Ask great questions, and Paul Graham’s How to Do Great Work

Imagine sitting at a dinner table.

Time is frozen.

Your friends or family surround you. This is where conversation happens.

What do you say?

Yesterday, I would have said something like “what book are you enjoying? Or “what have you learned recently?”.

I love learning- especially about people.

But today, I would say something very different.

I would say something similar to: “what is a good question you have been asking lately?”

Paul Graham has probably created more questions in my mind than anything else past 30 days.

His writing reminds me a lot of Derek Sivers. Reading their words feels like a longtime curious expert has paused in their work to explain something they thought was important. Like an expert chef has been creating some absurd levitating cheese foam, and then stops and turns — frothy cheese gently floating off their spoon — and starts talking about some important thing that changed how they worked with water when they cooked.

Here is a great example from How to Do Great Work

“Once you’ve found something you’re excessively interested in, the next step is to learn enough about it to get you to one of the frontiers of knowledge. Knowledge expands fractally, and from a distance its edges look smooth, but once you learn enough to get close to one, they turn out to be full of gaps

I’ve experienced a little bit of this already. Get close to the customer to find the real problems, ask them to show you. Ask why they do things, what they need and expect.

But Graham is talking about finding a way to follow other learners, learn what they found, and get close to the edge.

When I think about diving deep into something, learning to get close to the edge, where the gaps are…I sense fear and worry suddenly appear.

But what if it takes a long time?

What if I do all the work and get there, and I don’t find anything of use beyond the learning?

What if I don’t find valuable gaps?

How does the fear and anxiety “help” me? What protection does it serve?

Part of me feels drawn to doing things the same way- repeating the same instructions that others did to get the same result. A safe choice. A known outcome. The same painting, different colors. My life the result of a borrowed franchise manual.

ADD versus Bullet Journal method

Why do to-do lists work better for some people? They dutifully check off their lists and seem to move ever-closer to their goals. What can non-listers do to improve their tasking? Kara Benz offered great tips in How to Craft a Better To-Do list


I’ve taken some of my repetitive daily, weekly, and monthly tasks and categorized them into two lists. The first is my “If I have lots of energy then I will…” list, and the second is my “If I’m feeling sluggish then I will…” list. Kara Benz

Great point. I know my energy isn’t always the same, and I should adapt my goals and method accordingly.  I liked how the author addresses how to have a list for when I’m feeling sluggish or I have a lot of energy. I can give myself permission to get out and walk or experience some sunshine to give myself a break. 

Listers and Forgettors

It is easy to separate people into list-makers or forgetters, and classify myself as the latter. I don’t list. I try to keep it all rolling around in my head. Ask me how that is working. It isn’t, thanks for asking. 
I’m not a list checker. I don’t enjoy going back and re-checking the list to re-center myself. Lists aren’t interesting to me. Remembering is interesting, enjoyable and unfortunately it is also unsustainable. Eventually things drop off my memory radar which causes stress and slows me down. 

It feels great to have all those thoughts rolling around in my head, like a big Halloween candy bucket. I can choose to snatch a snickers (memory: free A/B testing tools for WordPress blog headlines), or an Alexander the Grape (idea: web comic detailing the captivating life of a concrete sidewalk portion). Using this (failing) method, I am rich with ideas but poor in implementation- a memory hoarder that refuses to select a goal and stick to it. 
Sure, I get a shot of positivity when I get something done, but i think others get a more powerful high. 

Focus on the Goal: People

My method has been to focus on the thing I enjoy, and factor in how my task will point to that. 
I love helping people share their ideas. I think the world needs more people sharing and listening to others. Looking at my task list; my car needs oil, I need a haircut, the website needs updating and we need to make a more efficient email message. 

Now, to give myself motivation to focus on a goal I’m interested in, I reconsider those tasks in light of how it will help people share themselves. Getting a haircut will help me focus on my job and give me a boost of confidence. Updating our email email encourage people to engage with the website. Ok, I can do this. 
Hey Inbox, you suck (at prioritizing my goals)

Too often it is easy for me to sit down and start checking emails for things I need to do. Instead, I can write them down, thinking as I write and prioritizing as they go into the list. I can use the bullet journal method to make another list of the top three things I will commit to complete. 

My Add brain is already frustrated I am writing something down twice. This is inefficient! This sucks! Go answer random, semi-important emails and get frustrated nothing actually was completed!

In reality, writing and re-writing items probably gives my mind more time to consider a solution to the task. Which, in reality gives my mind more time to do what I love to do: think about interesting things that are important to me. 

Kara has a great site focused on helping people live goal-oriented positive lives at (Phew, that sounds like a dorky positive Hallmark card endorsement, but I believe the world is better when we examine life and focus ourselves on greatness.) Thanks, Kara!

P.S. Kara also wrote a post on Bullet Journaling + the Getting Things Done method, which sounds like it will be a hot mess of flapjack goodness. Stay tuned and I’ll provide my hot takedown from an Add mindset soon. After all, it is on my to-do list. 😉

To do list in journal
Bullet Journal attempt, again.

Use a blue pencil and force yourself to draw

Grab a soft pencil and a blank paper. Draw. Right now.

Inspired by programmer Jamis Buck’s willingness to take on a new hobby every year (namely, to write 1,000 words a day), I decided to draw. I was tempted to find a pencil so I could draw and erase. No, I want to force myself to be free- to put ideas on paper, to “draw” those hundred words like Buck.
So, I drew. I kept wanting to place things in an orderly fashion or to start a new page with a new idea. Nope. Keep drawing. Pretty soon, is filled a page with badly-drawn lumpy computer desktops, abstract waves from the 1980s, magazine layouts with man eating a massive sandwich juxtaposed to the letters WO LVES, four rock band posters for my daughters room, and four website layouts.


I was frustrated the pencil became dull. I was frustrated at the lack of contrast from the light blue of the pencil to the white of the paper, but I kept drawing. I have myself the freedom to come back to these ideas and expand on them and this I was freer to not make these perfect right now.