Q. I’ve been trying to find a job for over a year but it’s becoming harder each day.  I am losing faith that I will find a job in the near future.  What can I do to keep myself motivated when times continue to be tough?
It’s no consolation that what you are experiencing now with low motivation is something most people in your situation are feeling.  The economy is taking much longer to rebound than most projected leaving the job unemployment rate nearly 10%.  It’s not that companies are not hiring because they are.  It’s finding out where the jobs are and what sectors are building and re-challenging yourself to think creatively about how your experience can appropriately fit in.  Keeping yourself motivated for most is a personal thing.  Whatever stimulates you whether it’s setting and achieving personal goals, to meditation to aggressively pursuing your interests with a new optimism.  I find that when most people approach a problem they are likely to find solutions to ensure their survival.  Your job search is no different.  Try to take an objective look at what the issues are and if you can’t, seek the help of a trusted friend or colleague who can.  Knowing that every problem has a solution will help you focus on solving the reason you do not have a job as opposed to focusing on the reason you do not have a job.  It sounds simple, but taking yourself out of the problem will usually help you objectively focus on coming up with I’m sure more than one creative solution on finding and securing your next best job.
Q. Is it necessary to put the date I graduated from College on my resume?  I feel like it’s giving my age away.
Typically it’s important to list your graduation school and field of study.  If you graduated, you can state that in listing the degree that you earned.  However, keep in mind, companies do very extensive background checks these days so it’s unavoidable to try and hide your age before you are offered a job.  The best way to navigate around this is to knock ‘em dead on the in-person interview and to really emphasize your experience and that it will help you and the employer hit the ground running in a more efficient and ultimately cost-effective way.  Everyone loves to save money no matter how old you are!
Q. I like my job but the hours are killing me.  What’s the best way to raise this without jeopardizing my job?
Depending on how long you’ve been with your position, it’s best to raise this ideally BEFORE you take the job.  Assuming you have been in the position for awhile, decide how much of your job needs to be done physically in the office and what if any might be handle under a more “flexible schedule” arrangement.  Most companies these days look to accommodate employees particularly as office space continues to be a premium and employers are looking for cost-effective ways to handle work-life balance as well as physical office requirements.  If you can justify that it makes good business sense to ask for a more accommodating schedule, then the hours can be managed so that you are not “killing yourself” between long work days and even longer commuting time.
Q. Is it important to list my job history beyond 20 years?
Not unless you are into 4 page resumes!  I don’t think listing beyond 15 20 years particularly helps you argue that you have the requisite qualifications to do the job.  It’s best to list your accomplishments under the last five jobs in detail and then list the other positions you held and companies you worked for with dates and locations for anything beyond 15-20 years.  Too much is not always a good thing in a resume.
Q. How common is it to ask for travel allowance to and from work?
Depending on your position and whether the company has a policy offering a travel allowance to and from work.  Generally if you are eligible to receive a travel allowance it is only for time during workdays and not to and from your home.  If you are asking whether you should ask for money to travel to and from work the answer is probably not.  Your living arrangement and whether it’s convenient to your ability to commute to work is not really the problem of your boss or your company.  Find a way to make it work by either moving closer to work or finding alternative ways to commute and don’t ask for money when it’s really something you should be able to solve on your own.