The Annual Review

Merry Christmas Eve, happy holidays, and Bestest Festivus to all!

This is not the normal Vinethinking essay. It’s more important than that.

This essay is about the Annual Review.

The Annual Review is a process that I’ve been going through since 2009, during which I take the time to get secluded, get reflective, get analytical, get hopeful, and get set for a great upcoming new year. This new year being 2020, it’s cool say a new decade and for some of us, we need that energy of new and fresh. 

I’ve shared this process in years past, and I’ve heard from many about the good it brought to their lives.

This life-planning exercise was introduced to me by my friend and mentor Chris Guillebeau, author of The Art of Non-Conformity and best known today as the creator of Side Hustle School (a must-subscribe podcast in my opinion). On his personal site, way back in 2008, he introduced me to the idea of the annual review and what it entails. See the original post here. I’ve modified the annual review to my own ways of thinking and planning, and have used it effectively ever since.

And I want to share it with you.

First, some rules.

1. This takes time. Usually, at a minimum, one full day, preferably two. And those full days should be spent, if possible, alone and somewhere else. Get yourself out of your regular environment (in years past I’ve gone to Santa Barbara, Phoenix, Portland, Seattle, Duluth, etc. — this year I’m keeping it closer to home, I’ll probably head down to Rochester or Eau Claire).

2. Unplugging is essential. You must disconnect from the world. You don’t need to become a Luddite or a hermit, but during the process of going through the annual review, it’s essential to not have your digital distractions nearby. You can set up windows of time for that, i.e. “I’ll work on my annual review from 10 am to 3 pm, then I will allow myself my email and Facebook fix.”)

3. This is personal. By you and for you. Nobody else. 

4. The goal of the annual review is to chart paths, draw maps, set goals, learn a bit from the past without getting bogged into it, and go into a new year with planning as a superpower. However, these are not resolutions! This is a much deeper process of planning, outlining, and reflection.

Okay, so what is the Annual Review like?

The Annual Review is a structured process of analysis and planning, with the goal of measurable outcomes plus a theme for the year. There are fourteen pages to the packet, and each has a goal of helping gain clarity. Print the pages, get pen to paper and take your time to do it right.

The power of the Annual Review lies in a couple of things. First, looking back to learn from the past twelve months — what went well, what did not. What did you have control over, and what was out of your hands? I try to keep the “looking back” part to about 20% of the total process, or else I find myself swimming in my mistakes (there’re a lot of those, and I’m extremely good at dwelling on them).

Second, accurate planning and goal setting. Goals need to be concrete and preferably measurable. 

Once you start working on the packet, especially if you’re by yourself with no other commitments for the day and away from the digital communication devices, you may find yourself in a zen-like state of reflection, planning, and power. Having control over your own destiny is a big part of this whole thing.

What can be achieved through the Annual Review?

Everything. And I don’t say that lightly.

We are all guilty of missteps. We all have our own demons and secrets. Some years are up, some are down. If you’re like me and deal with anxiety and depressive episodes, sometimes the weight of day to day life feels suffocating. There is no better antidote I’ve found than a carefully completed annual review, revisited monthly over the course of a year. It helps to reduce the problems to manageable little piles, it helps to give you a compass to bigger goals, and it helps to reinforce that it’s the journey that matters.

So I present the Annual Review template for planning an awesome 2020. You can download it here.

Let me know if you go through the process, especially if it’s your first time doing this exercise. 

Thank you to everyone.  Have a very Merry Christmas! Hug those kids, wrap those presents, and pop a great bottle of wine to celebrate your life.


Jason Kallsen