Taking Chances or Feeling lucky?

Andy Warhol

Day 17 of leveling up 

When the recruiter first told me how desperate the big bank was to hire me, I frowned. The last thing I wanted to do was to return to that environment. I had learned the difference between being lucky and in the right place at the right time. This offer was the latter. I thought the job description sounded ridiculous and so I told the recruiter they’d have to pay me a lot of money before I’d consider the job.

When they didn’t flinch I decided it wouldn’t hurt to have a fat paycheck. Within 12 months the pain of the experience far exceeded my wages. A friend suggested group therapy and recommended his group. As recovering workaholics, each of us struggled to find the environment that offered additional non-financial benefits. 

Whoops! I ended up in a group led by his therapists but the members were all victims of trauma engaged as  Manhattan creatives struggling to make ends meet. I was a fish swimming in the wrong waters until we talked about professional dissatisfaction. 

At this group’s urging, I took the plunge to start my own business. Why had I amassed such a large nest egg, if not for the purpose of creating a bigger safety net? When I went to graduate school both my parents reminded me that I was investing in myself, and wasn’t this a natural extension? The only safety net is what we create, and now needed to up the ante and bet on me by investing in a venture self- defined and self-directed. 

The therapists and group talked me through many of my doubts and reinforced my self-esteem, and confidence to give me the courage to act. Yes, I did trust my vision, believe in my abilities, and sense my product concept aligned with others’ needs! So what was stopping me?  

The group got me to launch which was great. Like the other participants, I needed support to stop the pain from my experiences and start fresh. What they didn’t know about business wasn’t important. They support got me out of my corner and out into the wider world again. I stopped complaining and found I had energy again to face new challenges and bounce back. 

Now the challenges I faced were of my own making. I took command and control, became the pusher, not the pushed or pulled. It was all up to me. Was I capable of skating to where the market was going fast enough with enough energy in reserve to take a shot powerful enough to make my goal? 

That’s just it, my dream of creating a tool fell significantly short of what was necessary to launch a business.

The group had helped me replace one weakness with another.  I went from unsure to self-possessed just short of smug. Now the fear was someone would steal my idea because I didn’t realize that my conceptions were mine just as much as my execution of them.  

There are multiple reasons why no other software attempted to do what I had envisioned for decades. 

One, I didn’t push myself past what I knew, I wasn’t willing to learn the balance of what it took to launch a business beyond the technical aspects of product development. 

Two, impatience was just as much my problem as it is for anyone else who wishes they were lucky. 

I was not alone in my vision of how the internet was the enabler of different processes and modes of information exchange. In 1995, the crowd of tinkerers in NYC called the World Wide Web Artists Consortium (the WAAC) all recognized that when the pipes grew, the types of information that could be transmitted instantly would completely change how people behaved.  Everyone was tinkering with some aspect of building for that future, and I was no exception. 

Few people notice, follow or appreciate the links between what happens around us is only in part related to us. Success is when the line between cause and effect is so short and takes so little time that there’s some surety in both our initiation and the result. 

Wayne Gretzky was great on ice because he mastered the equations and control of his movements in coordination with the other elements in a fixed arena. In business, that’s nearly impossible.  

Was Jeff Bezos success with Amazon luck, or  Bill Gates success with Microsoft? Steve Jobs naturally attributes success to something else. Not luck but developing sensibilities akin to those of a great orchestrator/ conductor.  Jobs famously learned through his failures how to ably recruit and conduct the right players for his orchestra.    

When things we try don’t  work, naturally we feel like victims of the situation and circumstance. I have used my practice to tinker at the edges. I can assert greater control and gain mastery as long as I use my own hands-on objects within arms reach. People are much harder, even when I see and hear their responses, I’m just as likely to get what they feel or will do wrong as I am to be right. 

Decades of practice required me to stop reacting or taking control as these behaviors got in my way of seeing and understanding the situation. The patience my parents exercised came slowly for me, but in time I developed it.  How? I discovered it necessitates waiting, listening and letting people proceed at their own pace.

Learning is the reward of the patient, as it allows time and space for others to reveal what they see, know and for me to increase my understanding of a situation, the circumstances in excess of my own perceptions and conclusions. 

Each of us love to exercise control and giving others control even if they will make mistakes, doesn’t make a situation riskier. Trick is to give them the opportunity to learn when to try and when to let others who are better go first.  

We don’t and thus can’t control everything. Chances left untaken do create rewards and some are indirect. I’ve benefitted by thinking things through but also realize like the error term in my regression equations, the unknown is just that. Being at the right place may be luck but it can also result from waiting, patience and practice. 


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