My Annual Plan is a big deal. For years I’ve worked to develop and refine my own annual planning process. I set aside the month of January to reflect and plan. I would create a long document that contained all of my roles, goals, plans, and responsibilities. I had my wife and friends review it, and gave them permission to correct it, or add to it. Then, each year, I turned it into an actionable plan that I fed into my task management system. It’s been really valuable and worked for me.

Until it didn’t. This past year my January was interrupted with several big life events for our family. So the planning simply could not happen then. It took months to get back on track, and when I did, the process was really difficult. It was more time-consuming and ultimately unhelpful. For the first time in years the whole exercise felt forced, false even. What had once worked well was broken. That’s no surprise really, it’s the way of the world. But now it’s time to fix it.

One of my favorite podcasts is Cortex, a podcast that is marginally about productivity, but aimed at my particular kind of nerd. For the last several years on the show the hosts have used used the idea of yearly themes to organize and guide their plans for each year. On this year’s annual themes episode something in particular struck me. One of the hosts’s theme was the “Year of [Re]Order.” He recognized that his previous theme, “Year of Order”, was not successful and it needed to be readdressed. It was a simple and honest admission—one that regular listeners were surely not surprised by, and yet it struck me as profound and—in the limited sense of this subject—brave. It’s hard to admit it when things do not go as planned, especially for those who are planners. It’s even harder to admit it publicly when you have people that look to your for help on planning. Listening to CGPGrey’s analysis of his theme choice, I realized what my own theme needed to be. I need a clean break. I need a hard reset across several areas of life. I need to reboot.

There are many reasons that my annual planning failed, but a post-mortem to figure them out would not be helpful. The question that matters is, how do I get back on track? That’s the goal of the “Year of Rebooting.” I will inventory all areas of my life, examine and reflect on each one, and then do a hard restart of it. Like any good reboot, there are some processes that need to be killed for good, and there are others that require significant changes. But none should be left untouched.

The process starts this month, January 2019. I am in the process of making several hard decisions that lay the groundwork for the rest of the year. The first decision I made is to leave Facebook and Instagram because of privacy and social concerns I noted in another post. The second was to start writing on the web more, partially to document this journey. The next decision in front of me is how to approach my Year of Rebooting. It’s not an annual plan. It’s not what I have done in the past. It will be something new, and I will build it as I go. But I do know one thing, it’s a fresh start.