How To Be More Comfortable With Guilt, Because You Deserve Happiness

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Last week, I was catching a flight from San Jose to Boston when I passed a vending machine full of makeup. "What a useless thing to have in an airport," I thought. My next thought was, "I should get something." You see, I'm trying to get comfortable with guilt. And few things make me feel guiltier than buying useless products.

Of course, I went for the least practical item in there: a $30 set of four lipsticks. My mind did gymnastics to try to justify it. Having good-looking makeup could be good for my career when I make public appearances, I figured. Or maybe I could give it to my friend as a birthday gift.

Then, I remembered what Christina Salerno and Toku McCree, executive coaches for Unexecutive, taught me: If you try to assuage your guilt by justifying your actions, you'll never learn to live with guilt. You'll also miss the whole point of the guilt-inducing decision you made: to do something just because it makes you happy — because you deserve happiness. Once I embraced the fact that I was buying completely pointless makeup from this oddly placed vending machine, my whole mood changed. I felt like I was treating myself. I felt respect for myself. I was having fun.

It was striking how this simple action affected my behavior. It was as if something had been unblocked — as if whatever was blocking me from buying things just for pleasure had also been blocking me from everything else I enjoyed. Suddenly, I was joking around in my work emails, excitedly texting my friend in preparation for my visit, offering her two of these useless lipsticks, and lending another friend money because I was just feeling generous.

This perfectly illustrated something Salerno and McCree taught me as my life coaches: When you get comfortable with little things that make you feel guilty, the big things become less intimidating. Once you can master buying makeup or eating sweets without guilt, for example, you can move on to defying your family's values or saying "no" when your friends ask for favors.

Toward that end, here's a list of little ways to practice feeling guilty. Try one each day and soon, other people's opinions will have no sway over your decisions.

1. Turn Down An Invitation

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An invitation is by definition something you can say "no" to.

2. Upgrade Your Travel Arrangements

Getting a five-star hotel may be expensive AF, but what about paying $25 extra for an Airbnb where you can really let your hair down?

3. Do Nothing

Become capitalism's worst nightmare and spend a set amount of time — even just five minutes — doing nothing at all.

4. Ask For A Sexual Favor

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Don't offer to do anything in reciprocation. You deserve pleasure unconditionally.

5. Play

Get out your arts and crafts supplies or old toys, or go to the playground. Playing seemed worthwhile when you were a kid, so why shouldn't it be now?

6. Take Up Space

Get your womanspread on, because god knows the guy next to you doesn't feel guilty about manspreading.

7. Say "No"

Then stop. Don't apologize. Don't explain yourself. "No" is a complete sentence.

8. Masturbate

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Your to-do list can wait.

9. Buy Pointless Products

Bonus points if they're from an airport vending machine.

Once you've tackled these, you can move on to the big stuff, like following your dreams. They're all the same skill, after all: living for yourself.