Imagine yourself in this scenario:

You own and operate a successful business and you decide now is the right time to sell. According to your advisors, you’ve done everything you need to position yourself and the company for a transaction. You’ve completed all of the pre-sale planning — taking care of those aspects of the business that were important to you personally, while also structuring entities and employing strategies to mitigate the tax implications of a transaction best suited for you. So you proceed and you and your deal team negotiated very favorable sale terms.

The sale closes, and the proceeds will more than support you and your family for generations to come.

Now what?

You knew that you would not remain active in the business post-sale. You’re not someone that can work for someone else or work within a larger corporation. You also had no plans to retire.

But, like most entrepreneurs, the unknown didn’t bother you — you would just figure out your post-sale life, well, after the sale. After all, how many times did you tell yourself not to count your chickens before they were hatched?

So, now here you are. Your company has sold, you took that dream vacation and you’re back home. You’re well-rested, refreshed, ready to start upon your next endeavor… and you’re bored. You’ve reached out to contacts and friends you developed through your old business, but they are slow to return your calls, if they bother to return your calls at all. You find yourself puttering around the house, being disruptive to your family. Even your dog is starting to wonder why you’re always around.

And then it happens… you start to miss your old business. While you’re thrilled with the payout, a feeling of seller’s remorse starts to creep in.

You worked hard, built momentum in the business, and earned the payout you could only have dreamed of when you started the company. But you’re longing for the adrenaline rush from your jam-packed schedule before the sale. You want to get back in the game.

So what led to this post-sale derailment?

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