Round Up
A YNAB celebrity prepares for a big life change
— September 8, 2025 —
There comes a time in a person's life over and over again when one needs to reassess their spending. With baby #2 on the way, Hannah sits down with her real-life husband, Mac, to discuss the seven questions that any YNABer should ask when anticipating a big life change. It's a glimpse into how partners reshuffle priorities and features Mac's valiant decision to lessen his Frisbee golf spending. 🥲
Speaking of reassessing your spending, Jesse talks about why the idea of "lifestyle creep" can cause people to feel guilty about natural changes to their spending as their life becomes more "expansive." And September seems like a fine time to check in on your holiday categories with Ben B. 🎁
PS: We're hiring! We’re looking for a delightful Delight Specialist to join our fully remote, award-winning team. If you have experience managing external vendors, complex logistics, and might be the world’s best gift-giver, check out the job opening. (Application closes September 14, though it may close earlier depending on volume of applications received.)
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Quiz question:
When Disneyland opened in 1955, you would have been able to pay for a day's entry, rides, and food for four people by raiding which of your categories?
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A: Monthly mortgage
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B: A week’s worth of groceries
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C: Monthly clothing target
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D: Gas for the Chevy Bel Air
(Answer at bottom)
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Watch
Seven Questions You Need to Ask Before a Big Life Change
Is life about to change for you in a big way? Has it already? Hannah walks through the seven questions you should ask yourself to get your YNAB plan ready for what's to come. This one's extra fun because Hannah and her husband, Mac, discuss the questions as they prepare for baby #2!
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Read
Plan for Holiday Spending Right Now
No, you don’t need to run out and buy a Christmas present in September. But you do need a category for holiday spending in your YNAB plan. In this blog post, Ben B unpacks the often-overlooked costs of the season—last-minute gifts, decorations, food, travel—and shows you how to set up targets that make the holidays feel a lot less stressful (and a lot more joyful).
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Watch
Why Everyone Feels Financially Behind
Here's a familiar feeling: you're worried about money. Behind on retirement goals, student loan payments, keeping up with the neighbors—you name it. Ben M explains why feeling behind on your finances is more a product of cultural pressure than personal failure, and how you can regain your confidence.
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Listen
It's OK to Move Your Goalposts
People often buy different furniture when they're 23 than they would at 53. Some call it "lifestyle creep," but if your financial resources have strengthened over the years, isn't it natural for your tastes to change as well? Jesse explores the way spending will evolve as you do.
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Quiz answer: $30, or a week’s worth of groceries
When Disneyland opened in 1955, a family of four could enjoy admission, rides, and food for around $30 according to a recent New York Times article. That was roughly equal to the cost of a week’s groceries for a median-income family at the time. Hot diggity dog! 🐭
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