It's absolutely worth while and it's relatively easy to set up.
Without it, all emails you send/receive are in plain text and if I knew where you were and could get onto the same network as you I could easily packet sniff all the emails you send and receive. So if you were to send someone a password for example, I would be a happy hacker.
First you need an SSL Cert. You can issue your server it's own for free, but you'll get warnings when you try accessing webmail and in your email client saying it's not trusted, so it's recommended you purchase an SSL cert from a trusted authority such as my PickleHost GoDaddy Reseller system (shout out) or GoDaddy or any other should be fine. I also recommend just purchasing a Wild Card SSL Cert for your server's primary domain that way you can encrypt everything you access on your server, WHM, cPanel, WebMail, etc.
Next, (optional) I recommend you force webmail users to use HTTPS over HTTP, which is a setting in WHM. This also will apply to WHM and cPanel access making everything you access encrypted.
Then in any of your email clients (Outlook, on your cell phone, thunderbird, or whatever you're using) switch to TLS encryption. If you choose that Wild Card SSL Cert mentioned earlier you'll set the servers to your server's primary domain so you won't get any certificate warnings.
KH support can easily assist with those requests if you need any help and I'm happy to walk you through the process of getting an SSL Cert from PickleHost if you decide to purchase there.