Maybe I'm strange but I quite enjoy the SE side. Maybe it's because I come from a service background and enjoy meeting the customers.
Maybe it's because I blend well and I don't believe I look like your stereotypical computer geek or computer security geek - that makes it easier.

But the general comments here are correct - SE is probably the easiest way to get into a system or at least to get close enough to get into a system!

As for getting into a client site, don't aim for the server room. Aim for other parts of the organisation and include the server room if necessary. If you can get access to a live network port, you're 90% there anyway.
Sometimes, using a toilet just off reception can get  you the access you need - you might be suprised the route ethernet cables take - access is often just a ceiling tile away...

Not all SE requires either phone or face to face contact but if it's required then either hire someone or work on those people skills. If speaking to strangers or in public is an issue I would suggest starting to do presentations to your work colleagues about topics you have confidence in. This will get you comfortable speaking in front of people. Move on to doing presentations in your local infosec chapters (ISSA, ISACA, etc). It teaches you how to prepare and stick to a script and to have responses for possible questions that might be asked.

Even if you choose not to actually interact with a user directly and decide on the email/website route for SE attacks you will still need to make sure that the emails/websites are well written and convincing, that they have the correct layout and graphics. ie: all links work, images/company colors are correct. This is just as difficult (or easy) as standing in front of a real, live person.

If you're not comfortable in front of people how do you present to a room full of clients about the results of the pentest? That aspect of being a pentester is as important, if not more so than being technically proficient.

dean

@ dean -- Thanks for the info...

Dean,

I think you are right on with the SE and in getting comfortable with presenting. I'm lucky enough to be in a job where presenting is a recurring theme. I got to go to a conference that was primarily for the powers that be in the Air Force enlisted aviation community to brief on the policies and procedures here at the Community College of the Air Force. Every one in that room out-ranked me. One of the things that helped me get through was the knowledge I had of our procedures as well as some of the prep I did before going down there with people that had done these conferences for their career fields (MOS in Army talk). Being prepared for a presentation is by far the best confidence booster you can have. That and surviving a room full of folks that have been giving each other a hard time all week long before you get up to speak.