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You're in good company! TONS of it!!!!!!
Caitlin,
Your post brought tears to my eyes. I'm in my mid-fifties and only recently learned that I have ADD. I've been struggling with bosses like yours all of my adult life. I know many, many, many of us have.
Actually, I've been a consultant doing leadership and interpersonal skills training all of my adult life, so when I refer to bosses I'm actually thinking of the client people who hire me. I've always been highly successful at standing up in front of groups of people (it brings out all the the strengths ADDers tend to have, and it's always active and interesting!) but I've always felt like a bull in a china shop with the clients who hire consultants like me; always ten minutes late, mistakes in my invoices, having to call back to reschedule things because of calendar disorganization, etc, etc, etc. One client person fired me even though I was training executives (at a much higher level than hers) who loved me-- just because she was so rattled by my seeming lack of concern over the details of the process. I was devastated, to say nothing of the fact that I lost thousands of dollars of income.
But the biggest reason I'm responding to you is how deeply sad I feel for all of us who have spent so much of our lives feeling not good enough, and being perceived by others as not good enough. As far as I'm concerned, having ADD makes us "less than" no more than does being shy, left-handed, bad at math, whatever. It just so happens that most work places, and the tasks within them, are structured such that the things we can't do well are expected as "normal" behaviors.
I can't count how many workplaces I've been in consider attention to detail a sign of professionalism. But when you stand back and look at it objectively, that's completely senseless! It'd almost be like saying right-handedness is a sign of professionalism!
On the other hand, I've worked with paralegals, and lawyers, and I know that happens to be a world in which detail matters a lot... So it seems you're 90% great at a job that requires attention to detail that'll never come naturally to you. The way you feel about your job performance, and your boss' perception of you, are situational. They are NOT a function of how smart and talented you are, or how dedicated you are.
But I'd be VERY careful about telling your lawyer boss that you have ADD. Rather, I'd start looking for on-the-job resources to help you with details in the future. Are there co-workers or subordinates who could proof-read your work in exchange for something you could regularly do for them? Or are there other ways you can get back-up for your areas of difficulty?
Also, think of this: Is your boss good at every aspect of his job? Aren't there specific aspects of his job that he has others do for him because he doesn't do them well? NONE of us is 100% good at our jobs. So, in regard to that, I think you should sit down with your boss for an informal evaluation of your performance in which you outline your strengths and your areas of development. Make sure he knows--and he knows that you know--what you're great at. And when you talk about your areas of development, talk in terms of finding ways around them. Don't be ashamed of them, be matter-of-fact. But also be realistic about the importance of getting everything done well so there'll never be a doubt in his mind about how much you care.
ALL the best to you-- Try to put this into perspective and not let it get you down so much!!
--Bonnie.
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