Don't Should On Yourself (0 to Time Hero Part I)

This blog post is the prelude to a series of practical, step-by-step guides designed to help you transform from struggling with time management to mastering it like a pro.

But before diving into the nuts and bolts, we need to address a common mindset block that hinders almost everyone I’ve encountered.

You’ve got to stop should-ing on yourself.

You know what I mean: saying things like, “I should do this,” “I should eat that,” or broadly, “I should be better.” The same goes for should’s equally tricky cousin, shouldn’t.

I’m writing this in mid-January, a time when many New Year’s resolutions are starting to lose steam, decaying into regrets we promise not to repeat next year.

No judgment—I’ve been there. Here’s how it happens:

Towards the end of the year, riding the wave of "I made it through," we start creating lists of who we think we should be. For a few days or weeks, we might even embody that idealized version of ourselves.

Then, inevitably, life throws a curveball, and we deviate from our meticulously planned intentions.

That’s when the problems begin. You had a plan based on the person you think you should be, but when you’re no longer acting like that person, the plan feels irrelevant.

Even worse, you might convince yourself that planning simply doesn’t work or that you “just can’t do it.”

The root issue?

You’re comparing yourself to an idealized version of you that doesn’t exist and then beating yourself up for not being that person.

What does this have to do with time management? Everything.

Effective time management is grounded in a clear, accurate, and honest understanding of your reality.

Take me, for example. As I write this, I cannot physically run a marathon. I’d probably struggle to walk a full marathon. That’s just reality.

If I started thinking I should be able to run a marathon or if I planned to run one, I’d be setting myself up for failure. Instead, I plan to walk a mile a day for the next month.

That’s something I can do.

Notice the difference?

It’s not about what I should do. 

I will walk a mile (or not), and that’s it. If I’m sick or injured, I won’t walk.

But I also won’t waste energy thinking I should have walked.

As Byron Katie wisely says, “Arguing with reality” is a battle you will always lose.

This shift in mindset is critical because no amount of planning can override reality. By aligning your plans with who you truly are and what your circumstances actually allow, you set yourself up for sustainable success.

In the next posts, I’ll share the practical, actionable steps to manage your time effectively.

But it all starts here: Stop should-ing yourself, embrace your reality, and build from there.

Until next time, slay!