how long is too long to be unemployed?

If you’re going that long without work I think you have to question a couple things:

-Are you in the right location? Some areas simply do not have design work, and at that point unless you can freelance long distance finding a job will be hard (because there aren’t any to be found).

-Are you maximizing your networks? Design conferences, meet ups, all provide opportunities to get your name out there and meet new people who might be able to help you.

-Are you actively pushing your design work in your free time, or waiting for work.

The recession in 2008-2011 was pretty rough for all jobs in general, but coming from the position of someone who looks for hires there are two possibilities:

-Your resume was blocked by an automatic filter or internal recruiter, and a real designer never saw it. That is especially common for large corporations.

-Your resume made it through, but your portfolio didn’t match the level of expectation so there was no callback

Ultimately you need to be in a market that has design work available - if you are then the next piece you really need to focus on is your portfolio. Once you’ve got a portfolio you’re really proud of and feel is competitive you can start to make contacts and work on getting your foot in the door.