built with this software that allows us to stay alive, that keeps us from being happy." So the goal isn't to be absolutely happy every day. It's to be reasonably happy. It's to be grateful. It's to wake up and feel good about what you're going to do that day. And that's good enough. I think that's a good goal. And having reasonable expectations is actually far better than thinking you're going to be rich and famous and have a million Instagram followers. And that will make you happy because it generally doesn't.

Dr. Richard Shuster:

Well, actually, the research is pretty clear that it doesn't, but what I like about this, Paul, is there is this pragmatism around happiness. You know, we've all met the person who, if they jumped out of an airplane without a parachute, you know, I'm thinking of the Bugs Bunny cartoon, but you know, like, "My life is great. Everything's cool." It's not. Like you're toast, right? And so, everybody has good days, bad days. Everybody has challenges, having family, having drama, being a parent, whatever it is, right? And there's things that are inside of our control and there's things that are outside of our control, but it all affects us.  And to say that it doesn't is impossible. 

So, I'm already digging the vibe of this book because it's essentially saying you can have happiness, but you don't have to live in this delusional world that everything is wonderful, when sometimes there's stuff that isn't.

Paul Ollinger:

Yeah. And the more you read, the more you come to the conclusion that past a certain point, right, because we all need a fundamental level of resources to feed ourselves and to feed our kids and to pay our rent. So, I don't wanna… and you know, more than half the country lives on a financial edge, and so I don't wanna minimize how stressful that is. But beyond a certain point, happiness is a choice, that we can decide to be as happy as we wanna be.

And you know, we were talking about earlier, what are some of the guidelines of… what are some of the touch points is, you know, in Buddhism, there's just a couple of fundamental concepts that if we think about them, we can really see the sources of our own happiness, you know. Desire is the root of all suffering, you know. And the difference between pain and suffering is that suffering is pain that we ruminate on. And if we can kind of separate ourselves from the workings of our brain and understand that we're causing a lot of the suffering in our lives, we can minimize it and we can make room for pleasantness. I was going to say pleasure, but it's really like… you know, it's like, okayness.

And okayness sounds really boring, but okayness is what it's all about in my book. Like, man, you wake up and you're, like, I'm good with where I am. I'm good with who I'm next to. I'm good with, you know, the struggles that I deal with every day. You know, I'm not as famous a comedian as I'd want to be. I would love for this book to sell 50,000 copies, but I did the book because it's worth doing in and of itself. And the outcomes are, to some degree, outside of my control and so why worry about them? 

Dr. Richard Shuster:

So somebody's listening to this, they're nodding along. Hello somebody. We love you somebody. And so, they're asking this question, Paul. They said, "Okay, I'm digging this. I'd like to be more happy than I am okay. I'd like some okayness in my life,"  andI know it's different for everybody, but what are some of the things you might suggest to somebody? Of course, they're going to read your book, but what are some…

Paul Ollinger:

Of course.

Dr. Richard Shuster:

Of course, right? But what are some of the things that you'd say, "Hey, here's a good way to get started into figuring that out, finding what makes you happy."

Paul Ollinger:

You know, I think it all comes… and it's gotten to a point, like, it's a cliche. You know, everybody's got a gratitude, you know, image on their Instagram right now. But I do think it starts and ends with gratitude. And I don't journal personally, but I think if you want to be grateful, you can just start by making a list of things in your life that you're grateful for. 

Here's the conundrum. Here's why people focus on money is because you can count money. You can count your Instagram followers. You can count the number of pounds you've lost since you started your workout routine, but you can't count how much people love you. You can't count the health of your children. You can't count your value as part of a tribe or as part of a group of individuals. And as you know, you know, all the studies point back to what really matters in life is the quality of your relationships and what you do every day. 

That's what drives our happiness, but you can't count those things unless you really sit down and write down all your friends. You can't count yourself. You won't notice how much satisfaction you get from the funny people that you work with unless you write it down. You won't notice how you feel respected and valued in your work unless you take the time to do it because that's not the thing that our brain calls attention to.  So, I would say it starts with just thinking about and writing down is a great way to do it, write down the things you're grateful for and do it every morning or every night or every Wednesday afternoon, carve out a time to reflect on what's valuable to you. 

The other thing that I find very helpful for me, because I've got an extremely active brain, is meditation. And when I say meditation, I don't mean shaving your head and sitting under the Bodhi tree. I mean, even using the Calm app, or whatever app you have, or just playing the nature sounds on your phone, and sitting in a quiet place and focusing on your breath. Start with five minutes. Five minutes, that's all it takes. And see the nature of how your thoughts are racing through your brain and try not to pay attention to them. But at the very least, it will give you some separation or at least a window through which to see how your brain is focusing outside of your control. 

And if you can recognize those thoughts as being separate from yourself, you'll start to go, "Oh! Well, I'm…" It'll also demonstrate what's driving you crazy, whether you know it or not. And you go, "Oh, apparently I'm really concerned about Barbara at daycare, who's driving me crazy." Well, why? What's Barbara doing? What is it? What part of you is Barbara threatening that you're letting her spend so much time in your head rent free?  And you can start to notice that you go, "Well, I don't really have anything against Barbara." Well, maybe you do. Maybe you should think about letting that go.  And so, meditation is a really helpful way for me to see what's driving me bananas and what I can let go of.

Dr. Richard Shuster: 

A lot of people say that they understand gratitude. And like you said, it has become a cliche. I was actually thinking about a story that a mutual acquaintance of both of us, John O'Leary, said on the show, and he said he was speaking to a group of individuals who were on death row at prison and was asking them… there was one guy in particular, if I'm remembering the story correctly, who was going to be executed pretty soon and was asking, what are you grateful for? And, you know, he initially said nothing. But then, with reframing, he was able to say, "Well, I'm getting food. I'm not on the streets. You know, I've made peace for what I did." So he was able to find things to be grateful for. 

So somebody who committed murder was, I believe, the charge and was going to be executed, could find things to be grateful for. Any of us can find things in our life to be grateful for. 

Paul Ollinger:

Yeah, I remember in Sheryl Sandberg's book, Plan B, talking about the death of her husband, who was a friend of mine, she was talking to Adam Grant. And Adam said, you know, well, you know, find things to be grateful for. And here's this person who's just lost her husband and the father of her two young children at the time. And you know, she's like, what in the world do I have to be grateful for? And he said, well, the fact that Dave didn't have a heart attack with your kids in the backseat while he was driving, you know, and that you still have other people in your life that you love and who love you. 

And I mean,  I've never suffered loss like that. And I hope I never do. I'll leave that growth on the table. But I think even in the worst of circumstances, you know, that's one of the ways out is looking for things to be grateful for despite whatever horrific loss and legitimate loss. 

You know, when I talk about the difference between pain and suffering, it doesn't minimize the pain. It doesn't, in any way, say that pain isn't real. Pain is real. It's just the degree to which we focus on that will determine how much we suffer. So, yeah, I mean, O'Leary's, that's a great example of how, even in the bleakest of circumstances, gratitude can help us find meaning in our lives. 

Dr. Richard Shuster:

Absolutely. And I want to pivot just a bit. I know that, you know, comedy is a big part of your life. The book is written, to say the least, in a humorous tone.

Paul Ollinger:

I like to think so. 

Dr. Richard Shuster:

Yeah, I would hope so, right? If you didn't,  you'd be a pretty terrible comedian. But tell me about that piece, right? Like, I'm curious because I think humor is so important in so many ways. It defuses tension. It's good for us. Talk to us a little bit about, first, if we could spend a minute just talking about how you became a comedian. And then, let's talk about how comedy is used in the book.

Paul Ollinger:

So, I grew up in a very practical household, right? Like it was… The career path, as I understood it, was we're going to send you to college, you're going to get a degree, you're going to get a job, and then you're going to go work for 40 or 50 years, and you're going to retire and die. You know, that's the greatest generation career path. So, I did plays in high school and I was always a bit of a ham. And I remember being on stage in high school and thinking like, this is the most fun I've ever had, but this isn't real. This isn't a real job. This isn't what real people do. 

And so, I never thought about performing again until I was in business school, I'd borrowed $80,000 to get my MBA in 1995. So, that would be twice as much today. And I went because I wanted to get a job to make more money. And then, my friends invited me to host a talent show at school, and I just made fun of them for 10 minutes in front of 300 people, and I got this massive narcotic wave of laughter coming back at me. And I was like, "Oh, this is what I'm supposed to be doing." And it was like, okay. 

I was not the greatest student in my class. I was firmly entrenched in the bottom 25th percentile of kids at the Tuck School of Business. But I was like, among all these really smart people, I'm like the funny guy. I have the sort of this sardonic take on all the things that our life entails, and our ambition and all that stuff. So I was like, "Okay, well, I want to be a comedian, but I had borrowed all that money. So I got to go get a real job."

And I said, well, at some point if I've saved some money and I am not married. I'll go be a comedian. And eight years later, I had worked right out of school for a company called Launch.com, which is a music website founded by Dave Goldberg, Sheryl Sandberg's late husband. The company went public, we crashed, and we got bought by Yahoo! for no money in 2001 at the bottom of the dotcom bubble. But then Yahoo! stock appreciated greatly over the next four years. I was able to pay off my student loans and put some money in the bank. I went out to LA to do comedy full time and that's where I started. 

And then I got engaged to my wife 17 years last week. Thank you very much.

Dr. Richard Shuster:

Congrats!

Paul Ollinger:

Thank you. And I thought, well, I really want to have a family and I don't want to be a deadbeat comedian living off my wife's modest salary in the hotel business. And about that time,  I got a call from a buddy of mine I'd worked with at Yahoo! and he said, "Hey, do you want to join this little social network company called Facebook?" And that's how I got…  that's where the two stories meet. 

Dr. Richard Shuster:

Perfect. And so, talk to us just for a minute or two about, you know, how you use humor throughout this book to help people find their okayness. 

Paul Ollinger:

You know, I have a lot of… my closing bit is about how my wife loads the dishwasher and how it drives me crazy. And people are always saying, "Well, you make fun of your wife a lot." And I'm like, "No, no, no, no. The object of that joke is me. The object of that joke is my rigid need for control over a chaotic world." And  the point is to demonstrate how the littlest things in life and so many couples have… and always, when I do the dishwasher bit, they're always pointing at the other person because you know, one person loads it, like there's a meme going around says something like one person loads the dishwasher like a Swiss engineer and the other person loads it like a raccoon on methamphetamine or something like that. And I think that's true. 

And so, it demonstrates that rigid need for control, that is a futile attempt to control an uncontrollable thing, right? And so, I use humor to make sense of the world as I see it. And hopefully, it connects with a lot of other people who are sitting there fighting the same battles in their head that I'm fighting. And I mean, the most successful people are fighting the same battles that the median person in this society, and maybe more so. The more super successful people I meet, the more I realize that similar to me, we've always used achievement as a coping mechanism. We've always wanted to say, "Well, if I get these grades, or if I have this job title, or if I make this amount of money, then I'm okay," right? So, it's just a different means of coping than what some other people do. 

Dr. Richard Shuster:

Got it. The book is Reasonably Happy: Essays on Money, Work, and Other Things that Piss Me Off.  It's available everywhere. This is awesome. Paul, our time together has flown by. I knew that it would. As you know, I wrap up every episode by asking my guests a single question. That is, what is your biggest helping, that one most important piece of information you'd like somebody to walk away with after hearing our conversation today?

Paul Ollinger:

Take the time to be grateful and be specific. 

Dr. Richard Shuster:

Short and to the point, but I love it. Paul, tell us where people can find you online and learn more about what you're doing. 

Paul Ollinger:

The best place to find me is words.paulollinger.com. And Paul Ollinger is P-A-U-L O-L-L-I-N-G-E-R. 

Dr. Richard Shuster:

And for those of you in the car at the gym, we got you covered. Everything Paul Ollinger, including the link to buy his brand new book, will be found in the show notes at drrichardshuster.com. Well, Paul, thank you for joining us today. I had so much fun. I'd like to think you did too because we got some okayness and more from our conversation today. 

Paul Ollinger:

Thank you for having me, Dr. Richard. It was great to meet you. 

Dr. Richard Shuster:

Absolutely. And for those of you who took time out of your day, I want to thank you as well. If you liked it, if you're inspired, if you're going to go pick up this book, go give us a follow on your podcast app of choice and leave us a five star review because that is what helps other people find the show. But most importantly, go out there today and do something nice for somebody else, even if you don't know who they are, and post on your social media feeds using the hashtag #mydailyhelping because the happiest people are those that help others.