Hi friend!

It’s no exaggeration to say I’ve been a fan of Susan Cain for years. Thanks to her mega bestseller Quiet: The Power of Introverts in a World That Can’t Stop Talking, I was finally able to articulate something I’d always kind of known about myself but didn’t have the language for: I’m an introvert! And I’ve heard from many, many people who had the same experience after reading Susan’s book.

Despite all evidence to the contrary (hello, career as an author where I legit have to be extroverted a lot of the time), I’m sensitive. I need quiet time! Most nights, I would much rather crawl into a throw blanket with a book than go out. And that doesn’t make me bad or weird…it just makes me me. Which is why it meant so much to actually sit down with Susan for my show, A Little Thing That Helps.

Looking for rituals and tools to help you get through the tough times and ultimately live a life you ACTUALLY enjoy? That’s what this newsletter delivers every single week with guests like Susan Cain. Coming up, we have Elizabeth Gilbert and Yung Pueblo (!). Make sure you’re subscribed so you don’t miss an episode.

During our conversation, I discovered Susan and I actually have a very similar career path. Susan started as a corporate lawyer on Wall Street, and she was good at it. In a lot of ways, it suited her nature as a wordy introvert. But by the time she was seven years into her career, she realized she had another, bigger dream - and one that she’d repressed for so long that she forgot about it. Deep down, in her heart of hearts, what she wanted to be was a writer 🤦‍♀️

When she said that, I was thunderstruck. I TOO had a great job - at Comedy Central, running shows like Key & Peele - and yet…it felt deeply wrong until the moment I remembered, “Wait! I wanted to be a writer, what am I doing?”

Susan’s turning point in realizing she was in the wrong career wasn’t some dramatic lightning-bulb moment; it was discovering a career book at her local Barnes & Noble called Do What You Are. This book actually listed other careers she might have. It opened the aperture of what she thought was possible for her life.

Susan found the start of a new life on a shelf at Barnes & Noble. Then she went and became that book for the rest of us.

Here’s what she said in our conversation that I can’t stop thinking about:

Wear the costume to work if you have to

Susan spent years being genuinely good at a job that was not true to her. And she shared a very specific image for how she got through her office door every morning: “I remember during that period of time [being a Wall Street lawyer], literally thinking every day as I walked into the office, okay, I’m putting on my metaphorical Superman costume now. This isn’t who I really am, but I’m just donning this costume for the purposes of this job,” she told me. That’s a perfect suit of armor if I’ve ever heard it.

While it would be great if we could all quit our day jobs tomorrow to pursue our TRUE calling, Susan pointed out that that isn’t a reality for most of us. We need to make money! We need to pay off our student debt! So it’s not a “disaster” if you find yourself in a job that isn’t quite “you.” Just make sure to protect yourself, wear your Superman costume, and keep moving in the direction of what’s actually right for you. Speaking of which…

Always have two stakes in the ice

Susan didn’t use those exact words, but here’s what she told me:

“Always, always, have a backup plan, a plan B.” I like to call this having “two stakes in an ice wall.” Whenever I have a dream that seems unachievable, I imagine I’m looking up at a giant wall of ice - impossible to climb unless I put one stake in, so that I can put another stake in and slowly hoist my way up.

That is exactly how my own career has gone. When I was at Comedy Central, my other stake was writing a book. When I was writing the book, my other stake was a coaching program. Out of the coaching program came this Substack Live series. We can use our “plan Bs” or “stakes in the ice” to move to incredible heights.

And Susan points out this is a GOOD THING. Instead of it being “a grim practicality, it actually unleashes your creative self.” “If you’re not up all night worrying about how you’re going to pay the bills, then whatever time you’ve been able to carve out for the creative project [can be put to good use],” she told me. PREACH, SUSAN, PREACH!

Do you know someone who feels their career is “wrong” for them but can’t practically drop everything to pursue their true passion? Send them this newsletter. I know it will help them!

Critical feedback is good IF it comes from the right people, in the right way

Susan told me about turning in the first draft of Quiet, a draft she wasn’t entirely sure about. Her own editor told her to throw it away (and if you want to read the actual letter she received - here it is!). But, “there was another editor who said to me, ‘You know, I read the draft and it’s fine. It’s a good book. I don’t know what they’re talking about.’”

It would have been VERY tempting to take that flattering advice. But, “There was the voice in my head saying, ‘No, it’s the editor with the criticism who is the correct one,’” Susan said.

She has one major caveat on receiving feedback, especially on your creative endeavors, though: “You have to be really honest with yourself about who you are and who that other person is and what your dynamic is.” Only take feedback from people you actually trust to give it, delivered in a way that makes you want to keep going instead of quit.

Susan spent seven years being excellent at a life that didn’t exactly suit her. Then she found a book on a shelf that told her there were other options, and that set her off on an entirely new path.

I don’t want to be grandiose… but I hope this episode and Susan’s words can be that book on your shelf.

Testify

Now I want to hear from YOU: Is there a dream you’ve pushed aside for something more practical that pays the bills? I’d love to hear from you in the comments. Do you need help figuring out how you can keep climbing up the ice wall? I’d love to help - I read and reply to every single comment.

Susan’s fantastic episode wraps the first season of A Little Thing That Helps. This season has been beyond anything I could have imagined - I literally thought I was just going to do a six-episode series and then be done with it. But these conversations have been so fulfilling for everyone that we’re coming back on Tuesday, September 8, for a second season. My first guest? Elizabeth Gilbert. Yes, you read that right! Elizabeth. Gilbert! I’ll see you there.

Hi friend!

The first time I ever heard Wilco, I was 17, speeding down Lake Shore Drive in Chicago, the windows rolled way down, music tumbling out of my rented Ford Taurus. I had picked up Wilco’s album Yankee Hotel Foxtrot a few days before because a) what did that title even mean? And b) the dude at the record store in Chicago said it was rad, and who can deny “rad?”

I was on a “college tour,” which is a decidedly optimistic activity, because I was bummed the f*ck out. You see, I had survived a mess-wreck-disaster of a childhood (neglect! psychological abuse! enough material for a book! Oh my!) and just about the only thing I believed was that life was a series of crises to endure. I was a very fun seventeen-year-old.

As I pressed play on my new CD (remember those?)...I couldn’t really understand what I was listening to. Was it music? Was it drums? Was it some kind of electricity? And what exactly was an “American aquarium drinker?” Little by little however, I was transfixed, hooked by the lyrics, and oddly comforted by the foreign world the music created.

Want small tools and rituals for getting through the hard time and living a life you ACTUALLY enjoy? That’s what you’ll get every week in this newsletter with incredible guests like Jeff Tweedy. Subscribe now so you don’t miss an episode!

I didn’t know people made music like this, that music was allowed to sound like this…And for the first time in a long time, I thought that maybe, just maybe, there was a bigger world out there that wasn’t quite as doomed as I had imagined.

And that is exactly why, twenty-three years later, I knew I had to talk to Jeff Tweedy on my show A Little Thing That Helps. Every week I interview people who have “made it” to ask how they actually get through the hard stuff and…I don’t know about you…but I’m finding…kind of everything to be the hard stuff lately.

And so I asked Jeff (PS I do not know him by Jeff, wish I did though!) what was helping him through this very special moment in time. He had SO many pearls of wisdom to share:

“You shouldn’t let those a******s have the joy.”

When I asked Jeff how he was letting in the light lately - because today’s world feels super dark! - he told me, “You should be a participant not just in fighting…and resisting the things that are destructive, but you should be a participant in making a world that’s worth saving.”

Let that sink in a minute.

He talked about being inspired by the iconic musician and civil rights activist, Mavis Staples, and the “radiant joy and fearlessness” she always showed, no matter how hard times were. In Jeff’s eyes, this is an example we should all follow, and we should think of joy, of creating art, as the ultimate act of resistance. “That’s not sticking your head in the sand; I think that’s what we need to survive darkness, and that’s what has always been necessary.”

Try Not to Believe Your OWN BS

In his book, Let’s Go (So We Can Get Back), Jeff wrote,

“It was a revelation when I started to be able to see that there were choices to make, and it was a hell of a lot easier to do the right thing when you’re aware that you have a right thing and a wrong thing to choose between. (256)”

I LOVE this quote. But how, I asked Jeff, do you actually habituate yourself to “doing the right thing?” He explained, “The great gift of being an addict is you have to keep working at being straight with yourself. You have to keep working at being…aware of yourself and those kinds of internal choices…you have to work on not allowing yourself to be deluded,” and ultimately, “maintain some curiosity about yourself.”

The advice to get curious about ourselves, slow down and say “Wait a second. I didn’t mean that. Why did I think that?” is invaluable. It helps us have the space to choose differently. “You better know yourself, or you’re kind of screwed.” Touché, Jeff Tweedy, touché.

Above all, “do not postpone happiness.”

The news cycle is overwhelming, and a lot of us feel like we’re living in the worst time in history. Jeff rightly points out that the problem might actually be the level of access we have to the news cycle, versus this really being “the worst it’s ever been.” “We have access to [the news] 24 hours a day, every second, all of the world’s suffering. If we’re looking for it, we can find it. And it’s a lot,” he said.

It can feel almost unfair to experience happiness and joy when others are suffering so much, but Jeff says our responsibility during these times is finding happiness and making art so you can create the world you want.

He pointed out that throughout history, there’s never been a time without beauty. “I think most of the people that survive most of the horrible things we know of from history, one of the ways that they survived those was to make art. Stay together. Lift each other up. It’s what Aristotle says - flourish. Despairing is, to some people, a sin.”

And further, falling into your own pit of misery won’t lessen the suffering of others. “I don’t know what good it does anybody to withhold things from yourself or withhold joy,” he said.

Do you know someone who has a hard time breaking away from the 24-hour news cycle and thinks they don’t deserve happiness right now because others are suffering? Send them this newsletter to remind them that the best thing they can do is flourish!

As for what’s bringing him joy?

“All the [same] stuff that sustained me when I was a little kid,” he told me. “Listening to other people’s records, going for walks, going for hikes, being around green, landscapes.”

When he puts it like that, it all sounds really simple, doesn’t it? Maybe because it is. Jeff ended our conversation with humility and wit, reminding us that if he’s our guiding light…well then… “it’s tough times all over.”

Jeff Tweedy, thank you for being someone in the world who shows us there is more possibility and that a better world already exists today, if we are willing to see and participate in it.

Testify

I want to hear from you: What’s one super simple way YOU find joy today? And what do you think about finding joy and bringing beauty into the world as an act of resistance?

Please share with me in the comments - I read and reply to every single one ‘cus that’s me!

Coming up

Next week, we’re wrapping up Season 1 of A Little Thing That Helps with author Susan Cain. You might know her for her mega world-influencing book, Quiet: The Power of Introverts in a World That Can’t Stop Talking, but I know her as a friend who lives soulfully and honestly, and who always encourages me to escape my perfectionism. Susan and I are chatting at 4 p.m. ET/1 p.m. PT. Don’t miss this intimate conversation with one of the great thinkers of our time!

We’re kicking off our next season in September with some incredible guests - I’m talking Elizabeth Gilbert (what???), Dan Harris, Joanna Goddard, Yung Pueblo…it’s going to be a stellar lineup, friends.

Hi, friends! How are you?

First, I have something to tell you…

I have been jealous of Bess for YEARS

THERE, I DID IT! I SAID THE THING WOMEN ARE NOT SUPPOSED TO SAY! Here’s why I was jealous: Bess and I went to the same college but went two different paths. I was too scared to become a comedy writer (don’t they pay you in soup cans?) and instead built a career at Comedy Central.

Meanwhile, Bess skyrocketed within the comedy world. She did it all: Jimmy Kimmel Live, best-selling books, even testifying in front of Congress about book banning…I mean, get yourself a writer who can do it all. From my perspective, she was living a lot of the dreams I’d been too afraid to chase myself.

And that’s exactly why I wanted her on my show, A Little Thing That Helps, where I interview people who MADE IT about a struggle they went through and the tools that helped them get through it. Hearing these stories really helps me feel less alone and less of a f*ck up in addition to learning amazing tools.

I asked Bess to tell me a story of when everything looked good on the outside, but she was struggling on the inside, and I had no idea her story would be so moving…

Being on stage, literally accepting an award, while your body rebels against you

Bess, it turns out, while she was crushing it in her career, was also living with an autoimmune disease that flares under stress and that seriously affected her life. This illness required injections and caused so much discomfort on top of “prednisone moon face,” a condition where your face becomes swollen due to steroids. SO OF COURSE, this was the moment, mid-flare, that she won a Writers Guild Award in 2017, and had to get on stage. “That was me having an autoimmune response on the inside,” she said, “while literally holding a trophy on the outside.”

A brilliant line - and I think one that will resonate no matter what career you’re in.

If you enjoy learning how Bess Kalb, Jeff Tweedy, and other folks who “made it” get through the hard stuff, subscribe to The Good Life. I’ll never spam ya and I’ll always love ya.

Comedy as a metabolic function

When I asked Bess what tools she uses to cope with that kind of pressure - dealing with a literal chronic illness flare while accepting an award is not for the faint of heart - she told me a story about her parents, both doctors working on the edges of life and death. I’m talking SUPER high-stakes jobs.

She told me comedy was never just a career for her, it was how her whole family survived and processed after her parents’ long days. “It became a liver,” she told me. “It became a metabolic function to be able to take sorrow and take reality and put it into this filtration system that had a sort of happy byproduct.”

This makes my little comedy-loving heart so happy.

A little thing I’m taking with me…

Laughter gives us so much, even during the hardest and darkest of times. Comedy has been my toolbox for coping,” Bess told me, and it was the reminder I needed. If you can find a way to laugh, even when life is almost too terrible to bear, you’re doing okay.

The whole (short) conversation is up now, and if you are interested in how the comedy industry works, how Bess has overcome her struggles, and why she stans for Raisinets, you must watch it.

Bess called comedy a liver: a filtration system that takes sorrow and reality and turns it into a happy byproduct. That’s the best description I’ve ever heard of what I try to do every Friday, when I write an essay about my messiest true stories (the epically bad breakup, the rejected chapter, the year everything looked fine and wasn’t) and filter them into something you can laugh at and actually use. If your liver could use backup, come join us.

Oh, hello my friend,

For your viewing pleasure, you can either watch, listen, or read today’s edition!

Today, I want to tell you about the time I almost completely lost it over a hunk of steel that would not make me an espresso if its life depended on it. This “time” I’m referring to was actually a few days ago, the day after I got back from an incredible, stress-free, JOY-filled trip to Paris with The Boyfriend™️.

You see, in a fit of pre-trip optimism, I had ordered myself a real, big girl, espresso machine, so that when I landed, I wouldn’t have to lose thirty minutes of my morning trekking to my local coffee shop for a coffee I could make at home. And I was in SUCH a good mental place setting it up, happy from Paris, relieved thinking of the time and money I would no longer be pouring into my caffeine habit.

And then…

It would not work.

I’m not talking about a little troubleshooting that an instructional YouTube video could fix. It was demanding something from me that I did not understand. A steam button! A milk button! Some kind of two-step sequence, like the machine itself was quizzing me on whether I deserved espresso. I read the manual twice, unplugged it, and plugged it back in…NOTHING. And if you’ve read Lilies, you know I am FAMOUSLY GOOD AT MAKING COFFEE MACHINES WORK!

For more chaotic stories (not always about espresso machines) followed by simple lessons that will actually help you ENJOY your life, subscribe below.

Somewhere around the fourth attempt, still in my kitchen, one literal day after the most romantic trip of my life, I felt my whole body go hot. My jaw clenched so hard I could have cracked a tooth. I was fully on the verge of tears over a KITCHEN APPLIANCE. And underneath the fury was a thought so old and so familiar I could recite it in my sleep:

I cannot get my needs met. Even the small ones. Something is wrong with me and the universe. At large…

I was in a BAD mood, generalizing and catastrophizing about how this espresso machine actually said something larger about my life. And then I started criticizing myself. Did other people get this bent out of shape about something so petty?

But! Thank GOD, I had the perfect person to reframe my overwhelm and walk me through exactly what was going on in my brain. That person was Melissa Urban on my Substack show, A Little Thing That Helps.

Melissa gently reminded me that…

Nobody Has Their Sh*t Together

Melissa has eight bestselling books and has built an empire out of The Whole30 and has an excellent Substack which I am actual reader of! If anyone has earned the right to say they have their life together, it’s her. So I asked her the question I want to ask every wildly successful person: was there ever a time your life looked perfect from the outside while you were falling apart on the inside?

So Melissa told me a story. The year was 2015, and The Whole30 was everywhere. I’m talking Good Morning America, Dr. Oz (before he was a quack), and a ten-city tour. The View wanted some B-roll of the power couple, so they asked her and her husband (who was also her co-author and business partner) to walk down a New York City street holding hands for the camera.

So many people could benefit from hearing Melissa’s story of having to put on a happy face while things were literally falling apart behind the scenes. Share this with someone who could use it!

What the camera didn’t know was that they were in the middle of a divorce. Not a fight. Not a separation but a FULL BLOWN divorce. She was text-fighting the man at night, then sharing the stage and business the next morning.

On TV, they looked like they had it extremely together and living this picture-perfect life, but as Melissa so wisely told me, “Nobody has their s**t together…I don't care if you're talking about this billion-dollar company or your favorite celebrity or that person on Instagram whose life just looks perfect."

I asked Melissa to share the tips that got her out of the moments our lives become a “swirling tornado of doom” (her words, not mine), and here are three of the secrets she shared with me:

There Are Three Ways Out of the Tornado

1. Ask: Is this true?

This is the one I skipped in the kitchen because I was already too far gone, and it’s the most important one. My thought was, I cannot get my needs met. But was that true? Standing there, phone in hand, with a million people who love me a text away, and a coffee shop blocks from my door? No. It was not true. It was an old thought, borrowed from a younger me that had MUCH less agency. As Melissa put it, “always ask yourself, ‘Is this true? Can you absolutely know this is true?’”

2. Say the worst case out loud until it shrinks

Unnamed, a fear is a looming black cloud. Named, it’s usually just annoying. Melissa’s worst case in 2015 was: “He (her ex) takes the business from you. You can’t do Whole30 anymore. You have no stream of income whatsoever. And you have no money.”

She said it out loud and immediately could answer that scary thought with: “I still have my son. I have a family that’s super supportive of me. I have friends who are really supportive. I have a college degree.” As for my worst case, it was not getting to have coffee at home. Said out loud…it’s just funny.

3. Know which plates are glass and which are plastic

During her divorce, Melissa kept exactly three plates spinning: her son, the book, her health. Everything else she let hit the floor on purpose, because plastic bounces. As she told me, “You need to know which of the plates are glass and which of the plates are plastic.” That morning, the espresso machine was a plastic plate. The right move would be to let it drop, not stand there obsessing.

I am so grateful to Melissa for her wisdom and leading by example - she was so real with me, and made me feel less alone in the world. I hope you feel the same way too!

Testify:

Do you find yourself mistaking glass plates for plastic? Are you able to reality check yourself in the swirling tornado of doom? Let me know in the comments. I read and reply to every single one - it’s the best place for us to have a conversation, so let’s get it going!

My dearest friend!

We’re back with episode 2 of A Little Thing That Helps!

Want the small tools, rituals, and mindset shifts that have helped people who “made it,” actually make it? Subscribe now so you don’t miss an episode of A Little Thing That Helps!

In this week’s episode, I spoke with Minaa B. Minaa is a therapist, author, and mental health educator whose work has been featured in Oprah Daily, Cosmopolitan, and Essence Magazine. She also has her own Substack, All the Hard Things, which I highly recommend (fair warning: she will call you out in the best possible way).

I look at Minaa and I see someone who has unambiguously made it (and by the way, she’s one of 13 kids. How insane is that???) What I didn’t know until we sat down together was what it actually cost her to get here. You can watch it above, or listen to the podcast version wherever you get your podcasts!

I’ve been thinking about the lessons she shared all week, and I KNOW these tips will help you, too.

The Little Things That Helped Minaa

1. Don’t Isolate. Find Your People!

When Minaa’s first book, Owning Our Struggles, came out, she was caregiving for her mother during the exact window she needed to be pushing pre-orders. When the book didn’t hit the best-seller lists she’d hoped for, she started beating herself up. What shifted her wasn’t a solo mindset exercise; it was her people.

“I had a wonderful community of friends who are also fellow authors who understood where I was coming from, but also friends who were there with me before any of this, who literally saw me while I was working a full-time job, watched me get through grad school, and saw all of my dreams come true.”

The people who had witnessed the whole journey, not just the public-facing part, were the ones who could actually remind her of how far she’d come. My instinct when something goes wrong is to go quiet and figure it out alone. Minaa’s lesson: go TOWARD your people instead.

2. Remember the Ends, Not the Means

Minaa came into publishing with one idea of what success looked like: the list. New York Times, USA Today, Wall Street Journal! If the book didn’t make a list, it didn’t fully count.

I cannot throw stones. Buy Yourself the F*cking Lilies didn’t make any list its first week. I know EXACTLY what she is talking about.

What she eventually realized is that she had confused the means for the ends. The list was never the actual goal. The actual goal was to reach people.

“I realized that is what the true accolade is. That is what the reward is, for people to actually find value in the book and to say, Minaa, I picked this book up and I learned so much from you. And I realized that was more meaningful to me than just the stamp of approval by hitting a bestseller list.”

Three years later, people are still DMing her to say they bought it for a friend, a family member, a client. THAT was always the destination. The list was just a door she thought she had to walk through to get there.

3. Build a Practice That Forces You to Be Present

When I asked Minaa what she enjoys in her life right now, she told me she walks her dog every morning for 30 minutes without headphones, a podcast, or phone calls.

“I think sometimes our problems cause us to go inward, and we don’t really pay attention to how life is literally just surrounding us, but sometimes passing us by.”

What I love is that it’s not some big, expensive, fancy thing. It’s just an intentional moment every day where she’s fully present. And honestly, a lot of my days just blur together, and I don’t even remember what happened - that’s not really an enjoyable way to live.

So Minaa’s third tool is one I’m taking to heart: can I have one intentional moment every day where I’m present? It could be journaling, it could be exercise, but it could also be as simple as walking down the street without my earbuds in and smiling at people.

Thank you so much, Minaa, for joining me and for being so generous with your story. You can find Minaa at her Substack All the Hard Things, on Instagram, and her podcast This Feels Familiar is available wherever you listen.

I want to hear from you:

Have you ever gotten so fixated on a specific version of success that you lost sight of why you wanted it in the first place? What helped you come back to the actual goal? I’d love to know! I read and reply to every comment, y’all!

My dearest friend!

Our show launches…NOW! Welcome to A Little Thing That Helps!

Want the small tools, rituals, and mind-set shifts that have helped people who “made it,” actually make it? Subscribe now so you don’t miss an episode of A Little Thing That Helps!

I’m OBSESSED with hearing the real origin story of how people who “made it” actually made it. I’m so tired of the sanitized, Instagram-ready version of events where success comes naturally and quickly. Those narratives either 1) make me feel bad about myself (why not me?!) or 2) stop me dead in my tracks because CLEARLY, if I were talented, things would have been more effortless for me, right?

It’s why I started A Little Thing That Helps, my new show where I sit down with people who look utterly put-together on the outside and ask them about a time they were genuinely struggling, and the small, specific tools that helped them get through it and ultimately enjoy their lives.

For my very first episode, there was one person I wanted to talk to: Gretchen Rubin. She’s a 7x NYT best-selling author (you might know her from The Happiness Project, amongst many others), host of the Happier Podcast, and has her own hugely successful Substack. She is a woman who has, by any measure, made it. I mean, look at her dog, Taffy! Who has this much success and a dog this friggin’ cute?!

The small, anyone-can-do-it tools I learned from her have already had a HUGE impact on me (esp #3!) and I hope they help you too!

The Little Things That Helped Gretchen (and That I’m Stealing Immediately)

If you want tools, rituals, and little things that help you to live a good life, then I hope you’ll subscribe.

1. Gretchen’s Flop Changed Everything

That Happiness Project is a MEGA best-seller, but what I didn’t know was that it was her FOURTH book, and that she had been writing seriously for ten years before anyone paid attention.

The book right before The Happiness Project was a biography of JFK that she loved writing and that completely bombed. It didn’t even come out in paperback, which, in traditional publishing, is basically the publisher saying they’ve given up on a book.

The flop made her desperate to find another way in - a direct connection with readers. So she started a blog when blogging was a thing, then got on social media when social media was just becoming a thing, then started a podcast, which was also just becoming a thing.

One tool at a time, she didn’t give up, but instead, she added to her empire because she felt like she had no other choice. That infrastructure is EXACTLY what launched The Happiness Project into the stratosphere when it finally came out. The failure of the JFK book built the foundation for everything that followed.

“Had this book not really flopped,” she told me, “I don’t know that I would have done any of that because I would have thought, well, the system’s pretty much working for me.” [5:30]

2. A Life Unplanned Isn’t Worth Living* (*okay, Gretchen didn’t say that, but Aristotle kind of did)

Gretchen spent more than a year figuring out the structure for her best-seller Life in Five Senses. She had eleven senses, then nine, then eleven again, before a friend finally suggested: maybe it should just be the five senses. THE FIVE SENSES. A concept you learn in kindergarten. That is how hard structure is - it gets in your head! And I say this as someone who spent six months writing the first twenty pages of my second book. [16:24]

Loving Gretchen’s lessons? Go ahead and send them to a friend who could use them!

But she wasn’t just talking about books: Gretchen told me,

“Scheduling is life. Whatever is on the schedule is what is going to be my life.” [23:10]

There is an Aristotelian philosopher named Edith Hall who frames it this way: a life unplanned isn’t worth living. I AGREE WITH THIS. Structure isn’t the enemy of a good life, it IS the good life.

So instead of just thinking “I should go to the gym,” you put your shoes out the night before, you put it in your Google Calendar, you make it part of the actual architecture of your days.

I just moved to San Francisco, and I want to build community, so I am going to start hosting Shabbat dinners on Fridays. These will be on the schedule every Friday, because that’s how it becomes real. Structure, while honestly a little boring and hard to implement, is a friend to an enjoyable life.

3. Annoyance Is the Price of a Rich Life

Confession time: the morning of this recording, I was SO annoyed at The Boyfriend™️ about something he did. Just completely in my feelings about it, going in circles, unable to let it go.

And then Gretchen shared a lesson that created a major reframe for me: if you’re social and engaging with other people, it’s natural that you will feel bad sometimes. You will:

* Put your foot in your mouth

* Feel left out

* Feel paranoid

* Feel annoyed

“There will be awkward moments and angry moments and moments where nothing lands right, and that is just the price of a rich social life, the cost of having people in your life who actually matter to you. [21:22]”

“The richness of it,” she said, “is that some of it’s going to suck.” [22:54]

When she said that, it made me realize that the goal isn’t to eliminate the friction, it’s to stop treating the friction like a problem to be solved and instead treat it as proof that you’re actually living - and building a life you f*cking enjoy! I actually let the Boyfriend ™ off the hook because I remembered, Okay, I’m annoyed by this thing, but there is another 99% I’m not annoyed about with him. We have a rich relationship. Not a PERFECT one.

Thanks so much, Gretchen, for joining me and sharing so openly. You can find Gretchen at gretchenrubin.com, visit her Amazon author page here, listen to her podcast here, and see her cute puppies on Instagram here!

I want to hear from you:

Now I’d love to hear from YOU: What FLOP ultimately led you in the right direction? Are there any flops you continued to pursue and now see you could have pivoted sooner? I have a few of those myself…

A Little Thing That Helps is a six-episode conversation series where I speak with people who’ve “made it” about the small, specific, anyone-can-do-it tools, rituals, and mindsets that have helped them through their struggles to enjoy their lives. Hosted by Tara Schuster, best-selling author of Buy Yourself the F*cking Lilies