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Obligation-Resentment-Entitlement Cycle

There’s a framed print of this reminder sitting near my desk.

And yet somehow I seem to be caught in Time Optimism a lot lately.

Right now, for example, my to-do list for the day includes writing this newsletter and 2 client writing projects.

I have about 30 minutes left in which to work today.

Did the me of this morning not see how unrealistic this all was?

Some reasons I fall into time optimism:

  • I forget to leave space for rest.

  • I forget that gathering my things and getting ready to leave the house takes a few minutes.

  • I forget to plan time for cooking and/or eating.

  • I estimate drive times based on best-case memories, not right-now conditions.

  • I don’t want to feel the fear or grief of saying No to projects or opportunities so I minimize how long they’ll take when I agree to them.

  • I don’t zoom out to make sure every important task is on my to-do list.

  • I seem to have an aversion to finishing something too far ahead of its deadline.

  • I genuinely underestimate how difficult something will be, especially when I’m doing it for the first time.

  • I don’t factor in time for administrative stuff, like making appointments and coordinating with collaborators.

  • I base my estimates on what I think I SHOULD be able to do.

So what to do about it?

👉 A mentor of mine recommends blocking time on your calendar to actually complete every client project as you commit to taking it on.

👉 I’ve heard someone else who started doubling their time estimates for everything, and somehow it magically worked out.

👉A “No” Diet seems like a good step; stop taking on new things and feel the feelings about it.

I haven’t solved this for myself yet. 

I suspect “the dread of being early” is a part of it for me. 

Maybe I’ll teach my drama class about how to feel perpetually behind.

Then I’ll do the opposite, and see what happens.

What about you? Got any Time Optimism mitigation strategies?

Belatedly yours,


PS – Does this describe you? If so, hit reply; I wanna ask you a couple questions about a program I’m considering cooking up.

  • You’re tuning into your inner knowing to create a business that feels like a calling

  • You like writing and want to learn to write for your business in an effective, authentic way

  • You have an offer that you’ve sold at least 3 times for least $500

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