In the past week, I began questioning the purpose of the journey I have embarked upon. What did I really want from this period of freedom and exploration? Did I want to build a company that would change the world? Or did I simply want to establish an independent and fulfilling lifestyle? Did I want the life of the rich and the famous? Or would I prefer a modest, simple, uncluttered existence which would provide the right conditions to establish a serene, warm, and constantly grateful state of mind?

These questions have been near the surface of my mind for a while, but in the past week I came to an answer which completely altered my plans for my current journey. This blog post is a feeble attempt to capture those ruminations.

A brief recap of the journey so far

First, a brief recap of the journey so far. A few months prior to quitting my job at Yahoo!, I was working on an idea for a 'new kind of social network' with a close friend. We wanted to build a network which would enable and enrich deep, exploratory, conversations on the Internet. I quit my job to build this network. Soon after I started, the idea was whittled down to focus on building a platform for a specific community, ie. for the community at These were the people who could make good use of the communication tools we had in mind.

So I started working on the product for this audience from the 'outside in'. I started designing and coding the user interface for the first version, testing the ideas with the community, and then working backward from there. Once I started, I learnt that my half-assed front-end design skills would pretty much guarantee a half-assed product at best! I also realized the enormity of the task ahead: doing design, front-end, back-end, and community development work alone would be crazy!

Taking the path to its logical end

It was at this point that I began questioning my choices, and began thinking about where they would lead. Here is a summary of my thoughts:

So far, not so good. I was essentially operating on faith that this 'hobby' (ie. non-remunerative activity) would convert into a business (ie. an activity which creates and captures value).

But even worse, if I did get into a position where I could realistically raise money, my life would almost certainly lose all balance. Getting funded as a first time entrepreneur is mind-numbingly difficult. And once you do have investors, they don't make the nicest bosses.

And then, even worse: in the rosiest (and almost impossible scenario), this path would would make me a millionaire. But then what? Is that a solution to any meaningful problem? Who wants to be a millionaire?

So I began thinking: is there an alternative to this?

An alternative emerges

Another development in the past few weeks has been the discovery of 'underground' software developers. These are people who love to build software and value staying small and independent. They either work alone, or have companies of very few passionate and like-minded people. They may not be multi-millionaires, but they do make enough to live comfortably doing work they enjoy; work which is personal, meaningful, and challenging; work through which they can discover and express themselves fully; work which does not feel like work.

The folks at 37signals, Carbonmade, Kalzumeus software and are some examples. A non-software example is the story of the couple behind Great Bread Harvest Co.. All of these people bootstrapped their way to profitability, minimizing (or in some cases eliminating!) their exposure to outside investors, and set their own rules.

I am sure that none of their stories are fairy tales and that there was a lot of hard work and perseverance behind the scenes. I am sure there were stressful and uncertain periods --that is a part and parcel of life.

However, there is something about the quality of the independent journey that is very appealing to me. Without the shelter of a large organization, with primarily yourself to rely upon, you are quite vulnerable. But you are also free. Free to make your own mistakes, free to discover things about yourself, free to explore and express your own ideas.

Making an independent small-business work is exacting in it's requirements for resourcefulness, diligence, discipline, intelligence, patience, and humility. It is a daunting challenge to be sure, but I think undertaking it gives one the chance to become a more aware, balanced, and bigger personality. And this aspect is the main motivator for me.

After all, you learn a whole lot more by going wrong in your own way than by going right in somebody else's. And being small and independent provides ample opportunity for making the right kinds of mistakes!

What now?

All these thoughts have completely changed the way I look at my own life. When I started this journey, I was focused on building a product and (hopefully!) a business around it. The question was: what do I need to do to make this product a 'success' (in other words, what do I need to do to transform this idea into a product that could get funding and become a company?).

Now, my thinking is different. I feel that the quality of the journey is more important than the outcome. Establishing a sustainable and balanced life through doing work which one finds challenging, meaningful, and enjoyable all at once is a goal worth pursuing. And that is the goal I have begun exploring.

The question now is: what business can I build that will add value, is personally meaningful and challenging, can be realistically bootstrapped, and which ideally utilizes my most developed skills? If I can't do it all alone, who do I need to partner with? How do I find these people? etc.

The road has been thrown wide open, the flavor of the journey is now completely different, and I am only starting my second month of this adventure! This promises to be quite a ride!