I’m a saver. Like… a SAVER. I check our credit card and bank apps so often it should honestly just live on my forehead. My thumb has muscle memory at this point — Chase, Amex, Discover, repeat.
Meanwhile… my wife Danielle? Full-on spender. I love her — but she’s the kind of person who has mastered Amazon shopping to a disturbing level. Throw pillows, 17 snacks, four candles, and a shirt that was “basically free because it was on sale.” (It wasn’t.) When I question all the Amazon boxes, I’m told “don’t worry I’m returning it.” Same excuse for years and she still thinks I fall for it.
But, I gotta admit something:
While I’m sitting there steaming, worrying about inflation, interest rates, and whether we remembered to cancel that free trial before it auto-renews — she’s just… living. Relaxed. Laughing. Enjoying the moment. And I can’t help but wonder: Am I doing it wrong?
I have anxiety issues to begin with (this is a safe space, right?). Like, serious anxiety. I worry about everything. I play everything out to its worst conclusion. One thing goes wrong and I have us homeless, unable to eat. It’s bad.
Danielle and I have been married for 117 years (not a typo). She knows me. She knows when I’m spiraling over money. She walks over, all cool, and says “what’s the worst that’s gonna happen? We’ll be ok. Let’s enjoy the ride.” In the moment, it infuriates me.
Live stream inside my head: “WTF ARE YOU TALKING ABOUT?! WE NEED TO SAVE IN CASE OF EMERGENCY!”
But here’s the truth: Maybe she’s right?
Every relationship needs a saver and a spender. Maybe it’s nature, maybe it’s nurture, maybe it’s just Target’s fault — but the balance weirdly works. The saver brings stability. The spender brings joy. And when it’s healthy, you keep each other in check.
But what happens when one of you goes too far? When saving turns into hoarding or anxiety… or when spending turns into real debt?
So let’s break it down — Rossen Reports style — with quick signs you might be going too far in either direction:
If you’re a SAVER… beware if:
You stress over every purchase, even small ones (shit, guilty)
You deny yourself joy “just in case” — constantly (every day)
You say no to experiences you can afford out of fear (not often, but yes)
You check financial apps more than you check on your kids (I’m screwed)
If you’re a SPENDER… watch out if:
You’re hiding packages from your partner
You don’t actually know what’s in your checking account
You’re always swiping now and worrying later
You justify every purchase with “I work hard, I deserve it” (even if it’s true — dangerous pattern!)
Here’s the good news: You don’t have to change who you are. But knowing your type — and your partner’s — is the first step to balance. Set boundaries. Have money check-ins. Use tools like budget apps (we love YNAB and Rocket Money) Talk openly. And maybe, just maybe… find a little room to grow.
Danielle is teaching me to let go a little. And I’m teaching her that 17 candles are, in fact, too many candles. (Even if they’re “Buy 3, Get 3 Free.”)
What about you? Are you the saver or the spender? How does it work in your family? Leave a comment and tell me.
Case in point: Uber.
Danielle just orders it. Doesn’t check the price, doesn’t compare, just taps and goes. Meanwhile, I’m over here yelling, “WAIT! Did you check Lyft?! What if it’s cheaper? What if there’s a promo code?!”
She calls me stingy. I call it smart consumer strategy.
So, I wanted to answer the question once and for all — Uber vs. Lyft: Which is really cheaper? Which one’s faster? We tested them in real time — and there’s a clear winner!
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On My Mind
Why Am I Tipping a Guy Who Didn’t Say Hi?
I dropped off my laptop the other day at a repair shop. No warm greeting. No smile. The guy behind the counter literally didn’t say a word. I handed over my broken computer… he took it and walked away. That was the whole exchange.
Later, I came back to pick it up. Same vibe — zero eye contact, no “have a nice day,” just plopped the laptop down and spun around the little iPad register on the pedestal. And there it was: the moment of shame.
TIP 15%? 18%? 22%? 25%?
For what, exactly? There was no “service.” I didn’t even get a sentence.
AND TO MAKE IT WORSE…
I got home and the laptop still didn’t work.
It’s official: tipping culture is out of control.
We’re being asked to tip on everything now — not just meals or haircuts, but:
Grabbing a pre-wrapped muffin at a coffee shop
Clicking “pickup” for takeout we’re carrying ourselves
A self-checkout kiosk (yes, really)
And now… handing off a broken computer to a silent repair guy?
And don’t even get me started on the pressure.
They spin that screen around, and suddenly you’re on a game show called “How Much Do You Care About This Person’s Livelihood?” — with the cashier standing two feet away. What am I supposed to do, hit “No Tip” and be the villain of the day?
I tip well for real service. Restaurant servers? Yes. Drivers? Yes. Barbers and hairstylists? Absolutely.
But it’s gotten ridiculous — and it’s adding up.
So what should we do?
Tip where it matters.
Sit-down meals: 18–20% for good service
Delivery drivers, rideshare, barbers: Yes
Hotel housekeeping: Yes (few people do, but you should)
Don’t feel guilty skipping it when:
It’s a retail counter
It’s self-serve
You’re just buying something, not being served
You had bad service (hi again, laptop guy)
Final tip:
If the screen flips around and you feel pressure, just say, “Oh, I’m good, thanks.” Or select “No tip” and own it. You’re not a monster. You’re just refusing to be guilt-tripped by a screen.
We can’t stop the tip screens from popping up, but we can stop reflexively hitting 20% out of fear.
What do you think? Are you fed up with this? Have you ever been asked to tip in a weird place? Hit reply or leave a comment. I want to know!
Talk soon,
Jeff
Jeff, you are a brilliant guy. Always, one of your key traits. Never change! I look forward to watching you thrive in the years to
come! You and your wife are adorable! 🥰 Keep navigating the ups and downs — it’s a journey!!!!
They don’t call me “The Cheapskate” for nothing, lol. But I’m trying to do better at worrying less about spending, especially for things like travel. That said, I still struggle to enjoy eating at restaurants because the prices ruin it for me. Like, $20 for a burrito, are you kidding me?! 😂