I’ve been talking with my friends about the experience of leaving Microsoft to start my own projects. We all have different thoughts and I’m throwing my own into the ring.

Most articles on career happiness spout abstract quotes about following your passions. Sure, those thoughts are nice (and I’ll link to a few), but I want to share the specific details with you:

  • Keep a Feel Good list
  • Keep an Idea List
  • Read the “experts”

And above all: Don’t trick yourself.

Starting off: So…what do you want to do?

Ah, the tough question which started your quest and the one you may dread: Why do you want to go off on your own, anyway? What are you going to do? Isn’t the regular life good enough?

There’s no easy answer. Even months after leaving Microsoft to try entrepreneurship, the decision isn’t crystal clear. Only now, after looking backwards for half a year, am I comfortable with my choice.

Thinking about it more, I don’t want there to be a solid answer to “What should I do?”. Imagine being told your life’s work at age 12: “You’ll be a Molecular Biologist”. Sure, that job may be great for you, but wouldn’t you at least wonder about the other options?

I want life to be more of a surprise, though I realize not everyone is like this. I think it’s ok to be lost, fight through some tough times which inspire you to search for what you enjoy.

You need rain to appreciate sunshine — and both are needed to make the beautiful, brilliant, one-in-a-million flower of your heart grow. Said another way, you need to touch a hot stove to know deep down inside that hot stoves aren’t for you. Take your pick of analogy, the “I’m a special snowflake” stuff isn’t really my style.

Don’t trick yourself

Beware the traps of justification and attribution when thinking about your life. Many people justify past decisions because they want them to make sense and feel better. “Yes, I like wandering around and then finding my passion because it makes me appreciate it more,” you might have heard someone say. For some, it seems that no matter what happens, it was the “right thing” or that it was “meant to be that way”. I’m on the fence about whether this is a coping mechanism, optimistic viewpoint (I’m an optimist), or whether it makes you appreciate life more.

Yes, most clouds have silver linings. But sometimes getting hit in the head with a shovel is just getting hit in the head with a shovel. It’s not fun, there’s not much educational value, and your life really is better without it.

Other people attribute every effect to a cause. They see an effect and start looking frantically for its cause. While I believe in cause and effect, I don’t always believe in mankind’s ability to interpret them. Do police officers cause crime because cities with more police have more murders? Surely not, but most arguments aren’t as easy to disentangle. Many people love to dispense advice and pretend they know why things happened the way they did. I tend to be more skeptical of this.

I’m aware of but not immune to these faults (neither are you, most likely), so take this with a grain of salt. Take each person’s experience as just that: their experience, with their mindset, their background, and their situation.

Also recognize that we aren’t always perfect snowflakes all the time. Have the courage to admit where you need to improve. Now let’s get onto the tips.

Step 1: Keep a “Feel Good” List

I don’t remember where I read this, but I love the idea. Keep a simple text file on your computer, mine’s called feelgood.txt. Whenever you have an experience that really makes you happy, put in an entry, even just a few words or a sentence. Here are some of mine:

2/4/07: Ron said I was good at thinking of big picture stuff! Remember when we went snowboarding, that was awesome.
1/27/07: I got capistrano + mongrel working! Wow, now I understand what it all means!! Amazing. Crazy. Awesome.
9/12: I got graphs in instacalc!!! Wow!!!
8/31/06: Great toastmasters speech! Enthusiastic! Had good feedback, think I did a good job. Feeling more and more that I can teach, etc. on my own.

Some days you’ll have five. Sometimes I’ll go a week or more without writing in it. The goal is to start keeping track of what makes you get excited about life.

Here’s the rub: if you try and sit down and name your favorite things, you might think of a few off the top of your head. But this is in the moment. You’ve forgotten about what made you happy last week, last month or last year.

The feelgood list lets you look back and see patterns in what you like. Here are a few patterns I noticed:

  • Intuitively understanding technology
  • Thinking of new “big-picture” ideas
  • Improvements in teaching, communication, and education
  • Creating content that people find useful

These trends seem “obvious” to me in hindsight… but how do you get hindsight without looking at your past? Our memories aren’t perfect and it’s hard to see trends in your own experience.

The feelgood list is also a great way to pick yourself up when feeling down: reading the old entries recreates the feeling I had at the time. Sometimes a “minor” word of encouragement (from the giver’s perspective) can have a huge effect on you. One small compliment may really stick with you and encourage you try something new or keep going (like Ron’s comment while snowboarding — he likely doesn’t remember).

This can work both ways — an offhand, snide remark can turn you off from a subject forever, so watch out for this. It’s hard to predict what has an impact on you — just write down what does.

Keep a feelgood list. Review it peridiocally. Repeat.

Step 2: Keep an “Ideas” List

More lists! Keep another file (ideas.txt, .doc, .xls, .etc) to write down your awesome ideas.

“Uh… what ideas?” you’re probably thinking. You have them, probably a dozen a day. The problem, again, is if I ask you for your ideas you’ll give me a list of 5, the things you thought about just now. That’s not good enough, chump. I want dozens, hundreds.

If you’re like me (all I know is my own experience), your head is constantly buzzing with thought. You’re in line at the grocery store — you’re thinking of stuff. You’re driving — you’re thinking of stuff. You’re “zoning out”, or so it appears — you’re actually thinking of stuff.

You’re doing all this thought, some about new ideas, and nothing is saved. No “Untitled Document (1)” is sitting around in your brain. And that’s a problem.

InstaCalc, BetterExplained, and a few unreleased projects are the result of these idea lists. Sure, not every idea is a winner — but you need to have some in order to pick and choose. Out of 50+ ideas in my list, perhaps 5 or 6 are “winners” that I feel really excited about doing.

And speaking of winners, remember that the idea isn’t judged when you write it down. You are capturing version 1 of the thought. If it’s interesting to you, you’ll come back a week later and make version 1.5. Then version 2, then version 10. InstaCalc is probably on version 500 in terms of the number of enhancements and features I’ve added since when I’ve started. And “a faster online calculator” doesn’t sound that sexy as a V1 idea, but it can still become something useful with some iteration.

You can’t get to version 500 if you don’t start with a version 1.

Your ideas are another insight into your mind — the things you think about, enjoy, and want to make better. Most of my ideas are around services that I’d find useful as a programmer or learner, and enhancements to existing tools. They are mostly software-related because that’s my background, though some are around education and communication.

The best part about keeping a list is that your ideas multiply like rabbits in your notebook. Each idea new idea can be combined with each of the old ones, leading to even more variations. Next week when you have yet another idea, it can enhance the older ones and the cycle keeps going.

I also keep a stack of index cards by my bed — I sometimes have brainstorms before going to sleep. I can remember nights where I’d be lying on my pillow and then bam, I’d get up a dozen times to write down a thought. It was a bit annoying at the time (“I just want to sleep!!!”) but my brain kept firing. I’m thankful now — most of those thoughts turned into features for InstaCalc.

So keep a text file and notebook (for offline use) to track those ideas streaming from your unique snowflake head. I prefer a plain text file because it’s simple, reliable, and fast. I need speed when pumping out thoughts.

The more ideas I write down, the more I seem to have. I’m sure you’ll be the same.

Step 3: Read the “experts”

I originally started by reading the experts, but found a lot of value from the feelgood and idea lists. I really value self-learning and I prefer these techniques.

But you’re reading this article, and I’m writing it, so I recognize the role of external tips and advice in getting started. Here’s what helped me:

Understand Your Personality

The point of personality tests isn’t to put you into a box. It’s to recognize the talents you have. The irony is that because we find something easy, we assume others do too, and therefore believe the skill is not valuable.

It’s not always the case — some things that come easily to you (talking to strangers, using computers, doing math, writing, humor, relating to others) may be really hard for many other people.

These tests can help you step back and realize what you do that others don’t.

  • Now, Discover Your Strengths – Understand what you do well and work from there. (My top 5: Strategic, Ideation, Learner, Achiever, Intellection).
  • Myers-Briggs test – puts people into one of 16 boxes. I fit best (not “am”, I “fit best”) with INTP. This has led to additional insights: “… not likely to place much value on traditional goals such as popularity and security…”.

Get Inspired

Sometimes it helps to remember why you are on this quest in the first place — to be happier and live a better life.

Parting Thoughts

The wonderful and frustrating thing about understanding yourself is that nobody can do it for you. After a year of thinking about this seriously, I know what I like (learning and technology), what comes naturally to me (thinking about ideas and intuitive understanding) and what my ideas are about (improvements to software and education).

I had hunches about these things (obvious in hindsight, remember), but thinking about them solidly is very useful.

These insights aren’t set in stone – I don’t want them to be! Some of my greatest joys have been from seemingly random decisions and paths, like deciding to join karate or do toastmasters. These clues have given me a fulfilling direction to follow, and I’ll correct the course over time. Software happened to be the first field on the list of what I enjoy, and I’ll continue pursuing it as long as it keeps me excited.

There’ll be more articles on the mechanics of going on your own — a better understanding of what you want is a good staring point. Happy soul-searching.