Start small, this way you do not find yourself out of your depth and it will encourage you to keep going. I used to admire people who where travelling alone and always wondered how they did it. Here is how I started and its my own experience, it might work for you , it might not. Take what intrigues you and add a bit of your own spice to the recipe to make it your own
Remember, Travelling Alone takes a lot of courage so give yourself time. It took me 14 months from going out for coffee by myself to going away for a weekend. The steps above has worked for me and I hope it helps you.