This ISSUE is a world traveler's NUMBER ONE concern and dilemma BUT take it easy this stressful topic also helps bring travelers together while "on the road" like no other. I took off on extended trips with vague knowledge of places around the world where I could work and make a few bucks like harvest season in southern France or Australia, skiing season at various resort towns in the Alps, teaching English in Barcelona, and especially East Asia ( the BEST highest paying gig going for "WT"s) and odd house improvement jobs in the summers in Scandinavia.
Also there's a number of smalltime profit equations which exist between countries where you can buy a bag full of "trincets" and sell them for more elsewhere. Streetselling or "busking" playing an instrument and / or singing for donations or performance arts like a Mime or a juggler can be more profitable you casn imagine in some cities. Also I met 2 British guys selling their scenic paintings of the Portugese coastline to tourists on the street( who had NEVER considered themselves painters but hated the idea of going back to look for jobs in UK they thought WHY NOT TRY IT? }
It really depends on what job and income options you have and how much you hate going back "home" to find work before you decide what's your BEST option.