Use career mapping to manage your career proactively

How do you eat a whale?

đź›  R2
7 min readSep 14, 2021

If you ever wondered what’s next for you, whether after enjoying a great success, plateauing at the current company, or being in between jobs, chances are you had also made one or two career decisions that you then regretted. You might have been in a situation where you found yourself in the middle of a job that didn’t give you what you wanted. Or, inverse of that, you were doing your best and feeling great, but the company had evolved, and suddenly your skills and experience weren’t as relevant and worthy of recognition. That’s unfortunate.

While luck is definitely a component in your movement along the career path, it’s also possible to be smart and disciplined about it.

Similar to how a team would break down a big project, defined as ambiguous one-sentence business objective in the beginning, into smaller and smaller parts until each of them can be accomplished deterministically, your career can be unfolded from a vague wish into something you can follow almost deterministically.

A reasonable way to proactively manage your career is to lay it out as a sequence of steps, where each step can be reached from more than one preceding step. Like paths on a topological map.

The process of getting there is career mapping: taking a critical look at what’s been happening and what lies ahead, extracting the important parts, and reducing them to a smaller version that leaves out noise.

A career map, then, is a tangible result of the career mapping exercise. Let’s talk about it for a bit.

Career map

The easiest metaphor that helps visualize a career map is a topological map of territory.

A topological map.

You typically also know your position on the map and you can put things that surround you at the moment onto a map accurately. But the it gets interesting when you want to draw a map without having walked some of the paths. We’ll get to that.

Before you go on to draw all the landmarks and roads and junctions, think about this: you probably want something from your career. It should lead somewhere, and you can only be in one place. Or, you could be in one of many places, but then each of them has a certain benefit of being there and a cost of getting there.

So where are you going?

Define a (potential) big goal, or a few of them

To set a big goal, ask: “If I could do anything in my career, what would I be doing?”

No need to limit yourself to current role or company. Think as big as you can. What is something that would simultaneously be the most rewarding and the most engaging activity for you?

Think about multiple possibilities.

Take them out of your head and put them somewhere so you could see them with your eyes. I found Miro to be a great tool for visual thinking, and that’s what creating a career map is about, but your tool of choice can be different.

If I were an engineer, my goals would be to hang out with smart people, be part of a global community, and help my peers grow faster.

Got the goals? Good. Next step is to define the current state.

Determine current state

You can’t reach a destination if you don’t know where you’re going, but you also can’t navigate a territory if you don’t know where you stand. Similarly, it’s important to determine your current state when doing a career mapping exercise.

How do you define your current state? By things you do or don’t do in your current role at your current company.

If you are a software engineer, you can’t just define your current state as “software engineer”. The definition of that varies greatly from company to company and even sometimes in one company from year to year. Instead, define that by what you do and care about.

Be specific.

Do you do code reviews for your team members? Even though everyone might be doing that, add that.

Maintain a lib that a bunch of teams use and that isn’t really part of any formal group’s responsibilities? Add that. Even if it is, add anyway.

Cover the team’s operational work, collaborate on a regular basis with your product manager to align team’s engineering strategy with product roadmap? Add that.

Support your engineering manager at hiring or staffing? Add that.

Collaborate a lot with someone? Add their name.

Tip: distinguish the points on your map based on what they mean; reserve different colors for people, activities, and (later) outcomes.

Doing this alone will give you a good overview of the things that you do and should be proud of. If your manager isn’t involved in the team operations enough to be aware of all these things, you might as well use this information to explain the value you create for the company and the organization in a comprehensive way without downplaying them.

Once you’re done with the current state, it’s time to connect the two.

Connect the current state with the big goals

You’re about to get the most value from the career mapping exercise: understanding how to get there. As in, what to do, what steps to take, what to focus on and what to ignore, in order to eventually achieve your big goal (or goals).

Defining possible paths requires work.

You can’t know what to do, otherwise you’d have done it. There’s a couple things you can do to define the middle layer:

  • find role models in the organization: who, among your peers, is doing what you want to be doing?
  • find role models on the internet (I head tech Twitter is still solid)
  • do a research of what they did prior to getting to where they’re at — ask them, it’s an absolutely normal thing to do

Among other things that might help get more information:

  • find job postings for the roles that fit your big goals and study the “requirements” section — after some time (after 50th job ad, I guess) this should give you an average that is likely to be close enough to the truth
  • observe people with whom you’re likely to be collaborating as you progress towards your goal: what do they care about, how do they speak? — and yes, it’s very likely you’ll be working with an increasingly wider range of roles, sometimes people who are foreign to your regular circle (say, salespeople to engineers)
  • and collaborate with your engineering manager: they can and should give a pretty accurate extrapolation of what you’re going to be doing as you progress in your career at the current company

As you do your own research, you’ll start seeing a lot of actionable things: a book you can read, a person you can follow, a project you can take on, a colleague you can support. Place them on the map — you don’t have to have done all that, because the point of the exercise is to determine possible ways, not yet walk any of them.

Over time, you’ll start connecting the points together, and paths will start forming over what had previously been a collection of accomplishments, activities, ideas and resources.

When this starts happening, it’s a sign that you’re making sense of your own career, — congratulations!

Now it’s time to focus.

Pick one path (or more) and focus your effort

The paths can be many, but you only have so much time, so it naturally makes sense to pick the least amount of things to do that would most likely lead to the desired outcome. To pick a path that, if you walked it effectively, would lead to your goal.

What I found curious is that people don’t pick the path of least resistance. Most of the time, folks optimize for fun and curiosity, which means that they are ready to put more effort and do more work to get to exactly the same goal.

Why? Seems like the process of working towards a goal, in a smart and informed way, is already rewarding enough.

There are also occasional circumstances, like the need for downtime to recuperate from a super challenging project or getting a new teammate on board who is passionate and energetic about things that belong in a “suboptimal” path on your career map.

Finally, in reality, you’ll likely be walking several paths at once, either due to existing commitments or to gain more knowledge about things. It might also happen that your goals change, while circumstances do not, which forces you for some time to handle two or more paths at once, spinning plates and putting more energy into that than, intuitively, you should.

That’s okay, the point is to always be clear on the goals and how to get there.

The concept of career mapping is heavily inspired by the inversion mental model. The visual representation is inspired by all the visual thinkers out there, — you are awesome! Finally, eating a whale only makes sense if you’re absolutely sure that’s the whale to eat; when no longer sure, change the whale.

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