Career Planning: The Complete Guide

Do you have a career plan?

I’m sorry, that was a loaded question. Most people think they have a career plan, and according to everything they’ve been told their entire life, they do.

The problem is we’ve been lied to. As a child, you were taught two things:

  1. How to set a big goal for your life. You wanted to be POTUS, CEO, a star, or a fireman (obviously, the coolest choice.)
  2. How to do the work you’re assigned. In school, you learned how to be on time. How to complete assignments. How to follow instructions. You learned that the path forward in life is to do the work you are given until the person in charge says, “Okay, you can move forward now.”

As a result, most of us plan our careers the entirely wrong way. We set a big goal for our life, and then show up to work every day and grind. The path forward to us is, “Work harder and I’ll get there.”

That’s not a plan. That’s a dream.

Dreams are great. You need something to aim for, and you should never sell yourself short by aiming small. But when you wake up from dreaming big, you need a plan to get there.

Over more than a decade of research I created a five-step system that is designed to get you from where you are in your career and life today, to wherever you want to be.

Step 1: Define What You Want

When you get in your car, you know exactly where you want to go today. You’re not thinking about where you want to drive tomorrow or 10 years from now. You know the exact location you’re headed to, and you know how you’re going to get there. Even if you don’t know the route, your GPS only works if you give it a specific destination.

Without a plan, you’d just be driving aimlessly — burning through gas, wasting your day — using a bunch of energy for no reason whatsoever.

As obvious as this seems, most people approach their workday the same. They know where they want to be ten years from now, but they have no idea where they want to be tonight.

Most people are aimless because their goals are outcome-oriented.

In my article on how top CEOs set goals, I explained the approach that separates real winners from the rest of the world. Top performers set goals that are process-oriented.

For example, let’s say you’re just starting your career in sales. You’re working in an entry level position, doing a lot of cold-calling. You probably have a monthly goal you’re trying to hit, a sales quota, or dollar revenue number.

If you just decide to show up every day and work hard hoping that you hit your number, you might, but it’s more likely you’ll fail. You can’t drive today if you’re thinking about where you’re driving every day for the next month, and you must drive your success in the present.

Instead of focusing on the big number at the end of the month, change your goal from an outcome to a process.

Don’t think, “I’m going to make this many sales this month.” Instead, commit to a goal like: “I’m going to call at least 20 leads today, with the goal to ask at least 5 questions, keep each of them on the phone for the duration of my script, and close more than I did yesterday. At the end of the day, I’m going to reflect on my process and look for improvements.”

Do you see the difference? You’ve set up a repeatable process for yourself that you can execute on every day, and you’ve also baked in a way for you to continuously improve. 
Define what you want by the process that will get you there, not just the ultimate outcome.

Step 2: Know How You Win

Look, in the end, success is easy: Are you better than your competitors? In a foot race it’s simple, and in every facet of life it’s the same. Winners get clear on what it takes to win, and they build themselves into the person who can do it.

This requires getting very skilled at building and putting to work your winning strategy, which demands that you collect a lot of information about the world around you, and more importantly, about yourself.

Studying how other people win is very useful, but at the end of the day, you aren’t other people. Sure, Arnold Schwartzenegger’s strategy led him to Mr. Universe, but you aren’t Arnie. You have your own unique goals and makeup, that requires you to build your own unique strategy for success.

This might seem complicated, but I’ve broken it down into three key steps that make building your own system incredibly simple.

1. Find Your Role Models

Success leaves a trail. Follow it.

In every pursuit in life, someone else has figured out how to win. Ask yourself what they did, and do some of that too. Now, we’re not just talking about what makes other people successful, you also want to know what leads others to lose.

You want to go as deep as you can on this, collecting as much intel on winners and losers, but you also want to recognize this isn’t just a cut and paste job.

As I wrote about in my article on effectively using role models, the key here is to have multiple role models who each individually exhibit the winning qualities you like, which you then combine into your “Composite Role Model,” or “Character.”

Doing this you might find that you can grab the charisma of one person, the self-control of another, the work ethic and fight of a third, and the wit of a fourth, which you then use to practice these “Character Traits.”

2. Know Your Guiding Principles

In his memo Principles, revolutionary thinker and leading hedge fund manager, Ray Dalio defines principles as “…concepts that can be applied over and over again in similar circumstances as distinct from narrow answers to specific questions.”

You may have a million different methods and strategies to get what you want, but if you’re doing it right, you will only need a handful of principles to guide those choices. In my work on Wall Street and with my clients across industries, I’ve come to see these five principles as the most crucial to professional success:

  1. Performance. Nothing else matters if you can’t deliver. This doesn’t mean you need “30 Productivity Hacks!” It means you need to figure out how you win and show up and crush it every day. For example, if your performance is nearly entirely driven by calling more sales leads, clear your desk and start dialing for dollars.
  2. People. Every professional business is a people business. Literally, nearly every aspect of business involves people so if you want to get good at business, well, get better than good at working with people. I’m not just talking about mastering the basics — How To Win Friends and Influence People, Influence — systematically become excellent at the skills you need to create success with other people.
  3. Process. Every thing in your life happens through process, an example of which are habits. You don’t need to think about how you get ready in the morning. You don’t need to think about how you get from the start of a project to the end, when you are a master of process. Every day, look at your winning process the same way a mechanical engineer looks at a manufacturing process — focus on sequence, steps, and workflow while continuously enhancing efficiency, effectiveness, and quality.
  4. Destiny Control. Jack Welch said it best, “Control your destiny or someone else will.” If you’re not taking control of your career, then nobody is, and your career is out of control. Not only is this crucial to guiding your career to where you want, but in my article about being recession proof, I talked about the many rounds of layoffs I’ve been through and those people who landed on their feet: They were the ones out ahead of it, preparing their resumes, seeking their next gig. They took control.
  5. Managing Perception. If your firm doesn’t perceive you as valuable, you aren’t. This runs contrary to a lot of traditional advice, but it is a simple truth of business. There is simply no definition of “value,” which is why it’s not completely stupid for Snapchat to be “worth” $20bn. Stupid are the people who form that perception, and smart are those who can create such perceptions of value in others… Constantly be aware of how you’re perceived and what you can do to manage it.

3. Develop YOUR Strategy

Whatever you learn in the previous two steps is about as helpful to you in getting what you want, as reading the thousands of mostly useless self-help books…

Sure, it might be the best way that I can imagine to build your strategy, but until you have your own custom-built strategy that is specifically tailored for you, you’ve got nothing!

Seriously, LeBron might have looked up to Jordan his entire career. He might know every single one of his plays. He might have rehearsed them billions of times. But until LeBron takes what he learns and develops his own unique style of play, he’s never going to win.

You don’t win by knowing how your role models or even you win. You win when you take that knowledge and build your own bespoke strategy that is built specifically for you:

  1. Aggregate the models and principles you’ve defined to create a list of strategies that could work for you. Look at your role models, and reverse engineer each quality you want to emulate according to the five principles we covered. You should see many different ways you “could” win.
  2. Mix-in what you already know. If one path forward requires you to learn an entirely new skillset, and another requires only the skills you already have, the choice should be obvious. Double down at what you’re good at and reject what you are not.
  3. Tailor your strategy to your exact needs. Take your best strategies for winning, and build the specific strategy that is right for you. For instance, what works for LeBron or Jordan might help a point guard come up with many ways to win, but when they blend that with their unique attributes — such as speed, height, leap, accuracy, etc. — now they have a bespoke winning strategy.

Always remember, this is about figuring out how YOU win.

Step 3: Build A Plan

I insulted the school system earlier for its pathetic deficiency in helping any of us create the careers and lives that we want, and I will continue to beat that drum. But there is something very powerful we learn throughout our education:

You learn methodically.

You spend the better part of the first two decades of your life in school. From learning your ABCs all the way through your SATs you develop an enormous amount of knowledge. Looking back on decades of learning you see that knowledge was built up for you in a methodical way that enabled you to keep progressing year after year.

Can you imagine how you would learn if all that knowledge was simply thrown at you in one year? What about one week? Instead, it was planned out and fed to you one chunk at a time.

One big reason people fail to get value from planning is that they craft elaborate plans that they are unwilling to execute. Like a drunk idiot at a bar, their mouths write checks that their bodies can’t cash.

Right now just pull out a sheet of paper, and draw out a plan you are actually willing to execute by following these two steps:

First, visualize your plan. Even before you put anything on paper, just sit back for a few moments and think about your career and life path. Imagine all the way out to the end of your life and see your life for what you dream it to be. And from here, look back and see the many steps that came together for you.

That’s step one. Easy, right? Well, step two is the easiest career plan you’ve ever seen. Like those unfortunate people who develop elaborate business plans that are out-dated even before they get started, you only want to plan as LITTLE as you need to keep you moving.

Do this by drawing four boxes on a page. In the top box, write, “Winning!” Then, draw the three boxes coming off this like an organizational chart, which you then label:

  1. External Workstream. These are how you will drive success external to your firm (e.g. with customers). Get very clear on the specific actions that are required here, and, if you choose, draw some more boxes, framing out how you’re driving your business.
  2. Internal Workstream. Career success is about far more than delivering top performance, it’s also having the support you need inside your company. Ask yourself, whose support do you need? How do you get it? Plan it out.
  3. “You” Workstream. This is your personal development track. If you want to win, plan how you are getting better. What skills do you need? How do you plan to build them?

Keep moving down layer after layer, adding more nuance until you have a clear plan of attack across all three workstreams.

Step Four: Execute Your System

If you’re reading this article, I know you are already someone who takes action. To have successfully made it to a good job, execution is something you know how to do.

That’s why I expect you will find execution to be the easiest step in this guide. So instead of sharing with you what more you can do, instead, we are asking: What less can you do?

Thoreau wrote, “Simplify, simplify, simplify.” That’s why I’ve broken execution down into five principles:

  1. Get Started. If you’ve ever seen a Rube Goldberg Machine, you know that amazing chain reactions are often spawn from the slightest initial movement. Executing is the same: Get moving. If you’re still struggling, again, I highly recommend the book Eat That Frog!
  2. Process Excellence. Execution is about process. Like a good production line, good execution comes from good process. This comes down to sequencing, prioritization, and efficiency. Get clear on it, and, well, keep moving…
  3. Momentum. Newton’s first law of motion states that an object in motion stays in motion until acted upon by an opposing force. To win, you must be willing to endure perhaps many years of opposing force, and again this comes back to process. Jerry Seinfeld had a calendar in which he’d draw an X over each day he wrote new jokes. Once he had a long chain of X’s, he had so much momentum he never thought about missing a day.
  4. Persistence. Will is everything. I asked a former Navy SEAL client of mine what’s the difference between people who wash out of BUD/S and those who succeed. It didn’t come down to skills or preparation, everyone there was a high performer. It came down to who would rather die than quit. If you don’t have the grit to move forward, someone else does, and they are going to eat your lunch.
  5. Propulsion System. This is a fancy way of saying motivation. Close your eyes and imagine you are at your desk whining about how you lack the time to create the life you truly want. Then imagine a voice comes over the intercom and tells you there is a bomb in the building that will detonate if you don’t take a step forward on your plan today. You’d get it done, right? That’s an “away from” motivator. A “towards” motivator is to know that when you get it done, you get the reward. Combined, these two “Motivational Directions” are your propulsion system, and the source of all your best juice.

Definitions of words like “execution” can get nebulous and ambiguous very fast. It’s critical that you break it down to composite parts that are actionable and concrete.