More Unsolicited Advice From David Cain

David Cain has many thoughtful and carefully observed posts on his blog “Raptitude: Getting Better at Being Human.” Here are excerpts from three posts that offer practical advice for entrepreneurs.

More Unsolicited Advice from David Cain

This a follow up to a blog post I wrote last year, “Some Unsolicited Advice From David Cain,” that extracted seven key insights from “67 short pieces of advice you didn’t ask for.”  It was triggered by his “Question for Regular Readers” asking for his best posts. ”

Relationships of All Kinds Take Initiative and Work

“It began when I went hyper-frugal to save up a job-quitting fund. I didn’t want to spend money on booze or restaurants or parties any more, so I said no to almost every invitation for nearly a year. Eventually the inviters stopped bothering, and I lost track of my biggest circle of friends. […]

Relationships of all kinds take initiative and work, and because that work was somehow getting done in my relationships, I never saw it as a responsibility. I got away with it for so long only because I was blessed to know so many people who did.”

David Cain in “A Common Habit That Costs Friends“

I think different relationships require different levels of investment. For family and close friends you have to have frequent interactions that are mindful so that you are available to them when they need you. Not every conversation has to be deep or serious, but you have to be open to the possibility of a real need.  I am reminded of a couplet from Simon & Garfunkel’s America where the narrator his worried about sharing his fears:

“Kathy, I’m lost,” I said, though I knew she was sleeping
I’m empty and aching and I don’t know why.
“America” lyrics by Paul Simon

But I think it’s also very important for entrepreneurs to keep track of former co-workers, partners, and others they have collaborated with successfully. This “extended tribe” is valuable because they know you and may run across relevant information and new people you should talk to. When you run across people or information that may be relevant to their current efforts it’s a good reason to reconnect, and to keep track of the last time you spoke so that you talk or exchange email at least every 6 to 9 months or so.

How to Avoid Four Common Causes of Procrastination

In the “Four Horsemen of Writer’s Block” Cain identifies four common causes of procrastination: “I’ll do it tomorrow”, “I’ll do it later”,”This is cool–even if it’s not what I set out to get done”, and “I realized I am not good enough to be able to do what I set out to do.” He decodes them in some detail and offers a counter-move to break yourself out of the procrastination loop.

1. Tomorrow: When you recognize that it is actually impossible to do work tomorrow, then you know to stay with your work until something starts to take form. Today is the only day you can ever work, and once you see this truth, he is defeated.
2. Later:  Work only gets harder throughout the day. Don’t use the day’s freshest hours to do its least demanding activities. Never accept gratification before you’ve done enough work to be proud the day.
3. Distraction: Avoid enchantment by learning to recognize what the in-the-moment sensation of becoming distracted feels like, and when you notice it, return your attention immediately to what you were doing, without “resolving” the distraction. It is easier to learn to do this in small stretches. Set a timer and declare the next thirty minutes distraction free. Snap back to the task at hand the moment you notice you’re not doing it anymore. This is a muscle you have to work.
4. Self-Doubt: bad work is unavoidable on the way to good work. Embrace your bad work as a necessary component of getting to your good work.

David Cain in “Four Horsemen of Writer’s Block“

Distraction takes many forms and is probably my number one blocker.

• Inability to prioritize. One counter-move is to make your short to do list up at the end of the day before avoids “tomorrow” and “later” and the distraction of prioritizing and re-prioritizing.
• Worrying about things undone and what you are not working on. Cain suggestion of a variation on Francesco Cirillo’s Pomodoro technique in #3 can counter this and belongs on anyone’s list of procrastination blockers.
• Trivial and unimportant victories. The equivalent of junk food on your shopping list, junk items that don’t belong on your plan for the day or week. For example re-organizing either on-line or physical workspace, solitaire games, reading news or other ephemeral content. In addition to timed sprints picking some relatively important pre-cursor activities can be a way to move the ball forward instead of dissipating efforts.

Meditation

5) Minute-for-minute, nothing I do is more rewarding than meditation. Even after just a very short session, it reliably makes me better at everything, especially making decisions. It lets me do my best. Yet I still do it only intermittently.

David Cain in “16 Things I Know Are True But Haven’t Quite Learned Yet“

I think mediation can partially offset lack of sleep but good sleep hygiene is probably an important precursor. I agree with Jorn Barger’s assessment that meditation is a key self-debugging technique:

“I believe that real meditation is about detecting self-deception.”
Jorn Barger in An Internet way of self-knowledge

And self-deception is one of the roots of fruitless distraction (as opposed to exploration and tinkering that may unlock new insights).

Pick What You Resist Most, Focus,
And Keep Starting Until You Finish

In “16 Things I Know Are True But Haven’t Quite Learned Yet” Cain offers a trio of habits that are mutually reinforcing:

10) The quickest and most reliable path to personal improvement is to do the things on my list that I resist most. Internal resistance should be taken as a big red sign guaranteeing rapid growth and new capabilities.

11) All you need to do to finish things is keep starting them until they’re done. The idea of doing something in its entirety always seems hard. But it’s easy to commit to simply starting on something, and then you’re past most of the resistance. Continuing is just as easy. (Thanks to Leo Babauta for this one.)

13) Ultimately, to get something done you have to forget about everything else while you do it. The mind is always telling you that 85 things are on fire and you need to do everything now. However you respond emotionally to it, to move things along you have to pick one to deal with, and let the rest continue burning while you do.

David Cain in “16 Things I Know Are True But Haven’t Quite Learned Yet“

I would rephrase #10 slightly to focus on the tasks that is most likely to move the needle or have the most  impact. It may also be the one that you resist most but it may not be. Also I think I have three or four kinds of hours:

• Most productive:  normally first thing in the morning (or sometimes late at night. Perhaps 2-4 hours a day or 10-15 hours a week. Often has a discovery or exploration focus.
• Productive:  Revising, refining curating activities that leverage prior productive work. Perhaps another 2-4 hours a day or 10-15 hours a week.
• Grinding or following a checklist or process: I can do this for many hours in a day if I can get into a rhythm. It’s an execution focus or fueled by checking things off. On a good day this is half my time, on a bad day I do this first thing to build on prior work and never get to truly productive work.
• Recharge: relaxing, exercising, reading, sleep. Time that enables more productive work in the following days.
• Distracted:  anywhere from a quarter to three-quarters of any given day. My fantasy is that I find a way to drive this to zero.

Family & Friends, Health, Frugality, and Personal Growth

16) Few things matter long-term other than relationships, health, personal finance and personal growth. Crises in almost every other area turn over so quickly there’s not much reason to get upset at them. Interestingly, those four are the areas that probably contribute most to happiness in the short term too.

David Cain in “16 Things I Know Are True But Haven’t Quite Learned Yet“

He leaves out faith, community, and satisfying work–or at least finding satisfaction in your work–but it’s a good list. Arthur C. Brooks suggests these four in “A Formula for Happiness“

• Faith: thinking about the transcendental, the things that are not of this world, and incorporating them into your life.
• Family: having solid family relationships; the things that cannot and should not go away.
• Community: cultivating important friendships and being charitable toward others in your community.
• Work: marrying our passions to our skills, empowering us to create value in our lives and in the lives of others.

Related Blog Posts

• Some Unsolicited Advice From David Cain
• The Intelligent Pursuit of Happiness
• Startup Advice in Three Word Doses
• Dharmesh Shah’s Pithy Thoughts For Startup Co-Founders
• The Challenge of Advising Entrepreneurs

“Squirrel Interrupted” photo © Kevin Murphy, all rights reserved. Used with permission. I picked this as a metaphor both for distraction based Dug the talking dog‘s repeated joke “Squirrel!” in “Up” and for moment when you have the sudden realization you have wandered far off the plan you had for the day.