Hi James
I have started up 4 times now it's not as bad as you think.
In fact I think it gets easier in some ways 'cos you have experience and mistakes and lessons learned.
I went on holiday to Ireland when I was 29 fell in love with the place - put a deposit on a rental house and we were back within the month everything sold up!
Never regretted it.
I am on my forty something postal address now and loads of the lads I went to school with are in the same town, still at the same jobs.
Not knocking them if they're happy but most have regretted not taking the plunge and the risk of doing something different than the old formula of steady job, mortgage, kids.