I’ve been reading the recent posts on Hacker News where people have discussed their income successes this last year and been very inspired to do more of what I love (writing and creating software art) and earn a good living out of it.

I also recall some of the wisest words I’ve heard, 15 years ago, from my friend Ken Kraisler. I was a newly minted software engineer at Claris (a subsidiary of Apple) and earning $32,000/yr approximately at the time. I told him “if I can just get to $X dollars, I’ll have enough money for everything I need.” Ken sagely responded by telling me “your needs almost always expand faster than your income.” I paused when I heard that. He was telling me that what I thought was enough in the future would probably turn out to be less than I needed as my needs expanded, unless I was very mindful about it.

Perusing the Wisdom 2.0 conference speaker list for this year, I recalled Premal Shah’s talk last year where he spoke about shifting from living an accomplishment driven life to a purpose driven life. What impact do my expectations of income have on my capacity to do do the things I love? What boxes have I put myself into because I have to earn a “respectable” income, where I have defined “respectable” as over $100,ooo a year? I know that now that I have crossed over the $100k/yr mark, I never want to go back below it. And, I find myself feeling frustrated when back of the napkin calculations for any new venture don’t fit that. There is definitely a large gap between $0 and getting a startup to pay you $100k, grown organically or with investment. Anyone that tells you it is easy is trying to sell you something, not that that is a bad thing.

This year I am in an interesting position to investigate this question for these reasons:

  • This is the last year of payments of the three year buyout of my company, so I have about $40k before before taxes which comes to me spread out over the year.
  • AirBnB has been phenomenal for me the last 1.5 years. I’ve earned $39,017 on my house so far. While this is basically break-even when all expenses are accounted for, it still means I don’t have to worry about a mortgage.
  • My wife just had a baby. We are talking about my role in the family once we move back to Oregon. My wife is a doctor, so she will likely be the primary breadwinner in the family. Staying home with our son Roosevelt for a few years sounds like an amazing opportunity. I’ll be honest it is terrifying to think of leaving entrepreneurship and software development and step into a completely different set of responsibilities. But, I believe when you see something terrifying in front of you, there lies the biggest potential for growth as well.

So, my goal is to get to $0 this year. I’m not clear how I’ll define this, but I really want to see how little I can earn while maintaining my financial commitments, and now that I put it that way, clarify what are my financial obligations, and which have I created, and which are inevitable.Some immediate things come to mind:

  • I’ve been putting off switching from my long contract with T-Mobile with unlimited data to a prepaid plan. The fact that somehow my bill just went up to $105 from $95 two months ago with no changes to my service should give me incentive to call 611 and shift to a $50/mo plan. I’ve tracked my data on my Android phone, and I know I never go above 2 GB, and I bet most of this is via wifi anyway.
  • I have a server on Rackspace for $105/mo which I use for hosting all kinds of things, from Rails apps to Wordpress to Node.JS apps. How many of these could I shift to free plans on Heroku (Rails), AppFog (Node.JS and Wordpress)? Could I completely shut down this server?
  • Where else can I look to get myself to zero? What other things am I paying for which I could remove and reduce my bills and increase my options for doing what I love?
  • By far the scariest of all: could I ask people to donate a place to stay when I travel for a conference? Could I ask people to donate server space for my Wordpress blogs? Could I rely on someone providing these services to me out of strictly goodwill and giving up control? This is one of the things I love about my experiences at Burning Man, and could I find a way to bring the gift economy to my life full time?