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Tuesday, August 22, 2017 Leer en Español

How to Map Your Ambitions and Navigate Your Career

This strategy will work for people in all stages and all walks of life.

One of my deepest fears is waking up one day and living a life that I did not create. I’ve met far too many people – young and old – who realize they are living a life that they fell into rather than one they consciously created only too late to do anything about it.

I’ve written about the dangers of lifestyle inflation and the golden (and copper) handcuffs for this reason and worked with people from dropouts to Ivy League grads for whom this is a problem. It doesn’t need to come as waking up as a homeless person on the street or as an overworked executive, either.

The ambitious, hardworking high achiever is particularly apt to fall into this trap as he often has more doors open to him and more choices available than the passive slouch. His labor and time are of higher value to all parties at the table so they expend more resources to get him to work for them and to convince him that it’s in his own best interest.

Large established companies – from Apple to Goldman Sachs – pour hundreds of thousands of dollars into recruiting a handful of candidates from specific campuses, convincing them that their paths together are the candidates’ destinies.

Until they’re not.

Otherwise happy and successful, a person living this life is by all means better off than somebody fending off feral cats under a bridge somewhere but lives a life of sacrificed opportunity. Going by salary or by earning potential, things look cheery. Going by unique contribution and autonomy expressed through work and life, a gloomier picture emerges.*

How does this happen?

The Labyrinth of Life

To get an idea, imagine a labyrinth full of doors. This labyrinth has plenty of exits and different paths you can take. Some paths even lead to the same exits as others, although it may take a little longer. As you progress down the labyrinth, you get the option to keep on the given path or to take a door as you pass it. You can always go through a door again later but only if you can find your way back to it in the labyrinth. You also have an idea of who else has gone through which doors but only when you get to the door. You may see that John, your friend with the fancy investment banking job, has gone through door 6 when you get to it, but you aren’t told which doors he went through beyond that until you get to one.

In itself, getting to a specific outcome is difficult enough. When you come upon a door and you see who else has gone through it, you’re tempted to take the door for fear that you won’t have another, higher-value door open to you later upon the path. You see people you admire (or worse yet, envy) on the door as past entrants and figure, “that’s pretty good,” and pass through.

There’s nothing inherently bad in the labyrinth of life.

Eventually, you get an ad hoc collection of door choices. Doors 1, 6, 26, 367, 368, 391, and 503, for example. The only thing they have in common is you. In and of themselves, they each present a decent life or set of possibilities for what you want but they are certainly not actively chosen.

If this were how life plays out and how we can make choices for our future, there’s nothing inherently bad in the labyrinth of life – but it isn’t how life plays out and it isn’t an accurate way of thinking of your choices.

“The open road still softly calls, like a nearly forgotten song of childhood.” – Carl Sagan

Life is more akin to a labyrinth with a map. If you’ve ever played a maze game in a magazine, you know that in order to win, you have to start at your destination and track back to the starting location. Unlike most maze games, your starting location in life is different depending on your circumstances, so it may take a few attempts at tracing backward from the destination in order to get to where you are.

If you watch a child or somebody unfamiliar with maze games try to solve the maze, they start where they are and then work forward, guessing and inferring what the best directions are in order to get to the destination. Ultimately, they get frustrated, give up, and say how playing a maze game is stupid anyway. When you’re playing with a magazine, you can throw the game down and walk away, but when you are playing in life, if you walk away, you stay the course with the path you are on.

Everybody else just takes the choices available to them like the child playing through a maze.

This is how far too many people play through the labyrinth of life. For planners and over-achievers, they base their path off of other people (who often base their path off of other people basing their path off of other people basing their path off of other people…etc.)**, for everybody else, they just take the choices available to them like the child playing through the maze game.

But what if you had the map?

Ambition Mapping

If you had a map to navigate a labyrinth, you know you should trace your way backward based on your destination. You adjust your path based on where you start relative to where you want to go. People know this when playing a game and know it in general when choosing a career (i.e., if I want to be a doctor, I should go to medical school) but rarely re-examine their path using this through their careers.

This process of regularly looking at where you want to go, evaluating where you’re starting, and working backward from the destination to where you are now is what I call ambition mapping.

Ambition mapping is the process of continually reevaluating where you are right now relative to where you want to go. Rather than starting where you are, though, you have to start with the destination and work backward. Unlike conventional mapping where you have nicely labeled doors, exits, freeways, and street signs, other people who have gone before you are the closest things you’ll get to a guidepost. You end up using a process known as reverse induction to figure out what turns and twists you should take.***

You have to constantly ask, “What do I want to be when I grow up?”

The problem is that most people only do something like this once or twice in their lives. “What do you want to be when you grow up?” is a question asked of young children and people getting ready to leave school. “What is your major?” becomes a heuristic as you get older, but after college, this question is never really asked again.

You have to constantly ask yourself, “What do I want to be when I grow up?” if you are going to get to the right destination in the labyrinth. Unlike a maze in a magazine, this labyrinth has different destinations and is constantly changing. The map you put together upon entering graduate school may no longer be relevant and new paths present the best options forward. You, too, change while going through it. You may follow a map that, at 15 or 16, made the most sense to you but at 21 or 22 terrifies you. Failure to reexamine where you are relative to your ambition and the routes available to you results in you living out somebody else’s path.

How to Practically Use Ambition Mapping

Once you understand that getting where you want to go is a constant process of evaluation, action, and reevaluation, you have to actually use it. Consciously setting time aside to review where you want to go and where you are is the best approach. Doing this while multitasking or working on something else is something I think most people actually do but get so caught up in the mechanics of life that they never act on it. You realize, “this isn’t the path I want to be on,” but then the phone rings, there’s somebody at the register, or you have to run to an appointment. Take the time to think solely about this, undistracted.

Your ambitions are your destination.

Your ambitions are your destination. The big, lofty, inspiring things you want to accomplish during your life require certain achievements to happen. The more details to your ambitions, the better. While something is better than nothing, more specific outcomes require more specific actions. “Live like a millionaire” can be done without actually being a millionaire. “Run a business with 3,000 employees and have an office on the top floor of the tallest building in town,” is better but can be even more specific. If you have a specific job or title you’d like to achieve, note that. It doesn’t matter if you do this collectively across goals (i.e., financial, personal, professional, health/wellness) or individually for each category.

Then, work back from the goal. What big, significant milestones would have to happen in order to achieve that goal? If you want to start your own contemporary art museum, for example, you may need to to collect art, get buy-in from artists, assemble a board and donors, raise money, find a site and property for the building, gauge interest – there could be any number of significant steps.

Write these down and put them in the best logical order. You’d probably want to raise money before purchasing a site and opening the facility. You’d probably want to get artists to agree to have their art exhibited before going and putting together a board. You may even want to collect art for the first showing first. Even easier, you may want to organize a community art event to show traction.

If you can’t figure the events out, do research.

Be as detailed as you can be. The further off the milestones are, the less-detailed they will naturally be, but the more you can figure out has to happen in between milestones, the better. If you can’t figure the events out, do research. Talk to people who have done it, read their books, listen to their interviews and start filling in the blanks.

Order these events in reverse chronological order, then. The ones that have to happen last are furthest in the future. The ones that have to happen first in order for later ones to happen are listed sooner.

Now ask yourself: Are there any things on this list you can take immediate action on making happen?

If the answer is no, you have two options.

Either: you need to do more research and make your action items and milestones more specific. Generality is the enemy of overachievers. Make clear, definite, finite tasks that can be assigned to somebody and have clear standards of success and failure.

If you do this and you still can’t act on anything, then comes the Or.

Or: Your ambitions and your current life setup are off. You need to make adjustments in your current life setup in order to align it with your ambitions. This doesn’t require quitting your job and backpacking across Europe. You may simply need to start attending events run by people in a specific community you want connections in, or you may need to pick up freelance clients in between your day job, or you may need to get a gym membership and block off time in the morning to work out. Whatever it is, the gap in between your ambition’s action items and your current setup is a signal that you need to adjust the setup of your day-to-day life. This realization should be uncomfortable – the lack of discomfort is what allowed the ambitions and the life setup to get out of whack in the first place.

How to readjust your life is the subject of another post.

*This doesn’t even take into account darker scenarios where the person we’re considering is at the force of negative life forces. When you drift into success you are more apt to drift into failure. An economic downturn, an unexpected loss of a client, some family problems, or health issues come out of left-field when living a life created by others.

**Finding role models and imitating people who have achieved things you want to achieve is actually a good thing if you know why you are choosing them. To know why you have to know where you are going in the first place. Envy makes for ad hoc models, planning makes for deliberate models.

***See my interview with Jason Brennan, Ph.D., here for a great example of reverse induction. Jason knew he wanted to become a prominent philosopher and started with essentially nothing. He looked towards people who had become prominent philosophers and knew he had to at leastimitate him to get to that place.

Reprinted from The Mission.

  • Zak Slayback is a venture capital and private equity professional and a small business owner. He is the author of How to Get Ahead (McGraw-Hill, 2019) and wrote the foreword to John Taylor Gatto's Dumbing Us Down (New Society Publishers, 2017). He lives in the United States and writes at He is a Eugene S. Thorpe Fellow and FEE alum.