My December: Reflection & Deciding What To Work On

Last time I mentioned how I typically spend part of December doing a sort of strategic check-up. Today I’m going to go through my process. Hopefully it’ll inspire you to put something together that works well for you too.

The first thing to be aware of is that It’s incredibly easy to get trapped in the planning process and never actually start executing. However, it’s also not hard to get so in the weeds with your project that you don’t step back and check your direction. It’s tough to find a good balance between these, partially because the amount of time you need to spend on each changes depending on how far you are in your project. I don’t have a good formula or anything to help out with this. The best I’ve been able to do is to manage it by feel. I try to set priorities weekly, do a quick “am I on track?” check quarterly, and do a sizable strategic review and planning process annually. These timeframes shrink or lengthen based on how lost I’m feeling.

My Annual Review:


The first thing I try to do is spend some time alone going through all the projects that I’ve come up with over the year. I use Evernote to keep track of possible projects and I use this time to come back to them and try to flesh them out a bit more. I ask how each fits into the overall picture? What’s required to make them work? Are they even feasible in the next year or two? Then I take some time and get anything that’s been lingering in my head down on paper. Most of these are pretty shitty ideas. Either because they’re distractions which don’t contribute to the overall goal or because they’re simply too far from possible at this point that it’d be a waste of time to work on them. Get your ideas out of your head and spend some time sorting through them.


I try to take stock of how I’ve changed over the past year. I need to understand what my strengths and limitations are. Where have I become stronger/weaker? Over the past 3 years I’ve really focused on my sales skills. I used to be shit at this for a number of reasons and now I’m pretty comfortable saying I’m competent. While I’ve gained there, I’d say my financial modeling skills fell off a bit. I don’t feel like I’m at the top of my game here but it’s not something that’s super important to my current projects so I’m comfortable letting it slide a bit.

Asset Assessment

What am I working with? What tools do I have at my disposal that could be useful in the next year. What things do I need to develop or build out? Take an inventory of what you have to work with. This can be capital, key relationships, an already started project, anything. Then tag them with the various projects where they could help. Because I’m working on a number of different things at once, it’s here that I start to identify what can be repurposed or used better of other projects.


This is where I really get going. I absolutely love the research process. For whatever you’re doing you’ll want to really get to know the lay of the land. Who is involved, how are they involved, what market forces are at play, what kind of trends are you seeing, and what are the driving motivations of the key players? I really like using mind mapping software here but I haven’t found one that I really like so I’ve settled for a bulleted outline with a ton of links to various articles and data sets.


If the Research section is where things got interesting, this is the part where the work starts to become tangible. Here we’re combining the first four sections and we’re looking at the market and determining what we can influence with what we currently have or with what we can build out within the next few months.

There will be spots that jump out that you’ll say “why the hell isn’t anyone doing this already?!” It’s when you come across these that you’ll want to dive deeper into them. Maybe there’s a reason no one else is there. Commonly, it’s that there are some serious market or political forces at play, but on rare occasions, you come across something that’s perfectly suited for you to move into. This happened to me last year with Promethean Research; it happened the year before that with Launch League, and the year before that with the Tech Lab.

Some key things that I’ve looked for here are finding areas where the talent is lacking, the market forces are shifting, or the vision is poor.


Attempt to identify where challenges will come from. Does it look like competitors are gaining steam? Have they changed their strategies over the last year? Where are these strategies likely to lead? There’s a bit of game theory at work here. It’s definitely not a science as I’m working with a very limited amount of info but it’s good to take a little time to get into the heads of your competition. If nothing else it’ll give you some confidence when you examine their quality of work. Here’s where you can pull out what will be your differentiator. What will you do that will 1) make people give a damn about your project and 2) make your work more valuable than what’s currently out there?

Goal Setting

How do I want to spend my time? This is the best question to really meditate on before you start setting goals. I tend to forego annual goals and instead make 3-5yr goals. They don’t follow the S.M.A.R.T. formula or any other conventions, but they’re incredibly clear. They’re not written down, but they’re something that I constantly keep in the back of my mind.

About 5 years ago when I did this my goal was that by the time I turned 30 I wanted to have options. I didn’t want to be tied down to any one thing. I used that goal to guide my decisions, often subconsciously, so that I’d end up at a place where I could do what I wanted. It took about a year longer than I expected, but now I can say that I’m pretty free from any single source of income or stress. I’ve diversified like hell and it probably looks pretty random from the outside but it has allowed me to spend time doing what I love with minimal strings attached.

I hope you take some of this and use it to influence how you spend part of your December. It really is a great time to step back and check your course.