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An Entrepreneur's Guide To Dealing With Disappointment

This article is more than 7 years old.

Everyone experiences disappointment at one point or another in their lives. Sometimes, it is over something as trivial as a missed business opportunity. Other times, it’s over something more meaningful, like an election.

Watching Hillary Clinton’s concession speech today reminded me of of just how challenging managing feelings of disappointment can be. I can only imagine how she feels; to lose an election after a lifetime of service, hundreds of millions of dollars of investment, and a grueling nomination and campaign must be devastating.

Still, despite the flood of emotion that Secretary Clinton must undoubtedly have been experiencing, she handled the situation with characteristic intelligence, class, and grace. Her example of graciousness in defeat should serve as an example to anyone forced to manage disappointment, especially entrepreneurs.

Entrepreneurship is a roller coaster ride unlike any other, especially for founders. When you think about a business, there are two kinds of capital: money and emotional investment.

Founders usually have the highest emotional investment of anyone in the organization. After all, the business is their baby—and for entrepreneurs, life is work and work is life. For better or worse, everything that happens to or in a business is somewhat personal.

When disappointment comes—and it always does—it’s easy to let it get you down on a number of fronts. However, for the sake of the company, the team, and your sanity, you’ll have to learn how to deal with the situation in a positive manner.

I’m not an expert on many things, but one area where I have plenty of experience is dealing with disappointment. I’d like to share what I’ve learned over the years so that my fellow entrepreneurs are better equipped to deal with the challenges they face in their lives.

Stay strong and keep a good poker face

Attitudes are highly contagious, especially inside small organizations. This is true on many fronts, but it’s especially acute when you’re dealing with the leader’s attitude. If a team sees a leader in a depressive mood, it will spread like wildfire. It’s critical for leaders to maintain a good poker face.

I don’t view this practice as a method of hiding the truth, far from it. Instead, it’s a matter of not allowing your fleeting feelings to affect the morale of those around you. It sounds corny, but good leaders don’t have the luxury of whining.

I’ve had plenty of experience dealing with disappointment over the course of my career. One incident in particular stands out in my mind. I had the opportunity to do a transformative deal with a group that I trusted, respected, and admired, and it ultimately fell through thanks to forces outside my control.

It was painful, but I realized that I could not allow my personal disappointment to affect my performance or the morale of my team members. The only way to deal with the disappointment was to recognize it, accept it, and move on to bigger and better things.

Be graceful in defeat

Failure is never fun, and it’s all too easy to let emotions to get the better of you. No matter how sad, frustrated, or angry you may feel at the moment, the ability to demonstrate grace under pressure is one of the most admirable qualities a leader can possess. However, it rarely comes naturally; it must be nurtured over time. When faced with disappointment, always seek to handle the situation with poise, understanding, and respect.

When I receive disappointing news, I strive to make sure that the other parties involved recognize my appreciation for all the work put in along the way. While things don’t always go the way we want, when everyone involved handles the situation with honor, respect, and transparency, the future remains bright with opportunities to work together again.

Handling the disappointment of the moment with grace and dignity goes a long way in cementing ongoing mutual respect.

Keep moving forward, no matter what

Business, like life, football, and politics, is a game of inches. As I’ve noted, most successful businesses are defined by the sum of all of the little decisions and interactions that happen each day, not by grand strategic moves.

This simple truth puts the responsibility on both leaders and teams to make every single moment count. When faced with disappointment you can either crumple up in defeat or keep moving forward. Successful people demonstrate true grit and keep moving inch by inch, moment by moment, even in the face of disappointment and setbacks.

Regardless of how you feel about Hillary Clinton, I can’t think of a better modern example of a public figure demonstrating grace in the face of defeat and disappointment. Entrepreneurs should take note, and strive to respond to their next disappointment with half as much class.

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