Depends largely on your specific field....if you have one. Some lend themselves to short stints of work interspersed with time off, and some are perpetually seeking skilled and motivated workers. Sometimes, both are true of the same field.

OP's question comes up a lot, and not just on traveler's forums like this one. I gather that in some fields it's considered highly suspect to have taken long periods to travel, but I can't say it's ever gotten in my way. I used to do construction labor, then various skilled trades; I'd work three to twelve months, then take a month (or six) off. I lost ground financially, but I was never terribly ambitious in that realm anyway. It didn't stop me from progressing from the very bottom to somewhere within reach of the very top within my little world....following which I took five (5) years off to go to college, then grad school.

These days I'm a licensed professional. After my last long trip--a couple of years of intermittent travel and little honest work--I found a job within a few months of my return, and stuck that out for 3+ years before setting up my own business. Now, almost 4 years later, no one cares about any of that. Why would they? I'm measured by my performance--or at least, by my customers' beliefs about my performance.

It all changes if you're supporting other people, especially kids. It all changes if you return home to a major recession, or if you've chosen to live in an economically-depressed area, or if you're in a field for which there is little demand. And of course it's more difficult to get your footing in an area where you don't know anyone or have any previous employment history. But the main thing is the nature of your work and your level of skill. If you happen to be a skilled carpenter, you could probably move to my town and have a job within a week regardless of your travel history. If an art history major just out of college, maybe not so easily.

Hope that's helpful.

Mark