What’s the most important question to ask yourself in order to succeed?
Not long ago I read a novel by Meredith Schorr. At the peak of the story, the protagonist had sunk to both professional and personal lows, but before long she manages to dig deep and rise up once again.
She had lost the love of her life, and circumstances were such that she might never see him again. In a last ditch attempt to make things right, she went all-in and took a huge chance to get her man back. This character was not prone to such behavior, but the moment she realized she really had nothing to lose, she was free to unleash all that she had to offer.
Janice Joplin, in her posthumously released 1971 hit, Me And Bobby McGee, told the world, Freedom’s just another word, for nothing left to lose. This is something I have found to be absolutely true.
I have worked in sales and business development for much of my career. In my third job after college, I worked for an IT consulting firm in New York City, selling computer consultants.
In New York in the 1990s, selling was a simple proposition … pick up the phone and call, call, call. The more people you called, the more likely you were to find someone who was interested in buying what you were selling. It required little skill to win at this simple numbers game. We had some access to email, but the first line of communication was still the telephone.
Most of the people I sought out had gatekeepers. A gatekeeper is a secretary or assistant who protects a senior individual from, well … salespeople. In New York, executives work longer hours than their help. The trick was determining if the person I was after, was an early riser or a night owl.
Once I got past the gatekeeper, I had a pretty high success rate for closing deals.
A couple times a week I would come in early to the office and try to get through to any of my targeted individuals. If they answered, I knew they were morning people. If they didn’t, I put them on the night owl list. Other days I stayed late and called the folks who failed to answer at sunrise.
One way or another, I was able to get through to everyone eventually … except for one particular guy.
In the IT consulting world of the 1990s, we all knew where the work was. Our talent were mostly independent contractors, so through conversations with each of them, we learned which companies were making calls.
Several consultants I placed with other companies told me they had been approached about slots at a large, internationally famous company across the river in Queens. They had all wanted to stay in Manhattan, but I had many talented contacts in Queens, so I set my eyes on that company.
Through careful research, I was able to determine the name and number of the hiring manager, but his gatekeeper was an absolute bulldog. No matter how I tried I couldn’t get any time with her boss. On my next early morning, I called the man, only to hear the voice of his gatekeeper at 7:15am. Off to the night list he went.
The next night I placed another call at 6:45pm, and what do you know – I got the gatekeeper again. How many assistants work a twelve-hour day? As unusual as this was, the optimist in me assumed this was a sign of how busy they must be, which of course convinced me of how desperately they needed what I had to offer. I had to find a way to get through to this guy.
The next night I left the office on time and headed home through my normal ninety-minute commute. I got home, made some dinner, watched some television and at 8:45pm, picked up my phone and dialed the number of the elusive executive.
On the seventh ring, he picked up.
I quickly introduced myself and began my pitch. Ten seconds in, he interrupted me by shouting, “I DON’T TAKE COLD CALLS!” The phone went dead.
I was sad, but I had done what I set out to do – I got through to the man and he rejected me outright. I went to bed. The next morning I got to the office and decided to move on to other prospects.
However, only a few hours into my day, I was chatting with one of my consultants, when again I was told that same company in Queens was actively looking for consultants. As I rode the subway back uptown to my office I had an idea.
As I had done the day before, I left the office at the normal time and worked through my evening routine.
Again I picked up the phone at 8:45pm, and again the man answered on the seventh ring. I began to speak just as I had the day before and predictably he did the same thing, cutting me off by saying, “I don’t take cold calls,” but before he could hang up I quickly interjected, “this isn’t a cold call … you hung up on me yesterday.”
There was a moment of tense silence, which was broken by the man saying, “okay, I like your style, you have sixty seconds.”
I explained who I was, what my company did and how familiar I was with his needs. He agreed to let me send some information and to consider my company as specific needs arose. Anyone in sales will tell you … that was a win.
I ended up leaving that job a few weeks after this exchange, so I never had the chance to close a deal with my new buddy, but the lesson I learned has stuck with me ever since.
The realization I came to on the subway that afternoon was that I had absolutely nothing to lose by making the second call. Nothing. Since then, I look at every difficult situation through the lens that measures, “what do I have to lose?”
I had a theatre professor in college named Annamaria Pileggi. I will never forget the charge she gave to my acting class one day. “No matter what you do, make a strong choice and stick with it.”
I have also heard the following:
- The greatest thing one can do is SUCCEED BRILLIANTLY.
- The second greatest thing one can do is FAIL BRILLIANTLY.
- The third greatest thing one can do is, take the mediocre, easy, path.
From this day forward, assess all your challenges (personal and professional) by measuring what you have to lose. If the answer is little to nothing, get ready to go all in. What happens next may just amaze you.