If You Feel Guilty Spending Money, You're Doing It Wrong

Today I want to talk about saving money.

We Save Money

We recently took the YNAB team on a retreat. At YNAB, the retreat is a category, and we save for it all year long.

This is the YNAB team. In front of the ginormous cabin. This was our “fancy” picture.

We spent several days in the largest privately-owned cabin in the U.S. (Seriously, that is a thing!) We played laser tag. We learned how to curl, er, we curled, we tried curling—you get the idea. We played board games and Spike Ball and did a huge puzzle. A chef came one night and made us dinner. There was a ginormous, heated pool.

It was even more amazing than we expected—and we had pretty high hopes—but it was a big expense and worth every penny. I put money away for the retreat every single month and when it’s time to spend a big chunk, I do it without hesitation.

This was laser tag. Which all of the YNAB team loved except for one person who shall not be named and was always dead.

Spending Money You Saved On Priorities Feels Great

Spending should always feel great—unless you’re having to just pay your taxes, that doesn’t feel great. But when you buy something, it should feel enjoyable. The good stuff should feel good. Spending money on a vacation should feel good.

If you’re feeling guilty or second-guessing spending money on your vacation it might mean the spending isn’t totally aligned with your priorities, or that you don’t really have that money to spend because it’s earmarked for other things.

In my case, spending on the retreat is 100 percent aligned with my priorities. Our team works remotely, all over the world, and this is our chance to come together. Sometimes, we get to meet people we’ve worked with for years but have never met. It’s so important for our growth as a team and our work overall. It is so worth it for me.

Puzzles and coding and board games. Our coolness never ceases to amaze.

But when you’re feeling that guilt about spending money on a vacation or spending money on this or that nice thing or whatever, that guilt can come from one of two places: 1) the spending is out of line with your priorities, or 2) your priorities are out of line with your spending.

And you say, “Jesse, that was the same reason.” Yes, it was. There is only one reason why you feel guilty when you’re spending money, and it’s because it’s not actually in line with your values — that’s just it. And you feel guilty — that’s it.

We have such a great team. And it remains one of our top priorities to get them in the same room from time to time without any form of video chat required.

Know Thy Priorities—And Save For Them

So, don’t feel bad about feeling guilty. Don’t feel guilty about feeling guilty. Just recognize, “Hey, whoa! There’s a little signal. Let me slow down, analyze that signal a little bit, and see if I can separate noise from signal and get to the bottom of this.”

And you find out a lot of times that yes, your money’s just… you’re just kind of going with the flow. You’re going with the crowd. You’re a little bit of a sheep sometimes — I am too. And you end up doing stuff you didn’t actually really want to do.

So, these little guilt trips are sometimes good wake-up calls. BUT there was no guilt at the YNAB retreat. And it felt great.