Recently in calls with clients, I find myself digging into the assumptions and premises that form the foundation of any one person's plan to move a project forward.
For example, say a client comes in and says "I want to make a plan to finish this piece before I start teaching again in September." And I ask "what plan do you think will get you there?" or "what do you have so far?"
"Well, if I write 1k words per day for the rest of July and half of August and then revise 10 pages a day in the third week of August and then footnote and format everything and do every step for submission and my writing group gives me feedback in 24 hours or less, then I will be able to submit it on August 31 and also I have given myself 12 flex hours to spend how I wish between now and then."
[This is an exaggeration, obviously, but only slightly ;) ]
And so, as coach, I start to dig in:
"What outside people or things is your plan dependent on?"
"How many hours are you expecting to put in a day?"
"Where is your buffer time?"
"Have you ever worked at this pace before?"
"What things will you be doing to take care of yourself during this period? When will you fit them in?"
Try asking yourself these questions about your plan for the week, or the month, or the project as a whole. And if the answers are alarming, adjust!
Plans are just drafts - they're your best guess about how something might unforld, and what milestones you need to hit in order to make that happen. They aren't contracts you sign with your future self, nor are they they only possible path forward.
So if you find yourself in a cycle of making plans, getting off track, making new plans, and feeling pressure because of it, it might be time to examine the assumptions you're making about yourself, your collaborators, and the world that inform your plan. The best plans are those that reasonably address and accomodate for the conditions on the ground, not the perfect conditions you want, or wish, to have.