Winnable Deal

woman on smartphone

I like to amuse myself with word games or card games on my phone. Whether I’m waiting for an appointment or sitting at the car dealership, I will spend a few moments trying to win a hand of solitaire.

I recently downloaded an app that has many kinds of solitaire, including one called “Spider.” I’d never played this kind of solitaire before — after reading the rules of play and failing miserably at a few hands, the chase was on. I just HAD to figure out how to win at this thing.

I played hand after hand with no success, losing time and again, but each time getting a little closer to victory. Each time I learned a little about strategies I had tried that worked and those that didn’t. Now I win about a quarter of the games I play, often enough to keep me playing.

One day, while waiting for the game to load, I noticed a checkbox on the game set-up:

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Winnable deal.

It was turned on, meaning that every hand that I had been dealt was a winnable hand. Every. Single. One. But I was only winning about 25% of the time.

If every hand was a winnable deal, what was preventing me from winning? I could restart every game and keep trying until I won each deal before moving on to a new deal. Why wasn’t I winning 100% of the time?

  1. Tedium. Playing the same set of cards over and over again is not the most interesting thing to do. Many of the moves are always the same with no options for alternatives, so for much of the game I’m doing exactly what I’ve done before.
  2. Not remembering what I’d done before. When given options, I couldn’t remember if I had tried the move in the previous hand or not. Was I repeating exactly the same game as before, and would I have the same outcome? I had no idea.
  3. Not willing to put in the time. I’ve ended more than one game when my meeting began, I was interrupted, or otherwise had to stop playing. I did not have time to keep trying new strategies to win a hand. (This IS a game for leisure, after all.)

I realized that these same issues that kept me from having a 100% winning streak are the same issues that plague many in our professional lives.


During his career, my father spent many years at J.I. Case, which manufactured tractors and other machinery for the agricultural industry. While a general manager there, the company was going through a difficult time of slipping margins, poor quality control and labor issues. My dad worked hard through all of those challenges and was a key factor in the company’s turnaround.

He told stories of those days with fondness. Every day was a different battle, utterly unique from the day before. It was challenging and exciting, even the day that he tried to leave work and found that all four of his tires had been slashed, presumably by a disgruntled employee. Finally, the ship had been righted, labor demands appeased, and quality and margins began to increase. Now it was back to the tedium of managing day-to-day operations. He left the company shortly after, because, he said, “It was boring.” Some years later Case merged with International Harvester; I suspect he would have found that transition time to be fascinating to work through had he chosen to stay.

Not Remembering What Was Done Before

When I left my agency job to work for a nonprofit, I was fortunate enough to get in touch with the person who had held the job before me, even though he had already moved on from the organization. During my first week at the new job, he and I had coffee and I learned so much about what he had done to make the annual giving program a success. He had left careful documentation (in random folders, perhaps, but the documentation existed), of previous testing that had been done and its results.

Thanks to him and to this documentation, I did not need to make the same mistakes again. Despite the change in personnel, I was able to keep moving the program forward, increasing the number of donors and revenues, and also build a strategy for a grateful patient program.

Five years later when I left, I wrote a 7-page document for my future replacement, outlining previously tested strategies, where to find documentation, the direction of the program and challenges to be addressed moving forward. Unfortunately the organization decided not to replace my position until months after my departure, and much of the documentation did not survive the other changes in leadership that were happening at the same time. Now that they’ve got new personnel in place, they are re-tracing steps previously taken to prove to new leadership that the program that had been put in place was indeed effective before they can further advance.

Not Willing to Put In the Time

In my agency days we hired a lot of people right out of college or who only had one or two year’s experience. We were a growing company with a lot of entry-level positions.

For a time, we went through countless recent graduates; our turnover rate for entry-level positions was awful. We would post the position, carefully described the job through the interview process, hire someone in, and this person would begin work. Being an entry-level position, the work was…well, tedious. Detailed. Repetitive and sometimes frustrating. Invariably, within 3 to 6 months, our new hire would ask when he or she would get promoted out of the position.

We were a growing company, but not growing so quickly as to need to promote within the year every single person who started with us. We would re-direct to the job at hand: there were nuances to be learned, improvements to be made, more to do in the current position than simply moving past it.

For a time, the majority of our entry-level people walked back out the door about a year after they’d walked in. The few who stuck it out did indeed get recognition and promotions to move on to the next level. Those who were willing to put in the time were rewarded.

I think of conversations I’ve had with people over the course of collective careers, and the decisions I and others have made throughout our lives. A job that was tedious, a boss who was weak, a co-worker who made work miserable, who forced our hand to make a decision to either stay or ride it out. Was that a “winning” decision? What would have happened had different decisions been made?

What is keeping you from winning your winnable deal?


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