I went through this last year when I decided to apply and geez-louise were the jobs for freelance writers depressing and/or annoying and I had a sinking feeling that even though I'm a spry 56 going on 57, once you are over 50 (45?) it's kinda pointless to re-enter the workforce unless it's Walmart. There's always Upwork....it's possible to find decent clients if you put the time in. Whether they have regular work is another story.