Gretchen Rubin • Gretchen Rubin Media

Gretchen Rubin is a NYTimes best selling author and one of today’s most influential and thought-provoking observers of happiness and human nature. In this Chat episode, she shares the details of her journey from law clerk of Sandra Day O'Connor to her current role as author, podcast host, App creator and more. Learn how she transitioned to life as a full-time writer and how she navigated structuring her business so that she can remain focused on creating, not managing.

This episode is a roadmap for all the creatives and dreamers that are considering leaving their day-to-day behind and following their dreams. Gretchen's "Life in Five Senses" is the perfect book pairing to the episode for those seeking to get out of their head and back into the moment. We celebrate the release of the paperback version launching the same day as this episode.

Thank you for listening! Subscribe to our YouTube page to be notified with new content. In the meantime, feel free to explore more accounting and business resources. If you think your entrepreneurial story is a perfect fit for an Accountfully Chat, reach out to the marketing team to talk more.

Transcript

Brad Ebenhoeh: 0:08

Welcome to the Accountfully chat another episode here this week today we have Gretchen Rubin, New York Times best selling author. How're you doing today, Gretchen?

Gretchen Rubin: 0:17

Pretty good. I'm very happy to be talking to you.

Brad Ebenhoeh: 0:20

Yes. And we're very excited that you're here chatting with us today. So you've been a client of Accountfully for several years. And it's been great working with you and your team. On a lot of aspects from accounting and taxes. But really, we want to focus on your journey, becoming a creative and an author as well as then you know, how you've grown a business and what systems and processes you put in place today. So before we get started, can we get a background of kind of where you came from, you know, where, how you decided to become an author and all those things there.

Gretchen Rubin: 0:52

Well, I started my career in law, I went to law school, and then I was actually clerking for Supreme Court Justice Sandra Day O'Connor, when I decided that I wanted to be a writer. I started out by having an idea for a book before I even thought about being writing that book, I was going for a walk on Capitol Hill one day, during my lunch hour. And I thought to myself, well, what am I interested in that everybody in the world is interested in, and I thought, well, power, money, fame, sex. And it was like power, money, fame, sex. And I just ran out and started researching those subjects, which to me felt very tied together. And this is something that has happened to me ever since I was very young, I'll get intensely interested in something and do a huge amount of research and writing and note taking. So that was a very familiar process for me. But with this project, it just got bigger and bigger and bigger. And finally, I thought, well, this is the kind of thing people would do if they were going to write a book. And then I thought, well, you know, maybe I could write that book. And so I went to the bookstore and got a book called "How to Write and Sell Your Non-Fiction Book Proposal|". And I pretty much just followed the directions. But you know, I was fortunate because it one point I thought, you know, at this point, I'd rather fail as a writer than succeed as a lawyer. I didn't really know what I wanted to do in law, but I very much wanted to write this book. It wasn't even that I just wanted to be a writer, I wanted to write this book. So it was sort of like, okay, well, let me take my shot, I'll succeed or fail. And then I'll figure out what to do next. And fortunately for me, I got an agent. And that was indeed my first book. So so it all worked out, which makes it sound much easier than it was, but that that's how I became a writer.

Brad Ebenhoeh: 2:40

That's, that's an awesome story. Did you while you were writing the book, and and following the steps in the instructions of that book that you bought, were you still working at the law firm? Or did you like quick cut it off, or kind of what did that process are, I

Gretchen Rubin: 2:54

Well I actually never worked at a law firm. So I was clerking. I was clerking on the Supreme Court. So I did that. Then I went to go work at the Federal Communications Commission, I was a senior adviser there. So I was sort of, you know, in, in the government doing that. And so I would still be doing the work, you know, on the weekends at night and my free time. And then, so, my husband, I were living in DC, and we decided we wanted to move back to New York. And at that time, he decided to switch from–we met in law school–he decided to switch from law into finance. And I decided to try to get an agent. And so that's when I started, I sort of started full time, trying to be a writer. And that's why getting an agent was so exciting, because I felt like getting an agent made me a professional, sort of, because somebody was investing in me by giving me their time. And if you're an agent, your time is your money. And so that was a really important step for me. And at that time, I, that was just at the time, when I had really gone to be I didn't at that time have a full time job. But for most of that period, I was working full time in one way or another.

Brad Ebenhoeh: 4:04

Was there any point in the journey when you were basically all in with the agent writing your book, no job where you were like, Oh, I messed up, I need to go backwards and start over Are you just kind of, you know, moving forward?

Gretchen Rubin: 4:17

I was pretty much moving forward, I had a very clear sense of what I wanted to do, and it was unfolding. But of course, I was fortunate that I was married. I think anytime that like there's two of you, it's a lot easier to take a risk because you've got that buffer. So I feel fortunate that you know, I wasn't just you know, out there hanging solo as I was making this big jump.

Brad Ebenhoeh: 4:38

So then as you move forward in that journey, and you know, your book got published and all that aspect, how did all that unfold over time in terms of Alright, I've made it or I have a book now what's next? Now I need to build a team out, a business, you know, how did all the that like process and your mindset work and what those aspects

Gretchen Rubin: 4:59

Well It's interesting because my time as a writer has really overlapped with just immense changes in the world of writing, the world of the media, the world, the way that people communicate ideas. And so because my, I'm best known probably for my book, The Happiness Project, and you know what a lot of a lot of people assume that was my first book. But of course, like many people, I worked very hard for 10 years to then become an overnight sensation. And what happened with the hat, what what happened with the Happiness Project was the book that I wrote before, that was called 40 ways to look at JFK. And this was a book that I loved. And if you have a book that flops, what they tell you in publishing, as they say, your book didn't find its audience. That means your book was a big failure. So my book did not find its audience. And what that really got me convinced of was that I needed to have my own way to reach an audience. Because I was convinced that there were many people who would be interested in my book, there was an audience for the book, but they were not finding it. Because at that time, you had to go through, you know, TV and book reviewers and all this. And I really thought, wow, I wish I had my own way to communicate with readers or people that I think would be interested in my subject. And that was right when blogging was becoming something that a person who was not very tech savvy could do. So I started a blog. I was then beginning work on the book that became the Happiness Project. And I thought, Okay, well, I'll do a blog alongside that one of the one of the things I needed to test that Happiness Project is all my experiments and how to be happier. And one of the things I needed to experiment with is doing something that was novel and challenging. So I thought, well, something novel and challenging would be to start a blog, because I have no idea what that was. I've never written short form like that. I'm not tech savvy. You know, writing every day sounds incredibly challenging. But I was like, Okay, I got to do it. It's part of the the experiments of the Happiness Project. So I did it. And that was a huge, that was a huge engine of happiness for me. And it was a way to connect with people about my subject before the book even hit. And so then when the book came out, there were a lot of people that I was already in communication with, and I could tell them about the book. And so, you know, you never know, if it's good news or bad news when something happens. And for me, the failure of the 40 ways to look at JFK was really fortunate, because I think if that book had been, had even been a mediocre success, I wouldn't have thought, Okay, I need to be able to connect with readers myself, I would have just thought, Okay, this system works for me. And so then it worked great. So then I did have this project. And at this, this was when all of social media was slowly coming on board. And I feel fortunate because I was able to add these tools gradually. And now I think, when new writers sort of asked me for advice, they see that I have all these bells and whistles, and I have, you know, all these things going on, and it seems so overwhelming. How do you how do you do that from the beginning. And I was fortunate because I could just add it piece by piece by piece like, something's this new tool. Okay, what am I going to do with this new tool? And, and also, I had the luxury of time, so something like my newsletter. Well, I have more than a million subscribers to my newsletter, but I've had my newsletter for I don't even know how long I've had my newsletter. Yeah, time immemorial, it feels like that, of course, it's changed tremendously over time. But I but I've had that, that, that that start, you know, that kind of compounding interest that you get when you start something early. And so So yeah, so I've just been gradually adding tools. So I one point, I think about nine years ago, I started having a podcast, that's all that, you know, when I started out as a writer, podcast didn't even exist. So I didn't think of myself as becoming a podcaster. Now that's a huge part of my identity. Having a newsletter, I have a you know, weekly newsletter, five things making me happy. That's a that's a huge engine of happiness, a huge part of my professional identity. And then, of course, I'm still writing books all the time. And then I do courses. Now I have paper products, like journals and a card deck and the Muse machine, which is this like, cool thing that I created. So yeah, but I'm still at my core a writer, but I have all these new ways of connecting with an audience around ideas.

Brad Ebenhoeh: 9:26

That's, that's awesome. It's interesting, because you're talking about everything you did pre social media when you started blogging. And basically, it's a very similar concept what a lot of folks do today on social media, they want to create, you know, it's the chicken or egg, right? Like do I started a business then find my customers or create a community of prospective customers, figure out what they like connect with them, then sell a book or sell a service or sell. So I feel like once you build that community, then you connect with them. I think that probably makes it easier to sell but also then iterate or do another Project are in Apple replicas, you understand what they need? And you're probably getting a lot of consistent feedback and communication from them. Right?

Gretchen Rubin: 10:05

Well, the app, how did I forget my app? Yes. Thank you for reminding me. I also have an app. Yes. I mean, no. Right? Well, yes, it's very fortunate. And one of the things that's fortunate with me about my subject is that it is the subject where I can learn a tremendous amount from other people's observations, insights, examples, resources, I feel like the world is my research assistant. And if I'm curious about like, Oh, does an idea, is this like, my idiosyncratic Quirk? Or is this something that resonates with other people, I can sort of test the idea out. Now, when I was writing a biography of Winston Churchill, I don't think that lends itself quite so naturally, to that kind of deep engagement. But fortunately, not because I had any great foresight, but just because I happen to be very, very interested in happiness. That was, that's my subject and just sort of human nature, generally, I guess, as my is my larger subject. And that is something where connecting with an audience does come very naturally. And people have a lot to say. And there's a lot, there's a lot to talk about, that lends itself to social media and other, you know, other kinds of technology platforms, as well as ye old books are my favorite. But I like the other things, too.

Brad Ebenhoeh: 11:17

So was there. You know, as you move forward, your journey sold, books created, communities kept going more and more new books. Was there like a pinch me moment, or like an I made me moment, or I've made it moment or anything that you remember?

Gretchen Rubin: 11:30

Well, I was getting ready to do an event in Seattle. And my editor called to tell me that my book had hit number one on the New York Times bestseller list. And that is a big dream as a writer, that is really great. And so I remember that moment very, very well. But if there was a moment, that's the most important it was really getting an agent because as I said, that's what made me go from being just like somebody was writing a book, and every time to somebody who was really, like, I felt like that I was on. I say, the first rung, but it's actually it's such an important step. If you're a professional writer, to have an agent, it's such a crucial step. It's like, the it's like rungs one through 10. So that was a really, really important moment as well.

Brad Ebenhoeh: 12:13

Awesome. And then, you know, as you again, have been growing, you need to focus creatively, right, and it says, consistently stay above all the, the nuances in the administrative tasks and everything that's going on from a business owner and entrepreneur, you know, throughout your journey, how did you over time, stay creative, delegate tasks, hire people, like what was your process with that, and as you build out your team, as you, you know, continue to grow your business?

Gretchen Rubin: 12:43

Well, I really made a huge mistake. And I urge other people to learn from my mistake, which is I waited way too long. To put together a team, it was really just me for years and years and years, then I had like one person who sort of helped me she was she was terrific. But she was doing way too much work for one person. And she was just sort of executing on things that like seem that were very fairly low level. And then I hired someone as the COO, and then she Anne Mercogliano, and then she was so outstanding that like that I was like, Okay, let's make you CEO. And then she was able, because because I'm a writer, really like I'm I'm a that's what I but she's like a person, she's a business person. So she was able to say, these are the jobs to be done this is if you want to take it to the next level, and the next level and the next level and add these things to your portfolio of things that you're creating, these are the people that you would need to hire in this order. And this is how you create the money that would pay for this team. And let's put the systems in place because I was just very much like a DIY, you know, I didn't have a sophisticated system. And I paid my taxes and everything. But it was all very rudimentary, because it was just me and kind of one other person, sort of. And so it was really that getting that keeper. It's funny that when I hired some I was asking someone who's kind of similar to me who had had, but had gone way deeper into kind of building out all her stuff. And I was talking to her about this problem. And she said, Well, I'll tell you why you'll hire somebody. And the first thing they'll say to you is now you have to hire more people. And I and that's exactly what happened. Because the fact is, if you want to do a lot of things really well, one person can't do that. And I think the thing is like I know what I do really well and what I want to do, and then there's other things that I would like to do as part of that, but I don't have the expertise to do them, to do them to execute them. I don't have the time to do them. If I did them, I wouldn't be doing them particularly well. There are other people who could do those tasks much better than I could much faster than I could. And then that means that I have more time to do what I wanted to do which is like read a book like Life in Five Senses where I am going to be doing a lot of research and writing and thinking about the five senses, which is something that only I can do. But then if I want to, like, you know, do a like do a video, you know, for Instagram about the wonders of Heinz ketchup because it is one of the rare foods that has the five tastes of sweet, sour, salty, bitter, and umami, then somebody can like, put that together, I tell them what to do, but it's my idea. But somebody else can can can get it over the line for me, which is an in a way that would be much better than what I would do on my own. So that's, it's really a delight to work with a team. Now.

Brad Ebenhoeh: 15:44

It's an interesting tidbit on Heinz ketchup,

Gretchen Rubin: 15:47

I am the biggest fan, everybody dismissive, we've all got packs with Heinz ketchup, like lying around everywhere, right? But I go home, put like one taste on your tongue. really notice the way it tastes. And you will be astonished by how sophisticated and rich it is, if you can find all five tastes, it's that's why it's the secret ingredient in so many food and why so many people love it, like some huge percentage of Americans have Heinz ketchup in their refrigerator. Because it's this extraordinary, it's this extraordinary concoction. It's very rare, very hard to get all five, some get all four, like a margarita, it's all four. But it's hard to get all five, if you're not like a combo like apple pie with cheddar cheese, something like that. That's just kind of cheating, right? There's a lot going on there. Ketchup is ketchup.

Brad Ebenhoeh: 16:38

So you've been doing this for a while, you know, writing about happiness and different themes and everything that we're talking about here. How is like society, not how society changed since you started to where it is now in terms of maybe just general happiness, not how people consume what you're doing. We all understand reading versus internet and all this stuff, but just general, like, Are people happier? Are people not happier? I mean, do you have a gauge on that?

Gretchen Rubin: 17:04

Well, there's a lot of ways to analyze that it depends on your time horizon. And then you know, everybody took a big hit after the pandemic, because that's such a such a disruption. Um, so you know, it's interesting for me what I'm interested in, I'm not interested in like, like, trends or societal trends, or like, Are you happier if you live in the United States? Are you happier? If you live in Japan? Like, that is not what I'm interested in. I'm interested in Brad. If you're Brad, what are the things today, tomorrow, next week, next month, are the things that you can do within your conscious thoughts and actions without taking a lot of time, energy or money that would be likely to make you happier, whatever that means for you. Because some people are like, it's peace, contentment, satisfaction, joy, bliss, like, whatever it is for you. What can you do with your conscious thoughts and actions that will help to make you happier? And so I'm very focused on like, the what's within the individual's control? And so the idea of like, well, but what if Brad, were Brad in 1975? What would that be like? Well, gets complicated. What about this? What about that? Or, you know, Brad living in Costa Rica? Well, it's like, well, this or that, you know, what if Brad were honest. Well, you could say this, you could say that. These are questions that are wildly interesting to many people. There's a huge amount of academic research into these things. But I just have to say, for my purposes, I'm very interested in the individual, like, what can I do on my own? I'm not saying that the other stuff isn't important that institutions and organizations and even nations and cultures don't play an enormous role they do. Of course, they play an enormous role. But they're not something that we can like change today. And I'm like, what can you do this week? So that's what I focus on. And I think just for just about everybody, there is a lot of low hanging fruit of things that we can do without spending a lot of time or energy, it's just part of our ordinary day, to make us happier. And, and so that's, and I think, I think that is very manageable and possible, not for everyone of course, and not in all seasons of life. We go through periods of our life where we're not happy and we probably wouldn't even seek to be happy. It's not appropriate to be happier. But a lot of times we can.

Brad Ebenhoeh: 19:24

Yeah, that rings true to me just from you know, even your journey from corporate and corporate from you know, being a clerk, but working and then moving on to your own path and your passion. My journey of corporate world being just not happy and then freeing myself and the power of the individual and the power of the consciousness of doing little things like to your point hanging around with different people going on walks, you know, moving to a warmer climate place, or whatever it is that kind of over time it does feel like things just add up and over time you just become more positive, more happier and more Like seems to kind of, you know, roll more organically that way. So definitely rings true to me in terms of just, you know, the little things you can do you know, you can move forward in your life and your journey. Yeah. All right, as we kind of go here and wrap everything up, what do you have in your horizon moving forward outside of the 86 things that you have going on anything new, anything, you know, exciting, outside of everything you got going on on your website and your social media and everything?

Gretchen Rubin: 20:28

Well, one of the one of the things that I talk about a lot on that on the podcast, Happier with Gretchen Rubin is how we have to know ourselves. Because when we know ourselves better than we can shape our lives to be happier. So I love quizzes, and I've created some really interesting quizzes to help people know themselves better. And that's been really fun. Because it turns out people love a self knowledge quiz. And so I get so many people that are like, love these quizzes. So if people like a quiz I have, I have a quiz that will tell you, I have a personality framework that divides people into upholders, questioners, obligers, rebels, so you can take that at Gretchen rubin.com/quiz You can find out what's your most neglected sense and your most appreciated sense that comes that's from research that came out of my book Life in Five Senses, also a Gretchen rubin.com/quiz. I have a quiz that is about if you because people want to be like, I want to be happier. But I don't know where to start. There's so many things I want to work on or like what should I do first? So this is the quiz that will tell you what should you Brad do first now should not what should one do first? But given Brad? And how Brad answers the question, what should Brad do first? And that's the Habits for Happiness quiz. Also Gretchen rubin.com/quiz. So this is something that's really fun. I'm getting ready to do another one based on design your summer. For people who are wanting, you know, like, we're coming up on the summertime. And for people who want to get more from their summer, I think a lot of times we have all these, these kind of plans and expectations for summer. And then like you, you blink an eye and it's over and you're like, wait, we were gonna go on picnics. And we were gonna go to the state fair. And we were going to do that new hike, and we were gonna go to the lake and it's like, okay, if you don't, if you don't design your summer, none of that happens. So this is a quiz that's going to help with that. So if people like quizzes, go to the quiz. And, and then I'm also working on a little book that's called Secrets of Adulthood. That's all about its aphorisms, sort of one, like big ideas and a few words about all the lessons that I've learned about about happiness and human nature. And so that will probably come out next spring. So I'm working on that. And then the paperback of life advice census is just coming out. So that's really, it's always really fun to have a paperback out. A lot of people don't like to buy hard backs, they're like buy paperbacks. So the paperback is coming out now for the people who, who want that version of the book.

Brad Ebenhoeh: 22:52

Well, but I'm gonna take a quiz or two here after the chat. I'm very interested in I love how you're like customizing it to the actual individual taking the quiz. That's always, that's always helpful. So as we wrap up this interview slash podcast here, we typically end with two questions from a small business perspective. So for you know, you talk about small business owners out there, what does one do or recommendation from your journey of being an entrepreneur that you provide to them?

Gretchen Rubin: 23:23

I would say ask for help. I like I don't know why it's so hard to ask for help. Or sometimes you don't even realize that you need help, or that you're facing a problem. But so often, I found that whenever I would ask for help. You know, there's an old saying, when the student is ready, the teacher appears and for the teacher to appear, you kind of have to articulate what it is that you want to learn. And so I would just say, like, really try to understand like, what's the problem? What do you need? I think that's part of why I didn't get a team is I didn't really articulate to myself, just really how frustrated and limited I was, so I didn't ask for help sooner. And if I had asked for help, I think I would have I would have made that that transition. sooner and more easily.

Brad Ebenhoeh: 24:08

Yeah, it is interesting in terms of the prospective clients or business owners I talked to how like embarrassed or ashamed they are about their accounting or bookkeeping or tax, like, hey, that's why we're here. Like, we're here to help if you have it down I wouldn't have a business so whatever question or anything you need, there's people out there that are experts or can help you. And then what is one, you know, don't don't do as a business owner.

Gretchen Rubin: 24:32

Okay this is gonna sound like you planted this with me and told me to say this, but I promise you we have not discussed this before. I am not slacking. But I'm just saying like this is why something like Accountfully is so important. Don't But the larger point I would say is don't create messy systems. Don't assume yourself. Oh, I'm such it's just little teeny tiny old me. It doesn't matter if I don't have like an official password keeper and I just write it down on a little piece of paper. For or I don't have copyright clearances for these photos, but it won't matter. Because, you know, no one's ever going to look at my blog, or I don't have, you know, oh, yeah, maybe I should be playing this taxes, but are they ever really going to come looking for it? Or, you know, I'm not keeping track of all of the, you know, my contacts, but I can always just like flip through my texts and find it. It's like, create systems, maintain systems, and keep them as early and as clean as possible, because so often, I have just been like, oh, my gosh, if I had set this up properly, at the beginning, it would be so much easier. Or if the minute that I realized that there was a problem, I had kind of like stopped and said, at least going forward, let's clean this clean. And maybe we'll go back at some point and clean up the beginning. But just sort of telling yourself, Oh, this is fine. This is doesn't matter, I can just kind of like use some scotch tape and chewing gum and it'll be fine. The province that's very limiting. And as you grow these systems, like, you know, it's like if you're, if you're assuming that those will always be satisfactory, you're just assuming that you will never grow. And that's, then that's too bad. So you set yourself up for growth, make it easy to grow. By having systems that are robust. I learned that the hard way too.

Brad Ebenhoeh: 26:13

I love it. I love it. That's definitely how how my mind operates is process system workflow. So that's definitely helped us grow. And I think that's a huge recommendation to everybody out there. And it's never been easier with all the tools and the apps and everything. But it's also you can be the hardest because it's just to your point in text messages.

Gretchen Rubin: 26:34

Yeah, you just throw everything in a Google Doc and it's like, okay, at some point that's going to become a hot mess.

Brad Ebenhoeh: 26:41

Well Gretchen This was awesome. Thanks again, so much for your time and your information and knowledge and just sharing your experience and your journey. This has been awesome. Once again, Gretchen Rubin, the Accountfully Chat. Hope y'all enjoy. Take care.

Gretchen Rubin: 26:55

Thanks.