When things don’t go quite as you hoped, it’s human nature to look backwards and question your decisions. If you had done something different maybe the outcome would be better. If you didn’t do the other thing, maybe you’d be in a different spot. We all do it. Some more than others. It’s almost impossible to not wonder what would have been.

But you have to be careful playing Monday Morning QB. If you wallow in a situation you end up stuck in a house of pain after a decision doesn’t go well. You probably don’t have a time machine, so whatever happened is already done. All you have left is a learning opportunity to avoid making the same mistakes again.

hindsight can be painful

That is a key concept, and I work to learn from every situation. I want to have an idea of what I would do if I found myself in a similar situation again down the line. Sometimes this post-mortem is painful – especially when the decision you made or action you took was idiotic in hindsight. And I’ve certainly done my share of idiotic things through the years. The key to leveraging hindsight is not to get caught up in it. Learn from the situation and move on. Try not to beat yourself up over and over again about what happened. This is easy to say and very hard to do. So here is how I make sure I don’t get stuck after something doesn’t exactly meet my expectations.

  1. Be Objective: You may be responsible for what happened. If you are, own it. Don’t point fingers. Understand exactly what happened and what your actions did to contribute to the eventual outcome. Also understand that some things were going to end badly regardless of what you did, so accept that as well.
  2. Speculate on what could be different: Next take some time to think about how different actions could have produced different outcomes. You can’t be absolutely sure that a different action would work out better, but you can certainly come up with a couple scenarios and determine what you want to do if you are in that situation again. It’s like a game where you can choose different paths.
  3. Understand you’ll be wrong: Understand that even if you evaluate 10 different options for a scenario, next time around there will be something you can’t anticipate. Understand that you are dealing with speculation, and that’s always dicey.
  4. Don’t judge yourself: At this point you have done what you can do. You owned your part in however the situation ended up. You figured out what you’ll do differently next time. It’s over, so let it go and move forward. You learned what you needed, and that’s all you can ask for.

That’s really the point. Fixating on what’s already happened closes off future potential. If you are always looking behind you, you can neither appreciate nor take advantage of what’s ahead. This was a hard lesson for me. I did the same stuff for years, and was confused because nothing changed. It took me a long time to figure out what needed to change, which of course turned out to be me.

But it wasn’t wasted time. I’m grateful for all my experiences, especially the challenges. I’ve had plenty of opportunities to learn, and will continue to screw things up and learn more. I know myself much better now and understand that I need to keep moving forward. So that’s what I do. Every single day.


Photo credit: “Hindsight” from The.Rohit

Security is changing. So is Securosis. Check out Rich’s post on how we are evolving our business.

We’ve published this year’s Securosis Guide to the RSA Conference. It’s our take on the key themes of this year’s conference (which is really a proxy for the industry), as well as deep dives on cloud security, threat protection, and data security. And there is a ton of meme goodness… Check out the blog post or download the guide directly (PDF).

The fine folks at the RSA Conference posted the talk Jennifer Minella and I did on mindfulness at the 2014 conference. You can check it out on YouTube. Take an hour. Your emails, alerts, and Twitter timeline will be there when you get back.

Securosis Firestarter

Have you checked out our video podcast? Rich, Adrian, and Mike get into a Google Hangout and… hang out. We talk a bit about security as well. We try to keep these to 15 minutes or less, and usually fail.

Heavy Research

We are back at work on a variety of blog series, so here is a list of the research currently underway. Remember you can get our Heavy Feed via RSS, with our content in all its unabridged glory. And you can get all our research papers too.

Resilient Cloud Network Architectures

  • [Design Patterns]
  • [Fundamentals]

Shadow Devices

Building a Vendor IT Risk Management Program

SIEM Kung Fu

Recently Published Papers

Incite 4 U

  1. Still no free lunch, even if it’s fake: Troy Hunt’s post is awesome, digging into how slimy free websites gather personal information and then sell it. But it turns out all that glitters isn’t gold, and some of those records are total crap. It’s very interesting to see how Troy pulled a number of strings to figure out which sites were responsible, and then figured out that a lot of their data is fake. Which makes sense given that no one can really check 5MM records, so they confirm a small sample and then pad with nonsense. Now you can’t even believe the fraudsters that are selling records to perpetrate more fraud. That’s totally shocking! – MR
  2. The flaw: I’ve never been a fan, but since I have neither deep experience nor data to show whether the Bi-modal IT model is good or bad, I have shied away from commenting on it. Jez Humble does not mince words, and his recent analysis of Gartner’s Bi-modal model for IT practices is no exception. He states that Gartner’s model is based on the idea that reliability and agility are at odds. I think frameworks like this were created by philosophers who grasp a specific problem, but lack the practical experience to understand why idealistic solutions don’t work in the real world. But when you examine a confounding, anti-intuitive approach like DevOps on paper, it looks reckless. In practice it has shown that speed and quality can be synergistic. Much the way Toyota demonstrated how their manufacturing approach allowed them to make cars better, faster, and cheaper; DevOps is blowing up assumptions of what’s possible with IT operations and software delivery. A few years down the line, we won’t call it DevOps – it will just be how we do things. – AL
  3. Smokin’ hot job: Based on the latest ComputerWorld Salary Survey, security folks are in the catbird seat. Information Security Manager is the hottest job in IT. No kidding. The survey states “security pros are paid well, rate job satisfaction high, and will make a move for money.” No kidding. Salaries were up 6% or so, and it’s probably more in metro areas with high demand and lots of options for practitioners. Though I can’t say job satisfaction is a highlight in the (very non-statistically significant) sample of folks I talk to regularly. It’s a tough job, and it’s worth a lot. So once again Mr. Market wins. And if anything salaries will continue to move upward because it’s not like a bunch of security personnel are about to come online anytime soon, if ever. – MR
  4. Subtle: Google’s announcement last week on encryption and email security nearly put me to sleep with their understated blog post and crappy “Safer Internet Day” tag. Let’s be honest: “Safe Browsing” has been around for years, and has allowed me to go to dangerous sites without protest. But not those sites. I don’t do that (doh). Flagging sources already using TLS is handy, but few use content encryption, so it’s hard to say that content is not being read by some government entity which subpoenaed an Internet provider somewhere. But what got my attention was the new warning about “state sponsored attacks”. When you realize the route your email takes to get to its destination, you realize this is agnostically targeting your government, regardless of where you sit. Very subtly backing the recent swell of support for user privacy and encryption. – AL
  5. WhatsApp’s one-finger salute: Whereas Google has taken a more subtle approach to telling the feds who want full access to customer data to bugger off, Facebook’s WhatsApp has basically stood on the proverbial table to give them the one-finger salute. By integrating the Signal protocol into their app and stating in no uncertain terms that all messaging traffic is encrypted from device to device, Facebook is making it clear that they cannot access user content, regardless of subpoenas. Although law enforcement can still access who spoke to whom, they cannot get anything else. We have written quite a bit about privacy and the slippery slope of backdoors and special operating systems. I applaud Facebook for taking a stand here, knowing that bad folks can (and do) use their network to plan bad things. But either there is monitoring or there isn’t, and by not providing any wiggle room, WhatsApp has clearly decided against monitoring. But you have to wonder if Facebook is forgoing a huge advertising stream by providing truly private messaging. – MR