Recently, I was talking with a friend of mine who’s decided to take the leap from a traditional 9-to-5 job to working for herself. Knowing that I myself had experienced both sides of the employment coin, she asked me if I could offer any words of wisdom to ease her transition. After pondering her request for a moment, I knew how to answer: “The most important lesson I’ve learned,” I told her, “is that the grass is always greener.”
By no means was this statement revelatory, for me or for my friend—most anyone who takes a moment to ponder how it applies in a professional context can see what lies on each side of the fence. On self-employment’s front lawn, you have somewhat flexible hours, no boss, the power to say no to any project, unlimited vacation time, no commute, and a bunch of tax write-offs. What you can’t count on are the steady, guaranteed paychecks, health-care and retirement benefits, peer companionship, and paid time off that await you in traditional employment’s yard. And to say whether one set of perks outweighs the other is nothing short of impossible—only you can know which lifestyle is right for you at any particular moment, let alone whether you’re even curious about how the other half lives.
What is astonishing is how readily the saying “the grass is always greener” seems to apply to people of all races and ages, across all socioeconomic strata, all over the United States. In short, it’s the great equalizer—no one escapes its impact altogether.
Take the sticky predicament of the modern-day working mother, for example. A woman with a full-time office job may feel intellectually, financially, and socially stimulated by her career but is devastated to realize that all that fulfillment comes at the expense of watching her kids develop and progress each day. By the same token, if that mother quits her job to stay at home with her children and enjoy the privilege of witnessing each milestone in their lives, she then might sorely miss participating in a professional community and practicing the vocational skills she’s worked hard to hone.
In addition, no matter how much parents love their offspring, they often equate having children with a loss of individual freedom and therefore tell their childless friends how lucky they are that they can do “whatever they want”—be it sleep late, spend money indiscriminately, leave the house without a stroller and diaper bag, and so on. Yet the friends with all that free time and money might look back at those people with kids and long for the pure, continuous joy that parenthood evokes—a sense of satisfaction that far surpasses the instant gratification of being well rested or having a wild night out on the town. In fact, a person who knows he or she wants children but hasn’t had the chance to have them yet, for whatever reason, would likely gladly sacrifice those more frivolous activities in exchange for achieving the goal of bringing another life into the world.
Then there are the people faced with choosing money over family. For a single parent who can’t find steady work and is having a hard time making ends meet, the grass can look mighty green in the high-paying world of, say, corporate law or investment banking—what that struggling mom or dad wouldn’t give for a corner office and the ability to pay for a child’s college tuition with a single check. But while those attorneys and financiers are depositing hundreds of thousands of dollars into their bank accounts each year, their bodies are shutting down from exhaustion, they never see daylight, and when they finally do come home, it’s often to spouses and children who feel neglected and bitter, whereas the parents with less money on their hands can devote more of their energy to bonding with their kids and earning their respect.




