How to Craft Your Career Map

Navigating one’s career is a lot like planning a long road trip.

Before I embark on a road trip — no matter if it’s a one-day cruise along California’s Highway 1 or a month-long motorcycle journey across Vietnam — I always take a few common steps.

First, I open up Google Maps and carefully study the geography at a high level.

Then, I strategize about my constraints. Do I want to take the most direct route or make indirect stops at particular attractions along the way? Do I want to avoid the highways? How much time do I want to spend driving each day?

Taking into account these considerations, I start plotting out my route on the map.

This may be surprising… but I take the exact same steps when charting my career.

I reflect on where I am now, where I want to go, and how I’m going to get there. I form constraints that clarify what my next role should be and influence what actions I need to take.

In previous articles, I have written about the four essential elements of career mapping: values, superpowers, curiosities, and needs.

Values are your core principles or standards of behavior. Superpowers are the abilities you perform well. Curiosities are where your fascinations lie. Needs are the lifestyle non-negotiables you have.

The result of leveraging all these elements is a lasting, fulfilling career that gives you energy — instead of sucking your energy.

So how do you synthesize these elements into a map for navigating your career?

It’s a lot simpler than it might sound.

What it comes down to is…

Creating your criteria.

In this piece, I’ll first explain the two-step process for translating your career map elements into actionable criteria. Then, we’ll walk through how to use these criteria in your job search or career advancement.

Two Steps to Creating Your Criteria

You want to first start off with a list of your top values, strengths, curiosities, and needs. If you don’t know what these are for you yet, then follow the links above in the intro to complete these exercises.

For each of these elements of your career map, try the following two steps:

1. Create an “If… Then…” Plan to define the minimum threshold it takes to feel like you’ve fulfilled your values/superpowers/curiosities/needs. 
2. Run an “Actionability” Test to evaluate if you can actually use the if/then plan you just created to make a decision. In other words, is the if/then plan clear enough that you can answer yes or no to the question, “Does this decision (e.g. applying for a new job) meet my if/then plan?”

I know what you’re thinking…

“Creating standards for myself — this sounds hard!”

I’m not going to tiptoe around the issue, it’s not going to be easy to do this exercise. In fact, pinning down what you truly care about can often feel like wrestling with your mind.

With that said, the mental clarity you’ll get after you have your criteria laid out in front of you is well worth the effort.

Let’s discuss a practical example to help you see how these steps work in reality.

Case Study: The Value of Freedom

Let’s take Freedom — one of the value shared by several of my coaching clients (and myself). From my observations, Freedom as a value translates into a very different set of actionable criteria for each person.

For parents, Freedom means building in more flexibility into their day-to-day schedule so they come home at a reasonable hour for their family. Their if/then plan may look like, “If I have to regularly work evenings during my family time, then I will feel unfulfilled in terms of my Freedom.”

For younger nomads, Freedom means setting up a lifestyle where their work affords them the ability to travel for long, uninterrupted periods of time. They might decide on the following if/then plan: “If I can work remotely while I travel internationally for 1 month each year, then I will feel fulfilled in terms of my Freedom.”

As you can see, both groups share Freedom as a top value but express it in unique ways. 

If you run their if/then plans through the “Actionability” test, it’s also clear when each group has passed the threshold of their criteria.

Let’s say each group is evaluating new roles. The parents will know exactly when a role violates their Freedom criteria because the hiring manager requires them to be regularly on-call after 5pm. The nomads can easily identify which roles are going to give them the flexibility they seek based on their remote policies.

Synthesize Your Results

Once you have all of your criteria in front of you, synthesize similar ones and do one more prioritization. Choose the 5-7 most important criteria to you in your next career decision.

Take one of my own job searches as a tech product manager. I first reflected on each element to arrive at the following outputs:

• Values: adventure, freedom, curiosity, relationships, and courage
• Superpowers: creatively analytical, systems thinker, high emotional IQ, communication
• Curiosities: building new product, management, emerging markets/industries, personalization technologies
• Needs: minimum compensation

Then I converted these outputs into this prioritized list of my top criteria:

1. Target Knowledge Areas: If I get the opportunity to build my expertise in one or more of these areas — building new product, management, emerging markets/industries, personalization technologies — then I’ll feel like I fulfilled my curiosities.
2. 3/4 of Superpowers: If I get to use at least 3/4 of my superpowers (creatively analytical, systems thinker, high emotional IQ, communication), then I’ll feel like I’m making the most of my strengths.
3. Relationships at Work: It’s critical for me to work in a casual, personal environment that is conducive to developing healthy relationships. This is more a gut check of how I perceive the workplace during my coffee chats and in-person interviews.
4. Flexible Lifestyle: This criteria is a merge of my Adventure and Freedom values. It’s important to me to have enough time outside of my day job to work on my own projects and travel. Specifically, this means I want to have my weekday evenings free at least 80% of the time to work on my own projects and ability to work remotely 1 day per week if needed.
5. Minimum Compensation: I want to have enough income to save a healthy amount of cash and investments. Omitting the numbers here, but I can tie a range to this criteria.

You’ll notice that I tried to distill down these elements into just 5 criteria while still trying to be as specific as I could, which ultimately helped me take action during my search.

Putting Your Criteria Into Practice in Your Career

Congratulations! You now have a list of your most important criteria.

The next step might be intuitive to you now. But if you’re wondering, “how the heck do I use this?”, don’t fret. I’ve got you covered.

We’re going to show you how to use your criteria as a set of filters for two situations: job search and career advancement.

Job Search

There are two stages in every job search process: discovery and search.

In the discovery stage, you’re doing mostly inner work to identify what role or career path you want to pursue next. In the search stage, you’ve clarified your target role or career path and now you’re reaching out to people, applying to jobs, interviewing, and negotiating to get to your target.

Your criteria comes in handy for both stages.

Discovery: Career Path Venn Diagram

During the discovery stage, plot your potential career paths on a venn diagram of your values, superpowers, curiosities, and needs using your criteria.

In one fell swoop, you can triangulate which career paths align with who you are as a person.

Search: Job Criteria Score

During the search stage, create a criteria score to use in your Job Application Tracker:

The criteria score is a simple math formula: # criteria met / total # of criteria

For each job posting, assess if the role meets the criteria you laid out. Mark an “X” in the columns that the role seems to fulfill.

What’s useful about having a numeric score like this, is how easy it becomes to compare one role versus others based on your criteria.

Career Advancement

Believe it or not, advancing in your current job involves the same discovery and search stages found in a job search process.

Strategically, you’ll be taking much of the same actions as in the job search — albeit just dressed in a different costume.

Shift, Expand, or Switch Your Role

Break down your role into its actual responsibilities and then ask yourself the following questions:

1. Where do each of the responsibilities fall in your Career Path Venn Diagram?
2. Where might there be gaps between your actual responsibilities and your career map elements?
3. What are experiences or projects that you can seek out to fill these gaps and align your role with what you desire?

While your answer to #3 may require you to switch roles, plenty of times you’ll discover that shifting or expanding your current set of responsibilities is sufficient for aligning your role with what you want.

Going Above and Beyond

There you go! You now have a foundational career map — a hallmark companion of thoughtful careerists.

Most importantly, you learned how to turn your career map elements into actionable criteria and have started putting them to use in your discovery and search processes.

What we covered were frameworks and skills that apply to every career transition you’ll make for the rest of your life (no kidding!), so you can pat yourself on the back for getting a head start.

There’s no doubt in my mind that you’ve already started noticing changes in the way you think about and plan your career. I’m excited to see how you use these tools in the future.

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