Okey so a basic rule to being anonymous is ofcourse using a VPN.
U can get a cheap one for about $3.00-$5.00 since this isn't going to be your main VPN.
What I did is buy one off digital ocean. I bought one in Amsterdam, Ubuntu 16.04 x64.

What you are going to do is check your email and get your VPS details.

Then you are going to need an SSH client such as PuTTY, KiTTy or MobaXTerm.
If you are on a MAC or Linux OS, u can just type the following in terminal:
Then you will connect without downloading additional software.

Now once you are connected, if you bought a server from Digital Ocean u will be prompted to change your password. Do so, use a good password for god's sake.

Now run the following code:
This will install the entire VPN.

It will ask you for your servers IP, by default, this is already filled in.
Then it will ask for the protocol u wish to use. I select TCP but UDP will work fine.

It will provide u with a port, just press enter.
Then it will ask for the DNS u wish to use, I use OPENDNS.
Now provide the client name (the config name. I just use client).

Now it will start pushing out random dots and plus'.

Now you can connect using the OpenVPN client and your config!

First off, NEVER USE SKYPE, just don't. Please.
Start using XMPP as your main IM service, due to its ability to use OTR (off the record messaging)
Which of course is then way more secure.
If u are into black hat/gray hat activities. Never talk to anyone about your activity's, u never know who will snitch. Don't trust anyone.

U can download Pidgin by a simple google search.
Then search for OTR. So you can install this plugin by simply running the Setup file u just downloaded.

Now you are ready to go, if somebody doesn't have OTR, get them to install it or just never talk to them again, being secure also means taking choices.

I would recommend getting a RDP to extra ensure your privacy. U can get one for as low as $5.00 which is really cheap.
I'd recommend installing a VPN on there (can be any vpn such as nVPN or something).
This will really make sure you are very safe on the internet.