I would check monthly or quarterly to be sure that the proper amount was being contributed to my account. The other checking would be investment related. Frankly, I probably would tend to recommend establishing an allocation that you stick with for a number of years. Everyone says I'm being foolish not to, but I truly live pay check to pay check. Saving definitely requires a committment.
Saving becomes the first priority, rather than the last.
Regarding your personal situation, I would suggest closely reviewing any expenditures that are discretionary rather than absolutely essential. That may be the equivalent of giving up a couple of beverages, packs of cigarettes, or some other non-essential item weekly. Once you get started, the most effective way of increasing your contribution level is to take a portion of any pay increase and dedicate it to the plan before you see it in your pay check. This decision has been driving me crazy for some time. I am 29 years old and already feel like I'm behind the times because I'm off to a late start investing in 401K retirment plans.