Every once in a while, I like to take on an impossible quest. There is a thrill in trying to do the impossible, or even highly unlikely — especially when you do it in such a way that you have very little downside, and lots of upside.

My friend David O'Meara is a great champion of this idea. He is the author of Creating Amazement, a book about how wonderful and life-affirming it is to find something we are passionate about and really go for it. In David's case, he constantly comes up with new ways to create amazement in sports, especially in order to inspire athletes over 30. He has run 20 one-mile US-based races in 20 weeks, in under 5 minutes per mile, at the age of 45. He then did a similar challenge overseas, and now he is doing it again at all of the great wonders of the world. This effort has attracted corporate sponsors and keynote speeches. Why? Because, unlike coaches who talk a lot about inspiration and greatness, he actually walks the talk. To him, it doesn't make sense to do anything unless we do it all out.

In my own case, as an executive coach to entrepreneurial companies, I constantly start up my own businesses and try to grow them to multiple millions of dollars. How else can I coach entrepreneurs about overcoming the challenges of running a business, if I'm not in the game myself? Many of the businesses fail, but many succeed.

Now, starting businesses is not an impossible quest. However, this past weekend, I decided to take on a truly impossible quest, just to stretch myself.

My tennis club hosts a wildcard qualifying round for a professional tennis tournament. The top 50 to 150 tennis players in the world compete in this tournament. This year, tennis great James Blake is in it.

What's great about the wildcard qualifying round at my club is that anyone can sign up, even a middle aged club hacker like myself. And why not? I had no chance of winning, but I was going to get at least one match with a top tennis player in the world. Some people would pay thousands of dollars for that privilege. There was no downside, and — if I happened to win a round or two or pull off an incredible upset — tons of upside.

Sure enough, I was the lowest seeded player in the draw of 32 players, and got matched up against a guy who has coached Andy Roddick, Venus Williams, and Jennifer Capriati. He played on the pro ATP tour for 10 years, and has beaten some top players. His name is Julien Link, if you want to look him up.

There was no doubt about it: This was an absolutely impossible quest for a player at my level and conditioning.

As the match approached, it was interesting to hear different people talk about my participation in it. Most tennis coaches said, "Way to go! You have guts!" Some people said, when they heard who I was playing, "Oh, that's too bad. You should just call and default."

In my mind, I tried to come up with ways I might be able to pull off an upset. After all, in tennis if you can win one point, you can win two. If you can win two points, you can win a game, then a set, and then the match. I got all sorts of advice about how to beat him, including from one pro player who had beat him. Advice ranged from hitting right at him to cut off his angles, to coming into net, to hitting low slices (apparently he doesn't like to bend).

When the match began, my opponent couldn't have been nicer. But he didn't hold back. Even in the warm ups, his topspin shots bounced higher and hit my racket harder than any shots I'd hit before. I felt embarrassed during the first few shots in warm ups, when a couple of my balls shanked out of the court.

But then something really great happened. I relaxed, surrendered to the fact that I was playing a guy five levels above me, and I just started cranking the ball.

He creamed me (and "creamed" might not even be a strong enough word), but I won some legitimate points. I took him wide on a great serve, he returned an easy return, and I put it away. He lobbed me once when I came to net, and I hit a winning overhead. I think I even passed him once when he came up to net. And it took him about 4 shots by each of us before he could put me away.

One game even went to deuce.

Yes, I lost 6-0, 6-0. But what an experience! I think I played better than I even have in my life. There was a sense of freedom, relaxation, and just pure joy at going all out. I left exhilarated, despite getting crushed.

So, what does all of this have to do with coaching? I think coaches need to have experiences like this in our own lives. At the same time, many of our clients could use an impossible quest or two — just to recharge and remember that we are on this earth for a very short time and need to make the best of the time we have.

What have any of us got to lose?