1. Anonymous, prepaid phone line
It might be possible to pick up an unlocked phone (no iPhones, Androids please - just a simple flip phone a la Motorola RAZR and the like) and a SIM card from a nearby country, for example, Panama, that is not registered to your name. Better yet get two phones and SIMs, one for you and one for your friend. The SIM cards from Panama won’t be registered to your names and as long as no one gets their hand on your phone, you might be safe. To be extra careful, don’t call anyone else with your special phone other than your other special phone.
Advantage: It’s cool to carry two phone around, people might think you are more important than you really are; not having a smartphone with Twitter and Facebook makes it virtually impossible to update your social media status with compromising photos
Disadvantage: You have to go to Panama to get a SIM card; you need to recharge the phones minutes A LOT since you’ll be roaming; someone in the CIA is probably already onto this tactic
2. Tin can phone
Advantages: Leaves virtually no trace of calls, makes you look kind of cool in the office; cheap and easy to assemble with household items; no need to worry about recharging the battery or finding a new plug adapter to fit the latest Apple docking technology
Disadvantages: Limited distance; wire can get tangled, sometimes cut; poor encryption technology (also known as pig latin)
3. Encrypted landline phone
We found a company selling landline technology with 256 bit encryption. If you and your friend have one, then you might be in the clear.
Advantages: Secure, don’t need to worry about charging the battery or topping up your airtime.
Disadvantages: It’s a landline. Your friends at work might wonder why you need an extra landline phone on your desk thereby raising suspicion
If you’re going to use email (mistake) and need things to be more secure, then we recommend exploring Tor. Tor is probably the only way that you can stay anonymous on the web but it requires a fair amount of attention to detail and vigilance in maintaining a cloak of secrecy.
Advantage: It probably works
Disadvantage: It’s not as easy as the tin-can phone