Austin Kleon has a short section, “Make Lists,” in his new book, “Keep Going.” He offers several suggestions for different types of lists; I have selected four to explore in some detail because I think they are most appropriate for entrepreneurs. 

Austin Kleon on Making Lists:
To-Do, Ideas, and Do’s & Don’ts

Austin Kleon has a new book out called “Keep Going.” He offers ten rules for artists to persevere; the first is “Every Day is Groundhog Day.” The first  chapter is devoted to that rule and has a short section titled “Make Lists,” where he offers several suggestions for different types of lists. I have selected four to explore in some detail because I think they are most appropriate for entrepreneurs. The book is highly recommended.

Austin Kleon on Making ListsTo-Do Lists

“Lists bring order to the chaotic universe. I love making lists. Whenever I need to figure out my life, I make a list. A list gets all of your ideas out of your head and clears the mental space so you’re actually able to do something about them.

When I am overwhelmed, I fall back on the old fashioned to-do list. I make a big list of everything that needs to get done, I pick the most pressing thing to do, and I do it. Then I cross it off the list and pick another thing to do. Repeat.
Austin Kleon in “Keep Going

I am a huge fan of “to-do lists” and use them regularly. Whenever I am not working to a list, especially in an emergency or crunch situation, I view it as a key indicator that I am losing traction–likely spinning my wheels—and effectiveness. Here are a couple of quick rules of thumb I use in making a to-do list:

  • I will often estimate the time needed for an item and use it as a budget; this can help to inhibit a creeping perfectionism and allows you to manage your time for completing an item and getting a number of items done in a block of time.
  • Pay attention to items that keep getting transferred from an old list to a new one. Often it’s an indication of a lack of importance or a poor understanding of how to get started. Sometimes it makes sense to mark it “dropped” or “not important” (or “no longer important” if you’ve missed the deadline) and cross it off the list.
  • There is a risk that writing something down can release the energy needed to get it done. But, writing it down at least forces you to acknowledge you are not getting it done and does not allow you to “forget.”
  • Once you have the list and the time estimates for each item, you can determine your priorities for the morning or the day or the week. Assigning a priority to the top N tasks can force you to acknowledge what’s likely not to get done–which may trigger a new appraisal of priorities.
  • Making a list in a team setting, where members take ownership for items and confirm or update the time and priority estimates, is a great way to build shared trust and shared momentum.

Explicitly scheduling time for tasks can be a natural follow from a to-do list. You can start with time box exercises where you allocate a short amount of time (e.g., 5-20 minutes) to force yourself to make at least a small amount of progress. Or you can start with longer uninterrupted blocks of time to make significant progress on key items.

Good Ideas, Sparks, and Someday/Maybe Lists

When there is something I want to do in the future but don’t have time for it right now, I add that to what productivity expert David Allen calls a “Someday/Maybe” list. Writer Steven Johnson does this in a “spark file”–every time he has an idea, he adds it to the file, and then he revisits the list every couple of months.
Austin Kleon in “Keep Going

I think there are a number of ways to leverage this concept:

  • In a sales call or software demo, it’s useful to maintain a “parking lot” list of items that are written down on a flip chart, whiteboard, or Notepad file in a webinar. They should be discussed at some point, but not immediately. Some of these may become follow up items for a follow-up call, email, or meeting. A public list allows everyone to have their requests and questions acknowledged and followed up on without sidetracking the conversation.
  • Enhancement requests from customers are also worth capturing and reviewing: both in the context of all of the requests from one customer and all requests from all customers.
  • I keep a list of product and service ideas for SKMurphy that we may implement someday.
  • I also keep a list of “problems worth solving” and look for startups that we can help to address them.

Do’s and Don’ts Lists

When I need to keep myself on track spiritually, I’ll make a list of “Thou shalts” and “Thou shalt nots.”
Austin Kleon in “Keep Going

I see several ways to apply this concept to individual and team level productivity (in addition to making spiritual progress):

  • A don’ts list identifies the behaviors or practices that you are trying to extinguish is a good idea. For each don’t, you should have one or more options for your “do” replacement.
  • Decision rules with an “until” requirement can also prevent problems. Two examples: “don’t make a decision until you have generated and evaluated at least three alternatives” and “don’t stop looking for flaws in a plan until you have identified at least three things that can go wrong.”
  • These lists are also a vital aspect of a project post mortem or after-action assessment. One simple approach has you make three lists: the continue or “what worked” list is incorporated into your do’s list, the stop or “what did not work” list is added to your don’ts list, and a start or “let’s try this as an experiment” list is added to your to-do list.
  • A don’t rule strictly adhered to can be quite powerful. Clayton Christensen observed in  “How Will You Measure Your Life“ that “It’s easier to hold to your principles 100% of the time than it is to hold to them 98% of the time. If you give in to “just this once,” you’ll regret where you end up. You’ve got to define for yourself what you stand for and draw the line in a safe place.”

Thanks For / Need Help Lists:  A Paper Prayer

“When I am stuck: I will draw a line down the middle of a piece of paper. In one column I will list what I am thankful for and on the other what I need help on. It’s a paper prayer.”
Austin Kleon in “Keep Going

Kleon’s approach can be especially helpful at a team level.

  • Take the time to point out recent accomplishments or contributions by other team members. Especially after a setback, it’s useful to celebrate things that have gone right–while acknowledging everything that has gone wrong.
  • Identify where other groups or people not on the team have supported your current progress or past successes and thank them.
  • Making a list of missing expertise or known shortcomings allows for a change in methods and targeted outreach for assistance outside of the group.

I find it very energizing to send handwritten thank-you notes, to write LinkedIn recommendations, and to count my blessings after a setback. Avoid serving a “crap sandwich” where you offer praise only to follow it immediately with criticism and then some more praise. Offer praise directly, not as a prelude to criticism. Provide constructive feedback directly and without apology (if you find yourself starting with “now don’t take this the wrong way” stop until you can phrase it in a way that it cannot be taken poorly).

“I make lists to keep my anxiety level down. If I write down 15 things to be done, I lose that vague, nagging sense that there are an overwhelming number of things to be done, all of which are on the brink of being forgotten.”
Mary Roach

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