I'm currently transitioning from 9 to 5 to being a full Digital Nomad. Could you share the most practical way you've done to achieve it in < 6 months?
And also how to know where to start? or handle feeling alone, and can't ask for help? would love to hear and learn from you, thanks
Then make sure you have good equipment and by that I mean stuff that you can work on anywhere. Maybe taking your work to a local coffee shop to test out how it feels. Personal I have a very hard time typing on a small keyboard as a larger gentleman. I take my keyboard with me when I travel for work, which I luckily don't do a lot.
Then you may need to plan your trips carefully. You may be without internet for days if not careful. This may not matter but if you hit a deadline while out of service your employer may not be happy about your lack of foresight.
Finally, if being alone is a concern then don't do it alone. You could find someone who wants to go with you, or just meet people as you travel by staying in hostels or what have you. Travelling by yourself will be lonely but for me that's a good thing.