Annual Reboot

I’m on the final approach to O’Hare on what I just realized is my 50th and (thankfully) final flight of 2015. For the entire flight from New Orleans, I did nothing but stare at the back of the seat in front of me and reflect on the busiest, most stressful, yet most amazing year of my life to this point.

I was in New Orleans for my my “Annual Reboot.” Each year I take a long weekend, usually in a fun city, just to reflect on the year ending, envision an ideal upcoming year, and put the plan together to achieve this vision. In addition to this self-reflection, I tend to get a lot of creative work done while I’m sitting in the coffee shops, cafes, museums, pubs, and taverns that I discover while exploring each city I visit. Most importantly though, I take the time to enjoy myself and meet new people wherever I’m visiting. It’s energizing, to say the least.

The name “Annual Reboot” is a nod to early IT jobs where I would have to reboot all of the Windows servers in our data center on a regular basis because the systems would become sluggish over time, but would return to peak performance after a reboot was performed.

This retrospective and planning exercise requires intense self introspection and honesty, but the process itself is as straightforward as it gets – I ask myself three simple questions:

  • What are you doing that’s working and you should invest more time and energy in? (Keep Doing)
  • What are you doing that’s not working and you should stop right now? (Stop Doing)
  • What are you not doing that you should start doing? (Start Doing)

This list is by no means a new concept or anything that I came up with on my own, more a pattern that I have recognized regularly in the books, articles, and blogs that I have read over the years. One interesting thing that I’ve observed during this exercise is that the “Stop Doing” list – the list of things I should cut out of my life – is the list that ends up having most profound impact on my productivity and well being. This sounds counterintuitive at first, but it makes total sense as time and energy are freed up to invest in the activities, relationships, and ideas that are going to provide a much higher return.

The “Start Doing” list seems to be where many of us fall into the trap of creating goals or plans that we never follow through with. How many New Years resolutions do we make with wild-eyed optimism that we end up abandoning because we don’t put enough thought into the emotional and operational infrastructure needed to support these goals? I’m finally getting to the point where if I do add anything to the “Start Doing” list, I follow it up with a comprehensive execution plan before I even consider moving forward. I can’t even begin to tell you how much time, energy, and emotional bandwidth this has allowed me to refocus on the things that matter most.

By no means should the “Keep Doing” list be considered a lower priority simply because things are working – maintaining the status quo can be a potentially fatal mistake. Believe me, I have felt the pain of telling myself things like, “no news is good news,” or “if it ain’t broke…” only to miss key signals that cost me after I took my eye off of things that I assumed would just keep working on their own. Life doesn’t work that way. Even what we may think of as “low maintenance” requires at least some regular investment of energy – like a plugged-in appliance that continues to draw power even though it is turned off.

All of this may seem like hard work…because it is. Being direct and honest with ourselves doesn’t come naturally, but with enough practice it will start to feel less like self-criticism and more like self-discovery. If anything, I recommend something like an “Annual Reboot” if for no other reason than to just disconnect from life and clear the mind. How often do we get the opportunity to just zone out, absorb the energy of a new place, and spend uninterrupted hours reflecting and planning…looking back to look ahead? Whatever that number is, it never seems to be enough. That’s why I fiercely defend this time and fall off the face of the planet even if just for a few days each year. It’s cleansing, it refocuses me, and it inspires me. I also know that it’s completely necessary to maintain perspective and see what lies ahead.

Do you have a similar process? What have you found that works? I’d love to compare notes – mike [at]

Mike Topalovich Salesforce Technical Architect in Chicago
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Mike Topalovich

Hi, I’m Mike. I help companies like yours do business in new ways with Salesforce.

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