On Dreams, Goals, the Big Why … and Serendipity

As part of my two month sabbatical this year I’ve been thinking a lot about where I’m headed. I’ve jokingly referred to this as figuring out what I want to be when I grow up, because in many ways I’m so very fortunate to have such a large palette of possibilities to choose from. It’s basically involved a fair amount of reading and a lot of thought and introspection. It’s also involving a fair amount of writing, some of which I’ll be capturing here.

The reading has been varied, and I’ll save the reading list for another day, but at around the end of the first month I had a realization that helped get me unstuck.

That realization?

I don’t have a dream.

And that’s OK.

My Serendipitous Life

As long as I can remember I’ve never really had any clear vision of “I wanna do that”, where “that” is some vision of a future life, lifestyle or accomplishment. I just haven’t.

And yet I consider myself incredibly successful.

And incredibly fortunate.

It’s in that good fortune that I’ve long realized that my life has been a series of fortunate events, a sequence of happy accidents, a collection of wonderful happenstances more than it’s been a drive to get to a particular place.
In other words, serendipity.

From my choice of career, to my wonderful wife, to my lengthy employment with Microsoft, to my associations and affiliations and to the last 10 years doing Ask Leo!, none of it was planned. All of it was, as best I can describe it, accidental.

Wonderful. But accidental.

I never set out to do any of those. They’re not things that I actively set forth as a goal or set out to achieve. They happened to me, not the other way around.

Now, I don’t want to minimize what I did accomplish, not at all. Microsoft didn’t hire just anyone, I bring things to Ask Leo! that no one else can, and I’m certain that my wife didn’t marry me on a whim. In each case, and in many more, it wasn’t that I went out seeking those specific things, but rather that I was somehow prepared for them when they came along, or I ended up becoming what was necessary once they caught my eye.

That’s not goal setting. Those aren’t dreams.

That’s being ready when opportunity knocks, and having the sense to open the door.

That I’ve lead a serendipitous life is nothing really new to me. It’s something I identified long ago, and as I said, something that I feel truly blessed by.

But when it comes time to get introspective, things can get frustrating.

Dreams and Goals and … Assumptions

As I said, I’ve allotted a significant portion of time to introspection and have gathered a number of books and other materials not so much to follow any preset programs, but rather to garner ideas (I call it “cherry picking” the best and most relevant ideas) and encourage thought.

The problem that I ran into very quickly is simply that the vast majority of self-help and personal growth materials make a very basic, often implicit assumption: that somehow, somewhere you have a dream of something that you’ve always wanted or that you have some sort of goal that you’re attempting to achieve with your life.

In other words, they start with your dreams, and move forward from there. (To be fair, some start by helping you to discover, uncover or expose your dreams and desires, since so many people repress them for assorted reasons, but the underlying assumption remains that there is something there to be discovered.)

That doesn’t help if you don’t have a dream. In fact, it can be downright discouraging and frustrating, and can lead you to think that you’re supposed to have a dream, all successful people have dreams and goals that lead to their success and if you don’t there must be something wrong with you and you’ll never be successful.


In Search of The Big Why

I actually had a model for what I was hoping to find out about myself, and that’s “the big why”. Basically what is your purpose? Why are you here? Why do you do what you do, and does what you do match what you believe your purpose is? What is it that you want to accomplish that gets you out of bed every morning?

A friend whom I deeply respect and admire, Jeff Walker wrote a blog post a couple of years ago now entitled The Future Of All Humanity, where he detailed what he considered his “big why”, and yes, it’s as big as the article title suggests. It’s big, it’s audacious, and it fits Jeff to a T.

So, I wanted a Big Why of my own.

After much reading, introspection and soul-searching I’ve come up empty, at least so far.

But I think I have something else that for me is just as good.

The Big What

You see, it’s not like I don’t know what I enjoy doing. Just call it “playing with technology”, among other things, for this discussion. The problem is that’s not a goal, that’s not a dream.

That’s not a destination.

It’s a description of the journey.

My revelation? My “goal” is my journey, not my destination.

I don’t really know where that journey will take me 5, 10 or 20 years from now, just like I didn’t know what today would look like 10 years ago. But I have faith that it’ll be someplace interesting, someplace valuable, and someplace successful, as long as I know and do what I enjoy and value to take me there.

The Little Why

Now, some may say that I do have a why, and it’s what I’ve described as my “what”.

Others may say that I can certainly use my “what” to make a “why”, and it’s true. In fact, it’s very likely that in order to provide some consistency to my work and my direction I will, indeed, manufacture a reason behind what I do that allows me to do the things I love in some productive way.

That’s not a Big Why. That’s not why I get out of bed in the morning.

I get out of bed in the morning so I can do the things I enjoy doing. If I pull together a framework, a reason, a direction and call that a “why”, it’s a “little why” at best. In a way, some would see it putting the cart before the horse. And I also acknowledge that others would say it’s exactly the right approach.

To me the difference is all about desire. My desire is, primarily, about what I do. Why is important, but secondary … and flexible.

It’s more important to me to enjoy the journey than to know where it will take me.