I can’t do deep, sustained work unless I’m under significant pressure (imminent, unmovable deadline, preferably with significant consequences).
This is how it’s always been since I was at school, but I’ve always delivered high quality results.
As I grow older, I don’t want to be under so much stress. I wish I could just be organized in advance and a good time manager gradually building my results.
Has anyone had success in combatting this? What did you do? Should I consider medication?

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Support groups like CHADD, coaching, therapy, etc. could be helpful for learning ways to work that work for you. Takes lots of willingness and practice. Accepting who you are is a huge part of finding your flow and loving yourself.

Meds help lots of people, but having support and skills is important as well.

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I have this same challenge. Always have. I’ve gotten by thus far but it always feel like the other shoe could drop at anytime. I am considering investigating medication to help me, but it will take time. So I would encourage you to at least look into it.

Outside of that, some things that work occasionally for me are working on those things as the very first thing I do in a day. Once I get started I tend to knockout the task faster than expected. I have to tell myself to stop thinking about how long it could take or how much I don’t feel like doing it and just do it. When I stop my brain even momentarily and take action I seem to be more successful.

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Medication, in my experience, doesn't change the fundamentals of my ADHD brain. It just takes the edge off, and makes it easier for my other strategies to work.

I still struggle to do tedious work on meds. I still need novel, interesting or urgent things to motivate me on meds. I still get distractible on meds.

However, I am able to come back from distractions more readily on meds. My other focus strategies are not effective on meds. You will still need to work with your brain on meds.

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Meds are very much a personal choice. If you’re willing to give them a shot, I would say it’s 100% worth trying especially if you are struggling. I struggle with the same things and put off taking meds for so long because I told myself I didn’t need them or that they wouldn’t help that much. Needless to say, I was wrong. So wrong. In fact I regret not going on them years sooner. But you need to weigh the pros and cons. Maybe try some different strategies to help without them and if you exhaust all of those then give the meds a shot if it’s something you’re hesitant about.

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I got way better at this skill through terror:

I was working in a high pressure environment on a new career track I wasn't confident in, and I needed the job to feed my kid and pay the rent.

There was a ton of office politics and difficult personalities on top of the overwork and professional pressure, and I had a manager who would ask me, "Pop quiz!" out of absolutely nowhere, and I had to know any random specific detail of a project, or else it looked like I wasn't on top of it.

I feared dropping the ball so badly, I started getting ahead of everything. I basically gamified (SquidGamified? It wasn't fun) staying a step ahead of every toxic team member who would throw me under the bus the second it looked like I wasn't 100% on it.

I finally got off that team, but the muscle memory of doing future me a solid stayed.

I don't propose you subject yourself to the same trauma and clearly killing your adrenal glands is what you're trying to get away from, but maybe you can flip it to doing favors for future you?

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This contingency planning and hypervigilence you describe is a pretty common trauma response neurodiverse people develop. We're told so many more times growing up that we're not living up to expectations that we do all of these things to anticipate everyone else's needs so we aren't punished for having a different way of engaging the world.

It's ultimately not a sustainable response, especially as we get older and the accumulated stress and anxiety starts showing up in our bodies as illness.

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Thank you all for providing your views and experiences - if anything, it makes me feel less alone in this situation.

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