Is trying to hammer a square peg into a round hole a cliché or what? Just for grins, I tried to do this once and had no problem. Of course, the hole was a heck of a lot bigger than the peg. But that is not the point. The more we try to force things that are not meant to be, the more likely we are to become frustrated and fail. I do know this from lots of experience.

Here is an example. In the old days I might have interviewed a great candidate for a position we had open. This individual had all the right qualities, the right experience and seemed enthusiastic about joining our firm. We would extend a job offer and perhaps there would be some back-and-forth dialogue over the terms, salary, etc. But then the candidate went dark and stopped responding. My tendency was for my sales instincts to kick into overdrive and really put the hard press on this person. Often the person might eventually come to work for us. But it usually was not a happy marriage and ultimately ended in divorce. What did I learn? If we have to “chase” someone and “sell” them on joining our company, then they probably are not the right fit in the first place.

Here is another example. I have a big decision to make. I am trying my darnedest to find complete clarity in this situation. I list all the pros and cons, but the answer still is not there for me. I talk to other people whom I trust, but no one grabs me by the hand and opens the door for me. I continue to press for a revelation, but none comes to me. The frustration mounts and I feel stress because the decision must be made immediately. The stupid peg just will not go into the hole! What did I learn? Complete clarity is often elusive and most of the time we must make the best decision we can after considering all the facts. And we need to trust our gut to some extent.

Here is the final example. Several years ago, there was an investor who owned a large apartment complex that our firm wanted to manage. I cultivated a relationship with this investor and met with him regularly. I tried everything I could think of to convince him to retain our services. He was self-managing the property, and I just knew we could improve his bottom line. All my creative marketing and sales methods were for naught. We never were able to win the business. I hammered and hammered and hammered, and the square peg never made it into the round hole. What did I learn? We are not going to win 100% of the time. If we are paying attention to the basics and fundamentals mixed with a sufficient dose of creativity, we have done what should be done. Sometimes we will succeed and sometimes we won’t. Trying to force success is a pathway to being demoralized.

When we force things and try to muscle through, we often flounder and fail. When we relax, pay attention to the details, and trust our instincts, we improve the probability that things will fall into place. And if they do not, we simply stop hammering and move on.

This blog is being written in tandem with my book, “An Entrepreneur’s Words to Live By,” available on Amazon.com in paperback and Kindle (My Book), as well as being available in all of the other major eBook formats.