Who Deserves a Holiday Tip Best Year-End Tipping Practices

22 Dec 2025 · 10 min

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

Earn Your Leisure Podcast Summary

Episode Title

Who Deserves a Holiday Tip? Best Year-End Tipping Practices

Hosts

  • Rashad Bilal
  • Ian Dunlap

Episode Description In this episode, Rashad Bilal and Ian Dunlap explore the nuances of year-end tipping practices, addressing a listener's question about who to tip during the holiday season. They offer practical tips, discuss common scenarios regarding tipping etiquette, and emphasize the importance of showing appreciation to those who provide various services throughout the year.

---

Key Concepts and Discussions

Importance of Tipping

  • Tipping is not just a monetary gesture; it's about acknowledging the efforts of those who make everyday life easier.
  • The hosts stress that tipping can improve service quality in the long run.

Who to Tip

  • Common Recipients of Tips:
  • Sanitation workers
  • Teachers (in certain educational settings)
  • Valets and doormen
  • Barbers
  • Cleaning staff
  • School bus drivers
  • Building concierges
  • Considerations:
  • The nature of the relationship with the service provider.
  • The quality of service received throughout the year.
  • Special considerations based on living situations (e.g., apartment vs. house).

Tipping Etiquette

  • Monetary Gifts:
  • Gift-giving is encouraged to align with the level of service received; great service warrants a higher tip.
  • Gifts can include cash or thoughtful items depending on the provider's role.
  • Gray Areas:
  • Discussion on whether to tip teachers, particularly in high school versus preschool settings.
  • The necessity of tipping based on service quality; poor service should not be rewarded.

Practical Tipping Advice

  • Tipping can lead to better service in the future, as service providers remember those who treat them well.
  • Examples from Ian's life illustrate tipping practices, such as rewarding cleaning staff and recognizing the importance of mail carriers and other service workers.

Building Relationships

  • The hosts highlight how tipping can foster better relationships with service providers, leading to personal connections that enhance service experiences.
  • They encourage listeners to think about who they rely on daily and consider these individuals when deciding on tips.

Influence of Culture

  • There is a recognition that tipping practices can vary significantly across different communities and that education about such practices is vital.

---

Episode Takeaways

  • Show appreciation through tipping to acknowledge the hard work of service providers.
  • Recognize the subtle differences in tipping etiquette based on relationships and service quality.
  • Make a conscious effort to cultivate better relationships with those who contribute to your life, which can lead to enhanced service experiences in the future.

---

Conclusion This episode provides a comprehensive look at the often-overlooked topic of holiday tipping. Rashad and Ian's insights remind listeners of the importance of gratitude and the role tipping plays in fostering positive relationships with service providers. The practical advice shared can help anyone looking to navigate the complexities of year-end tipping with confidence and appreciation.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:00This is an iHeart Podcast. Guaranteed Human.

0:31a.k.a. neurolinguistic programming. Is it a self-help miracle, a shady hypnosis scam, or both? Listen to Mind Games on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hello, hello, all my people. What's up? It's Questlove. Recently, I had the opportunity to sit down with the one and only ASAP Rocky. He reflects on his journey from Harlem roots to global icon status and discovering the hip-hop origin of his name. The Ledge was on the TV. Rakim had the bucket hat Kangol join on. My pops was like, that's Rakim. That's who you named after. I just was like, damn the f*** I swear.

1:11Listen to the Questlove show on the iHeartRadio app, Apple Podcasts, or wherever you get your podcast. A new year doesn't ask us to become someone new. It invites us back home to ourselves. I'm Mike Della Rocha, host of Sacred Lessons, a space for men to pause, reflect, and heal. This year, we're talking honestly about mental health, relationships, and the patterns we're ready to release. If you're looking for clarity, connection, and healthier ways to show up in your life, Sacred Lessons is here for you. Listen to Sacred Lessons with Mike Delaroach on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

1:49This is Dr. Jesse Mills, host of the Mailroom Podcast. Each January, men promise to get stronger, work harder, and fix what's broken. But what if the real work isn't physical at all? I sat down with psychologist Dr. Steve Poulter to unpack shame, anxiety, and the emotional pain men were never taught how to name. Part of the way through the valley of despair is realizing this has happened, and you have to make a choice whether you're going to stay in it or move forward. Our two-part conversation is available now. Listen to The Mailroom on the iHeartRadio app, Apple Podcasts, or wherever you get your favorite shows.

2:21Hey, it's Joel. And Matt. From HowToMoney. If your New Year's resolution is to finally get your finances in shape, we've got your back. prices, they're still high, and the economy is all over the place. But 2026 is the year for you to get intentional and make real progress. That's right. Yeah, each week we break down what's happening with your money, the most important issues to focus on, and the small moves that make a big difference. Kick off the year with confidence, listen to How to Money on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. This episode is brought to you by PNC Bank.

2:56A lot of people think podcasts about work are boring, and sure, they definitely can be. But understanding a professional's routine shows us how they achieve their success little by little, day after day. It's like banking with PNC Bank. It might seem boring to save, plan, and make calculated decisions with your bank, but keeping your money boring is what helps you live a more happily fulfilled life. PNC Bank, brilliantly boring since 1865. Brilliantly Boring Since 1865 is a service mark of the PNC Financial Service Group, Inc. PNC Bank, National Association Member, FDIC. Okay, let's talk about tipping.

3:39Who gets tipped? Who should you tip? What's the best practices for end-of-year tipping? You know, it's one of these things. A lot of service workers, this comes from Mike. He asked this question. It's a great question. Garbage men. valet parker, like if you live in a building that has like valet parkers, those guys, concierge service if you live in a building. But then it goes down. Teachers. It's a good, yeah. Then at what age do you, like preschool teachers, stuff like that. Are you giving money to your son's high school teacher? Like what, who really needs an end of year monetary gift? Well, valet, for sure.

4:25Shout out to the guys. Doorman, shout out to y 'all. For sure, because they keep a lot of chaos away. Teachers, if they are a good teacher. What age teacher? I don't know. But the ones that I've had has been now first through fifth for Xander. I like his teacher, his primary teacher a lot. So I definitely give them something tomorrow, matter of fact. But I think it depends on, but even in preschool, you may think that they were not doing a lot, but when I would just pop in, they were, and then it was a family-run daycare. They do a really good job. So I brought some stuff up there for Christmas too, and then cleaning ladies.

5:10That's like my second family. They make my life so much easier. So those are the ones that I take care of in my circle, valet doorman teacher um house manager and it depends on if you live in an apartment or if you live in a home too because sanitation that's a home thing that's a private home thing yeah if you live in an apartment you don't see a sanitation worker so that's not even a thought if you live in a home then yeah the sanitation guys come and you know they come every wednesday they pick up the trash. That's a more personable thing. I think it depends on your life because a valet parker, like I said, if you live in a building, that's important.

5:51That's a close relationship. Yeah. Work-wise, yeah. The mailman. The mailman. Maybe. It depends on the relationship. Well, it also depends on the service, but it's just like I feel like the mailman is important. Are people even getting mail like that anymore? Nah, nah, people still get mail. That was my... They get bills. True. True. What if mind control is real? If you could control the behavior of anybody around you, what kind of life would you have? Can you hypnotically persuade someone to buy a car? When you look at your car, you're going to become overwhelmed with such good feelings. Can you hypnotize someone into sleeping with you?

6:37I gave her some suggestions to be sexually aroused. Can you get someone to join your cult? NLP was used on me to access my subconscious. NLP, aka Neuro Linguistic Programming, is a blend of hypnosis, linguistics, and psychology. Fans say it's like finally getting a user manual for your brain. It's about engineering consciousness. Mind Games is the story of NLP. its crazy cast of disciples, and the fake doctor who invented it at a New Age commune and sold it to guys in suits. He stood trial for murder and got acquitted. The biggest mind game of all? NLP might actually work. This is wild. Listen to Mind Games on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

7:24A new year doesn't mean erasing who you were. It means honoring what you've survived and choosing how you want to grow. It means giving ourselves permission to feel what we've been holding and knowing that it's okay to ask for help. I'm Mike Della Rocha, host of Sacred Lessons. This podcast is a space for men to talk openly about mental health, grief, relationships, and the patterns we inherit, but don't have to repeat. Here, we slow down. We listen. we learn how vulnerability becomes strength and how healing happens in community, not in isolation. If you're ready to let go of what no longer serves you and step into the year with clarity, compassion, and purpose, Sacred Lessons is your companion on your healing journey.

8:14Listen to Sacred Lessons with Mike De La Rocha on America's number one podcast network, iHeart. Follow Sacred Lessons with Mike De La Rocha and start listening on the free iHeart radio app today. New year, new goals, and in this economy, a better money plan is more necessary than ever. I am Matt. And I'm Joel. We are from the How to Money podcast, and every week we help you to spend smarter, save more, and make sense of what's going on out there. If you want 2026 to be the year you finally feel in control of your money, we're here to give you the tools and advice to help you make it happen. Listen to How to Money on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

8:53Hey there, this is Dr. Jesse Mills, director of the Men's Clinic at UCLA Health and host of the Mailroom Podcast. Each January, guys everywhere make the same resolutions. Get stronger, work harder, fix what's broken. But what if the real work isn't physical at all? To kick off the new year, I sat down with Dr. Steve Poulter, a psychologist with over 30 years experience helping men unpack shame, anxiety, and emotional pain they were never taught to name. In a powerful two-part conversation, we discuss why men aren't emotionally bulletproof, why shame hides in plain sight, and how real strength comes from listening to yourself and to others.

9:30Guys who are toxic, they're immature, or they've got something they just haven't resolved. Once that gets resolved, then there comes empathy and some compassion. If you want this to be the year you stop powering through pain and start understanding what's underneath, listen to The Mailroom on the iHeartRadio app, Apple Podcasts, or wherever you get your favorite shows. This season on Dear Chelsea with me, Chelsea Handler, we've got some incredible guests like Kumail Nanjiani. Let's start with your cat. How is she? She is not with a thing. Great, great, great way to start. So this is a great beginning and hopefully you'll be able to, I don't know, maybe you will cry.

10:10Amanda Seyfried. Life is so short. If you feel something like that, you have that fire in you for this experience. It's not for a guy. It's for the experience of being in love. And like, it's bigger than a guy. Elizabeth Olsen. I love swimming naked so much. And I know you love taking pictures of yourself naked. I love to be naked. I just want to be in my brown underwear all the time. Ross Matthews. You know what kids always say to me? Are you a boy or a girl? Oh my God. All the time. That's so funny. I know. So I'm always like, hi. I try to butch it up for kids, you know, so they're not confused.

10:44Yeah, but you're butching it up. It's basically like Doris Day. Right? No, I turn into Bea Arthur. Listen to these episodes of Dear Chelsea on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

10:59But yeah, the mailman. Barber. Oh, yeah, Barber, for sure. Yeah, Dave Shands made that conversation go crazy about if they're charging too much, but definitely holiday time. You got to take care of the Barber. School bus drivers. That's a good one. The school bus drivers. Those guys are important, or women. They're important because they make sure your kid gets to and from. Who are you not tipping? Anybody that does a bad job. Just because you do something. If you're a bad sanitation worker and the trash is always on the lawn, no, I'm not tipping you. Or if you just have horrible energy. Yeah, if you're not a nice person.

11:43Yeah. But if you do your job well, how much do you tip? it depends on the relationship to be honest. Clean ladies, they make my life so easy. Nice gift every year. You know, because this goes back to the wedding thing. Remember we talked about the wedding? A lot of people don't know. A lot of people, especially, unfortunately, our community, they don't fully understand etiquette a lot of times when it comes to wedding gifts. A lot of people don't fully understand etiquette when it comes to year-end gifts, tipping, holiday tips. They don't even know you have to do that or that is something that is you know expected on a certain level right so it's like it's not even that they're trying to be cheap it never the thought never crossed their mind that to give a sanitation worker a hundred dollars yeah but people also what my thing is to do to others how you want them to do you so deep down i think some people know they just may not think it's a requirement even in business you should be sending gifts out in the year for the people that's taking care of you.

12:45Well, that's bonus. Year-end bonus. Yeah. And a gift may not be bad in addition to. So in combination, if a person has been exemplary for you. Yeah. But rule of thumb, anybody that you're relying on, either on a daily or weekly basis that has a high level of customer service throughout the year, should be getting a tip. So if you're relying on your sanitation worker, if you're relying on your valet parker, if you're relying on your concierge, got your building, if you're relying on your, on your, a FedEx worker, if you're relying on your mail worker, if you're relying on your barber, if you're relying on the lady that does your, your manicures, if, if, if you're relying on, you know, your, the bus driver to make sure that your kid gets to or from school safely.

13:32If you're relying on a, on a preschool teacher that has to stay with the kids all day, every day. And they don't, they don't get different classes. They only have one group of kids for the whole entire day. because A, you're thanking them, but B, you're also having some level of, let's be honest, preferential treatment going forward. Yes. They're going to treat you better. Pay it in advance. Let's be honest. Right. Like, I mean, it's just one of those things. Like if you have one, they're going to make sure that you get better treatment than everybody else because you went over and above everybody else.

14:10Especially in a restaurant setting, too. Like, one way to get great service is a tip as soon as you get there. Before dinner? Mm-hmm. Helps a lot. I went and had a reservation. That'll go away a couple of times. I used to have a little issue in Sexyfield. You don't have no pants? Don't worry about it. Thank you. You know, Jabril broke it down, Passport Heavy. Shout out to him. Shout out to him. He said what he does is he started tipping the hotel check-in people. It helps a lot. It helps a lot, bro, especially L.A., Mexico. He starts, he's like, and then miraculously, he just starts getting room upgrades, fruit baskets sent to the room.

14:54Even when I go to Cabo, like, they'll connect you with the other people that are moving the show. Hey, do you know such and such? He's a director. I don't know. I have no clue what that nature documentary was on BBC. Cool. Connect me. Because you're paying it for it first, and they may not be able to give you the gratitude back monetarily, but they'll be able to do it in service or another way. It helps. Yeah. And for your cleaning people and drivers and all that, if you don't treat them well, your information may end up on the dark web. So be careful. Take care of them. Take care of them, please.

15:28That's a fact. That's a fact. monetary gifts for everybody that's important earners what's up you ever walk into a small business and everything just works like the checkout is fast the receipts are digital tipping is a breeze and you're out the door before the line even builds odds are they're using square we love supporting businesses that run on square because it just feels seamless whether it's a local coffee shop a vendor at a pop-up market or even one of our merch partners Square makes it easy for them to take payments, manage inventory, and run their business with confidence, all from one simple system.

16:05One of the things we love most is seeing neighborhood businesses level up. There's this West Indian spot right in our community that started with a small takeout counter. Now with Square, they've been able to expand into a full sit-down restaurant and even started catering events across the city. That's the kind of growth that inspires us, and it's powered by Square. Square is built for all types of businesses, from the corner bagel shop that turned into a local chain, to the specialty market with thousands of unique items, to the stylist who's been holding you down for years. If you're a business owner or even just thinking about launching something soon, Square is hands down one of the best tools out there to help you start, run, and grow.

16:47It's not just about payments. It's about giving you time back so you can focus on what matters most. Ready to see how Square can transform your business? Visit square.com backslash go backslash E-Y-L to learn more. That's square.com backslash go backslash E-Y-L. Don't wait. Don't hesitate. Let Square handle the back end so you can keep pushing your vision forward. What if mind control is real? If you could control the behavior of anybody around you, what kind of life would you have? Can you hypnotically persuade someone to buy a car? When you look at your car, you're going to become overwhelmed with such good feelings.

17:24Can you hypnotize someone into sleeping with you? I gave her some suggestions to be sexually aroused. Can you get someone to join your cult? NLP was used on me to access my subconscious. Mind Games, a new podcast exploring NLP, a.k.a. neurolinguistic programming. Is it a self-help miracle, a shady hypnosis scam, or both? Listen to Mind Games on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

18:16Just damn the f***ing f***ing swag. Listen to The Questlove Show on the iHeartRadio app, Apple Podcasts, or wherever you get your podcast. A new year doesn't ask us to become someone new. It invites us back home to ourselves. I'm Mike Della Rocha, host of Sacred Lessons, a space for men to pause, reflect, and heal. This year we're talking honestly about mental health, relationships, and the patterns we're ready to release. If you're looking for clarity, connection, and healthier ways to show up in your life, Sacred Lessons is here for you. Listen to Sacred Lessons with Mike Delaroach on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

18:57This is Dr. Jesse Mills, host of the Mailroom Podcast. Each January, men promise to get stronger, work harder, and fix what's broken. But what if the real work isn't physical at all? I sat down with psychologist Dr. Steve Poulter to unpack shame, anxiety, and the emotional pain men were never taught how to name. Part of the way through the valley of despair is realizing this has happened, and you have to make a choice whether you're going to stay in it or move forward. Our two-part conversation is available now. Listen to The Mailroom on the iHeartRadio app, Apple Podcasts, or wherever you get your favorite shows.

19:29Hey, it's Joel. And Matt. From How To Money. If your New Year's resolution is to finally get your finances in shape, we've got your back. Prices, they're still high, and the economy is all over the place. But 2026 is the year for you to get intentional and make real progress. That's right. Each week we break down what's happening with your money, the most important issues to focus on, and the small moves that make a big difference. Kick off the year with confidence. Listen to How to Money on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. This is an iHeart Podcast. Guaranteed human.

From the publisher

In this insightful clip from "Black Out with Ian & Rashad," hosts Rashad Bilal and Ian Dunlap dive deep into the important—yet often misunderstood—topic of year-end tipping. Responding to a listener question, they break down who should be on your tip list during the holiday season, how much you should give, and why showing appreciation to those who make your life easier is essential. Rashad shares common scenarios, highlighting everyone from sanitation workers, teachers, and valets, to barbers, school bus drivers, and even your building’s concierge. Ian provides real-life examples from his own life, pointing out the value of tipping your cleaning crew, building staff, and even the mailman. The duo discusses the nuances of tipping based on the service received, relationships built over the year, and the importance of recognizing excellent customer service. They also tackle those awkward gray areas: Is it necessary to tip your child’s high school teacher, or does it stop at preschool? What if the service was subpar? Both hosts agree that monetary gifts should go hand-in-hand with outstanding service and positive energy—but getting the etiquette right can sometimes confuse even the most well-meaning among us. Whether you live in a home or apartment, rely on daily or weekly help, or simply want to ensure you’re not missing an important gesture, this clip is packed with practical tips, etiquette reminders, and candid stories about why tipping matters—not just for gratitude, but for better service in the future. Ready to level up your holiday tipping game and show some love to those who support you all year long? Rashad Bilal and Ian Dunlap have you covered! *Hashtags:* #TippingEtiquette #HolidayTipping #YearEndGifts #ServiceWorkers #BlackOutPodcast #IanDunlap #RashadBilal #Gratitude #PodcastClip #LifeAdvice #BetterService #SupportYourCommunity #Appreciation #CustomerService #MonetaryGifts

See omnystudio.com/listener for privacy information.

More from Earn Your Leisure

All 386 episodes
Who Deserves a Holiday Tip Best Year-End Tipping PracticesEarn Your Leisure · 10 min
Listen in VO