The Future of Work is Illegible

There is a growing gap between what young adults are told about what a career is, and what it actually is. The model of a career we learn at least one generation old, and when we reach the real world, we must rapidly update those models or lose out.

The current work world is weirder than we learned. Gone are the days where a university degree leads to a steady 9-5 at a big employer with career progression then an inevitable retirement at 60. Computers, the internet, and modern culture fragmented everything.

What comes with this fragmentation is illegibility. The work, roles, and companies that make up a career are increasingly unclear to outsiders. The illegible career they create comes with a new set of challenges and opportunities.

What Is an Illegible Career?

A legible career is understandable, measurable, and controllable (by managers). An illegible is the opposite of this. It is difficult to understand, measure, and control.

A sign of an illegible career is a challenge explaining what you do. The amount you must explain is inversely related to the legibility of your role. Anyone can explain the role of teacher, doctor, or waiter. It’s more difficult to explain content creator, entrepreneur, gig worker, nomad, or freelancer.

Illegible careers are also difficult to compare. The inputs and outputs can be radically different for similar roles or companies. “Software developer” can mean either working on frontend site design implementations or backend infrastructure wrangling. “Entrepreneur” can both mean unemployed and multi-millionaire. With the legible roles of the past, this would be easier to compare.

Of course, not every aspect of your work is illegible, it is a spectrum. Being a manager and sending emails is relatively legible, no matter if you do it at a government agency or travel agency. Legibility also depends on your target. For example, someone in tech knows the difference between a staff engineer at Facebook, an engineer at a seed-stage startup, and a UX designer at an agency, while your parents might not.

To sum up what an illegible career consists of:

  1. Uncommon role. Not a teacher, doctor, lawyer, or police officer.
  2. Uncommon company. Not a big brand, big company, or obviously related to a common industry.
  3. Uncommon work. Not 9-5, office work, writing reports, sending emails, doing labour.

The Illegibility Career Tax

The working world expects careers to be legible, and in many ways, is built for these legible careers. This means people entering illegible careers are going to face a bumpy start, and likely pay some “career taxes” along the way. You pay this in multiple ways, but it largely revolves around lack of prestige or status, they include:

  • No clear career progression. If your role is illegible, this also likely means your career path is illegible. What’s next is foggy at best.
  • People simply not understanding what you do. This means they can’t support you in your career, you don’t receive the benefits of status, and the full rewards for work. You constantly need to compare your illegible career to a legible one.
  • An illegible career is riskier. You must leap because you don’t really know. You might need to jump jobs, change your compensation structure, or go freelance. Having an illegible career is what Reid Hoffman likes to say “like jumping off a cliff and assembling a plane on the way down.” It can be scary.
  • Standard credentials mean less or don’t exist. There are rarely degrees or classes or institutions supporting your illegible career. The existing ones are built for legible careers and are less useful for illegible ones.
  • Problems when a process depends on legible status. Applications of all sorts, from immigration to university to future jobs, are a challenge because they expect a legible career.

Why You Should Consider an Illegible Career

After all these downsides, why would someone choose an illegible career? In many cases, they don’t have a choice. For the people who do choose an illegible career with other options available, it leads to better career-person fit.

The whole point of legibility is to make it easy for other people to understand you. This means shaping your career to be understandable to other people. This causes a square peg-round hole situation. You constrain yourself to fit within a career that doesn’t fit you.

Having an illegible career enables you to find a career that better fits you. It creates internal consistency. You can better connect your interests and natural desires with what you’re actually doing.

Another benefit of having an illegible career is the ability create unique value. Because few people are doing what you are doing, you create a stronger competitive advantage and moat. You can demand more from your combination of skills because they are rarer.

The greatest rewards come from working on something that nobody has a name for. If you possibly can, work where there are no words for what you do. – Kevin Kelly

How to Succeed in an Illegible Career

When you have an illegible career, you cannot rely on a standard career path or tactics. Throughout my short career so far, I’ve been varying degrees of illegible, and now find myself in a role I enjoy and fit well (technical content marketer at PostHog). Here are a few tactics I’ve seen work for other people as well as have worked for me in my short, relatively illegible career thus far:

  1. Advocate for yourself. You are your own best promoter. Especially in an illegible career, you need to create your own luck and opportunities. Write, talk, ship publicly, and tell people about what you’ve done.
  2. Developing skills over credentials. The book “Seeing Like a State” (where I got the concept of legibility) talks about legibility destroying local knowledge. As career legibility declines, the importance of local knowledge increases. Having skills that apply across careers helps you navigate all of them better.
  3. Focus on projects and people. Legible credentials like “prestige” work experience or a college degree are less valuable in an illegible career. People can understand who you are, what you’re good at, and trust you to do work. Projects show the reality of your work. This combination is the new credentials for illegible careers.

People succeeding in illegible career paths is a good thing. It means people with roles better fit to them, and it makes the world a weirder, more interesting place. I know I’d like to see this happen. If you have any more advice for succeeding, let me know.

Let me know what you think on Twitter.

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