Paying for Privacy in a Cloud Age

Can I change my ways into a more secure, private, digital experience?

No one needs to be reminded that there is “no free lunch”, yet our digital society has continued to consume free services and push more data into the cloud. Myself included. Every time a Google search or a social media “like” turns into a “we think you’ll like” recommendation in my Amazon app, I’m reminded of my near perfect digital self that is floating out there, ready to be monetized.

I’ve committed in 2020 to do better, and with my experience in the information security space, hope to chart a sort of meandering path for others to consider in order to improve their digital selves. I expect that often times this will come at the expense of convenience, paying for services to limit a company’s interest in my data, or through new hardware purchases for the homelab (this may, or may not, be the real reason for all of this). How much will it cost, how inconvenient will it be, and will I feel better about my interactions? I don’t know, but seems like a good thing to track. So much data!

A little about the test subject

Growing up in the broadband boom, and being involved in technology for my entire career, I have built out a workflow that encompasses most of the largest cloud offerings. Dropbox? Yup. Apple Drive? Uh-huh. Google? Of course. Amazon? Where else do I get free photo backups?

To take back my world, I have some advantages on my side. As we move to an ever increasing subscription-based world, I’m more comfortable throwing the odd $5–$10 a month at a service if it provides greater value to me. In addition I have a small homelab with some good networking equipment that I can leverage for private solutions. And most importantly, I have time (thanks Coronavirus) and patience to make improvements.

Areas to review

I’m sure that there will be several more things that pop up, but I have started out with the following things I would like to explore:

• Password Management — The bedrock. I developed my own password management scheme several years ago, but it is worth a review, as well as comparing it to other players in the space.
• Email — The big one. As a heavy Gmail user with several accounts, how can I migrate to something more private, while not going overboard?
• Social Media — Having already uninstalled Facebook, I think this requires a review to ensure that I’m aware of all the aspects of dealing with different platforms.
• Secure Browsing — Excited about this. How can I browse better; from ditching Google, to cookie management and ad blocking? This will likely be the biggest “convenience vs. privacy” area.
• Networking — Reviewing virtual private network (VPN) technologies, configurations, and purposes. While I currently can VPN home, what can I do about outbound traffic?
• Multi-factor — Username and passwords are not secure anymore, and getting a code through text isn’t much better. What’s the benefit of moving to services that support better multi-factor capabilities?
• Backups — I need a better way to backup my network attached storage (NAS), without allowing someone to mine it all or have significantly out-of-date, off-site backups.
• Messaging — Is there a better way to chat across devices than normal texting and iMessage? This can’t just be me, so can I convince others there is value?

Blogging for science

I’ve had ideas for articles in the past, but always get hung up trying to pick a domain name and a content management system. I chose Medium after some research on the platform itself and spending time with some pages (Olaf Hartong and Blake Strom) that I keep coming back to.

Separately from the information above, I’m interested to see if the Partner Program can also defer some of the costs of a more private lifestyle. I’m committed to sharing the success and failures of this part of the experiment as well in the hopes of adding more data to the blogging zeitgeist.

Enough with the intros

Will I feel that I have more privacy in 365 days? Will I leave the perfect model of myself stranded in 2020? Will I be able to keep on schedule and recoup some of the inputs without offending everyone? Who knows?! But I’m excited to have a spot to at least get thoughts on paper, even if it isn’t my own domain.