The easiest way I think to get started, at least for me, is to play at retirement centers. They are very happy for you to be there. They will compliment you and it's not very hard to get the gig. Just go speak to the activity director.

Where I live, they tell me that they will pay $50 for just an hour. I tell them I'll play for the $50 but it has to be at least an hour and a half. That just makes them happier. I just started back playing a couple of years ago so, I‘d rather play longer for the experience even if the money isn‘t great. I‘m tired of just fishing all the time. After a few of these type gigs you’ll gain more confidence, which will help you to move on to other venues.

Of course it will help if you know the old standards and some country tunes.