The ‘Should’ Trap: Why Resolutions Set You Up to Fail

Hey Comically Human Tribe,

Welcome back! If you’re already regretting your New Year’s resolutions, don’t worry—you’re in good company. In this week’s edition, we’re diving into the history of resolutions, why they set us up to fail, and how to break free from the ‘Should’ Trap.

The Origins of Resolutions: From Gods to Grind

Did you know New Year’s resolutions have been around for over 4,000 years? Turns out, humanity has always been bad at follow-through.

• Babylonian Beginnings: It all started with the Babylonians during their Akitu festival. They’d promise their gods to return borrowed items and repay debts. So, if ancient Babylonians could remember to return a borrowed ox, surely your neighbor can manage to give back your lawnmower.

• Roman Glow-Up: Fast forward to Roman times, when Julius Caesar named January after Janus, the god of doorways and awkward double-sided faces representing past and future. Romans would vow to be better citizens while Janus creepily watched from both sides. No pressure.

• Medieval Makeovers: By the Middle Ages, knights made “Peacock Vows,” swearing to be chivalrous while a literal peacock judged their sincerity. Talk about a tough audience.

Resolutions can be summed up in one word: religion. A lot of unrealistic, unachievable rules designed to make you feel guilty for not living up to someone else’s standards. In other words, a bunch of rituals created for one purpose: to convince you that, on your own, you’re “not enough.”

Fast-forward to today, and resolutions are less about returning borrowed donkeys and more about hitting 10,000 steps a day or finally unsubscribing from that email list you forgot you were on (except this one, of course).

Why Resolutions Set You Up to Fail

1. They’re Unrealistic: "Lose 20 pounds in 2 weeks" or "Start a side hustle and make six figures by February." Sound familiar? We’ve all set resolutions so big they’re practically a recipe for disappointment.

2. They’re Rooted in ‘Shoulds’: The word “should” is sneaky. It sounds helpful but often leads to guilt. “I should work out every day.” “I should eat kale.” “I should be able to do this without crying.” Who decided these things? (Hint: not you.)

3. They Ignore the Bigger Picture: Resolutions often focus on surface-level goals without addressing the underlying issues. Want to work out more? Maybe it’s not about the gym—it’s about finding joy in movement.

How to Break Free from the ‘Should’ Trap

1. Set Intentional Goals: Instead of resolutions, focus on what truly matters to you. What brings you joy? What makes you feel alive? Let those answers guide your actions.

2. Start Small: Forget the grand gestures. Real change happens in small, consistent steps. Want to write a novel? Start with 10 minutes a day.

3. Redefine Success: Success isn’t a checklist—it’s a feeling. It’s the satisfaction of living a life that feels true to you, not one dictated by societal expectations.

Bake Failure Into the Plan

How to Plan for Life’s Chaos

Here’s a secret: I don’t expect perfection. In fact, I plan for failure. Here’s how I do it:

1. Placeholder Days: Three to four days a week, I go all in—weights, cardio, the works. The other days? Just 10-30 minutes of yoga or stretching. These “placeholder days” keep me consistent and out of the all-or-nothing trap.

2. Float Days: Once a week, I schedule a guilt-free “skip” day. If I don’t need it, awesome. If I do, no sweat—it’s already part of the plan.

When you bake imperfection into your routine, it’s no longer failure—it’s strategy. Life’s chaos doesn’t derail you because you’ve built flexibility into the plan.

Closing Note:

In closing, why is the word “should” a trap? Because it’s always rooted in comparison or someone else’s expectations. The truth is, you’re already enough. You don’t need a list of resolutions to prove your worth. As you navigate 2025, focus on progress, not perfection. And remember: the only person you need to impress is you.

Ditch the 'shoulds' and watch how your life transforms. Freedom starts when you stop living by someone else’s rules and start creating your own.

Did Today’s Email Change How You’ll Tackle 2025?

🌟 “I’ve already stopped ‘should-ing’ on myself—life is good!”
✨ “I’m considering it, but it’s hard to let go of the grind.”
🌠 “Still feeling backed up—might need a life laxative!”

Hit reply and let us know your thoughts! We’d love to hear how you're tackling 2025. Your feedback is our favorite resolution. Don’t keep it bottled up—let us know!

 P.S. If you’re reading this at work, consider it a sanctioned break. You’ve earned it.

Stay Curious. Stay Playful. Stay Spiritually Immature.