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)
- 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) - 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) - Do You Need More Time — Or Just Decide? (28:05)
Sometimes perpetual ‘preparation’ is actually procrastination. Make the call. - 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) - Question Your Assumptions (29:13)
Don’t let thoughts like "I could never use dating apps" go unchallenged. - 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) - 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. - Get a Buddy and Use Accountability (32:41)
For many, having a partner (gym buddy, quitting partner, etc.) is essential for staying on track. - Leverage Your “Tendency” (33:05)
Utilize Gretchen’s Four Tendencies framework — Obligers need accountability, Rebels need choice, Questioners need reasoning, Upholders need scheduling. - 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) - Script Hard Conversations (34:47)
Prepare what you need to say ahead of time for difficult talks. - 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.