If you work with a lot of entrepreneurs as I do, you see a lot of naked ambition on display. These are smart driven people, eager to disrupt their industries, move the needle on culture in some way, and hopefully, make a lot of money doing it. By all outward appearances, they are “crushing it.” And yet, many of the people I talk to, at least those brave enough to seek out coaching, do not feel remotely satisfied. When do you think you will feel successful, I sometimes ask? And here, the answers often become vague and faraway. When the next round of financing comes through. When we finally move into a bigger space. When the company goes global. When it blows up and becomes a unicorn. When we go public.

The Promised Land, like the elusive unicorn, is always out there in the distance, tantalizingly close, and yet somehow, just out of reach. But there’s a price to pay for living this way. The sun may be shining, but for the person in search of a unicorn, there’s always a big dark cloud hanging over everything that blocks out all light and makes the road ahead appear dark and uncertain. Present success is minimized, and past success, if it ever happened at all, is no longer even relevant. They do not feel successful, despite all outward evidence to the contrary. Part of my job is to point this out, and try to “look at the data” to see if any other interpretation of the facts is possible. While feelings can be very powerful, they are not facts – they are simply filters, and not always helpful ones either.

Having our “success” be contingent upon some hoped-for outcome is always a dangerous game, and one that can play havoc with self-esteem. It sounds obvious, but it’s surprising how many smart people fall into this trap, refusing to grant themselves the acceptance they would freely give to others. Women, in particular, are prone to holding ourselves to impossible standards of perfection. Men have their own issues to deal with: grandiosity and aggression some of the more common manifestations of low self-esteem. Healthy self-esteem, by contrast, is an internal sense of balance and worth that is not contingent upon any outside person or event. It says, “I have value simply because I AM…”

Diversify Your Investment

One of the things I often invite my clients to do is to “diversify their emotional investment” in any one area of their life. Sure, your work may be important, but are you having any fun? How are you doing in your relationships? Are you spending any time with friends and family? Sustaining healthy relationships with others requires that you first have a good relationship with yourself. Author Terry Real has a lovely phrase which I will sometimes borrow: he describes healthy self-esteem as “holding yourself in warm regard.” It means treating yourself kindly, with all of the compassion, warmth and understanding that you would give to someone you really cared about. You accept all of their faults and limitations. And you certainly wouldn’t judge them for what they have (or have not) achieved.

It can be hard to do this when the prevailing culture generally does not. Blame advertising or social media, but the message seems to be: “You are not enough, UNLESS….” Watch any hour of network television and what you will see is an entire world divided into winners and losers. Life as a zero-sum game, where one contestant wins a million dollars, and the other is cast off the island, banished from the kitchen, sent home without a rose. Most of us, if we’re honest, have some version of this ridiculous game show going on in our heads. We believe that if we could only build that unicorn, if we could just live in that house, then our lives would be perfect. All doubt, all fear, all self-esteem issues would instantly vanish, and our lives would be suddenly perfect. But this is not usually what happens, is it? Because being “enough” is really an inside job.

Some years ago (I’m totally dating myself here), there was a silly movie about the first Jamaican bobsledding team called Cool Runnings. The coach is played by the late great John Candy in his usual goofy role. The men on his team are desperate to win an Olympic gold medal, just as many of my clients are desperate to achieve their own version of a “gold medal.” I don’t remember much about the movie now except for one of the coach’s lines. In it, he says something like, “If you’re not enough without the gold medal, then you won’t be enough with the gold medal.” That line stayed with me because I think it says something very profound about the nature of happiness and success. We need, as human beings, something to hold on to. We need goals and ambitions and dreams. But as John Candy knows, our real value does not come in the shape of an Olympic medal. The world can’t give that to you. The good news is, neither can it take it away from you.