Things I Wish I’d Known/Done Differently

I once read that experience can be defined as “That thing you get right after you needed it.” Likewise, my dad used to have a sign in the bathroom that read “If you can’t be a good example, be a horrible warning.” I believe it’s very important to learn from others whenever possible, both the successes and failures. Why recreate the light bulb from scratch every time – complete with the failures – when someone already did it? It is with this mentality in mind that I thought I would take some time to look back at my early days of privacy and talk about some of my own successes and failures and things I wish I’d known or done differently.

I Wish I’d Been More Patient

I’m the kind of person that when I get a new obsession, I get really into it. My mother described my early years as “the child of phases.” I went through phases where I would only eat pancakes – breakfast, lunch, and dinner – wear cowboy boots, use a certain word at every opportunity, etc. I was notorious for latching onto something and running with it til the next thing came along. These days I tend to jump around less, but the intensity of my interests still remains. When I got into privacy, I jumped in headfirst, and while there’s absolutely nothing wrong with that, I do wish I had paced myself a little better because many of the things I ended up doing, I ended up rolling back and costing myself money. For example, I deleted Steam – the popular gaming platform. Well, this came back to bite me when I decided that while I don’t consider myself a “gamer,” I do still play casually. That meant that all the games I had previously purchased from Steam, I had to purchase again when I decided to go back. Likewise, I ended up needing Facebook for a short time after deleting it, resulting in me signing back up – and having to give up real information so I could make an account again.

Now it should be noted that there is something to be said for both of those examples. Getting rid of Steam, while it meant paying for things twice in the end, was easily reversible, and likewise getting rid of Facebook once was the stepping stone that made it possible to do it twice (and for good the second time). Often I encourage readers if they’re unsure to just do it and you can always step back later if it proves to be too much. But the opposite is also true: you can start by deleting Facebook off your phone, and then after a week realizing “wow, I’m doing just fine without it, may as well go all the way and delete my account entirely.”

I Wish I’d Done More Research

When you first get into privacy and security, you’re probably following the lead of one person. This may be because you don’t know any other resources (which is why I list other resources on my site), or it may be because that person resonates with you and explains stuff in a way you can understand. But this is dangerous. There is no one-size-fits-all privacy/security solution. If there was, there wouldn’t be dozens of products in the same space. (That’s also why my site is organized in “pro/con” format.) On the other hand, in many privacy forums and chat rooms you’ll find no shortage of opinions and while some of them may be valid and fact-based, many of them are still just that – opinions. While I’m fortunate enough to have developed good critical thinking skills that have helped guide me in the right direction, I still wish I had taken more time to evaluate different services myself rather than relying on popular opinion. It took me far longer than I care to admit to realize that all services come with a privacy policy and that’s a good place for me to start vetting things on my own. Or to use the search function (including open web searches) to find more information about a service’s history. Again, I was fortunate enough to not fall for any major misteps, but I could’ve done better if I had taken more time to think for myself and evaluate things on my own instead of taking them at face value because of popular consensus or what my own intro-to-privacy guru thought.

I Wish I’d Been More Fearless

This one kind of runs counter to the first one, but not really. I understand – and suffer from – the fact that life is busy and there’s more to life than just privacy or security. Bills have to get paid, the day job has to be paid attention to, there’s social obligations and relationships, and other interests that also typically cost time or money. But in almost every situation where I put off something because of the time and/or money involved, I end up wishing I’d done it sooner. For example: once I FINALLY pulled the trigger and bought a DD-WRT router, that meant I could start experimenting with it sooner and finding a privacy-oriented solution that works. Now, I can rest easy knowing my network is extra secure. Or similarly: recently I came into possession of a PinePhone. After a few weeks of tinkering, I am beyond convinced that this is not a daily driver for me. Previously I had been on the fence – “maybe I can make it work… I’m not sure.” No, definitely not. And now I know I need to invest in another solution of some kind, but I still have a PinePhone to keep an eye on in case it develops further. The point is that more often than not, when I put things off it’s primarily justified due to fear of the unknown: “this will be a lot of work.” “I don’t know what I’m doing.” But more often than not, I end up finally implementing something and going “wow, how did I live without this before?” (Ironically, this is also the reply I often get when I convince people to switch to Bitwarden.) Again, this also varies. Sometimes I put things off because I’ve truly got other stuff to focus on and pay for. With privacy, there’s always more to do. It’s important to prioritize and take care of things correctly: the rent needs to be paid before I buy a Pixel for Calyx, and date night comes before the podcast – it’ll still be there waiting to be edited afterwards. But putting things off because I’m scared of the work or fear of failure, those have never been smart and I wish I’d been more willing to rise to the challenge because the sense of accomplishment and security I get from those can’t be understated.


When I set out to write this blog, I expected to have a laundry list of things I wished I'd done differently, but I quickly found I didn’t have many regrets. I think this is largely due to my critical thinking skills that I mentioned earlier, but also my social skills. I’ve written a blog post about this before, too. If you’re new to privacy, I hope this blog post is still helpful. Remember: do your research and don’t be afraid to take it slow in some areas or dive in deep in others. Just remember not to go too far to the point of hurting yourself or your relationships, and take it slow to avoid burnout. Privacy is a marathon, not a sprint.

You can find more recommended services and programs at, and you can find our other content across the web here or support our work in a variety of ways here.