Living Your Dreams: Always Moving Closer

March 22, 2016

Are you where you want to be in life? Are you doing what you love?


Years ago, perhaps when I was a couple of years out of college, I was flailing around trying to figure out what I wanted to do with my life. I took a look at my friends and acquaintances, and when it came to this subject, I noticed everyone fell into one of a few groups.

The first group was made up of those most would consider the lucky ones. They knew what they wanted to do and they were pursuing it. These were often the people who had always known they wanted to be a _____. A doctor. A teacher. Fill in the blank with some career that generally has a pretty defined path to getting there. It might not be easy. It might take certain capabilities, it might take grit, it might take a ton of hard work, but the goal is clear and the steps are clear.

The second group was made up of those who had a pretty good idea of what they wanted to do, but didn’t have a clear path for how to get there. Someone who wanted a career in advertising but didn’t know how to break in, as an example. What I noticed was that the goals of this group tended to have more risk associated with them, or fewer guarantees of success. There were lots of people who wanted to pursue acting full-time, or to be professional musicians, or to be entrepreneurs in a certain area. There was just more uncertainty around the outcome.

The other thing I noticed was that the barriers that stood between those people and their goals very clearly came in a couple of flavors. Some people needed some external circumstances to work out in some way. They needed someone to take a chance on them, or even just a little bit of run-of-the-mill good luck. The other flavor, which was much more insidious, was an internal barrier… they just couldn’t get out of their own way. Take enough swings at the plate and eventually you’ll probably get a hit, even if you’re a tee-ball level hitter up against a major league pitcher. But if you spend your time concocting all sorts of excuses and complaints that keep you from even stepping up to the plate, you’re going to need a lot more than good luck. You might need a miracle.

The third group was made up of those people who didn’t know what they wanted to do. In other words, they didn’t even have a goal to pursue. They were lost. They might have been different degrees of lost, but they were lost.

I was a card-carrying member of this third group. If I’m honest, that’s where I’ve spent most of the years of my professional career.

At the time, I looked at the groups and remember clearly what I used to think. When it came to the people in the first group, the ones who knew what they wanted to do… I could see they were the minority. You might even say they were rare. But man, was I ever jealous of them. The sheer cognitive stress of not knowing what you want to do can be all-consuming. If you remove that and all that’s left is hard work? Hell yeah, sign me up.

As for the second group, well “the grass is always greener” applied there too. After all, how could I even get going when I didn’t know where I was aiming? At least these people had a goal. I was convinced that if I had a goal, I’d find a way to make it happen. That’s what I believed. So I lacked sufficient compassion for those struggling to get to their goal, or at least for those whose barriers were self-inflicted. It’s often easier to look at someone else’s situation and to see what they’re missing, but not to be able to see what you’re missing in your own situation. Sometimes it made me crazy. Just do this, I’d think to myself about their situation. If I actually said it to them, the response was often “But…[insert excuse].”

I’ve always had compassion for the third group though. No surprise since that’s been my home. Sometimes people spend time in multiple groups. (I have at least tasted what it’s like to be in group 2). But I’m convinced group 3 is the toughest. If you’ve ever spent adult years in group 3, after you’re allegedly supposed to have figured it out, you’ll know how painful it can be. Especially if you’re a passionate person, an idealist, or somebody who just really cares about this stuff in life. Because you’re stuck. And traditional ways of getting yourself unstuck are tough. You’re shooting in the dark.

I’ve written quite a bit about navigating through the challenge of being in that third group in the past. But today I want to talk about the second group… the people who have a notion of where they want to go (even if it’s a somewhat fuzzy notion) but aren’t sure how to get there. It’s just as easy to get stuck here. It’s a different kind of stuck, but it’s stuck nonetheless.

In my experience, there are only two principles of importance for people who find themselves in this second group.

The first principle is this: Keep your goal broad or flexible enough.

If your goal is too narrow or rigid, you are exponentially more likely to suffer because of it. Now notice I didn’t say anything about how lofty your goal is. Lofty goals are fine, as long as they are flexible enough. If you’re hell bent on being an astronaut, well, good luck I guess. I’m not saying stop trying. But if you are open to other outer-space-related dream outcomes, your odds of “success” go up, and more importantly, you’ll probably be happier as you navigate your path.


One other thing to mention about this first principle: Many people with overly rigid goals would think I’m somehow advocating giving up on their dream as they’ve defined it. Not at all. I’ve simply noticed that #1, you will probably be happier if you are open to a slightly wider target and #2, it’s often the case that we think one thing is the perfect outcome but it turns out we’ve miscalculated anyway. A little extra room for a little bit of trial and error goes a long way. And it’s good to keep in mind that external circumstances aren’t what we’re really after anyway—we’re after the contentment we think they will bring. There are shortcuts that take you straight to that contentment, and remaining flexible opens you up to one of those shortcuts.

But let’s talk about the second principle. And to do this, I’d like to take you back to my junior year of high school. This was the year I had the pleasure of applying to college. In the spirit of “wide target,” I applied to 11 schools in total. But some of these schools required you to apply to a specific program within the school. And my top choice had you apply to either their liberal arts school or their engineering school. In other words, you were being asked to narrow your playing field as a junior in high school.

I ended up applying to the engineering school. Truth be told, I didn’t even know what an engineer was or what they did. I was just told people who were good at math and science should do engineering. I was arguably only slightly better at math and science than other subjects.

Anyway, I went to the engineering school only to discover I didn’t want to be an engineer. But I didn’t want to start over and I was told by others “just because you major in engineering, doesn’t mean you need to be an engineer.” I was also told by my parents that it’s a great degree to “fall back on” if you have trouble getting another job. (Quite the risk-averse argument.)

Had I been paying attention in high school, I might’ve noticed that one of my favorite classes was sociology. I might’ve noticed that I had an interest in psychology. I might’ve seen that whenever I had free time after school and sports were done, I wrote short stories. Or I wrote music, played music, and played in bands. I did some theater. I wrote skits. I didn’t deconstruct a radio to see how it worked. I didn’t write code. I didn’t do anything a person with a true interest in engineering would do.

But so it goes, I was far enough down a path I didn’t want to turn back. Onward! Finished undergrad, and eventually enrolled in a Ph.D. program (in biomedical engineering) thinking I might like to teach at the college level. But somewhere along the way something like this happened:

Me:  I think what I really envision myself teaching is something more like psychology, or religious studies, or maybe sociology, but not engineering. I’m not passionate about engineering.

Someone:  Well then why are you getting a Ph.D. in engineering? Only a crazy person would hire you to teach those subjects with that kind of background.

(I dropped out of the Ph.D. program.)

Then somewhere along the way something like this happened:

Me:  I think I want to write professionally.

Someone:  With your background, you’d be a great technical writer, or maybe someone who writes about science.

Me: But I don’t want to do that kind of writing. That’s dry and boring.

Here is my point in sharing all of this.
I didn’t listen to some very important internal feedback early on. I pursued a path that on some level I knew didn’t fit, and believed I could right the ship later. But there was significant opportunity cost to that. Each day I spent heading down the imperfect path was a day I wasn’t making progress toward where I really wanted to be (even if I only had a vague notion of what that was, which is sometimes all you need).

There are so many hidden costs to this. You are learning skills that may be transferable, but often aren’t as useful as the ones you’d be building if you were directly targeting your real goal. You are building relationships and connections that are much less likely to help you reach your true goal. You are burning valuable trial and error time that could be spent feeling your way toward your real goal when your goal isn’t 100% clear.

And perhaps most costly, it gets harder to pull the plug and reset as time goes on.

I’m the first to stand up and shout to the world that anyone can rewrite themselves no matter how old they are. And I believe that down to my absolute core. I’m a huge cheerleader for that team. But I’m also the first to tell you that I’ve experienced firsthand how it gets harder to switch the further down the wrong path you are. There are forces of momentum at play. And certain phases of life add complexity. And if you’re not careful, success at the wrong thing really can lock you in forever. It almost did for me.

So the essence of the second principle is this: when it comes to your goal, always move closer.

Here is what I mean. We are continually faced with decisions. Some are the big ones that are obvious to spot (although not necessarily easy to navigate with this principle in mind) like where to go to college, what to major in, whether or not to take a job or a new role, whether or not to move… the list goes on.

But many decisions fly under the radar because they seem small. These involve how you choose to spend your time on a day-to-day basis, which projects you pursue, what you tell people about your goals and plans, what you choose to say yes and no to, and so forth.

And the orienting principle through all of these decisions is the same regardless of the magnitude of the decision. Does this seem like it moves me closer to where I want to be or who I want to be? If yes, great. Go for it. If no, have the strength to move in a different direction.

It really is that simple. Trust me, it isn’t always easy. I’ve made so many mistakes it’s unfathomable. But the principle is so basic that if you can train yourself to spot those moments and use the principle to guide you, you’ll be far less likely to write a blog post about your unfathomable string of idiotic mistakes a decade or two later. (You can call me in a decade or two and we can compare notes.)

And how about if you don’t know what your goal really is? What if you have one foot in group 2 and another in group 3?

Certainly it can make things a little bit more challenging, or more accurately, just a bit more subtle. But it still works. If you really listen, if you really turn inward and tune into what self-awareness is saying to you, even your vague and cloudy notion of who you want to be and the life you want to live lets enough light through to guide you. Listen to that. Treat even the small decisions like your dreams depended on them. And ask the same “moving closer” question. If the answer is yes, move in that direction. If no, have the strength to move in a different direction. Rinse. Repeat.

You don’t need your path to be a straight line between A and B. It won’t be anyway. But if you’re always moving closer, you’ll find yourself somewhere you truly want to be.

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