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Business catch-22

April 11, 2013

Question: We are expanding our business into a new area and the only way to make it work is to nab a new, big client. The problem is, because this is a new area for us, we are having a hard time convincing people that we can deliver. How do I get experience if I don’t have experience? Catch 22!

As we all know only too well, being an entrepreneur requires that you wear a lot of hats – you are the CEO, VP of Sales, and, not infrequently, the shipping and receiving clerk too. Not only is all of that stressful in and of itself, but that also means that you often end up doing things that are new and/or outside of your comfort zone, because, well, that’s the nature of the gig.

And the challenge there is that getting results is tougher when you are doing something new and unfamiliar. Pitching a big corporate client is a lot easier the tenth time than the first time, and in fact, it is highly likely that the tenth time will go a lot smoother and create better results than the first time.

This is true for all sorts of reasons: Experience makes a difference, of course, as does knowing what to expect. And because the learning curve has been curtailed, once you have mastered something, you are better able to concentrate on the little things – the important details – that can really make a difference.

But that first time? Man, that can be tough.

I first encountered this phenomenon back in the day when I was trying to get published. Back then, things were very different. There was no Internet, so you could not simply write a blog, post it, call yourself a writer, and say you had been published. No, back then, professionals, called editors, held the key to the publishing kingdom. If your stuff was good enough and passed muster, only then would they say yes, and only then would your writing appear in “print” (“print” is a way to make words appear on this strange, physical substance called paper.)

OK, I am really starting to sound like a curmudgeon, but you get the idea.

Anyway, I tried for 10 years to get an editor, any editor, to say yes to me and all I got instead was a slew of rejection letters.

And then it happened.

One day, I opened the mailbox, and there was a letter from a great publisher in New York, W.W. Norton & Co. Norton was offering me a book deal for a book proposal that I had pitched a year before (God bless you Starling Lawrence!) So, before I ever had a newspaper or magazine article published, or a letter to the editor for that matter, I got a four-book book deal.

The weird thing is that, after that, getting book deals came much, much easier, and faster. It took me almost 10 years to get that first book, but the second deal came a mere three months after my first book finally hit the shelves.

At that time, I relayed this phenomenon to my second father, Seymour, and he shared what became one of the most important lessons I have learned in business. Seymour said that business, like life, is sometimes akin to a jar of pickles or olives. “Think about when you first open the lid,” Seymour said. “ All of the pickles are jammed in there. Getting the first one out is hard.  But what happens after that? All of the other ones come out easy.”

And so it is in business. Getting that first pickle out of the jar is usually challenging. It takes time and effort.

But the good news is that if you are patient enough, getting the other pickles will be much, much easier.

The trick is to get the first pickle out of the jar.

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