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On a recent birthday I was looking back at the strategies that my friends from high school and college and I employed to get where we are today. We assumed that success would bring happiness, and as far I can tell, we were wrong. It turns out that the two are separate, even though marketers would have us believe otherwise.The slogan for Cadillac is “Life, Liberty and the Pursuit.” Of course what your mind fills in is Life, Liberty and the Pursuit of Happiness. As if a $50,000.00 car will actually make you happier. And maybe it will. But keep in mind, if your life fundamentally sucks, it’s gonna keep on sucking the moment you step out of the car and onto the concrete. So, if the two are different—if happiness and success are not the same—what’s the best life strategy?

We are certainly taught to believe that being successful will make us happy. Society tells us, our parents tell us, our teachers tell us, students in high school as young as 12 and 13 are already being lectured about college. I take it to an extreme. I have a 5-year-old nephew, I am thinking about his college, I am thinking about his high school. It’s ridiculous; I am missing his entire childhood because I am so busy thinking about making him successful in the assumption that thus will he be happy.

I also find that in career coaching new MBAs, they have an almost religious belief that they can plan out a 20-year career path. They say things like, “I will make my money and then I will be happy. Then I will do the things that are meaningful.” Then, then, then. As if, among other things, you can even control whether “then” ever arrives.

So strategy number 1 is: pursue success and hope for happiness. The other strategy is to pursue happiness and meaning and find a way to make a living doing it. This is the strategy where happiness leads to success. Which one is better? Let’s see…

If you go for success and you become successful and you find a way to be happy doing it, yeah, you’re happy and successful. If you go for happiness and find a way to make money doing it, yeah, you’re happy and successful. So, in the case where you can achieve both, it doesn’t really matter which strategy you choose, you end up happy and successful.

But the point we rarely consider is what happens if everything doesn’t work out. If you define your life as pursuing success but you don’t actually find a way to be happy while doing it, or you get to that point where you have the money and now you don’t even know what makes you happy because you have spent the whole time pursuing success instead of happiness, well, great. You’re successful, but you’re not happy. You walk into an empty house surrounded by beautiful gorgeous things. You have a lot of friends and they like you. Why? Because you have a lot of nice things that they want to borrow. You buy a cat, the cat puts with you because you leave its automated feeding bowl in place while you go work at office. It actually hates you because you’re never around. You are too busy working, but at least it will pretend to purr every now and then.

On the other hand, if you go for happiness and aren’t successful, at least you will be happy and you will have a life full of meaning. They found one of the big things that helps people be happy, for example, it is having family and friends and community. So, if you are happy, but don’t quite make it to successful, you may wander into your one-bedroom tiny apartment and be surrounded by friends and family and people who love you and a cat that purrs because it recognizes you—it knows who you are and it appreciates the fact that you feed it. You may not have the money, but you will be happy.

So, in the case where the future works exactly the way we want it to, it doesn’t matter whether you pursue success and then find happiness or whether you pursue happiness and then find success. But in the case where you can’t guarantee the final outcome, it makes so much more sense to pursue happiness and hopefully you can find a way to be successful doing it.

I have spent my life up until very recently doing the opposite. I have spent my life pursuing success under the assumption that it would make me happy and it is not clear that it’s been worth it. Missing a weekend with friends so that I can work hard and earn enough money that I can take time off and … spend a weekend with friends. Hello? This doesn’t exactly make a whole lot of sense.

What I would like to invite you to do today is to examine your own life and your own motivations—How do you work? Are you pursuing success assuming that someday will bring happiness? Are you pursuing happiness looking for way to be successful while doing it? Are you getting both? And I would invite you to play around a little bit. Try doing something from the other camp and find out if that works for you.

If you’re a Type-A Personality Workaholic, skip a day of work, call in sick and do something that makes you happy, that’s meaningful, and that could be a taste of the life you could be living right now, maybe in exchange for money but maybe not. Because when you pursue happiness, you never know what kind of opportunities arise.

I am now one year into a three-year experiment of living my life to the extent that I can get my Type-A Personality to do so. I pursue the things that make me happy and have meaning. The bizarre part is my life is less predictable than ever before. The things I am getting involved with weren’t even on the radar screen a year-and-a-half ago, however, some of them are grander and more exciting than anything I could possibly have planned. Make a choice. Pursue success and find happiness or pursue happiness and find success. Either way you have a shot at both, but in one case you guarantee you will be happy.

Happy or Successful? Which will you pursue?

read time: 4 min