It sounds like you’re in a good situation, having transitioned slowly and with a 2-year-old business already.
Once you start - and especially once you do connect with commnunities of people who have the same mindset, and who will inspire you to go even further - I think those fears will dissipate; the people who you surround yourself with will become the “new normal.”
About the fear of failing to sustain, it’s possible for location-independent entrepreneurs to fall into one of two traps:
A) Getting so distracted by travel and the delights of the place you’re staying that you fail to give your business sufficient focus and energy;
or B) Being so uptight about maintaining your business that you overwork and fail to enjoy the lifestyle.
Which one you’ll tend towards depends on your personality (I’m a “B” myself) but the remedy to both is balance and clearly defined work/fun separation. Some examples of various schedules you could adopt…
- buckle down and work HARD for 4-5 hours, then go out and have fun the
rest of the day
- work 3 hr in the early AM, go out during the day, then do a couple more hours in the evening
- do an intense “sprint” of 8-10 hr-days for a work week, followed by a week off
I’ve used all of the above at various times, depending on my business and travel situation. So to sum up, the best bet for following through or sustaining this lifestyle is two-fold - to surround yourself with likeminded people, and to have the self-discipline to establish a good work/life balance (whatever that might look like for you).
Good luck, congrats on booking the ticket, and make sure to update this thread after you’ve taken off!