We all want so many things. I want to be a bestselling author, a globe-trotting consultant, a retired president of a yacht club, an expert explorer of the Pacific Northwest featured on the cover of some outdoor magazine, a musician, and a graphic artist. A professional videogamer. The host of a popular podcast. A world-class chef. A tech executive. A data scientist.

I’m not kidding. I’ve actually wanted one and all of these things at some point. Anyone with a modicum of curiosity and the ability to dream has wanted even more. Yet, it turns out that most of us aren’t any of these things. We’re not failures, losers, or nobodies. We just aren’t these things we flirted with for some time.

Why haven’t we become our aspirations? Rudyard Kipling said it best:

If you don’t get what you want, it’s a sign either that you did not seriously want it, or that you tried to bargain over the price. — Rudyard Kipling

Wisdom Learned The Hard Way

A less-knowledgeable version of myself would have been offended by this line. Especially when it comes to the part about being an author. How dare Kipling suggest I didn’t want to be a bestselling author? I wrote multiple (unpublished) books. I submitted them to hundreds of agents and publishers. I did everything I could!

Except I didn’t. I didn’t do everything one could do. I didn’t go to conferences, network with people, didn’t self-publish and fund my own DIY booktour. I didn’t hire my own editor to help me with the fourth draft. Aside from an online volunteer writing group, I didn’t have anyone read the books when they were done. No one read my books prior to submitting them to an agent.

Which is to say, I bargained over the price. I wanted to do it my way, the way that emulated my favorite author of the time (Stephen King) as explained in his book on the topic (On Writing). I had one way that I would do it and brooked no conversation of any other strategy.

Then, over the course of ten years, the steady rejection fueled by this flawed approach caused me to stop. Because at that point, to Kipling’s claim, I didn’t seriously want it anymore. It was far too painful.

There is an inescapable truth to what he says in this quote and it might be the biggest reason I love the topic of strategy. Because strategy is the way we can better understand what, exactly, it will take to achieve the aspirations we so easily toss out in those moments of hope.

Thinking It Through

This is easily understood when you look at the central framework from the book Playing To Win. Though the book is focused on business strategy, it provides wisdom that is useful for any endeavor. To aspire is human; to build the strategy that can get you there is divine. As shown in the graphic below, our aspirations are the launching point for figuring out what we’re going to do and how we’re going to win. But from those aspirations, we must continue to consider the full cost of the approach, the steps along the way, and the dependencies that it entails.


There’s a lot here that deserves a lot of study. But for now, let’s just consider how this graphic makes it plain that the things we want (the aspirations) must be tested and simulated through a cascade of additional, integrated choices we must face. Most people, my younger self included, don’t think this way. We don’t “think it through” when we begin the pursuit of our dreams.

In my case, I just knew I wanted to be an author and so I started writing books. That can be enough, sure, but there is no reason to not think through these other questions. Even the last question, though it might seem like anathema to an aspiring artist. Management systems? What does that mean? We’ll cover that later.

For now, consider every aspiration that you have. With respect to Kipling’s wisdom, do you really know what the pursuit of that aspiration will cost? Are you willing to pay that price? If you’re going to bargain, why? And how much?

It’s Not A Plan

Now you might think this graphic is showing you the elements of a plan. It’s an easy mistake to make. We know that plans are a list of things that we will do. Anyone can whip up a plan at any time. And be deeply seduced by it the way a recipe will seduce me into thinking I can be a chef. To maintain skepticism, as well as confront reality on reality’s terms, you need a strategy.

A strategy is a plan tested against the element of competition and for the explicit aim of winning. The distinction is really important and easily misunderstood:

A plan defines what you will do.

A strategy defines how and why what you do, and when, will lead to success.

A plan gives you the price for doing what you want to do.

A strategy gives you the price for making what you do a success.

My earlier journey to become a bestselling author was built on a plan. But not a strategy. I knew I was going to write a book a year. It was going to take several hundred hours and six months’ time while writing two pages a day. When the draft was complete, I would switch to short stories for a six-week period while the book “rested”. Then I would return to the book and do a second draft over the next four months. This process would rinse and repeat three times before I would send it to a list of fifty literary agents so that they could reject it at their convenience.

That was the plan to write a book. That wasn’t a strategy for being published.

A strategy checks each of those steps and tests it against what is necessary to achieve the aspired success. If you went through the plan I just devised and asked the simple question “How does this step help Norm become a bestselling published author?” and “What other steps are needed to help Norm succeed?”, you could devise several more actions or sequences that would undoubtedly improve the odds.

But you can take it one step further and apply the cascade of choices model. Now the plan is tested against certain questions that are otherwise never considered. Have I really decided where I will play? In terms of genre category? And are my capabilities really, really in place? How do I know? What will it take to gain those capabilities?

I’m using the imperfect example of one person striving to become a published author. But it still works. The point is that this fantastic model helps us go beyond the simple planning of what we want to do and think of how and why, exactly, that plan will succeed. By honestly assessing these questions in the cascade, we can test the hopes and dreams, attack the assumptions, carve a real path, and call it a strategy.

One with a clear price that we can then either accept and move forward or abandon without any further investment.

Rudyard Kipling undoubtedly learned this the hard way. I did, too. But the wisdom is here for us to not make that mistake again. Do the hard work of transforming your aspiration into a strategy and you’ll learn what you must do and, more importantly, the price you’ll need to pay. Then you’ll know just how much you want it.

Does that spoil the dream? Not really. The dream is invigorated by this work because it gives you a real foundation for the dream to stay alive. A dream cannot be enough. So I’ll close with a pithy line of my own:

Strategy is a gentle attack on blind hope so that you can trade it for an insightful plan.

Photo by Ahmet Ali Ağır on Unsplash