Great questions! As far as downsides of a nomadic lifestyle and freelancing career are concerned, there definitely are some. You have to give up a lot of the conveniences you’re accustomed to living at home, and it can be more difficult to establish lasting relationships. When it comes to friends and family back home, I’ve found that my relationships with the people who I’m closest to hasn’t suffered due to my absence, and it’s actually helped me to identify the people who are most important to me. I’ve also made a ton of new friendships on the road, many of which I suspect will last a lifetime. Other downsides are lack of job security and general lack of a consistent cohesive team to work with. Also, experiencing something like a medical emergency will be much more stressful than it would be at home. Obviously for me these trade offs fall in favor of travel, but for others they may not.
With romantic relationships, it’s definitely much easier to live this kind of lifestyle if you’re single (which I am). However, I’ve met many married couples who’ve hit the road together, and even more people who’ve fallen in love while traveling.
As for how I land freelance jobs, I’m planning on another full write up on this so stay tuned!