Planning, removing obstacles which also create discomfort, and sustainability for real change?

Dear Brooke,
I, like many others entered your self-coaching program having several goals in mind. After our 2nd class I realized that commitment was necessary to one and one only at this point in time. I picked weight loss. Since Jan 1st, I am down 9 pounds, feeling great, clear headed, and most of the time manage to stay motivated (most….). I continually use the phrase “double down” in my head now. My goal is to lose 40 lbs. These 40 have been gained over a period of 13 years, and at least 15 of which were in the last two years (I am now 51 and hormonally erratic due to perimenopause).
So here goes the thought I am having.
I entered the month clear about my strategy for jump start. I am nutritionally very conscious, so that part is not so hard. Quantity of food definitely needed to change (live between -2 to +2). Going alcohol free for the month of January (small and attainable goal). I planned on not socializing at night (which has been part of my regular weekly life). I live in NYC, am a business owner, and often have to attend dinners and events where food and drinks take a primary role. I am already in a habit of preparing lunches, as I don’t have time to run out during the day. I have been a night eater and after a few drinks, I would also indulge in late night snacking.
So, when re-listening to your prior podcast on “diets” and this week’s podcast with Corrine Crabtree, I questioned the lines between over planning, allowing discomfort, and sustainability. I started to think that too much planning can remove you from the negative emotions that you otherwise need to feel in order to push through them. For example, I switched many appointments from dinner dates to breakfast meetings. This way, there was no risk of staying out late and indulging, as time is limited for breakfast before work. There would be limited risk of drinks, limited chance of overeating (as mornings are always filled with motivation), etc.
But, and here is the But…. By changing these activities and pre-planning, I question the sustainability of this way of life. At a certain point and actually next month, I will begin attending evening events, fundraisers, and dinners out, and now question whether I have gotten far enough in my discomfort and negative emotion work. Of course these feelings are simply doubt, fear, and possibly pre-planned excuses. So I understand that I should instead embrace the challenge that is coming and “run towards the dog” as the monk did. So, intellectually, I am prepared, but does over-planning in some ways put so much control over your life that you just postpone certain feelings & emotions, or is that just part of the process one goes through to continue to get stronger and re-enforce your desires, commitments, and build on the resilience needed to “change” for the long-term. So I am looking for line between planning and sustainability.

Have a great week! See you on Monday’s self-coaching call, and here’s to using our prefrontal cortex!