Having a headshot you love should never be that hard. Knowing your angles and how to dress for your body will make your session more seamless. One tip I'd recommend is finding a photographer that understands you and the concerns around WHY you don't like having your picture taken. Take the time to interview your potential photographers. Ask them ALL the questions, never feel like you're crazy or getting on their nerves.
You're hiring someone to help capture the best version of you. I'll let you in on a little secret, we, as photographers, HATE when clients don't tell us what they want, or hold back on information about what they like and don't like about their bodies. I can't tell you how often we get this feedback AFTER the session only to find out you're not happy. Many of us work hard to create something we think you're going to love only to hear that certain poses are not your favorite or you think they make you look pregnant.
Please ensure you have these talks and trust this person. If you've done your homework (looked at their website and scrolled their social media) and I trust that you have, you'll notice a consistent look and vibe around their work. It's these things that'll speak to you and are the reasons why you want to hire them.