If I recall, you won't even see stars to indicate the number of characters in your password. You just have to be a good typist and nail it. Assuming that you've tried and failed to enter all passwords you would have possibly entered when setting up the system, the next step is to simply reset it. You could try booting the system up and going to a root recovery shell. This is done by holding the shift key during boot. At the grub screen, select the highest kernel that says (recovery) or something similar to that behind it. You'll see some text fly by as it loads, ultimately giving you a set of options. Towards the bottom there should be a "root" or "root shell" option. Choose that.
By default the system loads in read only mode. Run this command to remount it as read/write.
mount -o remount,rw /
From there you can reset your user password. I'm recalling this from memory, but if I'm right, it should be:
"passwd jayce"
where jayce is the name of your user. Type in your password twice. Once done, enter "reboot" to reboot the system. Once you fire the system up you should be able to log in again.
While on topic, I'm curious. What are your goals with this system? Are you trying to get your feet wet with Linux servers? While I do highly recommend learning the terminal as much as possible, there are some web based GUI utilities you can look into if you'd like to further streamline the process. This will give you a web based frontend to manage different things, like software RAID, network shares, users, etc. I've been using Ajenti on my server lately. I don't use it heavily, but I like seeing the dashboard where I can view all of my widgets to see system health/raid health/drive health/temps/load/network load all in one screen. Ajenti works directly work the config files, unlike some other web frontend services that totally muck with the configs. Tools like this were helpful for me when I first started, as I could make GUI based changes and then look at the config files in terminal to see what changed. After that, the rest is history.
Just a thought.
Installing on Ubuntu / KB forum / Ajenti
Note: I see the documentation specifically lists 12.04, however I have it installed on 14.04 (which was 12.04, then I did an in-place upgrade) and have had no issues, so I'd *assume* it'd work on a fresh 14.04 install as well.