The lighting angle is too high by far for a "safe" portrait—it's the kind of thing you'd use when going for dramatic effect, preferably with someone whose complexion and features can handle it. I'm not saying that based on the bags under the eyes, but on the shadow the upper lid casts over the sclera, the corner of the eye and the lower lid. I suspect that if we were to see more of the image, there likely wouldn't be a distinct catchlight, but rather more of a diffuse glow at about the level of the upper half of the pupil.
Post processing can help to a degree; a quick run through the Portraiture plugin (from Imagenomics, and available in versions for Photoshop, Lightroom and Aperture) with the "normal smoothing" preset yields this:
That may be a bit much for the entire image (and even a bit much for this part of it), but you can work the image in sections using semi-transparent masked layers (in the Photoshop version—the RAW-processing versions obviously can't avail themselves of layers) and do the appropriate amount of smoothing for each part of the image. There is still a deep crease under the eye, but it looks more like experience than damage, if you know what I mean.
A good plugin for portrait smoothing and skin enhancement will run about $200 or so (there are several decent ones, but Portraiture and I are getting along very well at the moment), and can be worth every penny of that and more if it rescues even a single paid shoot. It doesn't matter what kind of a purist you want to think you are, if you're a professional (or want to be one), then you really can't afford to be without the tools that let you cheat a bit when cheating is the only way to win.
But post-processing is time taken, so it's better from a turn-around perspective to get things as right as you can at capture time. For that reason, I think the "strobist" approach in a studio setting is suicidal for anyone who wants to go pro. Modeling lamps exist for a reason, and that reason is so that you can spot things like this before they happen. (Oh, and there's not a lot of point in having the ambient cranked up to the point that you can't really see what the modeling lights are doing—ambient should be no higher than necessary to prevent accidents in the studio.) Speedlights can be great if you can predict the result, or if you're on location and really don't have a choice, but studio flash or continuous lighting will be a better choice whenever it's available.
If you're stuck with speedlights for one reason or another, try to keep the light within 45 degrees of the lens axis—unless the pose is very much out of the ordinary (or there's a hat or something in the way) it's very unlikely that you will run into really problematic shadows in an otherwise good picture. Using a bounce flash, that may mean you need to provide your own bounce surface (a reflector on a stand or being held by an assistant/bystander, for instance) if the environment won't let you get the angle more naturally.
And no, you don't have to go super-soft. Hard (or hard-ish†) lighting can be just the ticket, provided that you have the right angle for the main light and sufficient fill to get the contrast you're after. It really helps, though, if you can see what you're going to get before you get it.
Oh, and believe it or not, the way these things are usually handled in "model preparation" terms is with an over-the-counter anti-hæmorrhoidal ointment like Preparation H. It takes a few minutes to do what it do, but it does work, and it's a long-standing "secret" (it hasn't actually been a secret for a long time now) of the modeling industry. If you're going to be helpful and carry it in your photographer's kit, remember to carry a brand-new tube with the seals still in place. Your subjects are probably still going to have that "you gotta be kidding" look on their face, but there won't be any "I don't know where that's been" mixed in with it. Witch hazel ointments are pretty much the same thing, don't come with the WTF attached, but are generally quite a bit more expensive and harder to find.
† A beauty dish, by the way, is "hard-ish" light. The point of one of those machines is to accentuate the contours of the face, like the structure of the cheekbones, without unduly texturing the skin. If you use it at too steep an angle, its effect won't be significantly different from a smaller parabolic reflector.