You’ll Know When

When I was in college, a mentor taught me a lot about the world of business. He taught me subtleties like how to make your boss look good, how to lead people to the action you want them to take and how to read a person by the watch they wear. The latter of course turned into a shared affinity for watches. I remember one time, he was giving me tips about wearing a suit, tricks for keeping the collar stiff, your jacket pressed, etc. This was before my 3 year stint as a road warrior; those lessons were invaluable for packing a suitcase. It was wisdom that only years of experience could impart.

As with all things, mentors give us lessons that we never really understand until much later in life. He was probably about my age when I got this tidbit, but it has stuck with me for 25 years.  We talked about how when you wear a suit, there is an unwritten rule that you really need to be at a certain level, you need to command a level of stature, before you can acceptably wear a handkerchief in the lapel pocket.  He told me, “You aren’t there yet, but you’ll know when.”

My entire career I have felt that I was at that level, and I always used this as an internal barometer/metaphor for my career.  I always argued with myself that I just hadn’t been given the opportunity to exercise it.  Turns out that I really wasn’t there.  Over the past few years, now I know.  It’s the ability to walk into a situation and know how to take charge or be respectful when someone else is and be part of the team.  How to see opportunities for triangulation.  It’s knowing that if there is a subject in my wheelhouse, I don’t need to prep to present the idea.  One of my favorite Steve Jobs quotes is “People who know what they’re talking about, don’t need Powerpoint.”  It’s so true.  I work best when I am listening to the audience and giving relevant answers to pointed challenging questions, using context, career experience and humor to bridge a gap.  When I am asked to follow a script, it inevitably goes worse.  When you are confident that you can stand at the front of any room, then you are there.

Over the past few weeks I did Peak Pitch, a ‘marketing’ trip to NC, crafted multiple solutions to business and design problems and have worked to reformulate our entire delivery model.  I highly doubt that anyone working with me would would question my abilities for what I do.  People don’t believe I can do other things, but that is a different story. 🙂

I finally understand, and now I know.  Too bad I never wear a suit anymore.

About Josh Rutstein

I am an aspiring entrepreneur and hopeful political candidate. Father of 2 very special girls, husband to an amazing woman, and passionate American. I snowboard whenever possible and follow a 20x mentality for exercise. I also play golf and ultimate frisbee and am a die hard New England Patriots fan and season ticket holder. Everyday I wake up wanting to make this country a better place, someday I hope to actually succeed.
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