Ep. 550: Very Special Episode: Now Is the Time to Tackle That One, Big, Hard Thing

Summary

Podcast Summary: Happier with Gretchen Rubin

Episode 550: Very Special Episode: Now Is the Time to Tackle That One, Big, Hard Thing

Original air date: September 3, 2025
Hosts: Gretchen Rubin (New York City), Elizabeth Craft (Los Angeles)

---

Episode Overview

In this very special 550th episode, Gretchen Rubin and her sister/co-host Elizabeth Craft explore the idea of “the one big thing” — a major, intimidating task or challenge that, once faced, could significantly increase your happiness. While their usual episodes often deal with small habits, hacks, and lighthearted topics, this episode dives deep into why tackling life’s most daunting problems is so important, what those big things might be, and how listeners have navigated these moments themselves.

The hosts discuss common types of “big things,” share insights from their own experience and listeners, and offer actionable advice for anyone facing their own big challenge.

---

Key Discussion Points and Insights

Why Focus on “One Big Thing” (02:29 - 05:59)

• Paradox of Happiness: Sometimes the things we need to do for happiness don't feel happy in the short term. “Happiness doesn't always make us feel happy, which sounds paradoxical, but… sometimes to be happier, we have to do things that make us feel less happy.” — Gretchen (04:50)
• Prompt to Action: If you’re waiting for the sign that it’s time — this is it. “Often something that can be done at any time is often done at no time.” — Gretchen (05:30)

Categories of “One Big Thing” Challenges

1. Relationships (06:07 - 07:53)

• Breaking up, divorce, dating again
• Saying goodbye to a beloved pet
• Setting tough boundaries (e.g., telling an adult child it’s time to move out)
• Having difficult conversations with elderly parents (e.g., “you can’t drive anymore”)
• Reaching out to reconcile with someone or breaking off contact
• Deciding whether or not to have children (07:41)

2. Self-Related/Health (07:53 - 11:39)

• Addressing addiction (smoking, drinking, gambling, overspending)
• Facing health concerns or overdue tests
• Overcoming fear of medical appointments or procedures
• Seeking therapy for the first time
• Managing chronic pain or experimenting with solutions
• Letting go of old dreams or facing hard truths about oneself

3. Work & Career (11:39 - 12:57)

• Quitting a job
• Updating a resume or seeking new work
• Gaining new certifications or returning to school
• Starting a business
• Planning for retirement

4. Money (12:57 - 13:37)

• Facing overdue taxes or debt
• Having hard financial conversations with family/partners
• Accepting you’re living beyond your means

5. Major Life Logistics (13:37 - 14:06)

• The overwhelming task of moving (yourself or a loved one), downsizing, or prepping a home for sale

“There’s so many parts about moving, which means you have to clear out all this stuff... you have to make a plan for putting it on the market. It can feel overwhelming.” — Gretchen (13:52)

Listener Stories & Advice (16:12 - 23:33)

Listeners’ real-world stories provided inspiration and actionable guidance:

• Career Change: Megan became a flight attendant after 20 years as a homeschooling mom. (16:52)
• Citizenship for Love: Patty Ann became a Canadian citizen: “My advice would be to make the decision once and just keep plowing forward toward that goal as best you can and eventually it will all be worth it.” (18:06)
• Divorce: Linda filed after 23 years — “It was the scariest thing I've ever done... But going through with it has made me so much happier. My advice would be to take it one day at a time and don't be afraid to ask for help.” (18:22)
• Debt: Michelle confronted $35k in credit card debt — “Stop hiding from the numbers. ... The debt doesn't get smaller by ignoring it, but once you know exactly what you're dealing with, you can actually fight it.” (19:45)
• Addiction: Jacob quit smoking after decades — “What helped me was realizing I didn't have to quit forever, just for today. Tomorrow I could decide again. That made it less overwhelming.” (19:58)
• Late-in-life Education: Lee went to art school at 32 and it transformed her life (20:36).
• Parenthood: Laura shared the intimidation and happiness of choosing to have kids.
• Physical Challenge: Sandy, at 58, completed a triathlon with breast cancer survivors: “My advice is to face your fears, find someone who will support you, break that challenge into smaller pieces, look to that final finish and how great you'll feel.” (22:02)
• Performing in Public: Maria danced in an international show — inspired by the quote, “You must do the thing you think you cannot do.” (22:19)
• Driving: Kirsty, intimidated by driving, challenged herself (as part of her “25 for 2025” goals) to rent and drive a car twelve times that year, ultimately succeeding. (22:48)

Actionable Advice: How to Tackle Your Big Thing (26:20 - 36:45)

1. Ask for Help (26:20)
   “Why is it so hard to ask for help? ...When something is really big and intimidating, it can be very, very helpful to draw on other people for support.” — Gretchen (26:37)
2. Start Before You’re Ready (27:38)
   “We often have this idea like, well, at a certain point, I'll feel ready... Sometimes you just have to take the leap and trust the process.” — Gretchen (27:42)
3. Do You Need More Time — Or Just Decide? (28:05)
   Sometimes perpetual ‘preparation’ is actually procrastination. Make the call.
4. Break It Down (One Bite at a Time) (28:14)
   “Make a list of everything... organize it into groups... then just start tackling it one thing by one thing.” — Gretchen (28:47)
5. Question Your Assumptions (29:13)
   Don’t let thoughts like "I could never use dating apps" go unchallenged.
6. Imagine Your Future Self (30:35)
   “What will you wish you'd done now? ... If you think about what your life will look like if you put this extremely hard task behind you... that can be really powerful.” — Gretchen (30:45)
7. Match Your Style: Marathoner or Sprinter? (31:39)
   Tackle big tasks either in one long surge or in small, consistent chunks — whichever suits you best.
8. Get a Buddy and Use Accountability (32:41)
   For many, having a partner (gym buddy, quitting partner, etc.) is essential for staying on track.
9. Leverage Your “Tendency” (33:05)
   Utilize Gretchen’s Four Tendencies framework — Obligers need accountability, Rebels need choice, Questioners need reasoning, Upholders need scheduling.
10. Therapy is a Tool (34:17)
    “Going to therapy could help you tackle the task. ... A therapist could help with a lot of these things.” — Elizabeth (34:17)
11. Script Hard Conversations (34:47)
    Prepare what you need to say ahead of time for difficult talks.
12. Acknowledge the Difficulty (35:16)
    Facing big challenges is truly hard. Give yourself credit for even considering it.

---

Notable Quotes & Memorable Moments

• “If you start to feel sick to your stomach, if you start to feel really anxious, it is probably a sign that there is something that you really need to grapple with.” — Gretchen (03:31)
• “Often something that can be done at any time is often done at no time.” — Gretchen (05:37)
• “We often get pain either way. So what kind of pain do we want?” — Elizabeth (31:32)
• “Stop hiding from the numbers. ... The shame loses its power when it's not a secret anymore.” — Michelle, listener (19:45)
• “What helped me was realizing I didn't have to quit forever, just for today.” — Jacob, listener (20:25)
• “We think we know everything, but we don't.” — Elizabeth (30:32)
• “The feeling of, like, energy and greater efficacy and control might come much sooner than the absolute finish line that you think of when you're beginning.” — Gretchen (36:45)

---

Timestamps for Major Segments

• Intro / Theme: 02:29
• Why “One Big Thing” — the Case for Tackling It: 03:19 - 05:59
• Categories & Examples: 06:07 - 14:06
• Listener Stories: 16:12 - 23:33
• Advice & Strategies: 26:20 - 36:45
• Closing Thoughts: 36:45 - 38:59

---

Final Thoughts

The hosts acknowledge how challenging it is to face the “one big thing,” but emphasize the freedom, happiness, and lightness that often follow on the other side. They encourage listeners to reflect on their own “big thing,” take steps (however small) to address it, and share their stories with the Happier community.

---

If you’re waiting for a sign to address that major hard thing in your life — this episode is it.

Transcript

[Elizabeth Craft]

There's something about a love story that takes your breath away. Not because it's perfect, but because it's impossible. Imagine finding the person you were meant to be with in the very place designed to destroy you. Imagine choosing love when everything around you is hate, everything designed to strip away hope. That's not just romance. That's survival. That's destiny. That's exactly what you'll feel watching Bow Artist at War. The film opens September 26th and you can visit Baomovie.com to see the trailers.

[Gretchen Rubin]

If you were moved by Schindler's List or even the bittersweet hope in Jojo Rabbit, you'll understand why Bao is different. This isn't just about what was lost, it's about what was found. Artist at War tells the remarkable true story of Joseph Bao, a brilliant artist and master forger who risked everything to help others survive. Artist at War opens September 26th. Visit baomovie.com to watch the trailer and learn more or sign up your organization for a group screening. Again, that's Baumovie.com from Fitness Routines to.

[Elizabeth Craft]

Mental resilience, navigating personal goals to tackling burnout, we all need a little help being human. That's what the Life Kit podcast from NPR is here to do. If you're looking to move with more intention or just need thoughtful guidance on living better, listen. Life Kit delivers strategies to help you make meaningful, sustainable change. Life doesn't come with a manual, but every day you're making choices, some big, some small, that shape the direction of your life. Life Kit offers real stories, relevant insights and clear takeaways to help you meet those decision making moments with confidence and clarity.

[Gretchen Rubin]

The thing about Life Kit is I feel like so often the episodes are specifically what I need at the moment. Like they recently did a one about dealing with neck pain. When I was dealing with neck pain, the timing was so perfect to give me practical tips that I needed. With Life Kit, you get help tackling common issues like relationships, finances, parenting and your career. Then you walk away with a game plan you can implement right away. Life Kit isn't just another podcast about self improvement. It's about understanding how to live a little better. Starting now. Listen now to the Life Kit podcast from npr.

[Elizabeth Craft]

Lemonade.

[Gretchen Rubin]

Hello and welcome to Happier, a podcast where we talk about how to make our lives happier. This week is a very special episode because it's episode 550. Every 10th episode is a very special episode and today we'll talk about tackling that one big thing. I'm Gretchen Rubin, a writer who studies happiness, good habits, secrets of adulthood and human nature. I'm in New York City, and joining me today from Los Angeles is my sister, Elizabeth Craft. My sister, the sage.

[Elizabeth Craft]

That's me, Elizabeth Craft, a TV writer and producer living in la. And Gretch, I think this episode has a lot of sage advice from you.

[Gretchen Rubin]

Well, I hope so. We shall see. But this week, for this very special episode, we are going to talk about tackling that one big thing.

[Elizabeth Craft]

Yes. So we often talk about little things, fun things, whimsical things, hacks. We have done bingo cards before, but in this bingo, one square wins.

[Gretchen Rubin]

Yes. So today we are talking about something different. We are going to talk about something that is big and something that is very, very hard. Today we're going to talk about the hard thing that we may need to do to make our lives happier. Because the fact is, sometimes, if we're going to really make our lives happier, there is something really, really big that we need to tackle. And sometimes it's so big and it's so intimidating and maybe it's so upsetting that we don't even want to admit to ourselves that this is the one big thing that really matters. And as we discuss the one big thing, as you're listening, listeners, if you start to feel sick to your stomach, if you start to feel really anxious, it is probably a sign that there is something that you really need to grapple with, something that is big and that is hard, but that will do a lot for your happiness.

[Elizabeth Craft]

Yeah. And of course, I mean, the one big thing is different for different people. For some people, it's a relationship thing. For some people, it's going to be an addiction thing. There's all different categories. So we're going to talk about what some of those one big things are or could be.

[Gretchen Rubin]

And before we launch in, there's just a few secrets of adulthood that I think are helpful. One is that the secret of adulthood, that happiness doesn't always make us feel happy, which sounds paradoxical, but the fact is, sometimes to be happier, we have to do things that make us feel less happy. Like we need to deprive ourselves of something. We need to demand something from ourselves. We need to face something. But then once we do it, then we get that feeling of lightness and energy and possibility once we push through. And another thing, and this is the reason that we are doing this very special episode, is that often something that can be done at any time is often done at no time. And so it may be that there is One big thing. And you're just thinking to yourself, well, not now, not today, not tomorrow, not this week, but eventually, one day, I will tackle it. Well, we are here to say now is the time. This is the time. This is the prompt. If you are waiting for something in your life to say now we are that. We are that signifier that means now is the time to start thinking about it.

[Elizabeth Craft]

Yeah. And so the one big things fall into several different categories. So we'll divide them up as we go.

[Gretchen Rubin]

And these are just examples. This is not an exhaustive list. But just to give people a sense for the kind of things that are these one big things. Or maybe for someone to have that ring of truth when they hear something, listed out here are some of the major things that people face. And first, let's talk about relationships.

[Elizabeth Craft]

Yes. So if you need to break up with somebody or even get a divorce, that's big.

[Gretchen Rubin]

That's hard. Maybe you need to get on the dating apps. This is a thing that many, many people resist, but many people say is really important to try.

[Elizabeth Craft]

Maybe you need to say goodbye to a beloved pet who has no quality of life anymore.

[Gretchen Rubin]

Yeah, that's really, really hard. It's hard to face that moment, face that time. Maybe you need to set a tough boundary, like there's a child living at home and you need to say, hey, it's time for you to move out.

[Elizabeth Craft]

Also, having a hard conversation, like telling a parent about the fact that they can no longer drive or live without assistance.

[Gretchen Rubin]

Yeah, these are hard conversations that, you know, maybe you put off and put off and put off, but, you know, it needs to happen. Maybe there is a relationship where you want to reach out to reconcile with, with someone from whom you've become estranged. Or maybe on the other hand, maybe there is a relationship where you need to break off a connection with somebody. Either way, you need to assess a relationship and decide if action is needed.

[Elizabeth Craft]

Yes. And then there's deciding whether or not to have children, because eventually you do have to decide that sort of one.

[Gretchen Rubin]

Way or the other or circumstances will decide it for you.

[Elizabeth Craft]

Yes.

[Gretchen Rubin]

Then there are the one big thing issues that arise in relationship to ourselves. And then often these are related to our health, health measures. A very big thing in many people's lives is dealing with some form of addiction, which is dealing with smoking or drinking or gambling or overspending or any kind of addiction. It's realizing that it's gotten out of hand and that you need to tackle it.

[Elizabeth Craft]

There could be a health concern, a test, you need to take that you've been avoiding or a worry that you're hiding. I think many people might sense they're sick but not want to face it. And it only gets worse, of course.

[Gretchen Rubin]

Right. Sometimes there's just something that you really dread that you know needs to happen, and yet you keep putting it off. Maybe you're somebody just really, really, really hates going to the dentist, even though you need to go to the dentist. I have a friend who put off and put off and put off getting a hip replacement. And then she finally did it. And then, of course, she was pain free, and she was so happy that she had done it, but she delayed for a very long time before it got to the point where she couldn't delay it anymore.

[Elizabeth Craft]

Yes. And I will say with that, Gretchen, age is a real factor in that. So let's say you need to get a knee replacement. Sooner is better than later in terms of your recovery.

[Gretchen Rubin]

With many, many things on this list. Sooner is better than later.

[Elizabeth Craft]

Yes.

[Gretchen Rubin]

Yeah.

[Elizabeth Craft]

Maybe you need to start therapy.

[Gretchen Rubin]

Mm. Many, many people find it to be extraordinarily useful, but it can be hard if you've never done it before. Here's something maybe you need to grapple with persistent pain. Now, chronic pain is so draining and overwhelming, but dealing with it can be very frustrating. It can take a lot of trial and error to figure things out. I remember we had a listener who suggested if you've tried physical therapy in the past and it hadn't worked, maybe try it again. Because there have been a lot of strides made in physical therapy. I mean, our father has issues with his feet, and he has done so much to experiment with different kinds of footwear to get to the kind of shoe that really allows him not to have pain. It can be frustrating. Yeah.

[Elizabeth Craft]

Gretch. I mean, Adam, you know, has suffered from migraines since he was five years old, and he had to try all different kinds of things to take care of the migraines. And he would go years without even trying because he was so worn out just from dealing with it. But now he's found the right thing, and it is a miracle. Yeah.

[Gretchen Rubin]

Maybe you need to face the fact that there's something very hard to do that you're just gonna have to do on your own, that you were hoping that you would have somebody to help, but you're just gonna have to do it by yourself, and that's hard. Maybe you need to move or buy a house, maybe have a baby. You need to do it on your own, and that can Be hard to do.

[Elizabeth Craft]

That's hard to grapple with. Maybe you need to decide whether to let go of a dream. So you wanted to be a famous actor, but maybe you need to accept it's not gonna happen and find another path.

[Gretchen Rubin]

Now, one of the things that can be tricky about the one big things is sometimes they creep up on you. And they may not look like big problems, but you have to recognize that they are big problems. And since I've been thinking so much about the empty nest, I would say that one big thing to tackle is if you feel like you agree with a statement that my children have become my whole world, that is something to address, because that is too much pressure to put on your children. If nothing else, they're a big and important part of your world, but you don't want your children to become your whole world.

[Elizabeth Craft]

Absolutely, I agree with that. And then, Gretch, there's the category of work.

[Gretchen Rubin]

Mm. Maybe you need to quit your job. Maybe you've been thinking for a long time you need to quit, but you need to get around to it and actually quit.

[Elizabeth Craft]

Maybe you need to look for a new job, getting your resume in place. Maybe you need a new certification or to go back to school for a certain skill.

[Gretchen Rubin]

Yeah, along the same lines, maybe you need to go back to college. Maybe you've been meaning to get your college degree and you need to get that started so you can get it done.

[Elizabeth Craft]

Maybe you really want to start your own business. Gretchen, I happen to be reading a book called maybe We Can Make It after all, about Kate Spade starting her business. And it's a fascinating story, and it just. Some people just want to have their own business.

[Gretchen Rubin]

They do, and it's just like making that leap. Or maybe you want to face the future of what retirement will look like and really sit down and start crunching the numbers. You know, Social Security, pension, all that. Really look at what those numbers hold.

[Elizabeth Craft]

I think so many of us avoid looking at anything having to do with numbers of any sort of. Can be very intimidating.

[Gretchen Rubin]

Well, and speaking of that, that brings us to the topic of money.

[Elizabeth Craft]

Yes, money. Maybe you have overdue taxes that you need to take care of.

[Gretchen Rubin]

Maybe you have credit card debt that you need to deal with.

[Elizabeth Craft]

I think a lot of us have that. Maybe you need to face the fact that you're living beyond your means.

[Gretchen Rubin]

And, you know, another kind of hard conversation. Maybe you need to have a hard conversation about money with someone. For instance, maybe you need to talk to your children honestly about what you can or can't for college or other forms of support. Those are hard conversations to have.

[Elizabeth Craft]

Or maybe you need to talk to your partner. I mean, Gretch, I think there's a lot of people who are in relationships who don't talk about money with each other 100%.

[Gretchen Rubin]

Absolutely. Absolutely. Lots of difficult conversations. And then finally, just in life, one thing that is often a very big thing that people put off is thinking about moving. Because there's so many parts about moving, which means you have to clear out all this stuff in your house. You have to fix things up. You have to make a plan for putting it on the market. You have to figure out, well, where are you going to go? Maybe you're doing this for yourself or maybe you're helping someone else to move like a parent. That is just another big, big thing that can feel overwhelming.

[Elizabeth Craft]

So overwhelming. I don't even want to think about moving ever. All right, Gretch. Coming up, we're going to hear from listeners on the subject of tackling an intimidating challenge. But first, this break. For every move, for every mood, for every you, express your true self with JLab. No matter your mood. There's JLab headphones for every you. JLab believes in amplifying every version of you through superior audio technology, innovative design and unbeatable value. Their diverse range of headphones and earbuds are engineered to deliver exceptional sound quality, catering to your unique lifestyle and musical preferences.

[Gretchen Rubin]

Yes. Whether you're a discerning music lover, a fitness enthusiast or a casual listener, JLab's cutting edge audio performance ensures your playlist sounds just as the artist intended. I have the JBuds pods which have more than 56 hours of playback. Hybrid active noise canceling the very sleek design. You can get black or mauve. I have black and it's the lab quality sound. Look for the blue box at retailers everywhere or shop jlab.com and use code happier for 15% off your order today.

[Elizabeth Craft]

Feeling better in your body shouldn't be a full time job. That's why hers makes it easier to get started and stick with it. Backed by expert guided online care that puts your weight loss goals first. Hers is transforming women's healthcare by providing access to affordable weight loss treatment plans. They connect you with a medical provider who will work with you to determine the best treatment option for you. If prescribed, you get medication as part of a doctor developed weight loss program, complete with ongoing care check ins, dosage and medication adjustments and access to 24. 7 online support at no additional cost, no hidden fees and no membership fees.

[Gretchen Rubin]

Whether you want to lose weight, grow thicker, fuller hair or find relief for anxiety, hers has you covered. Visit forhers.com happier to get a personalized, affordable plan that gets you that's F O-R-H-E-R-S.com happier forhers.com happier weight loss by hers is not available everywhere. Compounded products are not approved or reviewed for safety, effectiveness or quality by the fda. Prescription required. See website for full details, important safety information and restrictions. Actual price depends on product and plan purchased okay, well, we've talked about what that one big thing might look like. We talked about a lot of different, very big, big tasks that people might face. And we also asked listeners this question about whether they'd ever face something like this. The question was, have you ever tackled an intimidating challenge? And if you did, did it make you happier? What advice would you give to someone finding it hard to face that one big thing? And the first answer came from Megan. She said, I became a flight attendant for a major US airline after spending 20 years, my entire adult life raising and homeschooling four children. That required me to go through an extensive interview process and live in a hotel for six and a half weeks of training. Okay, well, that's a big, big career switch.

[Elizabeth Craft]

Yes, Patty Ann said. I became a Canadian citizen to stay with the love of my life that I met here in Alberta. There were quite a few challenges and so much paperwork and other requirements like fingerprinting and medical exams. It felt intimidating, overwhelming, and took literally years of stages and steps. My mother reminded me of the how do you eat an elephant? Saying. So I took it one bite at a time. I did have a few doubts of how it would work out, but quitting did not go through my mind. I cried, cried with relief when it was all completed. And of course it has made me happier. My advice would be to make the decision once and just keep plowing forward toward that goal as best you can and eventually it will all be worth it.

[Gretchen Rubin]

Well, that's good advice. Yes, Linda said. I filed for divorce after 23 years of marriage last year. It was the scariest thing I've ever done. I didn't even know how to pay bills online or change the oil in my car. But going through with it has made me so much happier. I'm learning who I am again after being we for so long. I even took a pottery class, something I never would have done before. My advice would be to take it one day at a time and don't be afraid to ask for help. Friends and Family want to support you more than you realized. Oh, that's a very encouraging thing to hear.

[Elizabeth Craft]

Yes, Michelle said. Ugh. Credit card debt thing. $35,000 in climbing. I was literally hiding mail from my husband because I was so ashamed. Finally sat down and made a spreadsheet of everything we owed. Cried for about an Then we both got serious about it. No more eating out, no more impulse purchases. Everything extra went to the cards. Took forever, but we did it. Worth every sacrifice. My advice? Stop hiding from the numbers. I wasted months being scared to even open statements. The debt doesn't get smaller by ignoring it, but once you know exactly what you're dealing with, you can actually fight it and tell someone. The shame loses its power when it's not a secret anymore. Well, this goes to so much of what we were talking.

[Gretchen Rubin]

Right? Right. About the fear of numbers, about the fact that things get worse if you don't deal with them. And that's a great thing to share with somebody because the shame loses its power. That's a great reminder. Jacob said. I quit smoking two years ago after smoking since I was 16. What worked for me was switching to those little toothpicks first, then gradually weaning off those two. Sounds weird, but keeping my hands and mouth busy was key. Still reach for my shirt pocket sometimes, but I don't miss the smell or the coughing. Definitely happier. And my wife is thrilled. She doesn't have to smell it on me anymore. What helped me was realizing I didn't have to quit forever, just for today. Tomorrow I could decide again. That made it less overwhelming. So that's interesting. That's sort of the opposite. One person says decide once and then just plow through. And then for somebody else, it's like it's just for today. So different ways work for different people.

[Elizabeth Craft]

Yes, lee said. At 32, I went to art school and the challenge was whoever won best portfolio at graduation got an internship at the most the most prestigious advertising agency in South Florida. So intimidating is there were so many talented artists it drove me night and day. And I did end up winning best portfolio, which was a springboard for a career in advertising that were the happiest days of my life.

[Gretchen Rubin]

So this is a good reminder. There's been a couple things about doing something at an older age than maybe people typically do it, but you can still do it.

[Elizabeth Craft]

Yeah.

[Gretchen Rubin]

Laura said.

[Elizabeth Craft]

Kids.

[Gretchen Rubin]

So intimidating. Pregnancy, childbirth. All scary. But yes, happier. Oh, yeah.

[Elizabeth Craft]

Well, that is very true.

[Gretchen Rubin]

That's very true.

[Elizabeth Craft]

Sandy Sundays. At age 58, I joined a group of breast cancer survivors to train and complete a sprint triathlon. Team Phoenix was a six week program to train to complete the try of swim, bike and run. We'd already completed the try of treatment, surgery, chemo and radiation. I had never done anything like it, had to borrow a bike. I completed my try with 25 other women and it was life changing. I'm not only happier, but I'm thriving. I went on to complete 12 more triathlons over the years and fell in love with the biking. It opened me up to other challenges. A half marathon, century bike rides, 100 miles in a day, as well as actually working part time in a bike shop. My advice is to face your fears, find someone who will support you, break that challenge into smaller pie, look to that final finish and how great you'll feel. Well, that's a very uplifting challenge.

[Gretchen Rubin]

Absolutely. And so much great advice. Maria said, I danced in an international charity show. It made me incredibly happy. I thought of Eleanor Roosevelt's you must do the thing you think you cannot do when I was asked to participate. And I immediately said yes, Gretch.

[Elizabeth Craft]

I have to mention here that my sister in law Olivia did this, a ballroom dancing charity show. And it was was so much fun. Adam and I went and watched and we were very proud of her because it is not easy.

[Gretchen Rubin]

Oh, that's so fun.

[Elizabeth Craft]

Kirsty said, I did my driver's license when I was 18. However, I never drove a lot and up until this year I had pretty much given it up completely. We live in a big city. Everything is super easy with public transport. Plus we only have an old VW camper van that I find difficult to drive. Then this year, as part of my 25 for 2025, I challenged myself to drive a car. 12 this year, I always rent a car that I find easier to drive. And by now I have already completed the 12 times. I did it because I wanted to be more independent and set an example for my kids. So that's facing something that's very intimidating. Sometimes you find it less intimidating than you thought it would be.

[Gretchen Rubin]

Yeah. Well, as somebody who's kind of a fearful driver, I really, this really strikes a chord with me. And yeah, it's a good example of facing a fear and it might be something that other people would not find fearful, but if for you it's something that's really intimidating, it could be your one big thing.

[Elizabeth Craft]

Yeah. All right, Gretch. Coming up, we're going to talk about other ideas that might make facing this one big thing easier. But first, this break this podcast is sponsored by Naked Wines Gretch. You know I want to entertain more. I am absolutely set on that but I have no idea what wine to serve. I will just be in the wine aisle looking around, no clue what to do. That's why I love Naked Wines. Naked is a wine club that directly connects you to the world's best independent winemakers so you can get world class wine delivered straight to your door. It's so great because I like white, Adam likes red. We can have a box with three of each bottles and we know what we get is going to be great.

[Gretchen Rubin]

Now is the time to join the Naked Wines community. Head to nakedwines.com happier click enter voucher and put in our code Happier for both the code and password for 6 bottles of wine for just $39.99 with shipping included. That's $100 off your first 6 [e-mail] happier and and use the code and password happier for 6 bottles of wine for just 39.99 I had such a wonderful time on my book tour for Secrets of Adulthood. This year I visited 15 cities without a single travel complication. When has that ever happened? I learned so much by road tripping across the country. First I learned how grateful I am for the kind people who help others stow their carry on bags. Hoisting my bag over my head is my least favorite part of the travel process and I so appreciate appreciated the thoughtful people who helped me out. Also, I learned the importance of airline apps. It makes a huge difference to have the actual app for an airline on your phone. In fact, these days, perhaps it's not really possible to fly without having the airline app.

[Elizabeth Craft]

Another app that's a must have while traveling Airbnb. Not only can you find amazing places to stay, you can also host your own space on Airbnb while you're away. It's just a smart thing to do. Bring in a little extra cash for yourself and open up a place for someone else to stop over on their cross country trip. Your home might be worth more than you think. Find out how [e-mail] host okay, we.

[Gretchen Rubin]

Got so many great suggestions from listeners who are speaking from experience. They went through this process, they faced the one big thing and they all say how much happier that they are having done it. A lot of great advice about how to make it easier, but here are just a few additional ideas or things to underscore. I think one thing that a couple people mentioned but really worth emphasizing is to ask for help. Why is it so hard to ask for help? This is so surprising to me. I have to remind myself in even the smallest things to ask for help. But obviously, when something is really big and really intimidating, it can be very, very helpful to draw on other people for support, for their encouragement, for just their help. For instance, if you're facing addiction, something like AA can be really important if you are trying to make a career change. There are all kinds of resources that are meant to help people going through a career change. And so it's to reach out for those resources and really avail yourself of them.

[Elizabeth Craft]

Yeah. I think one reason it can be hard to ask for help is because it is putting a name to something.

[Gretchen Rubin]

Yes.

[Elizabeth Craft]

Whether it's written or you're spoken, you are naming it. And then back to the shame. It may be something you feel ashamed about, which makes it even harder to put a name to it.

[Gretchen Rubin]

Yes. That's so true.

[Elizabeth Craft]

Another piece of advice is to start before you're ready.

[Gretchen Rubin]

Yeah. I think we often have this idea like, well, at a certain point, I'll feel ready, and that's when I will begin. But with all the things that we listed, probably a person would never feel ready to tackle them. They're just the kind of thing where sometimes you just have to take the leap and trust the process and not wait until it feels like the right time. Because it may be that no time will ever feel like the right time. Yeah.

[Elizabeth Craft]

And then ask yourself, do you need more time or do you need to make a decision? This is something you and I have discussed on a smaller scale many times.

[Gretchen Rubin]

Many times. Because a lot of times it is. You think, well, I'll be gathering information. Somehow things will become clear. There's just this idea that we have that in the future things will be easier or clearer or simpler. But sometimes you just feel like, okay, I just need to decide to do it and move forward and not keep finding reasons to put it off. And here's something I think can be useful if you're feeling really overwhelmed, especially if it's something that has a lot of moving parts. Make a list of everything that you can possibly think of that you need to do or that you need to find out anything that you can think of. So write it all down and then go back through it and organize it into groups. Probably there's categories of things and put it into some order and then just start tackling it one thing by one thing. A couple people mentioned this. Just take it one day at a time. Take a bite, Bite, bite. How do you eat an elephant? One bite at a time.

[Elizabeth Craft]

Yeah. And then, Gretch, question your assumptions. For instance, I could never use dating apps. Well, is that true that you could never use dating apps or just have you never used dating apps?

[Gretchen Rubin]

Right, right, right. Or sometimes people will say, like, well, I shouldn't depend on medication to help me get through this. Maybe it would help you to use medication to get through this. Question that assumption.

[Elizabeth Craft]

Yes. Or the assumption that it will be easier to do this hard thing next year. It very well may be harder to do the hard thing next year, not easier.

[Gretchen Rubin]

Right. Well, here's a really good example of questioning an assumption. So I had a friend who had to move her very, very frail, elderly parents from their apartment in the Midwest to be closer to her to live in an assisted living place here in New York State. And her brother lives very, very far away. And she just assumed her brother wouldn't or couldn't help, and she didn't even think to ask him. And then finally she was like, oh, well, maybe I should ask my brother if he could help. Maybe he could help pay for the cost of it, even if he couldn't help, or whatever. And he ended up showing up and really, really helping. Once she said to him, like, this is what the plan is in motion. Do you want to be involved? And he ended up being quite involved. But it took her a while to question her assumption that she had to do it all herself.

[Elizabeth Craft]

Yes. We think we know everything, but we don't.

[Gretchen Rubin]

Yes.

[Elizabeth Craft]

And then imagine yourself in five years. Think of your future self. What will you wish you'd done now? I find it helpful to think of my future self.

[Gretchen Rubin]

Yeah. I think if you think about, well, what will your life look like if you put this extremely hard task behind you and you really use your imagination to paint a picture of that and thinking about that future self and like, what you owe to your future self to get to that place can be really powerful. And this reminds me of another exercise that I love, and I often use this with habits, which is if you could wave a magic wand and you could solve one problem in your life, or you could make one task magically disappear, what would that thing be? Often you think, oh, my gosh, if this one thing were fixed, how happy I would be. And that's like, okay, so if that's what would magically do it, maybe you want to do the hard work of making it happen.

[Elizabeth Craft]

Absolutely. We have to remember that we often get pain either way. So what kind of pain do we want?

[Gretchen Rubin]

Yeah. I think sometimes it's just, it's one or the other. It's now or later. You have to face it. I think that one thing that can just in sort of the logistics of it, as you're. You're thinking about setting yourself up, as you're tackling this one big thing, is it's worth thinking about. Are you a marathoner or a sprinter in your preferred work pace? Are you somebody where you really, like, want to just buckle down and do it in like one intensive sprint in a weekend or a week or a month? Are you just really going to push, push, push, push, push through it? For some people, that is more energizing. That gives them the focus, and that's a way to set yourself up for success. But then for other people, they like small changes. They want to, like, pick away at something piece by piece by piece. And as we so often say, there's no right way or wrong way. But people really, they prefer to work one way or the other way. So think about setting it up in the way that works for you. Don't assume that one way or the other is the right way to do it. It's whatever works best for you.

[Elizabeth Craft]

Another thing that can be helpful is to do whatever that thing is with a buddy. Go through it with someone else. I mean, this is true for anything from quitting drinking with a buddy, to going to get your mammogram with a buddy, to going to the gym with a buddy. I mean, it can really be helpful. I mean, I know for me, as an obliger, a buddy helps with accountability, and that makes a huge difference.

[Gretchen Rubin]

Speaking of being an obliger, this is a place where you want to really tap into the superpower of whatever your tendency is. And again, if you don't know if you're an upholder, a questioner, an obliger, a rebel, or what we're talking about, go to GretchenRubin.com quiz and you can take the quiz. But again, like, if you are a rebel and you want to do this one big thing, you know, you don't want to tell yourself things like, I should do this, or everybody's telling me to do this, you want to say things like, this is what I want, this is what I choose, that will give me the life of freedom and possibility that I want. If you're a questioner, you really want to sit down and think about why this change is going to change your life for the better. Why are you going to be happier if you do it and, like, really run the numbers? When people quit smoking. Elizabeth, I remember when our father quit smoking, he said that one thing he did is he would just add up all the money that he would save. And then he's like, well, if I save this money and then I invest it, and then I get a standard rate of return, and then over a year and over five years, he would just run the numbers. And that gave him a lot of reason to quit and to really kick the habit. And then upholders put it on the schedule. It's on the schedule every day for a half an hour. I'm gonna do XYZ towards my one big goal. And obligers, of course, the accountability is the actual key thing.

[Elizabeth Craft]

I've often talked about how great I think therapy is, and we mentioned that one big thing you may need to do is start therapy. But I would also add that with a lot of these tasks, going to therapy could help you tackle the task. So anything from, oh, my gosh, I need to sell my house, I'm overwhelmed, to I need to quit smoking, to I need to talk to my parents about the future. I mean, a therapist could help with a lot of these things, right?

[Gretchen Rubin]

I think another thing that can help, a lot of these have to do with hard conversations that you have to do with people. One thing that can help with a hard conversation sometimes is just literally scripting out what you want to say when you're, like, in a calm, collected frame of mind. And it may not go the way you expect, but often sort of rehearsing it in your mind, and it can give you a greater sense of control. And then it also might mean that when you have that conversation, you're better at communicating effectively.

[Elizabeth Craft]

Yes, I think that's a great idea.

[Gretchen Rubin]

Look, here's the thing. It's easy to talk about these things. It's easy to list them, but this is hard. All the things that we're talking about that we've listed, that listeners talked about, these were really, really hard. We get it. You have all of our encouragement and sympathy.

[Elizabeth Craft]

Yes, it's easy to say, oh, get a divorce. But doing that, not so easy.

[Gretchen Rubin]

I remember a friend of mine, she was going through divorce, and she said to me, I really don't know that I can go through this. She's like, I don't know how so many people get a divorce. This is by far the hardest thing I have ever done in my life. And she was just so distraught at that moment. And then now I see her and. And it's so far in the rearview mirror, and she got through it, and now she's doing great. But when she was going through it, it was so, so hard. But often it is what we need to do to make our lives happier, healthier, more creative, and more productive. It is to just tackle that one big thing.

[Elizabeth Craft]

Yeah. And, Gretchen, I do wonder in tackling the one big thing, if the other side might come sooner than one imagines it will.

[Gretchen Rubin]

Yes.

[Elizabeth Craft]

Because sometimes starting the process of whatever you need to do. So let's just say, you know, you have too much credit card debt and that you have to pay it down. I think even before you get to paying off that full 35,000, you're going to feel a lot better when you've paid off 5,000.

[Gretchen Rubin]

Even having this spreadsheet. She cried for an hour, and then it's like, yes, I think that's a really good thing to remember that the feeling of, like, energy and greater efficacy and control might come much sooner than the absolute finish line that you think of when you're beginning.

[Elizabeth Craft]

And it's sometimes with health, for instance, the problem isn't as big as it might be in your mind. And you may be so happy when you find out that this is wrong, not that other thing you were worried about or if it is the big thing. Again, tackling it now is gonna be better than tackling it later.

[Gretchen Rubin]

Absolutely. Well, let us know if you do try this at home and how tackling one big thing works for you. We really want to hear your experiences. What did you tackle? What have you tackled in the past? What did you learn? This is something where we can all benefit from each other's experiences. We're really eager to hear what people have to say. Let us know on Instagram, Threads, TikTok, Facebook. As always, you can drop us an [e-mail], or you can go to happiercast.com 550 for everything related to this episode.

[Elizabeth Craft]

Yeah, it'll be really interesting to hear what people have to say.

[Gretchen Rubin]

Absolutely. And that is it for this episode of Happier. Remember to try this at home. Tackle that one big thing.

[Elizabeth Craft]

Thank you to our executive producer, Chuck Reed and everyone at Lemonada.

[Gretchen Rubin]

And here's your rhyming reminder. If you like the show, tell others you know.

[Elizabeth Craft]

Until next week. I'm Elizabeth Craft.

[Gretchen Rubin]

And I'm Gretchen Rubin. And thanks for joining us. Onward and upward.

[Elizabeth Craft]

Gretch. What's interesting is even if some of these items aren't in our life now, they could be later.

[Gretchen Rubin]

Oh, yes, absolutely.

[Elizabeth Craft]

There's always one big thing coming around. The corner.

[Gretchen Rubin]

That's why I think it's so great to learn from other people, because I feel like I'm learning so much that I can use it now. Or maybe use it years from now.

[Elizabeth Craft]

Yeah.

[Gretchen Rubin]

From the Onward Project.

[Elizabeth Craft]

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. 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?

[Gretchen Rubin]

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.