What’s keeping you awake at night?

Sleeplessness, caused by the inability to turn off the mind, is one of the most common side effects of business ownership. In my many years of helping entrepreneurs perform at a higher level, I’ve observed that a number of shared issues repeatedly make their way into the conversation as reasons for tossing and turning once the lights go out. Here are five questions I hear over and over again:

  • What is my business really worth?
    Are you building wealth or just treading water? Do you have a realistic notion of the value of your business? Are you setting yourself up for disappointment when it’s time to exit? What can you do now to improve your chances of leaving with enough money to live the life you want?
  • Is my organization and family protected if I — or my business partner — get divorced, become disabled or die?
    What is the likelihood of any of those events happening? What protections can you put into place? How much will it cost? Do you have a contingency plan? A succession strategy? Are you training the next generation of leadership?
  • Can I honestly measure my success in achieving my goals and aspirations?
    Has the business lived up to your expectations? Is it producing the desired results? Do you own the business or does it own you? Are you focusing your time and effort where it matters most, or do you spend your days putting out fires?
  • How well is my strategic business plan being carried out?
    Do you even have a written plan? When was the last time you updated it? Are you innovating and adapting to market changes? How do you develop new customers or clients? Are you retaining your current accounts, or is there a revolving door? Are your employees performing at optimal levels?
  • Why are we always short of cash?
    Is making payroll a challenge? Are your customers paying on time? Do you have ready access to additional funds? Are you able to upgrade needed equipment?

My guess is that you have found one or more of these questions uncomfortably familiar. Please keep in mind that being familiar with these questions makes them no less daunting.