Lesson #39

If the Flame Starts Flickering: How to Tell If the Fat Lady Is About to Sing

One of the biggest dilemmas for any entrepreneur, CEO, or business owner, big or small, is to know when enough is enough. Many times it gets down to the age-old question: Do you work to live or live to work?

Way too many entrepreneurs have worn out their welcome and crashed and burned after reaching a high point, only to precipitously fall from grace in the eyes of those who matter—associates, investors, sometimes customers, and even family. There are many waypoints along the journey to establishing, building, and running a company. An entrepreneur who can come up with a killer idea may not be effective at building on it once its strategy is fleshed out and ready for execution. In other cases, a leader might be a good builder but a failure at running day-to-day operations. The challenge is to understand when it's time to fade to black, and either leave permanently or bring in another executive to run the show—altogether or day-to-day. Perhaps an even more important decision is not whether to wear the hats of innovator, builder, and operator, but instead when to step up to the cashier's window.

There are peaks and valleys in virtually every company and industry. The trick for an owner is to understand these vacillations and know when to hit the bid. This essentially means either accepting an offer to sell and cash out or, in some cases, creating a scenario that results in an offer. This is where ...

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