Getting Older and Improving

Getting Older


I can not escape the reality.  I am reminded of it everyday. In the early-stage tech world, I am old.

Even the rare day that a colleague (average age 28.5) doesn’t throw an arthritis or senility joke my way, just working at Neverware forces me to acknowledge the unspoken. It goes well beyond our different interpretations of a “Big Saturday”. I communicate, prioritize, and operate differently. I still write my to-do list with a pen and paper. I still have cable TV. I still pay for… (cheeks reddening)... a landline. I try to adapt, but it doesn’t help to join Snapchat when I have no one to send a Snapchat to.    

The worst part? The fallacy that because I’m old, that I often have “the answer”. As if living life has somehow made me wise. Somewhat ironically, my experience has been the complete opposite. At the age of 42, I have never known less. A decade and a half ago, when I was their age, I knew SO much more:

Then: I knew exactly how to grow and run a company (management experience:  None)

Now:  Each day brings a new issue or challenge that I feel wholly unprepared for

Then:  I knew exactly how to mentor/inspire my direct reports (total career direct reports:  0)

Now:   I am confident I learn twice as much from my team as I teach them

I miss that certainty and assurance. Reality can be sobering.  

So, rather than wisdom, I believe the highest value I can provide is transparency to a lifetime of mistakes. By shamelessly sharing, my hope is that I can convince my colleagues to 1) not make the same errors, and, more importantly, 2) take risks and feel comfortable screwing things up.

Therefore, in the spirit of the transparency we always aspire to here on 27th Street, I’ll share what I believe to be my most consistent and damaging mistake.  I….am….too…..slow. At almost everything.  Its a track record too lengthy to detail, but in summary:

In the first ten years of my professional life...

  • I was too slow to pursue a career path I was interested in, but didn’t know how to enter
  • I was too slow to quit jobs I hated
  • I was too slow to shut out the external peer pressure to achieve standard “success”

While the type of mistake has changed, the volume has increased. Now….

  • I am too slow to tell people they are awesome and doing great work
  • I am too slow to tell people where they need to be better and help them get there
  • I am too slow to adapt to new ideas and too slow to accept when my ideas stink

An overused piece of advice these days is to “Fail Fast”, but based on my experience, I would say the real trick is to do EVERYTHING faster.  Decide faster, move faster, try faster, ACT FASTER.

Ironically, the advice to “Act Faster” feels pretty damn non-actionable.  Here’s some tangible areas that I always try to focus:

  1. Communicate faster:  Especially when it came to bad or difficult news, I procrastinated as long as possible.  Maybe, just maybe, the problem would solve itself.  Perhaps the employee would suddenly hit their stride and begin achieving their goals.  Perhaps the colleague would magically realize their tone and attitude was destructive and turn a new leaf.  There’s always a reason to wait just one more week, because, well, you just never know.  But, in your heart, you DO know.   Personnel challenges just don’t resolve themselves.  Have those hard conversations quickly - otherwise those weeks (or months) become wildly less productive (at best) or organizationally destructive (at worst).

  2. Reconsider faster:  One of the most challenging aspects of working in an organization with so many smart people is that they have spent a lifetime being the one that is generally right.  That leads to quite a few “spirited discussions” and too often, people (myself included) dig their heels in and spend more time constructing their next rebuttal than they do actually listening to the other viewpoint.  Sometimes, you need to just force yourself to shut the hell up and really listen and reconsider alternatives.  If you are fortunate to be surrounded by talented individuals, like I am, you will find that many times, someone else has the better idea.

  3. Change faster:  Now that you know the intellectual sparring that goes into getting a decision made, you can only imagine how painful it is to acknowledge that may not have made the best choice.  But, this is the area that moving slow can be the most deadly.  If a product, or a feature, or a sales channel or whatever does not feel like it is panning out, try something else - fast.  If you can A/B test or parallel process, great.  Figure out a winner anyway that you can.  But don’t sit with that idea one minute longer than you need to.  Especially if it’s just your ego you are protecting.

So now my colleagues can finally understand why I seem so tired all the time. It's not just that I’m ancient.  It's not just those three young kids at home. It's because I am trying to move so damn fast.  Now, I have to run and cancel that landline. (My wife is going to kill me….)

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