Iin summary – to reduce perfectionism:
- be curious of my MO
- get clarity in expectations
- pacify my ego
- be smart about my resource allocation
- build empathy: what does this person want / expect (and this includes mentally stepping into one of my “selves”, treat them as another person, hear them out)
- and most importantly: ask, ask ask.
Or more succinctly: getting clear on why I’m doing it, what does it need to look like, and to whom.
Was reading this thread https://news.ycombinator.com/item?id=30223559 and I suddenly wondered –
When I find myself chasing my own tail in an episode of perfectionism, have I ever stepped back and ask myself, “what do I really want to feel / hear / know after I shipped this?” and try to imagine the bare minimum version that will get me that. And then try getting that result / sensation / feeling / validation in advance as much as possible. Doing this will do a reality check on and calm my neurosis before even starting — giving it a snack before it got too rabid and ravenous.
Because if I haven’t, I should start doing it more often.
I imagine thinking strategically would also help: to remind myself / bring to awareness all the constraints I have at that moment and examine in what ways that I don’t have all the time, energy, or resource to get it done to the degree that I’d like .
The key here is to make my (and other people’s) implicit expectations explicit, make what’s still unconscious conscious.
Let’s say for example, I am about to work on a proposal. The minimum I’d like to hear after I presented the proposal would be for most of them  to say “You framed the problem really well, I understand your proposed solutions, and this captures the all key messages that I’d like to know. Great job“. Switching to another dimension: I’d like to be perceived as someone who thinks clearly, communicates effectively, and a visionary who knows her shit.
Then what I’ll do is share a quick and dirty listicle (ok, list of bullet points), send that over, say “hey does this capture all the high level points you’d like to see in the presentation?“. The next iteration is I’ll expand each bullet point, add one sentence for each. Then keep peeling the onion from then on. This ensures I’m on track and prevents me from going overboard, working on something that might just be overkill.
Yes all of this takes time — perhaps the same amount of time if I had just went into the cave and birthed it on my own, but I find it’s less painful to recruit some midwives in the process.
I’ve done many work in the past in a “big reveal” style. Some of them hit, most miss. But these days I don’t have much excess energy to spend on shooting darts in the dark anymore. I’d rather be working on the right thing and doing them right.
It’s an ongoing process, to make peace with my own mental dialog of “Heh, I know a lot but I don’t need to tell them everything. I only need to tell them what they need to hear now and gauge how they’d like to hear it. Asking them what they want to hear doesn’t negate the first fact. I want to show I am always one step ahead, y’all need to recognise the depth and breadth of my thinking, how much I have thought this through, and the edge cases I’ve considered. This is my magnum opus, bow down to my intellectual prowess, mwahaha“.
I’d say I am still dragged by my perfectionism 75% of the time, but it’s a muscle I’m developing.
One other muscle I will be forced to practice in this process is getting comfortable asking questions and asking for space / stage to share a WiP (Work in Progress) . It’s rooted in the courage to be vulnerable and exposed to risk of existential threat (most stress is brand / reputation management).
 If I somehow concluded that 1) I am actually quite okay / not really constrained at that point and 2) the deliverables are realistic in my opinion, then I don’t see why I shouldn’t just go ahead and indulge my neurosis once in a while.
 If I’m presenting to a group, it always helps to run through / get feedback from / give previews to the different stakeholders involved. Three benefits to this: a) it keeps the topic warm, b) I build trust, and c) I get myself sponsors who could back me up in that presentation because everyone would have seen and digested parts of the proposal by the time I actually presented it.
 WiP is not a brain dump. WiP is a brain dump with one clear ask / proposal / solution. So if all I have is laundry list, I’ll do another iteration on my own and extract my ask. This is especially effective when dealing with senior people with not much time who hold many other contexts in their heads.