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Lemonade I'm Gretchen Rubin and this is a little happier. As I've often mentioned, I love paradoxes, commas, parables, proverbs, secrets of adulthood, and teaching stories of all kinds. One very satisfying kind of teaching story is a joke. Some jokes have a moral teaching, just like a fable from Aesop or a parable from the Bible, even if that lesson is implied, not stated. For instance, you may know the joke about the two hikers who encounter a bear. The punchline is I don't have to outrun the bear, I just have to outrun you. If you'd like to hear the entire teaching joke and a discussion of it, I'll link to that episode of A Little Happier. One of my favorite teaching jokes comes from the world of lawyers. I started my career in law and my father is a lawyer, so it's understandable why I have a special fondness for the proverbs and teaching stories of the legal profession. But while usually I've heard this joke invoked by lawyers, it actually applies to many other areas in work and in life. The joke is Making partner in a law firm is like winning a pie eating contest and learning that the prize is more pie. This joke captures the idea that sometimes the reward for success is simply more of the same hard work that got you there. You think you're reaching the finish line and earning a reward, but instead you find yourself facing an even bigger helping of the same challenge. You work so hard to make partner in a law firm, but once you make partner, you have more work plus more responsibility. I remember being pregnant and dealing with all the errands, appointments and discomforts that came along with pregnancy. I kept looking forward to my due date and then reminding myself, wait, it's not like life is suddenly going to get easier and this experience will be over. It's going to get much bigger and much more challenging. A friend of mine who never exercised decided he needed to get in shape. He's very competitive, so he decided he wanted to run a marathon. He got very enthusiastic about this goal. He trained hard and ran the marathon. When I saw him soon afterward, I congratulated him and I asked him how he felt. He said, not the way I expected. To be honest, I was so happy to run the marathon, but now I'm realizing that if my real goal is to get fit and stay that way, the marathon is over, but the exercise isn't. I'm going to be working out for the rest of my life. Running the marathon is like winning a pie eating contest and learning that the prize is more pie. Sometimes a short joke can sum up a big idea. I'm Gretchen Rubin and I hope this makes your week a little happier from the Onward Project.
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Hi Gretchen, Craig Robinson and my little sister Michelle here. We host a new podcast called IMO with Michelle Obama and Craig Robinson. We know you're the queen of giving advice, so we wanted to get a few tips from you.
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You know Gretchen, a lot of our listeners are going through some major life changes. What advice do you have for folks who are trying to stay grounded in the midst of major life transitions?
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Craig and Michelle, I am so happy to be talking to you. Here are a few questions that might help us gain perspective. So consider questions like this what activities take up my time but are not particularly useful or stimulating for me? Do I spend a lot of time on something that's important to someone else but is not very important to me? If I could magically change one habit in my life, what would I choose? And here's a question. Would I like to have more time in solitude, restorative solitude, or would I like to have more time with friends? You know, just thinking about questions like this can help us start to figure out how we might make our lives happier. With greater self knowledge, we're better able to make hard decisions that reflect ourselves, our own nature, our own interests, our own values. In my own case, I have found that the more my life reflects my nature, the happier I get and the more grounded I feel when I'm going through a period of major change or transition. For more great advice, search for IMO with Michelle Obama and Craig Robinson. Wherever your get podcast you can listen to Issa Rae on letting go of certain friendships Keke Palmer on why disappointment is actually the key to career success, Seth and Lauren Rogan on caring for aging parents and so many more.
Episode: Little Happier: Why Is Making Partner in a Law Firm Like Winning a Pie-Eating Contest?
Host: Gretchen Rubin
Air Date: September 8, 2025
In this brief “Little Happier” episode, Gretchen Rubin shares one of her favorite “teaching jokes” to explore the paradoxical idea that achieving success often results in even more of the same hard work. Drawing from her legal background and personal life, Gretchen uses the pie-eating contest metaphor to illustrate how milestones, whether in careers, fitness, or life changes, are rarely finish lines but rather new starting points for continued effort. The episode aims to provide listeners with a thought-provoking lens on ambition, rewards, and the realities of success.
"One very satisfying kind of teaching story is a joke. Some jokes have a moral teaching, just like a fable from Aesop or a parable from the Bible, even if that lesson is implied, not stated."
— Gretchen Rubin (01:46)
"Making partner in a law firm is like winning a pie-eating contest and learning that the prize is more pie."
"This joke captures the idea that sometimes the reward for success is simply more of the same hard work that got you there. You think you're reaching the finish line and earning a reward, but instead you find yourself facing an even bigger helping of the same challenge."
— Gretchen Rubin (03:07)
"I was so happy to run the marathon, but now I’m realizing that if my real goal is to get fit and stay that way, the marathon is over, but the exercise isn’t. I’m going to be working out for the rest of my life."
— Gretchen Rubin’s friend, as retold by Gretchen (04:16)
"Sometimes a short joke can sum up a big idea."
— Gretchen Rubin (04:38)
Gretchen’s style remains warm, reflective, and inviting, blending practical wisdom with gentle humor. The episode uses relatable analogies and personal anecdotes, speaking directly to listeners seeking insight into life’s paradoxes and the nature of ongoing effort.
This episode of “Little Happier” offers a concise yet profound reflection on the nature of success. By weaving together a lawyer’s joke, her own life experience, and a friend’s fitness milestone, Gretchen Rubin highlights the truth that life’s major achievements often serve as a gateway to even greater—sometimes daunting—responsibility and continued effort. It’s a reminder to temper expectations about rewards and appreciate the journey as ongoing.
For those looking to reframe their perspective on personal achievement and persistence—Gretchen’s pie-eating contest metaphor will resonate long after the episode ends.