The Square Peg, Round Hole Entrepreneur

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. This I do know 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 have been 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 in paperback and Kindle (My Book), as well as being available in all of the other major eBook formats.

Square Pegs, Round Holes

Question: There are times when the harder I try to get something to work the less likely I am to succeed. Naturally this is frustrating but I don’t want to give up. Help!

Answer: Take solace – we’ve all been there at one time or another. Here’s what happens. We have a goal in mind. Let’s simplify it for illustrative purposes. We want to thread a tiny fishing line into a tiny eye of a tiny hook. We have the best of intentions – we just want to thread the hook. But our eyesight may not be the best; our fingers might be too big; the light might not be right; we may have trouble holding the hook steady (and maybe the line too) – all of these elements may be working against us. What do we do? We keep pushing that line at the hook’s eye and we keep missing. Over and over and over we do this with the frustration mounting.

How do we finally thread the line through the hook? We slow down. We make sure the light is right. We put our reading glasses on. We take a deep breath and relax. And guess what – the line goes right into the eye of the hook. The lesson here is that when we try and force things we often fail.

As entrepreneurs we need to use this simple lesson as we go about our daily business. I spent many years trying to “muscle” my way to accomplish my goals. There were times when I tried to “will” things to happen the way I wanted. This was a classic case of trying to pound a square peg into a round hole. It just didn’t work. Oh, there were plenty of times that I accomplished my goal. But that square peg may have been mangled in the process.

I finally broke the code when I realized that my “muscle” approach was actually causing me to be “muscle bound.” I learned that my high sense of urgency was causing me to plunge into trying to accomplish something without the necessary foundation being laid. I discovered that doing more research and creating a solid plan was a good launching pad. It also became apparent that maintaining a higher sense of awareness about what was happening along the way would serve me well. How were people responding to my approach? Did I need to provide better and clearer directions? By relaxing and keeping a positive attitude I was able to still maintain my sense of urgency, and the path to success was smoother and more certain.

When we feel as though we are running into walls it’s time to take a step back. Reassess the situation. Create a new plan. Relax. Then start again with a new and positive attitude.

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