Sometimes You Win, And Sometimes You Learn — John C. Maxwell

Two years ago, in the midst of a career change, I contacted someone I admired requesting a chance to meet, and to my surprise, he agreed.

Forgetting my wallet, and making him float the bill topped off a laundry list of mistakes I made during our time together. In addition to trying to act cool, I disrespected him at times by interrupting him in order to demonstrate my vast knowledge on the subjects we were discussing (probably something you should not do to a highly respected leadership and communication coach).

Despite this, he remained cordial, even humoring me at times, but even as thick as I was that morning, the message that I had blown an opportunity to build a relationship with someone who could teach me a great deal, came in loud and clear.

I left that meeting kicking myself for not living up to my potential, but after a few months I came to a hard conclusion; even if I was at the top of my game that day, I had not been prepared to meet with him, and that I had made the mistake of reaching out too soon.

Since that day I have used that conversation as a measuring stick to gauge my growth: Was I ready to contact him again? Was the work I was doing good enough to warrant a second meeting? Each time coming to the conclusion that the answer was, “no, not yet, get back to work.”

While this was happening, I began writing more in my blog. To my surprise, the one person who consistently checked in to leave an encouraging comment, was the very person whose time I had wasted months before.

Knowing that he was not the type of guy who wasted time on someone he did not see something in, the person who I had prematurely tried to impress, ultimately making me question my own confidence, was the very person who was building it up again, whether he knew it or not.

Last week I got a shot at round two. After speaking for 90 minutes I still had the feeling that I had much to learn, but I also felt like both of us had benefitted from the conversation, and that he had finally met the person who I thought I was a few years prior.

Since our initial encounter I have learned a great deal about myself, and through his subtle actions, much more about leadership and building relationships.

I have learned six valuable lessons since making the mistake of contacting the guy I admired too soon, President of Entrepreneurs Organisation (Spain) and Leadership and Communication Professor at IESE Business School, Conor Neill, which inadvertently, has turned out to be one of the best mistakes I have ever made.


If each of us lives a full life, the odds are high that we will work for 50 years, each year representing roughly 2% of our overall career.

By reaching out to Conor when I did, I demonstrated that I wanted everything at once, ultimately jeopardizing guidance from a person that could have helped speed up my learning curve a great deal.

Bill Gates said that, “Most people overestimate what they can do in a year and underestimate what they can do in ten.”

During our conversation Conor subtly reinforced this notion by reminding me to slow down.

I did not understand that then, but I do now.


Prior to meeting my wife, I had allowed my weight to get out of hand and I was stuck in a career that had I had allowed to run me into the ground.

Yet if during that time you had asked me to describe my “dream girl”, the words “in shape” and “successful” would have topped the list.

It was not luck that we met after I had begun to take care of myself again and begun to focus on work that mattered.

The same goes for my relationship with Conor.

I represented someone who had not yet done the work, expecting to connect with someone who already had without properly identifying how I could benefit him also, and you cannot do that.


The more people I meet like Conor, the more I have come to realize that success often comes down to the word, “AND”.

Good with numbers “AND” great at building relationships.

Inspiring writer “AND” patient teacher.

Even in relationships it is often the “AND” that keeps us awake at night; beautiful AND great sense of humor.

Successful people always have an “AND” , and observing Conor move from a successful blog to an incredible video series shows me that no matter what level of success he has achieved, he is still chasing the next “AND” to add to his skill set, and that I better keep moving if I hope to get that third conversation.


By not writing me off the first time we met, despite my embarrassing performance, Conor taught me that he was consciously listening with an empathetic frame of mind.

Too often we rush to dismiss an idea or an acquaintance based on hurried or shallow assessments, something I was guilty of in the past, but much more conscious of now moving forward.


Relationships and reputations are often build by what some would consider inefficient actions.

Conor is a very busy man with little time to waste. That said, his actions told me that he knows that we must be open to possibilities and that helping others always is the right thing to do in so many ways.

A favorable nod, a pat on the back, or a word of encouragement energizes and empowers others and through Conor´s subtle actions he reminded me of the golden rule in not only relationship building, but career building also: The best way to clear your own path is by helping others clear theirs.


Last December Fast Company contacted me about the bones of an article that I had submitted that they thought had potential.

I contacted Conor to get his opinion, and after receiving his feedback, I decided to go with my gut, contrary to one piece of his advice that he had offered.

It turned out that this point had been the tipping point for the editor at Fast Company in running the article.

This may seem trivial, but this was a big thing for me. But once again it came back to our first conversation where Conor encouraged me to listen to myself more than others, and for one of the first times in my life I went against the grain and it paid off.

A few days after our second conversation my feeling that I had indeed added something to the conversation was confirmed when Conor was kind enough to mention me in a part of his video series.

Having a guy who I obviously admire demonstrate that I am not wasting his time, but adding to it will be one of the highlights of my career.

The underlying lesson in my experience with Conor can be found in the title of John Maxwell’s book: Sometimes You Win, and Sometimes You Learn.”

The first meeting, I lost. But by Conor taking the time to guide me through the process, in the end, I learned, which the older I get, the more I realize is the same thing for winning.

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Originally published at on April 27, 2017.

Originally published at