You’re young, you’re motivated, you’re smart–but you aren’t really prepared. At the most difficult moments in business, there is no substitute for experience.  (This article first appeared here on

Let’s channel legendary coach Phil Jackson of the Chicago Bulls and Los Angeles Lakers for a second. One of the basic tenets of Jackson’s coaching philosophy was that you are more likely to perform well in a difficult situation if you’ve been tested in that very situation. That’s why Jackson put his players in game scenarios in practice, over and over. The thinking was that both the brain and the body need to be exposed to specific stresses in order to train them to react a certain way.

I think business works pretty much the same way. I’m sure there are some young entrepreneurs who are so skilled that they can process and react perfectly the first time they face a tough moment. I hope you are one of them. But I think probably not. Most of us need to face challenges in order to truly learn. We need to practice.

I think back to a situation where my older boss and I were pitching the CEO of our multi-billion-dollar public company for some internal investment dollars to kickstart a new digital business line. We needed a million dollars and had worked for months getting the approvals up the chain of command. Now we needed final approval from the CEO. I was 30. I remember sitting in the boardroom thinking to myself that I should be leading this pitch and not playing support guy for my 40-year-old boss.

Just a few minutes into our meeting, the CEO turned a light, informal, just-get-the-signature meeting into a serious, intense, why-do-you-deserve-this-money meeting. A very appropriate tack for this much investment, I would add.

My boss withstood the pressure with so much poise.

I walked out of that meeting thinking that I could not have handled that with even 50 percent of the poise that my boss had delivered. I still had a ways to go.

As I look back on that meeting, I realize it exposed me to a new level of business, where poise, strength, and durability under pressure are as important as intellect, preparation, and charm.

Get practice. Find ways to put yourself in situations that are far from your sweet spot. Pitch in front of an audience. Sit down with an investor, even if you are not ready. Find the hard-line, experienced local veteran and field his old-school questions. Talk to the banker and find out what he needs to make that loan. Put yourself under stress now, because someone else will definitely do it later.