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"Portofino 2" by Raymond Scott
Ch 1 – What is careering?
Ch 2 – How can individuals career?
Ch 3 – How can orgs change?
Ch 1 – What is careering?
Ch 2 – How can individuals career?
Ch 3 – How can orgs change?

Pull me
for choo's

Careering Fairgrounds

Theory Train




The Theory of Careering

Ideas on how we can play
through our worklives.

Volume One, Summer 2021


Choo chooo, all aboard!
Chapter One

How we build careers

Most of society builds careers for their worklife. By the time someone “enters the real world” they need to have chosen a lane, or industry, to pursue.

Once accepted into a lane through credentials like degrees or past experience, they’re given the opportunity to climb a ladder. The rungs of a career ladder are pre-defined roles. Someone has decided that these roles will both help the individual grow and provide value to a business.

A career lane with credential barriers

We call this way of working the The Career Model. It’s based around career as a noun, meaning an occupation undertaken for a significant period with opportunities for progress.

This model works for those that get enough benefit from fitting into pre-defined roles. Problems start to arise when:

  • an individual finds out that their chosen lane isn’t for them
  • an individual starts to discover new roles or lanes

How we career

Switching lanes to build a new career is daunting. The options an individual has are often costly or hard to find. They can:

  1. go back to school to “continue their education” (as if it had been halted!)
  2. find an organization that will pay them to learn and explore a new role
  3. start their own organization that provides a home for a nascent lane or role

When individuals “change careers” or “build a new career” they’re careering! They’re swerving to another lane, jumping over the high credential barrier to do so. This introduces the The Careering Model of working. Its based on the verb of career, meaning to move swiftly and in an uncontrolled manner in a specified direction.

Careering to another lane

When careering, it’s hard to know where you’re going to land. It takes courage to leap into the unknown. And so far we’ve just talked about switching from one lane to another, imagine trying to swerve between five lanes! Or how about swerving to a lane that doesn’t exist yet?

How easy it is to swerve, or career, is based on the environments we learn in. What barriers do they create that make it hard to discover new lanes and roles?

Our learning environments

There’s three main learning environments that influence how we career; Home, School, and Work.

At Home, growth begins as those around you may have ideas on what you could go into, what you could study, and what hobbies to try.

In School, lanes start to form in the shape of classes, departments, and degrees. Early Schools, like kindergarten and highschool, are careering friendly as they don’t require credentials to explore different topics. Later Schools, like universities, are more built to help you build a single career. Unless you have access to a build-your-own-major type of opportunity, you’ll be jumping through hoops to swerve into classes outside your chosen major.

At Work, we get lived experiences of what it means to play a certain role. Similar to Early Schools, Smaller Workplaces are careering friendly as role definitions are often ambiguous and ever-shifting as the needs of the business evolve. When Larger Workplaces start to want some sense of certainty they build up structures of accountability like teams and middle managers.

The crucial question for us to ask in all of these environments is:

Who gets to decide what we think about?

Is it you? Your manager or boss? Parents, teacher, government? There’s a web of influence that decides what we think about. As a society we fund what we value, so how much do we value the exploration of new ways of working?

In order to career, our Homes, Schools, and Workplaces need to support the discovery of lanes and roles that have yet to prove value. So how might they? And what can we do as individuals to move towards a new way of working?

A career lane with credential barriers
Careering to another lane
Please keep all hands inside the train
Chapter Two

Find your waypoints

In the Career Model, organizations may ask individuals to set career goals. “Where do you want to be in five years?” they’ll say. The problem with setting goals, is that they’re based on your current understanding of your practice. Your understanding of what’s possible changes as you grow, so you can find yourself somewhere unexpected once you start moving on a path.

This means that hitting your goals may not look like what you originally thought it would. In the Careering Model, instead of setting career goals we can set careering waypoints.

A careering waypoint is a point to head towards in your worklife. It gives you a direction but doesn’t focus as much on the destination, which makes waypoints more forgiving than goals. A waypoint could be a craft like drawing, an environment like school, or a role like researcher. It doesn’t matter if you’re “successful” in reaching a waypoint, because you’ll likely discover more waypoints that interest you along the way.

When imagining potential waypoints, it helps to draw them out. It could be a diagram with points in a journey map, or more like an illustration with a vast landscape that you forsee yourself exploring.

For some examples, lets look at contemporary careerers Ye and Virgil Abloh. Ye is organizationally careering through DONDA, swerving between many lanes including fashion design and city building. While Virgil is individually careering by swerving through different types of environments including architecture school and fashion organizations.

Ye’s DONDA waypoint map looking at its future
Ye’s DONDA waypoint map looking at its future
Virgil’s waypoint map looking at his past
Virgil’s waypoint map looking at his past

Here are some prompts that can help you think about what your waypoints could be:

  1. What do I want to think about?
  2. What environments do I want to grow in?
  3. What crafts do I want to explore?
Norm’s waypoint map looking at their future
Norm’s waypoint map looking at their future

Reflect on your understanding

How do new roles come to life? We believe they’re discovered by individuals before being practiced more widely. For example, the role of a User Experience Designer wasn’t always recognized by organizations. Roles like this were discovered by individuals careering into nascent lanes and finding new roles to play.

Your knowledge is unique, which makes your understanding of what you do unqiue. In order to learn by doing, we often need guidance to know what opportunities already exist. When first playing a role, we may rely on someone else’s understanding of it. Once you have your own lived experience of the role, you can reflect on what you do and how you play in it. You may find that what you see the role providing is different than those that initially guided you. If so, you’re likely discovering a new role!

Through careering reflections, individuals can start to shed light on how their path diverges from current definitions of a role.

Publish your roles

In the Career Model, our roles are defined by organizations. They could be a public service company trying to provide guidance on potential career paths, or a company posting a job on their careers page. Both are providing boxes for you to hop into. However, if individuals are the ones that discover new roles, shouldn’t individuals be the ones to define and publish those roles? We think so!

In the Careering Model, as you discover new roles you should publish them! Let others know about your understanding of the role, the tools you use, and the learnings you have while practicing the role.

We’ve created a Role Carousel in these Careering Fairgrounds as an example of how individuals could publish their own roles. It’s open for publishing for when you’re discovering a new role! Of course, you can also publish on your own site, as a book, or on a public bulletin board. What matters is that you’re taking the time to define your understanding of your role and sharing it with others.

Now that we have individuals careering and publishing their roles, how can organizations support them and uphold the Careering Model of working?

Ye’s DONDA waypoint map looking at its future
Ye’s DONDA waypoint map looking at its future
Virgil’s waypoint map looking at his past
Virgil’s waypoint map looking at his past
Norm’s waypoint map looking at their future
Norm’s waypoint map looking at their future