Advice on journeyman save

I'm currently managing Gainsborough in the Skrill North, with the aim of the save being to have a successful career by managing various clubs. I'm starting the 2015/16 season and the plan is to be the last season at Gainsborough, but I'm not sure how I should approach the hunt for jobs.

What does usually work best? Should I leave at the end of the season when my contract expires and then holiday until I get a new job, or should I wait and be approached?

I have always found it easier to get a job while already employed. I think your reputation takes a hit when you resign. You may have to approach teams with job vacancies, though. Teams who would hire you may actually deem you to be too good for them unless you apply for the job.

Not saying at all that Overmars is wrong, but in my personal experience I find it easier to get a new job when unemployed. I find teams in lower leagues are rarely willing to pay the compensation required to 'buy' you out of your existing contract. Obviously this doesn't become an issue once you've resigned from your job. Not to say I haven't been offered jobs, or been accepted for interviews/offers while still employed.