It’s The Mistakes That Make Us

It’s the mistakes that make us.  Not sure who said it, but it is true.  I cringe when I think of these three stories from my career.  None of them killed me, I learned from them and I want to share them so that others can avoid my mistakes.

Lesson One – Seize Opportunity.  Applying for my first job in NYC, I had spoken with Ursula Obst (can’t forget that name), then the admin to Phillip Moffitt, the highly regarded Editor In Chief of Esquire Magazine.  I was such a fan.  I decided to deliver my letter and resume in person.  Ursula wasn’t there, Phillip Moffitt came out (in a great shirt and tie as I recall) and asked me if there was something he could do for me — Ursula was out for the day.  Did I tell him I wanted to work for him?  No.  I froze, told him the letter was for Ursula and left.  I Kicked myself all the way down on the elevator, but I did get a great celebrity encounter on that ride.*

Lesson Two – Do the hard thing.  This one is more of a decision than a mistake in my book, but I do think about it from time to time.  Following an incredibly intense 3 years as the original Business Development work for IBM’s WebSphere brand, I was exhausted and feeling unappreciated.  I accepted an offer to leave IBM to start an Internet consulting practice in Westport, CT, Digital Idea.  IBM countered that I should run NYC WebSphere sales for the intimidating, but highly regarded Bob Guidotti.  The hours would have been insane, the base pay was not as good, and I had doubts that I would be successful.  But working at Digital Idea gave me the income that allowed us to renovate our house (a decision that I’ve never regretted) and I got to try my hand at building a business in my hometown.  Digital Idea flopped, I went back to IBM and got to do many more exciting things, but I always wonder what would have happened if I had said yes to Bob Guidotti.

Lesson Three – Don’t undervalue facetime.  As WW Marketing Manager for IBM’s Partnerworld Industry Networks program around 2007, my team was running marketing campaigns and spending millions of dollars around the world.  I was on dozens of conference calls from my office – but no-one who reported to me was located in my building in Somers, NY.  The policy came down that I was going to get a roommate. I was fond of speakerphones and privacy and did not like my commute so I decided to go work from home.  What did I miss out on?

  • Serendipitous, random meetings in the lunch line with execs and peers.
  • Knowledge of upcoming initiatives or nuances to existing approaches.
  • Opportunities to hear about new jobs before they got announced.

None of this hurt me at first, and I got to spend more time with Suzanne, Rose and Bennett, which is never a bad thing.  But when the big cuts came in 2009, I realized that moving home had in some ways been a career limiting move – one that could have been avoided with a disciplined approach to planning work days in Somers or other IBM locations, even when there was no reason to be there.

These stories and others are always on my mind as I work with entrepreneurs everyday. I encourage them to be prepared to tell a short story about their business to anyone who asks.  I try to help them make the right strategic move to achieve their goals – and I always encourage them to invest the time to meet people, to be present as we work to build an entrepreneurial community in Connecticut.

*celebrity encounter was when I boarded the elevator and Joan Didion and her husband John Gregory Dunne were on board.  Dunne turned to Didion and uttered the immortal words “No-one really goes to Fiorucci’s anymore, do they?”  At least those words are immortal to me…


Peter Propp is a business consultant focused on helping startups create and execute great strategies, especially in the area of strategy and marketing.  He is VP of Marketing for the Stamford Innovation Center in Stamford, CT.

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