Everything’s Perfect…Except I’m Broke from Tipping Everyone
Everything’s Perfect podcast with Autumn Calabrese and Donald Stamper (aka Sarah and Nell)
Episode Date: November 11, 2025

Episode Overview

This funny, honest episode dives deeply into the messy etiquette, emotions, and pressures surrounding tipping—especially during the holidays. Autumn (Sarah) and Donald (Nell) share their frustrations about “tip creep,” swap stories from years of working in the service industry, and break down who deserves a tip (and when), how much is right, and when it all feels like too much. Peppered with relatable anecdotes and candid confessions, the episode offers a fresh, practical take on generosity, gratitude, and the realities of modern tipping culture.

Key Discussion Points & Insights

1. The Overflowing Holiday Season and Content Creator Envy

• Early Christmas Content Fatigue

  • Frustration with seeing Christmas reels and decor in October, feeling pressured to skip over Thanksgiving and rush into Christmas for online content.
    • Sarah: “Do I have to bust out all my Christmas decor and start filming Christmas recipes? Because I’m trying to put Thanksgiving stuff out.” (02:14)
    • Nell: “I like Thanksgiving because it ushers in that… Christmas holiday spirit… growing up, we always drew names on Thanksgiving of our gift exchange for Christmas.” (11:15)
  • Acknowledgement of clever creators who make Instagram content look effortless (“I’m really just bitter that mine doesn’t work that way.” — Sarah, 05:06).

• Nostalgia for Slower Holidays

  • Stories about family traditions (post-Thanksgiving Black Friday, shopping in Cleveland, waiting until after Thanksgiving to decorate for Christmas).
  • Mutual appreciation for Thanksgiving being about gratitude, not gifts:
    • Sarah: “It’s not about gifts. It’s not stressful… just come together. What are you thankful for?” (09:31)

2. Black Friday, Marketing, and Sales Naming Fatigue

• Black Friday “Deals” Starting Early
  • Discomfort with stores and brands marketing “Black Friday” sales weeks ahead of the holiday.
    • Sarah: “Black Friday is the day after Thanksgiving… Just call it a sale.” (12:43)
  • The reality that retail brands earn a high percentage of their sales during the Black Friday-Cyber Monday window, prompting them to start earlier.
    • Sarah: “I think I read that her company does 40% of their total yearly sales on… Black Friday-Cyber Monday weekend.” (14:39)

3. Core Topic: Tipping Culture—Old Rules vs. New Realities

• Service Industry Background

  • Both hosts worked in restaurants/serving (“worked in the service industry half of my life”—Sarah, 15:40) and empathize with tipped employees, but see tipping culture as muddier than ever.

• Tipping as Essential Income for Service Workers

  • Explains how servers’ hourly pay is negligible; tips are their main income.
    • Sarah: “You got paid $2.15 an hour, which basically meant nothing… So you were only getting your tips.” (16:31)
    • Discussion of tip-outs: servers must tip out hosts, bussers, bar, sometimes leaving only half their total after tip-out.
      • Nell: “If you tip 20 percent, the server… is only getting 10 percent.” (20:17)

• The Gray Area: When, Who, and How Much Is Right?

  • Automatic Gratuities

    • Experiences with restaurants (especially in LA) that add 18%+ gratuity to checks, even for small parties, ensuring staff aren't stiffed by international guests or those unaware of tipping norms.

  • Tip Creep & Tip Pressure

    • Frustration with touch-screen tip prompts everywhere: coffee shops, to-go counters, bottle service at venues—where staff are often paid a regular wage.
      • Nell: “They just didn’t do anything… I still left a tip because that… I’m so bad about when that option’s there.” (30:02)
    • Agree that 20% is the minimum for full service, but don’t feel obligated for to-go/counter staff.

  • Delivery & Takeout

    • Food delivery services: tip based on distance, not just percentage.
      • Sarah: “If I order a steak dinner… I’m not tipping you $40… I do think about their gas money and their time.” (34:24)
    • Grocery delivery: frustration that tips are prompted before service quality is known; wish it could be edited post-delivery.

  • Other Service Professions

    • Hair salons: confusion over tipping multiple assistants; don’t tip owners.
      • Sarah: “If your hairdresser owns the salon, you’re not supposed to tip them.” (43:41)
    • Bartenders: always tip 20% (not just $1/drink), especially as drink prices have risen.
      • Nell: “Most people just think… $1 is enough, but it’s not.” (41:01)
    • Valets: $5 is standard.
    • Housekeepers (at hotels): often forgotten but considered necessary, more per day than per stay.
    • Bellhops: per bag or a flat $20 if bringing multiple bags.

  • Tipping vs. Direct Pay / Bonus

    • For house cleaners/contractors paid directly at a set rate, tipping isn’t necessary, though holiday bonuses are nice.
      • Sarah: “She gets holiday bonus, things like that, little things throughout the year.” (49:21)
    • Caution against companies charging high cleaning rates and then requesting additional tips (“I felt like I got bent over... For the price that they charged, and then… tip three women on top of that?” — 49:37)

  • Holiday Tipping & Gifting

    • Feel pressure to tip/gift everyone during holidays: hairdressers, teachers, mail carriers, etc.
      • Sarah: “By the time you just get through the taking care of the people that help take care of you at home, you’re like, okay, that was a lot.” (57:10)
    • Agree that big holiday gifts for every service provider is appreciated but not expected—don’t feel guilty if you can’t do everything (“I think it’s always appreciated, but it’s never expected.” — Sarah, 59:21).

  • International Differences

    • Express envy for Europe’s non-tipping culture; fair wages mean tipping is unnecessary and even odd.
      • Sarah: “They just pay their damn employees… servers are nice… they kind of look at you crazy if you tip them.” (53:12)

Notable Quotes & Memorable Moments

• On Creative Fatigue:

  • Sarah: “It really just pisses me off that I suck at it. If I’m being totally honest. Trigger is me.” (03:37)
  • Nell: “That’s not my journey, honey. I’m here to admire that, not to create that.” (05:21)

• On Giving Flowers (Instead of ‘Props’):

  • Sarah: “You’re not supposed to say props anymore. You say give flowers… I got to give flowers where flowers are due.” (02:25)

• On Restaurant Tipping Reality:

  • Nell: “If you can afford to sit there at that restaurant, you can afford to tip 20.” (21:21)
  • Sarah: “If you can’t afford to tip the person, then order differently. Order differently. Or go to a different restaurant.” (22:23)

• On Tip Creep:

  • Sarah: “It feels like everywhere you go, everybody’s got their hand out for a tip.” (29:31)

• On Tipping Counter Service:

  • Nell: “This is an opportunity for complete generosity. Yes, I do not need to tip here. But if I want… but it doesn’t feel the same as not tipping at a restaurant.” (33:04)

• On Housekeeper/Bellhop Tipping:

  • Sarah: “It’s usually about five bucks [valet]... If I do have somebody bring stuff up, I typically just give them a 20.” (50:38)

• On The Best/Worst Tipping Experiences:

  • Nell: “His bill was like $75… and he tipped me $200. And he was like… have a nice time, go buy the suit, whatever. Just enjoy it.” (60:29)
  • Sarah: “When I waited tables at the Cheesecake Factory, Ron Pompeo… would tip me $100 every time he came in.” (61:15)

• Holiday Tipping Pressure:

  • Sarah: “It was just—it’s November 30th. I didn’t even think about a Christmas present. And I know I’m not going to see him now until after Christmas. So do I bring a present after? Does it look like I tried to time it out to avoid them? Because I didn’t.” (58:38)

• On Tipping in Europe:

  • Sarah: “You don’t tip. Anybody… They just pay their damn employees.” (53:12)

• Podcast Humor Finale:

  • Nell [sign off]: “Until next time, when we talk about… just the tip. Just kidding. I can’t believe we went this whole episode without making a just the tip joke.” (64:02)
  • Sarah: “Actually, good job.” (64:05)

Timestamps for Key Segments

• Christmas & Thanksgiving Content Pressure: 01:56—09:29
• Holiday Family Traditions: 09:29—10:51
• Black Friday / Early Sales: 12:24—14:54
• Tipping as a Service Worker: 15:16—23:44
• Automatic Gratuity, Servers’ Finances & Tip-Outs: 17:31—22:03
• Gray Areas: Who & When To Tip?: 23:44—29:31
• Tip Creep in Society / Counter Service Debates: 29:31—36:35
• Bartender, Delivery & Takeout Tipping: 40:41—45:50
• Salon, Spa, and Personal Service Tipping: 43:04—48:06
• Hotel Tipping (Housekeepers, Valets, Bellhops): 48:29—53:04
• No Tipping Culture in Europe: 53:04—54:33
• Holiday Tipping, Gifts, and Guilt: 55:23—59:29
• Best Tip Stories: 59:37—62:33
• Final Thoughts & Listener Call For Input: 62:57—end

Summary Takeaways

• Tipping in America is both necessary and confusing. Both Sarah and Nell are generally generous tippers (especially as former service workers), but struggle with “tip creep,” unclear expectations, and feeling broke during the holidays.
• Fundamental tipping advice: If someone is paid as a tipped employee (waitstaff, bartenders, valets, hotel housekeepers), tip at least 20%. For others (counter service, delivery, salon owners, house cleaners paid directly)—use discretion and consider wage norms.
• Holiday season: tip more if you can, but gifts/tips aren't universally expected—cash and practical gifts are always best, but don’t let pressure “break you.”
• The wish: clear, European-style wage transparency would resolve much awkwardness. Until then, generosity is appreciated, but authenticity (and financial boundaries) matter most.

Connect with the show:

Instagram: @everythingsperfect.official
Email: everythingsperfect.podcast@gmail.com