Is Your Calendar Creating Chaos Or Cramping Your Style?

To wax slightly work-poetic: Calendars are like scaffolding for our work souls.

In an ideal world, they support our dreams, our goals, and the various activities we commit to daily.

Take a look at your calendar week. Does the time you’re allocating align with top priorities? Do you know what those are?

Or are they a bit blurry, undefined and constantly changing?

Intention is not an imperative.

And —

Clarity of intention is dynamite for creating change and doing the things our most inspired and highest performing selves want.

In my first year or two of entrepreneurship, I was constantly reinventing my goals. I had shiny object syndrome: Every time I tried to pin myself down to one thing I would change it or come up with ten more. A part of me knew the different ideas were on some level connected (and they were), but they weren’t clearly linked to higher or deeper intentions for my life, my work and my experience.

I confused the spirit with the form.

Coming up with a million things to do (few of which I finished) is a great way to stay busy versus productive.

It’s also a great way to miss the point.

As an entrepreneur, I’ve learned the magic in designing structures to support higher goals without being attached or lost in the structure itself. The structure serves the spirit — not the other way around.

Now instead of feeling like first world shackles or a chaotic treadmill of entrepreneurial lust, my calendar reflects and serves my true priorities. It’s a Swiss Army knife of self management and intentionality, not an imperative or a “must.”

5 quick tips for cleaning up your calendar if it’s creating chaos or cramping your style:

  1. Is it clear at a calendar glance what you/your team’s top 3 priorities are (priorities being associated with tangible goals)? Find a way to make it obvious.
  2. Do you have non-essential appointments and calls calendared? Take them off. If that’s too painful or impractical, create a separate calendar and hide the view.
  3. Aligned with your top 3 priorities, declare what you intend to complete in the next one to four weeks. Shorter periods are easier. Calendar only as much as you need to hit those goals. Use any spare time to move the needle on the same priorities, to recharge or to generate ideas. Reinforce your intent.
  4. Hire an executive assistant (or a time management specialist). Be clear on your priorities and conditions of satisfaction and keep the dialogue open.
  5. If you don’t have a system for how you manage and organize your calendar, come up with one. It can be as simple as dedicating 30 minutes weekly to calendaring and organization. When things are measured and done in a generally consistent way, you can see what’s working, what’s not and make tweaks or reinvent.

Calendars are great productivity and prioritization supports for the most creative of minds. If you’re an entrepreneur and haven’t embraced yours, it might be time to climb on up.

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Casey Onder, PhD

Casey Onder, PhD


Psychologist, success coach, believer in solid behavioral science and the power of tuning in.