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Reality, Common Sense and Snark: 50/50 Hindsight combines the enterprising wisdom and alternately compassionate or snarky insight of veteran Silicon Valley CEO, Marilyn Weinstein.

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The Day I Stopped Playing in the Failground

January 27, 2017 By Marilyn Weinstein

faiset realist expectations - not wildest expectations

I probably need to start with a bit of a confession, first: I was raised to be a failure. I know, that sounds strange.  But the concept of trying hard to fail, expecting to be a failure, and spending more time trying to dig out from an inevitable failure, than trying to succeed in the first place, is not all that uncommon, actually. But, as they say, the first step is to recognize the problem.  So, I like many others, believed I wanted to succeed. No one could tell me otherwise. After all, who would mortgage a home and feed a family of five without an obvious desire to grow her company and succeed beyond her wildest expectations? Well, the last few words are actually the operative part, “beyond wildest expectations.”

How many times have you said or heard this phrase, “succeed beyond his/her wildest expectations”. It’s as commonplace as any other colloquialism or cliché. But, think about it. If you expect to succeed at a high level to begin with, then this phrase would make no sense. Well, that’s really what I’m saying. Success is actually scary. It comes with a whole new set of burdens and responsibilities. It often outgrows you and your capabilities.  For many, it embodies the unknown. By contrast, failure is comfortable. It allows you to focus on comfortable topics like, “fault” and “blame”. It provides for “easier” work, like “fixing” and “solving”.

Succeeding at achieving a goal is wholly unrewarding. If you hit a bar, we raise it. If you achieve a milestone, we look to the next one. No award or reward can possibly equal the glory that is bestilled upon the failure. Whether you ride in on your white horse and save the (at risk) day, or spend countless hours setting a (failing) project back on track, the glory is unmistakeable

Now, no one really wakes in the morning and formalizes a well-thought out goal of, “today, I am going to fail.” Instead, everyone believes she is trying to succeed. But, perceived actions show an undeniable effort to fail, instead. Take, for example, a new technology that your team is to implement at your company. There’s a project leader and project team. There are stakeholders. There are direct and indirect internal customers, etc. There is usually someone whose job would be at risk, if the implementation were to fail. So, obviously, from the ultimate end user/internal customer to the project team, everyone goes into the project excited to succeed. But, what we quickly see are efforts to elucidate and deal with issues.

On its face, this does not seem like a “desire to fail”. After all, basic risk management principles require that risks be identified and dealt with early so as to mitigate costly issues. But, listen as the teams point fingers. Hear as teams vie for loudest issue enumerator position. Note, those who make it clear that the technology won’t work, or that the company won’t fully adopt it, etc.  Ask yourself which interaction was more memorable, the one with the team whose tasks were completed as scheduled, on time, and on budget, or the ones with the issues? Why was more passion and energy brought to the failground?

It took me a long while to figure out that in some ways, I was trying to fail. While failing, I got to talk about wishing I would succeed. I got to plan for fixing things, one failure at a time. I excused poor performance, missed milestones, failed targets, etc., by expecting that to be the case, and working on the proverbial, “plan B”.

Oh, and failures are also super likeable – for the most part. Successful people are intimidating, whereas those who fail are relatable and human. I was not intimidating, as long as my goals remained unachieved. And, again, the passion and excitement I could bring to a “heroic” tale of turnaround is far more interesting than the spreadsheet outlining success.  And, you know what? Failure begets failure. So, for as long as you have that mindset, you are inevitably going to hire failures, join companies with leaders who don’t succeed, coworkers who bask in their stories of how things should be, or should have been, etc. You’ll be immersed, as I was. You’ll be comfortable. You’ll be just unhappy enough to keep trying to succeed.

There is no quick or easy solution to this phenomenon. But, once you see it around you – if not in your own self—you start to see it everywhere. And then maybe, like me, you’re awareness will lead you to a desire to succeed instead.

Filed Under: And More, Career Development, Management and Leadership

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A proven leader in business strategy, development and people management, Marilyn is the founder and CEO of premier Silicon Valley IT staffing firm, Vivo. Named among the “Fastest Growing Privately-Owned Companies in the US” by Inc. magazine for three years, Vivo supports the tech staffing needs of many global Inc. 500 companies.

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