Sometimes You Need to Shake the Opportunity Tree

I ran into a good friend the other day at our kids’ baseball game. After the usual pleasantries, he said, “I’m glad you’re here, we really need to talk.” So we moved away from the rest of the crowd and he began to tell me about an incredible opportunity that he had been presented. His former employer had asked him if he’d be interested in buying the company.

Now, this wasn’t the first time they’d had the conversation about my friend taking over the business. But this time, it had progressed to a point where my buddy felt the owner was very close to pulling the trigger. So he filled me in on the details and the current state of the business and asked me what I thought.

He knew very well what I thought. Every time this discussion had come up in the past, I had encouraged him to go for it. My encouragement usually was met with a “You know me, I’m not much of a risk taker,” response, as it was that day. I realize that, in part, he came to me again because he knew what I would say. He knew I’d encourage him to do the deal. I left the ballgame that night thinking about his opportunity.

The next day, he again met with his former employer, and I received a phone call from my friend after the meeting. He filled me in on the conversation and the specifics of what the owner had proposed. I again encouraged him to pursue the deal, telling him, “This is too good to pass up!” He responded once again: “You know I’m not a risk taker.”

I spent the evening distracted by my friend’s dilemma. I knew that it was in his best interest to buy the company. I also knew that if he structured the deal correctly, he could greatly minimize his risk. I called him the next day to encourage him once again. I went so far as to tell him that I felt so strongly that he needed to do this that, if he wouldn’t do the deal, I would and then I’d figure out how to convince him to buy it from me.

He told me he was going for it. No more talk about not being a risk taker, he had stepped over the precipice and was on his way to making the deal. His focus and attention went from worry to action. My friend was now laying out the plan to get the deal done and make sure he had considered all the issues. It was music to my ears!

I was struck by how his whole demeanor had changed once he made the decision to pursue the deal. His energy was high, and instead of being driven by emotion, he was making rational plans about the steps necessary to close the deal. It was wonderful to watch.

Not everyone has the opportunity to buy a company, but that doesn’t mean that we’re not all presented with opportunities every day. The question is whether we’re willing to take the risk when those opportunities present themselves. It might be a promotion or a new work project. There are dozens of reasons not to take it — longer hours, more responsibility, pressure, risk of failure.

But if you consider the opportunity and focus on ways in which you can reduce the risk, instead of spending all of your energy on the negative aspects, you might just determine that the upside far outweighs the risk. Focusing on the negatives makes them seem bigger than what they are. And the more you focus on them, the bigger they become.

Instead, take a problem-solving approach to every opportunity.  Here are the basic steps:

Identify the opportunity. What is it that is being presented? Sometimes the hard part is identifying what really is an opportunity. They’re not always easy to spot. At times, they might even look like a problem.

List all of the reasons you would want to pursue the opportunity. This is usually the easy part. Come up with a list of all the things that make this opportunity attractive. Quantify your reasons if possible. Make sure you’re being reasonable about your assessment of the opportunity.

Assess and list all of the risks. If you’re not a natural risk taker, this might be the part you excel at. List all the reasons this is a bad idea and why you might crash and burn. Get them out there, but don’t stop there.

Determine how you can reduce or eliminate each risk. Here’s where you need to be creative. In what ways can you eliminate some or all of the risks you’ve come up with?  For those you can’t eliminate, how can you reduce them? Thinking positively about the risks makes it easier to resolve them instead of being intimidated by them.

Evaluate your lists. Evaluate your list of reasons you want to pursue the opportunity and compare it to your new assessment of the risk side of the equation. Then, try to put your emotion aside and make a rational decision about what’s best for you.

Consult a trusted adviser. Go to someone you feel is qualified to give you good advice. Sometimes a little bit of distance can give you a better perspective. You can come to a better decision when discussing the situation with someone who isn’t as emotionally wrapped up in it as you are.

There’s a great quote from Logan Pearsall Smith about risk taking: “What is more mortifying than to feel you’ve missed the plum for want of courage to shake the tree?” Sometime you need to muster the courage to shake the tree. Sometimes no fruit will fall. There will be times that when it does, it will land squarely on your head. But every once in a while, you’ll end up with a plum so sweet that it will make all those other times worthwhile!

Go shake some trees!