I have a good friend in need of advice who is afraid to ask himself .. 🤦‍♂️

He is a 1099 worker (not a w2 employee) does maintenance work remodeling homes and etc. He made in the past few years about 40k yearly average and didn’t file because he didn’t have any money to pay them. Didn’t handle things correctly and now is terrified he is going to prison for not filing. But also knows if he doesn’t start filing it could be worse. I guess I’m asking - what to expect. Should he ask the employer for the past few years 1099s and take them to H&R Block perhaps ? File and then see how much he is gonna owe altogether ? Then what start making a payment plan ? Cause he don’t have any savings. Please if you have any knowledge or ideas or directives etc … I would like to pass whatever I gather into him. Thanks in advance