Confessions from a hotel room at the stroke of midnight…

In the beginning all I wanted was a paycheck.

I had just had my first experience of wanting something bad enough to get to work for it. Unfortunately no amount of money in the world could buy what I wanted. I caught an early break and no one lovingly sat me down and cleared this little misunderstanding.

The biggest paycheck on the planet requiring the shortest path and smallest number of external dependencies was a big question to answer for a 14 year old.

Of the professions within reach, the pick that made the most sense was actuarial science. A set number of self paced exams. A structured well documented path to the top with regular merit based increments linked to your ability to pass exams. No shortage of employment opportunities and guaranteed above average pay checks. An added bonus; I was good with arithmetic and problem solving skills.

That lasted all of 7 years. (The actuarial piece, not the good with problem solving bit.)

To hack studying for actuarial exams, I sneaked into Computer Science as my major. In my moment of need it stepped in as my white knight. When I found actuaries to be boring, my development stuck at a fork in the road, struggling with external dependencies that I hadn’t expected, technology helped me regain my sanity. I had picked the actuarial profession because I hated dependencies. When I ran into them headfirst, I found that there was another door that would allow me to side step the entire debate. I opened it and escaped. It led to a very different path. Under ordinary conditions a dose of rational thinking would have had me committed. Should have had me committed.

While technology fixed one problem, it also created a significantly larger one. I now wanted more. More of the stuff that no amount of money in the world could buy. Perhaps technology could help, again? After all if money couldn’t buy happiness, toys were the next best substitutes. I ran a new set of experiments, thinly disguised attempts to earn a living, variations on the same theme. Dream, build, promote, sell. Destination Sky high. Switched gears from development to management, from domain to hands on guy, from analyst to product owner, from innocent bystander to guilty as charged. Wondering, wishing, praying, trying and preaching that we shall prevail. That technology will guide us to the promised land.

Fast forward 12 years. It didn’t.

By now I was getting the hang of the game. It was ok to want stuff that no amount of money or technology could buy. There was no shame in it. It wasn’t the safest or most recommended way of paying your bills but it was certainly the most interesting. A conventional family would self destruct with the choices you made, so you picked an unconventional one. One that understood that for you to remain sane and functional, you had to flee from one experiment to another. Sometimes chased by creditors, sometimes by chaos, sometimes by fame, occasionally by all three. A family that stood by your side, as you set fire to the world around you and was ok with it. With there being no ordered exits or structured shut downs, ok with you being an absconding father and husband.

When I read these lines after writing them just now four key words stood out. Want more. Experiment. Delusional. Family. That is the mix you want if you want your life to be a Petri dish of experiments. Some will go wrong, some will go missing, some will go wild, and then one of these days you will be hit by a lightning strike.

While most dreams and desires are unachievable, some are just within reach. The only way to filter and segregate them is to continue dreaming, experimenting and reaching. Aim high, shoot fast, ignore convention, do what feels right versus what everyone thinks is right. But most importantly value family. That is the way to do it, if you are tempted or interested, not that I recommend it. For everyone else there is Master card.

On a side note, I now juggle four interests or pseudo careers. Seams that can be traced back to decades old experiments. Teaching. Writing. Consulting. Building and growing businesses. Like reading three books at the same time. A tad more exciting and sometimes more rewarding.

Oh and in case you are wondering about the stuff that I wanted that I couldn’t buy with all the money in the world. I wanted to change it. Here is the lesson that I learnt. You don’t change the world with money or technology or a career.

You change it with the power of your will.

Originally published a year and few months ago at