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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
And to our right, we have infrastructure
Chapter Three

Center individual growth

Another way to say that individuals are discovering new roles, is to say that they are founding those new roles. They’re a founder of practice! In order to support careering, organizations need to foster environments that enable everyone to be a founder of practice. This will lead to more individual growth, which we believe leads to organizational impact.

The first way an organization can support careering is through hiring. Organizations that operate with the Career Model typically hire for organizational impact. Whereas an organization using the Careering Model should hire for individual growth.

Growth is a combination of opportunities provided by an environment, and the effort provided by an individual. If a past environment of one individual didn’t have as many growth opportunities as another individual, we can’t assess their past growth equally. So when hiring, we should ask, “How do they want to grow?” before considering, “How much have they grown before?” or “How much impact have they created before?”

Once an individual is in the org, they’ll need to be supported with enough agency and time to discover how they want to continue careering.

Make Roles project-based

Workplaces that operate in the Career Model define your role when you start a new job. Role changes after that are typically a big event that happens as a result of being promoted or changing teams. We can call these promotion-based roles.

Stages of Team Development and Stages of Role Discovery

What if the role you play was questioned more often, say at the start of every project? The start of a project is a friendlier time for a team to enter or re-enter the Forming stage, when new members join the team or roles are shifted. This beginner-friendliness time makes it best for discovering new roles, that individuals can then start to practice in later stages of the project.

When do you try out new roles?

When playing a project-based role and its working out, you’ll continue playing it for many projects. As soon as you notice there’s room to grow and try a new role, you’ll be able to do so at the start of the next project. Lowering the barrier of entry in expanding or changing roles would lead to more moments of individual growth. Instead of looking at a whole job as one stop in a career, we can provide many opportunities for individuals to career and swerve through roles during their time at an organization.

Encouraging individuals to explore roles on a per-project basis keeps the same reasoning as when an organization hires them. Promotion-based reasoning switches the narrative to, “Have they proven enough value yet?” while project-based reasoning keeps the narrative at, “Do we think they’ll provide value in this new role?” The same way we invest in individuals by hiring them, we should invest in them by giving them more opportunities to career.

Allow Managers to be Agents

You may have heard the phrase that, “people don’t leave jobs, they leave managers.” The role of Managers today can vary greatly based on the type of organization. We think most workplaces see Managers as accountability tools. The many layers of Managers are there to ensure that all individuals employed are providing value. Some Managers are more likely to see themselves as an enabler or educator. Following on our principle of centering the individual, what if the role of a Manager was to serve the individual first and organization second?

Managers are educators

We think this would result in a sort of Manager Agent. They would be responsible for helping individuals discover their new roles both in the current environment as well as any other environments. Manager Agents and Individuals could then move as a unit between organizations, creating more opportunities for the individual to career.

Manager Agents and Individuals career as a unit

This already happens today, its just not officially recognized. A manager could move to a new organization and establish the team from their previous working relationships.

Operate as a school

Constantly discovering new roles requires more educational moments in our lives. We provide and enforce oodles of educational environments for children and young adults, but we leave the rest of society to fend for themselves.

Knowledge separates our old self from
our new self more than age.

On top of this, most environments assume that age roughly equates to knowledge. If somoeone is young in age, we expect them to have young knowledge. If someone is old in age, we expect them to have old knowledge. This makes sense when we think that knowledge is gained through experience, and the older you are the more you’ve experienced. But when an individual is swerving into a new lane, they likely don’t have any experience in that lane. That individual is going to have young knowledge, no matter what age they are. Which is great, because young knowledge asks wise questions!

In order to support careering, Workplaces could help take on the responsibility of fostering educational environments and begin to operate more like a school. Some Managers already feel like educators. Coule projects be courses?

There are many learning structures already present in the day to day workings of an organization. A common relationship found in the Workplace today is that of a Mentor and Mentee. Typically someone with old knowledge helps provide guidance to someone with younger knowledge. How about a learning structure between two individuals that both have young knowledge?

Traditional Apprenticeships + Peer Apprenticeships

Every organization has the opportunity to help define new structures of education. One of these could be Peer Apprenticeships, where two learners are following their curiosities about a topic and helping each other learn. With the sustainability that revenue brings to Workplaces, they’re in a good position to use some of that attention to explore new learning models.

Stages of Team Development and Stages of Role Discovery
When do you try out new roles?
Managers are educators
Manager Agents and Individuals career as a unit
Knowledge separates our old self from
our new self more than age.
Journey of a learner
Journey of a learner
Traditional Apprenticeships + Peer Apprenticeships
Choo chooo, this is the last stop. Thanks for riding around the fairgrounds today.

Phew, you made it through the Theory Train! We hope you enjoyed your travels. We want you to feel ready to career, whether you’re individually careering or organizationally careering. It can be a scary and ambiguous journey, so if you’re looking for some careering peers along the way, give us a choo choo at swerve@careering.it

View research

~ Norm & Yatú

Swerve on

Many thanks to Grammy, Melquíades, Toby Shorin, Laurel Schwulst, Al Hertz, and everyone we've discussed careering with for laddering these thoughts with us!