Career Indulgences and Getting Real

I am sure 'career indulgences' appears an oxymoron, there can't be such a thing!

But in my quest to do things I love, and also to work with people I like, I have created, at least, the possibility.

At this time, a penny-dropping moment of sorts, I am reflecting when I started indulging in dreams! And, indeed, there are many forkways to look back at, like these:

1. Walking out a secure job and an impending promotion, I jumped on the dotcom boat in 1998: Not many people around me were doing that at the time and I had no idea how to deal with investors and their contracts. 

2. A couple of years later, when the enterprise became boring and investors became bosses, I pursued my dreams of adventure - going to a country in the middle of political turmoil and business decline - and lived through bomb threats, general strikes and all that. 

3. When all that was sorted out and I had won, four years later, I gave up yet another promotion and promises of a predictable life to become adventurer again, landing up in the UK without a job in hand. 

4. Several years on, I got a foothold in the UK, with a decent job, a good boss and relationships and networks in the e-learning industry, and yet, I left to pursue a global network of training and recruitment centres, with an objective of turning English language from one of privilege to that of possibility.

5. Four years of incessant travel, and I wanted to combine the e-learning expertise with my global networks, and build a new kind of competency-based education delivered through learning technology. But instead of starting up, I went and joined a private college in London, large but facing an existential crisis at that time, with a plan to re-engineer the business model.

6. Three years later, I managed to save the college and help them sell to a new owner, but instead of going with it and working for new bosses, I decided to finally start-up, boot-strapping and living precariously, exploring the same dream of creating a global network.

7. Finally, after two years of living on overdrafts and credit cards, I decided to let one of our Chinese partners to take over the students and deliver remote education that we planned. Perhaps I was being too cautious: Perhaps we could have lived on the student money and save the business. But we felt that taking on students for two years is too big a risk, and did not want to gamble on getting future students to continue providing services. So, I took on a job - one with similar objectives, but diminished scope - in which I lived for the last three years.

One could call it stupidity - or, stupidities, if you prefer - or one could it adventure. One could label them career suicide - one can't possibly have multiple suicides - or one could call them enterprises. One could see indulgences, or one could hide all that behind serial something (being something serially has become more respectable: Newspapers talk more about serial entrepreneurs than serial killers these days). But one thing for sure: This is not the usual path of a fixed career that people usually pursue, with variable goals. I chose a fixed goal and had multiple careers trying to achieve the same. 

Yes, my invocation of Edison there may be a little weak, at least till I figured out which are ways of not doing it. I did understand some of my mistakes along the way. Some of these mistakes are shared sins, jumping in to Dotcom bandwagon, reading too much Red Herring magazine etc, far too common at the time. Yet others were very specific to my circumstances - trying to start out in 90s Calcutta, which was no silicon valley, and expecting all investors to be Vinod Khoslas - which I have understood and tried hard to change. But, there are some other mistakes which I have done along the way, appreciation of which, I believe, would help me get real. In particular, I can think of three 'signature mistakes' which I committed more than once, and these are worth mentioning as they may be easily avoidable:
 
1. Optimism: Optimism is one of those things: Can't live without it, and with it. Any project that I love, I am attached with it: By definition, I believe it can work. That belief is essential to make me commit to it, and without that commitment, it doesn't work. But optimism has lead me down the garden path at times. One of my mentors used to say, 'Hope is not a strategy', and I have failed to follow this sound advice at times.

2. Attachment: This is somewhat like optimism, but these are with people. It may not be obvious from my short stints at work, but I do get attached to people and form long friendships. I often say with pride that most people I have worked with in the past would work with me again. And, often, my descriptions about colleagues at work start with - I like him - which is not what one would usually talk about in work terms. Not that I regret this style or want to abandon this; but this is another thing that has led me down the garden path at times. I stayed when I should have left, and sometimes spent inordinate time in the futile quest of being a responsible leaver. I ignored the sound advice, from the same mentor I quote above, that once you have made your mind up to leave, it is best to focus on the next thing. I often spent time worrying about the relationships.

3. Desirability of Change: A few times, I assumed that since an organisation is in trouble, they would want to change. It seems optimism is my original sin, but this is still slightly different as this may seem like plain business logic. But change is never easy, whatever the management consultants say. And, indeed, change is even harder from inside. People in organisations are always living their past lives in an infinite loop, because if you are not clinging to the past, you would be outside the organisation which is on the wrong path. And, hence, even if the need for change is obvious, no one really wants to change. In fact, as I have now figured out, if an organisation needs changing, by definition the people in that organisation hate changing.

Indeed, all the three mistakes I cite above are double-edged problems. How does one do anything worthwhile without optimism? Or without connecting with people, or believing in change? This is indeed my get-real part, as I attempt to look to future with fresh eyes. My get-real strategy is based on three principles, corresponding to the three 'weaknesses' that I describe above:

1. Details As Deliverance: How to guard against this natural optimism that makes my world go around? I have met enough people in life, as you will expect, who would advise me to be cautious, even pessimistic: But those are people who never tried anything themselves and wheeled away their life in doing other people's bidding. To be real, the guard against optimism is not pessimism, but Details: I have learnt along the way to focus on the details. This allows me to go beyond the sentiments - both optimism and pessimism!

2. People are different from Organisations: Personal relationships are not the same as loyalty to doomed enterprises. Say I like someone I work with, and would rather help the person achieve their objective. However, supporting that person when I know it is not sustainable for him or for me is actually about postponing an inevitable rupture, a failure. I know walking away from an organisation is often seen as disloyalty to people involved, but it is not the same. I, in fact, know this, as I count among my dear friends people I have worked with in the past, and people who I have worked for, and that walking away hasn't destroyed the relationship. In fact, the only people I have struggled to maintain relationships with are those who I worked with well past the time I should have, confusing my personal loyalties with organisational ones.

3. A Different Change: I had given up, irreversibly, my earlier ideas - very Indian ones, I admit - that gradual change in organisations is possible. I have now come around to the view - more American, I suppose - that change has to be quick and decisive. While I don't support President Trump's politics, I can see why he attempted to make such a decisive break with earlier administration. I used to be dismissive with the 'First 90 days' kind of thing: I don't do it anymore. There is no comfortable change: All change is painful. As I look to future, I don't want to take on any enterprise where I don't have the mandate to do a fresh start, and build again. Or, even better, build fresh!