If you asked me what I do, I’d probably give you a nondescript answer and get on to more interesting topics. Fact is, I “do” a lot of different things. This whole “What do you do?” question is a relic from an earlier era, before it was possible to “do” 30 different things. I am not salaried, so I work on my professional, personal, family, and global objectives each day. A little business, a little reading, a little history, a little art, a little self-discipline, a little philosophy, a little technology, a lot of different things.

But if you had to nail me down to three words, I’d say, “I’m a strategist.” Nine words? “I’m a strategist. I figure out how to win.” 15 words? “I’m a strategist. I figure out what is winning, and then how to get there.”

The first part of strategy is answering the question, “What is winning? What are even working towards? What are our highest level objectives, and why do we have them?” This is typically known as grand strategy.

Grand strategy is figuring out what the goals of an organization or a solo person ought to be. Arguably, this is the hardest part of strategy, because there is no right or wrong answer. It’s subjective. And if you work on the wrong stuff, it doesn’t matter how good of a job you do at it.

That’s worth saying again. It doesn’t matter how good of a job you do bringing your vision to reality if your vision was poorly chosen.

As Peter Drucker said, “There is nothing so useless as doing efficiently that which should not be done at all.”

Most people don’t think about grand strategy too often. They’re on the course they’re on, and they maybe try to optimize that course sometimes. But they don’t study, self-analyze, introspect, meditate, gather new data, get new perspectives, study history, look for parallel situations in history. Grand strategy is hard. Saying, “Out of every possible thing we could do, this is what we’re going to do.” That’s not easy. It requires a sharp, active, discerning mind, but more importantly it takes a lot of fortitude and courage. When you set grand strategy, you could be wrong. And if you’re wrong, a lot of stuff is going to go wrong.

On an individual level, grand strategy is probably called “goal setting” or “planning” or “dreaming” or “thinking big” – something like that. Most people don’t think about this very often, probably less than once a year after they’re solidly in their career. Me? I try to look at my overall large goals, dreams, and big plans at least once every week or two. When you’re firmly established in a good direction, you can do this slightly less – every two to three weeks, maybe. When you’re getting started on a new path, looking at and thinking about your grand strategy daily would be time well spent.

After grand strategy comes strategy. This is roughly “the big picture way that we’ll get there from here.”

I was trying to write to define strategy for you, and having a hard time. I looked up all sorts of definitions, and they’re all hazy and ugly and not very clear. After 20 minutes of thinking about it, I realized why.

Strategy are big pushes you’re going to try out to see if they get results.

Strategists and such like to pretend we’re doing a precise thing, especially when the stakes are high. But we’re not. We’re looking at the past, holding as many examples of similar-but-not-quite-the-same examples in mind, and trying to use that to make good guesses about what will work. Then we try those.

The reason strategy is so poorly defined is because to some extent it really is guessing. Educated guessing, yes, but guessing none the less. Now, I think a lot of people of my trade would disagree with that, probably because it implies anyone could do it and it’s not important. Oh, no, not at all. Because strategy is really educated guessing, that means you need very talented and broad-sighted people making those guesses.

It’s difficult to do, and even the best strategists don’t get everything right. The harder and more important the problems you’re working on, the less likely your first guesses as to strategy will pay the results you think they will. Thus, you need to adapt your strategy as you get more information. Many people get emotionally attached to the old strategy they put forwards – this leads to very bad places. But on the flipside, you can’t give up too easily. Figuring out when to tweak your strategy, when to scrap it in favor of a new strategy, and when to double down for results – that’s what a good strategist does. All the while, you need to be aware of your emotions and not let them cloud your judgment.

So you’ve got grand strategy – the highest level goals, the “why?” of the whole thing. Then you’ve got strategy, which answers the question “how?” Finally, you’ve got tactics, which answers the question “what?”

Tactics are the specific implementation of your strategy. Tactics are small-sized chunks of actions that are designed to put your strategy into action.

Good tacticians are incredibly valuable and are rare, but are slightly less rare than good strategists. That’s because the learning curve on tactics is shorter. You can figure out one or two effective tricks and get good at them in any field reasonably quickly, within a year or two. Becoming a strategist requires study of as many different fields as you can find, and how people won or lost in those fields. How a style of painting became dominant or how a religious organization became dominant through its use of missionaries – these might seem like trivial historical details with no bearing on the modern world, until one day you make a mental connection between a style of painting becoming dominant and a new sort of hardware becoming the technology standard, or realizing that the same strategies used to convert and expand a religion can be applied to get people to join your online service.

Strategy is difficult. I’ve said my goal is to be the greatest strategist of my generation, but I don’t expect it to happen any time soon. I study who wins and loses throughout history, and why. Anything from painting to theology to warfare to inventing to trade to dominant standards to government structures to banking and finance to morality to philosophy. Why this, and not that? Why here, and not there? Why this outcome here, with this totally opposite outcome there?

In truth, I’ve neglected my skills as a tactician a bit, and focused on the more abstract levels. This is an okay starting point, but it doesn’t pay the rent. Tacticians need to be more decisive and fast-acting, less ponderous. Outside of a couple fields where I have a solid expertise, I ponder too much – I should make mental divides between when I’m doing grand strategy (goals, highest objectives, “why”), strategy (gameplan, roadmap, “how”), and tactics (action, motion, “what”). Grand strategy should be built carefully and then committed to fully. Strategy should be decided less carefully – usually you can devote a small amount of resources to exploring a new strategy tangential to your main one, so long as it supports your grand strategy. So, strategy can be done a little more quickly. Tactics should be decided fast – there is an instinctual and reflex-based aspect of tactics, where something occurs to you that it might be correct. You need to listen to that instinct and try these new tactics as soon as possible, then document the results and refine. Good tactics should be tried, refined, and implemented lightning-fast, so long as they fit with the strategy, seem workable, and you’re not risking too much by trying them.

So, what do I do? I’m a strategist. I figure out what winning should be, how to win, and then put this into motion. I’m starting to get a grasp on strategy, the lessons I’m learning from history, business, culture, governance are starting to converge a little bit, I’m seeing patterns. My notions of grand strategy are developing more, but I expect this to take longer. Going forwards, I ought to become a better tactician. Specifically, a faster tactician. Failure at tactics is okay, especially if nothing is too much at stake.