Some Unsolicited Advice #24 (if we don’t know where we’re going, we’ll most certainly never get there)

A while back we started a series in which I share some completely unsolicited advice… if you’re looking to pick up from the beginning, you can do so here, or read all the subsequent posts here.

Long story short: I wrote a book that you can read here; however, instead of leaving it as an e-book that very few people will ever read (it is titled “Some Unsolicited Advice” after all), I figured it’s worth sharing the points and lessons learned in a more consumable format, as a rolling blog series where I add one or two new items every now and again (depending on how much time I end up having), making for quicker and easier reading than dumping an e-book and calling it a day. And in this way, over the course of a year (or less, depending on the cadence), all the points will get shared in bite-size, more easily readable chunks. Today, we’re moving on to #24… Let’s get to it!

24. If we don’t know where we’re going, we’ll most certainly never get there.

?Where do you want to be in six months? How about a year? Two years? Five?

This seemingly simple and innocuous series of questions was asked of me recently, and quite frankly, it took me by surprise. A lot.

My answers at the time were pretty weak. In six months, I more or less expected things to look the same way as they do now, just with maybe more money and responsibilities, or something like that. In a year, well, uh, I guess the same thing. Two years? Um, shit. The same again… just with even more money and responsibilities? And five… well, you get the idea.

None of these were awful answers. Continuing on my current trajectory wouldn’t be the worst thing to happen over the next period of time, but is that it? Is that who I’m going to be for the foreseeable future? Me, just older? That can’t be right. I have aspirations and want to do things… big things! But when were those things going to happen? At some point, I know I want to be a successful author, musician, and politician, but none of that is on any clear timeline. So, what happens between now and then? And how does my now help me achieve any of my later goals? This isn’t all that dissimilar from the very first point of this whole book (about living with intention), but despite the similarities, I’d never really made a connection in my mind.

At face value, it’s not a tough question, but I was a little taken aback by it. How do I expect myself to be different six months from now? What do I need to do in the next six months to help advance the things that I want to do in 12 months or beyond? And if I can get an idea of what the looks like at a macro level, then what do I now need to learn or do to get there?

These intuitive questions are ones that I’ve routinely failed to ask myself. If I hope to be X within Y years, then what do I need to be doing now to get there? In the back of our minds, when asked these questions, we all have some vague image of being retired on a yacht and hanging out with billionaires, but that’s nothing close to an actual plan (much less an even remotely realistic possibility). So, what job or position would I like to see myself in over the next few years? And this doesn’t have to just apply to work. What do I know, where do I live, who do I hang out with, and so on? If I don’t know where I want to be, then how could I possibly be taking the right steps right now to ensure that I get there? And the next 12-36 months do not hold a candle to the existential crisis of asking about five or ten years down the road! I’d somehow like for this book to sell a trillion copies and to play sold-out concerts across the globe, but even if that’s the moonshot plan, what do I need to learn or do over the next week, month, quarter, or year to have a shot at arriving there?

Things can also get interesting on the more macro time horizon if we abstract money from the equation (pretend you just won 100 million). What does life look like now? The ol’ career counselor question of, “what would you do if you didn’t have to do it for money?” Just like you, I’d like to be rich, but what happens when you get everything you’ve ever wanted; then what? It certainly sounds appealing to party every day, but after even just a few consecutive weeks of day drinking on your yacht, what comes next? As much as drinking, sleeping, playing games, and eating are fun, too much drinking will kill you, too much sleeping begs the question of what’s all this money for, and too much eating will just make you fat. So, what fills the time between the parties, naps, and dinners?

For most of us, we’d still engage in some form of work after all the galivanting and globetrotting ends, regardless of the form it takes. We probably wouldn’t choose to be coal miners, but even with infinite money, we’d likely end up doing some sort of work (or maybe it’s just me), even if it’s charity, writing, dancing, running ultra-marathons, or whatever. What would you choose to do, and how would you do it? What steps could you take in the next six or twelve months to do as much of that as possible? This isn’t me up on a high horse. I’m asking these questions of myself right now in real-time, and they’re not easy to answer.

At the end of the day, billions of dollars or not, if we don’t know where we’re going, we’ll most certainly never get there. If all I’ve got are vague ideas of being super rich with no defined route on how to arrive there, then you can be pretty damn sure that I’m not going to somehow magically become King Midas. And we all know this to be true (as we’ve discussed previously). Intuitively, we all understand that one cannot expect to start wandering in the middle of Ohio with the hope of arriving at El Dorado someday and then be confused or upset when they don’t arrive. That just doesn’t work, and it’s an awful life strategy because without a plan, ten years down the line, you’ll realize that you’ve more or less been going around in circles (or worse, going backward, or even worse-worse, chasing something you never wanted in the first place). If your answer is that you want to just do the same thing you’re doing for the rest of your life, I would challenge you to aspire to more, though I’m sure most people do. How many people actually dream of slow, painstaking, methodical career advancement? Not many. So, what are your aspirations, and what’s happening over the next six to twelve months to move the needle to get there? (again, I need to answer this myself)

What I’m driving at (and as it’s been alluded to in previous points) is that it helps a lot to have some goals and a clear understanding of where we’re going. Nothing has to be immutably set in stone, as priorities can (and do) change; but just by having our goals clearly outlined, we now have a point on the map that we’re moving towards, and we can then ask ourselves daily, “Have I, or how will I move the needle today towards said goal?” And in this way, we can hold ourselves accountable for what we aspire to - slowly but surely moving towards whatever our end goal is. Sometimes, by understanding what we’re after, we may even realize that we don’t really want it or that we don’t need much more than what we’ve already got in front of us. At the bare minimum, by at least considering it, we can recognize that there’s likely a whole lot more we could be doing to move the needle today than we originally thought.

We’ve talked about it in other places, but to say it again, by having clear goals, we can better understand what it takes to get there and then start doing those things. For instance, if my goal is to be a great singer, then it follows that I should probably be taking some singing lessons and practicing for at least a couple hours every day, even if I’m already a decent singer. If my goal is really and truly to be a great singer, and I’m not taking singing lessons, or working to improve my singing ability in a substantial way, then it has to call into question the seriousness of (and my commitment to) the goal. Maybe that’s not what I want after all? Maybe I just thought I wanted to be a great singer, or maybe I don’t need to be a good singer, and what I really need is a muse to sing about. Well, if that’s the case, what’s our goal with a muse, and where do we get started? And in this way, we can then revisit and adjust our goals accordingly as we go.

This feedback loop has an intensely powerful and potentially life-altering effect. For instance, one of my present goals is to publish this book in the next six months. However, if I really mean that, then I have to hold myself accountable for progress each and every day, asking myself: did I move the needle on finishing and getting this book published today? If the answer is ever “no,” then I have to critically evaluate where I chose to spend my time instead, ostensibly on something that I decided was more important than getting this book finished. Sometimes there are good reasons, but most of the time, there aren’t. Maybe I was tired, so I chose to watch a TV show or go to bed early; maybe there was a party that needed attending or a work matter that sprang up, and so on. Nobody said this shit was easy, but if I’m going to ever finish this damn thing, that means waking up day after day after day and getting after it. And hey, once I put a few hours into moving today’s needle, I get the added benefit of feeling pretty damn good about myself. Today, I’m one step closer to my goal, and that’s enough. And if we can just string enough of those tiny steps together, we’ll suddenly find ourselves a lot further along than we ever imagined we’d go.

As always, this (and every point) applies both in the macro sense (life, as a whole, etc) as well as in smaller ways as well (individual projects, etc). Knowing where we’re trying to go, regardless of what we’re doing, is an essential component to arriving there.

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And that’s it for this round! Of course, if you want to skip ahead at any point, feel free to buy the full book on Amazon here. Thanks!

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