I can't help career wise, as I'm struggling with the same thing as you.
Sleep wise, I'm somewhat an expert. have you tried a Zinc supplement? Really does wonders for me to achieve a deep, all-night sleep.
Being sleep deprived only makes things that are on our minds even worse. A good nights sleep does wonders.
I've had trouble with insomnia for so long I've been thinking of starting up a luxury soap business.
There's loads of obvious advice, routines, keep the bedroom dark, back off the caffeine late afternoon. Supplements (zinc, magnesium, almost aping the ZMA thing, 5-HTP). Mild / OTC sedatives / hypnotics (the usual fair of largely relaxant / anti-histamine based ones). The things I've often read about, in commentary for others, that have greatly helped them, in my inferred increasing order of effectiveness: zinc, magnesium, 5-HTP, melatonin.
Personally, I'm not looking for something to make me drowsy and put me to sleep - or leave me feeling drowsy or "hung over" in the morning. Ideal, for me, would be something that either helps me maintain sleep for longer than I normally get, or helps me then fall asleep again, once woken.
I've recently started using melatonin, and have to say I'm very positive about it - it's not perfect, but does seem to be helping (my issue isn't really getting off to sleep, more waking up then not being able to get back to sleep). On the plus side, seems to be something that has several all-round benefits and seemingly precious little in the way of side-effects or issues; on the minus side, it's prescription only in the UK - but available comprehensively in the US. The version available as a prescribed med in the UK, is 2mg sustained release - the amount, I'd say, is about spot on, sustained release probably no bad thing.
To be clear, that's not me advocating people suffering with insomnia to rush out and procure melatonin, just pointing out that after trying many approaches and supplements (but never going so far as prescribed drugs for the matter - I just don't want to get involved with serious sedatives / hypnotics - 'cos let's face it, entertaining they may be, but they all come across as a bit weird - and how's that for one of those subtle, obscure, tentative, fast and loose puns, that don't get made every day, eh?), I've read about countless things people have used, and tried many, and have personally found melatonin helpful for me. Reading / research, plus consultation with your GP is always the best way, anyways.
Truth be told, that's something I've often found quite odd, really - US society seems to be, officially at least, very risk-averse, and along with that, FDA regulation, plus the official rules about off-label usage of certain drugs / meds - yet there's some cases where they allow sale and use of various things that are prescription only in the UK, despite the UK not having anything so organised or central as the FDA.
Very comprehensive advice, Neil, or should I call you Tyler? As an Insomnia sufferer too I've experimented with all of the above. Melatonin didn't work for me, Diphenhydramine left me feeling spacey the next day. My problem is double edged, I find it difficult to get to sleep and stay asleep once I do nod off. Zinc doesn't help with the getting to sleep, but I find it does help me to stay asleep once I nod off. Plenty of exercise, cut off caffeine at 2pm, drink lots of water, no heavy meals late at night and nothing too stimulating an hour before bed seem to be working for me just recently. Then again the dreaded sleeplessness could strike at anytime.
A few years back the Doctor prescribed me Zopiclone, after I hadn't slept for 4 days. What a trip that shit is. Knocks you out cold. Not for long term use though and not solving anything in the long-run. Education is the key!
A good Indica used to help me sleep, but I gave up smoking years ago.