Getting great self portraits

Hi.

So I got some new flashes, and new umbrellas that I can shoot through. As much as I hate doing self portraits, its one way to test things out.

I didn't get too many shots well lit before I was exhausted (self portraits are also tiring), but every shot just brought out every flaw and every wrinkle. I didn't think I really looked that bad. I tried one light at 45 degree. I added a second light down low going up, to the other side at various angles and a reflector. I made myself look 15 years older. I can do good taking other's photos, even with the older equipment, but myself? No way. I did several sets of senior pictures this past fall that all came out great, so I'm capable of something.

I would figure that if I can't get the self portrait I am looking for, I'm not worth the salt as a photographer. Any tips to make it easier?

I think you are exaggerating the link between a quality self portrait and being a quality photographer. Focusing and lighting are much harder on yourself. Plus posing and emoting are harder when you can't see your subject.

Maybe the "selfie" is ruled by the phone camera. I wanted to flesh out something both sort of high key and dark and shadowish, but couldn't get near either. Maybe I'll work on it again tomorrow.

If you'd new to off camera flash the first thing I'd suggest is to start simple. Work one light until you've got it down. Only then start adding other lights to the mix. Being new to OCF myself I'm a bit overwhelmed by all the different lighting setups, so I've been focusing on what can be done with just one light and I'm constantly being amazed by what's possible.

Plus I think gonzogolf has it right, it took me forever to get a look or expression I was even close to happy with. I felt like an idiot trying to get a natural looking smile with nobody to smile at.

Keep the lighting simple. Learn one light until it's second nature.
As for selfies, go for it, it was the only way I could dial things in because of the amount of time I devoted to lighting, along with the fact that I have no kids to use for subjects, along with my wife not wanting to spend that amount of time.
Get the following for selfies:
a stool
a tripod
a remote shutter release

set up an extra light stand (or anything you can pre-focus on) in front of the stool at the height of your eyes and pre-focus on that.
shoot at f11 or f13 for plenty of DOF.