I’m a big fan of checking off boxes. There’s something satisfying about marching my way through a series of checkboxes and knowing I’m accomplishing some larger task. If you don’t already, I highly recommend using to-do lists as part of your daily routine of getting things done. (As a side note, the book Getting Things Done is great for how to organize these and generally how to be someone who gets shit done. If you’re already pretty good at this, I recommend just reading this summary of GTD.)

However, I noticed recently that I’ve been running into problems that I couldn’t seem to fit into a to-do list. Not that they were abstract things that couldn’t be broken down into tasks, but rather they were things I didn’t know how to do. For example, how to develop a product to sell in an online store or learn how to build a desk from scratch. I would sit down and start writing out my list and maybe get as far as, “Buy wood” then suddenly I’d be staring into the abyss of questions… what kind of wood? how much do I need? where do I buy it? do I really want to build a desk? what if I buy the wrong supplies and have to start over again? where can I find the space to build this? etc.?

What I realized though is that I’m trying to go from 0-60 without passing through 0-20 first. So what I did was took a step back, threw out my list, and started again with a simple entry: “Research building a desk.” The internet is an amazing place and a simple search turns up more information than I could ever possibly digest on this subject. In starting at a more logical beginning point, I can drastically reduce the number of show stopping questions I run into. This, in and of itself, presents a set of problems.

Many people, when faced with an near-infinite amount of information can become paralyzed by it, spending hours upon hours researching and never actually reach the task they’re researching. To quote Steve Jobs (and for those of you who know me well: yes it does hurt me a bit inside to do so.): “Real artists ship.” So let’s not let fear of imperfection stop us from completing the task we were previously driven to do. Let’s modify that original to-do list item to, “Spend 1 hour researching building a desk.”

This doesn’t mean you have to spend only one hour researching then go galavanting off to buy wood and screws and never ask any more questions. This means you have given yourself 1 hour to read up on generalities and use this knowledge to inform the next points. Maybe you’ll come up with the following:

1. Find a space I can use to build a desk.
2. Spend 30 minutes deciding what kind of woods to use.
3. Draw up general plans and measure the space I plan on using it.
4. Make a list of various pieces I need: screws, hinges, rails, handles, tools, etc.
5. Decide on dark or light stain or paint.
6. Head to the store and see what woods and materials are available.
7. Revise plans based on new information — go back to researching if needed.

From here I can start working my way forward. It’s natural that the list will expand and contract as I proceed forward and ask and answer more questions. As I run into the unknown, I can add more notes to research, using time limits, and trying to be as specific as possible (but remembering that it’s ok if I don’t know exactly what it is I don’t know — I’m just learning).

Ok, I’m off to research building things… as a last note, remember to embrace the investment in loss that comes with learning a new skill and adventuring off into the unknown. It’s a journey, enjoy it.