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Where are the kids? At home? In college? On their own? Are you still supporting them, or are they financially independent?
    Lifestyle: What do you want to do? Get involved with charities? Golf? Boat? Travel? Spend time with the grandkids? How much vacation time are you taking each year? If you’re spending increasing amounts of time away from the business and the business can operate without you (a good thing if you want to sell it), retirement time may be nigh.
    Finances: Do you have enough saved to fund the lifestyle you want? Have you actually figured out that number with a professional planner, or are you just guessing?
    As far as funding retirement, business owners usually have a rough, back-of-the-envelope number in their heads. Many times, that number is little more than a guess, and that guess often is a gross overstatement of what the owner really needs to fund his retirement. Sit down with a qualified wealth manager and talk about exactly what you want to do in retirement. That wealth manager should be able to determine what you’ll need to retire and live exactly as you want to live.
    Your personal drive: Be honest: How’s your energy and drive? Yeah, I know, that sounds like one of those pharmaceutical commercials, but in all seriousness, are you still the go-getter who originally built the business? Admitting that your drive isn’t what it once was and that you’re putting aside your ego to think about what’s best for the business and your employees is no cause for shame.
    If your position is no longer necessary to support the family, you have enough to retire, your lifestyle interests are increasingly outside the confines of work, and you’ve simply lost your mojo and desire for work, perhaps you’re ready to think about selling the business and retiring.
    Buyer, you can ask a reluctant Seller if she has planned her retirement with a qualified professional. Getting an owner to create a concrete retirement plan with an advisor can be a way to bridge a valuation gap (see Chapters 12 and 21 for more on valuation and bridging valuation gaps).
    Let someone else take the company to the next level
    Some owners choose to sell because they’ve determined that they’ve taken the business as far as they can take it. They may not want to retire, but they also may not want to run the same company anymore. This situation happens for a few reasons:
    Capital needs: A growing company, even a highly profitable company, usually requires more capital than the business generates from operating cash flow. Why is that? For most companies, cash flow lags behind revenue recognition, and revenue recognition lags behind expenditures required to support that revenue. A growth company that constantly needs to reinvest in the business (new employees, equipment and supplies, and so on) essentially has the capital needs of a much larger enterprise. Owners often decide they’re no longer willing to put their money at risk, and as such, they’re ready for another owner, perhaps a larger and better-capitalized entity, to swoop in and take the company to the next level.
    The segue: I’m not talking about those fancy two-wheeled scooters here. The segue refers to a natural phase during the life cycle of a company: the gradual shift from a entrepreneurial company to professional company.
    As a company grows, it needs more people to manage, oversee, and support the company’s new, larger size. With each new hire, the dynamic of the company changes; the entrepreneur/owner’s influence on the corporate culture is diminished. This move isn’t a bad thing; it’s normal. The company, by necessity, has to shift from a centralized, seat-of-the-pants, CEO-is-in-on-every-decision organism into a diverse, decentralized, and highly structured entity.
    Many successful entrepreneurs simply don’t have the ability (or interest) to design, implement, and run a highly structured company and thus