Does setting a "Debt Free" date work?

Does setting a debt free date work for you? You know, that day in the future when all your debt will be paid off? For me, I"m in so much debt I cant even fathom it. I feel like I owe so many creditors (and I don't compared to many other bloggers I read; I only have 5 plus the 3 savings accounts that used to be flush that I would like to repay to myself), the amounts of me debt are so high, and that there are so many variables to juggle that any debt free date would be complete magical bull-crap.

I used to know this date well. I knew exactly when I would have both my student loans paid off, and my mortgage. I would find it so exciting to calculate how an extra $200 per month on my mortgage would cut years off the total! I would run calculations of how much I needed to save to have $X in my account at x time, or when my mortgage payment would be more principle than interest.

But now a few months into Seriously Seriously getting my debt gone, I feel lost. I thought I was going okay a year ago but I had fallen into the trap of paying one debt with another meaning no real gain on reducing my total debt. Add that I'm about to "lose my job" aka go on maternity leave doesn't help. I know they are completely different, but my pay after October will be coming from the same office/place/rules*/guidelines. I don't get maternity top-up, and I can't quite tell what my income will be. I know I have to wait about a month, maybe more, before I will receive my first EI check. And honestly, when this leave starts depends on how long the baby wants to stay in. I can't control that!

*Main differences I detect being absolutely no work is allowed for the first 17 weeks on maternity, and there is no requirement to be actively looking for a job during the 52 week maternity/parental period. Travel is also acceptable during this period, where it would not be allowed on (regular) EI.

How can I even start to think about a debt free date?

Well, I'm taking the same approach as eating an elephant. I've got the end goal in my mind (debt free), I know I have some obstacles coming up (Maternity leave), and I know I've got some time. So, I'll just take it one bite at a time.

For maternity, my plan (until I know my income/expenses better) is to pay my minimums. Assuming I'm able to work as long as I want, I think I can pay these bills from the $1000 in savings that I will have. Current balance, $175. I'm also going to have an emergency fund (that might end up being used now or later for something like yearly car insurance that my EI budget can't handle) of $750, currently $383. I won't be able to be aggressive, but I *knock on wood* will be keeping up with the minimum payments.

Secondly, I'm focusing on my lowest debt, which has the second highest interest rate (by 0.75%) because I need a foreseeable win. My budget has me putting an extra $600/month on this guy. I calculated what will be left if I make minimum payments until December. I have transferred some of my debt from my line of credit to this loan so on January 1st, 2015, my little student loan will be gone! Hey, look at that, I do have a debt-free date. Might just be for one, but it's close enough to keep me motivated and pushing. My calculations mean this transfer will cost me about $90 in interest, on an account that I might have to dip into if my EI checks don't arrive when I hope, There are numerous reasons why this might not be the wisest financial move right now, but it's one that is keeping me motivated and pushing At this point in my journey, I need that motivation to keep my paycheck percentages to 49-60% debt payments, and to have a win before this year ends. I need this motivated to maintain the minimum payments I have now once I'm on maternity leave, because I don't want my debt to just wait around until I go back to work full-time.

What do you do when your debt (or goals) are so over-whelming the big pictures stresses you out?