Keyboard Philosopher

Yeah, sure, New Year’s resolutions, fine. Well I sort of missed it, so I gave myself until the end of January to plot my year.

I generally wanted to embrace the S.M.A.R.T. (Specific, Measurable, Attainable, Realistic, Timely) goal-setting concept where possible and practical, so what’s below is divided into the discrete, check-it-off-when-done tasks, and the more abstract goals I’ve haven’t wrangled into task form (or don’t want to take the time to track, like some of the dailies).

Here’s the blueprint to build a 2010 that I will find awesome in reflection:

Entrepreneurship

Know how to execute most small business plans so that I can rapidly convert ideas into experiments; know how to run a company successfully.

• ☐ Start another company
• ☐ Outsource some business tasks to solidify understanding, eliminate barriers
• ☐ Create a short document synthesizing what I’ve learned about marketing

Health

Improve and then maintain health, optimizing for longevity. Try for (and realistically achieve) the best health of my adult life.

• Resume running regularly
• Spend 30+ minutes outside everyday (weather permitting), for general sanity and for vitamin D
• ☐ Complete Couch-to-5K (stopped last year after getting sick and then hitting the cold winter)
• ☐ Experiment with meditation
• Synthesize, internalize, and share (☐) newfound knowledge of nutrition

Language Learning

Solidify Japanese, then start thinking about another language.

• ☐ Learn all 1,945 Jouyou kanji (meanings only), know ~400 at present
• ☐ Take the JLPT (level 3? 2?); December 5th, registration in July

Meta

Optimize and systemize personal processes.

• Incorporate more feedback and optimization (data and accountability)
• Systemize goal-setting process (even if a 90% solution)
• Create a heroic personal definition and attempt to live up to it
• Write personal stories (especially for 2009)
• Stick to GTD. In fact, do it better

Money

Develop sources of location-independent, automated, diversified income. Wisely manage the money I have.

• ☐ Create two more income streams
• ☐ Achieve net positive cash flow (even if this must include active income)
• ☐ Earn $1k per month in passive income by the end of the year

Social

Overcome anxieties (however small), make smalltalk, make more friends, be friendlier to strangers, be a better storyteller. Network better.

• Participate in more groups and be a better participant (more regular, more engaged)
• Embrace opportunities to enter new social circles
• ☐ Hang out with a new friend every month
• ☐ Re-engage an old friend every month

Travel

• ☐ Visit at least four new places
• ☐ Visit at least two new countries

Writing

• ☐ Write at least four blog posts per month
• ☐ Complete at least one longer project (15+ pages). Book? Ebook?
• Be more attentive to writing effectiveness

Other

• ☐ Read 24 books (19 in 2009)
• ☐ Learn to surf

The plan is to track these items on this template (plain-text, markdown formatted, Unicode encoded). If you’re tracking your goals you might consider stealing some chunks of the file. Or, if you have improvements, I’d love to hear about them!

A little over a month ago I released an iPhone application called Raconteur. And while It may not be especially groundbreaking, it was a hugely important for me because it’s one of the few things I’ve ever finished. On my own, with no external requirements, and no one driving me, I finished it.

Oh, I start things. I have 58 unpublished blog drafts (probably a dozen more on paper) and scores of projects in my version control repositories. I just don’t finish them.

Looking around in my life lately I keep seeing people who have great ideas but never seem to have the motivation to get them implemented. I know that I used to be one of those people too but I think I’ve finally broken away from the old ways. Here are my best tips for finding the motivation to do (and finish!) big things, many of which I leveraged while developing Raconteur.

• Know what you are doing. Have what you are making clearly laid out before you, written down, drawn out, or mocked-up—something physical. Solidify the goal.
• Know why you are doing what you are doing. Have a clear reason for the project. Write it down. With explanations if necessary. Write as if you were trying to convince someone else: when you hit the motivation slump you need to be able to look at this and convince yourself. As Seth Godin explains in The Dip, basically anything worth doing will have a tough period you’ll simply need to power through¹. You need to have decided up-front, for sure, if this was worth working on, and have laid out your argument so that you won’t re-evaluate in this state where you are less likely to be honest with yourself².
• Take baby steps. If you’re working on something worth doing, there will be times when you’ll look at the enormity of the task and feel overwhelmed. Instead of remaining stagnant and stressing, ask yourself “what is the simplest thing I could do that would move me towards my goal?”, then do that thing. As Lao-Tze said, “The journey of a thousand miles begins with a single step.”
• Embrace detours. If you’re like me, you find that day-to-day you don’t have the “psychic energy” to power through certain tasks, but others don’t seem too bad (David Allen talks about this). To make this style of productivity work, you need to know what steps you can take from here. Keep a quick (non-exhaustive) list of things you need to do soon so you can cherry-pick what you are up for. If almost nothing seems palatable, look for a research task you’ll eventually have to tackle before you’ll be able to deal with some future “real” work.
• Accept some slack time. Down days happen. Sometimes you get sick. Sometimes you’re just not up for it. Accept it—don’t even be upset with yourself. Just try not to let two or three happen back-to-back and you’ll be OK.
• Track your progress. Whether it’s a paper checklist or a Github page, you need something to show you how far you’ve come. If you can chart it, graph it, log it, or list it, you’ll know you’re getting there and you’ll realize that it is possible.
• Leverage inspiration. Keep a list of things that inspire you. With Raconteur this was a list of iPhone apps that I felt were top notch; I’d fire them up, fiddle with them, explore the tiny little style touches and know that I wanted to make something that stylish, that well made. Maybe I didn’t get there, but it brought up the quality of my work. My RSS reader is often a source of writing inspiration for me. If you’re a visual person, consider a vision board.

Do you have any motivation tips to share?

Footnotes

1. That doesn’t make the converse true! Everything hard is not necessarily worth doing.
2. Unless, of course, new information comes to light.