a guide to unconventional careers

Part II - Career Agency

Over a year ago, I did something that raised quite a few eyebrows: I quit my “prestigious” job as a tenure-track Economics lecturer to work for a YouTuber.

Over a year into this transition, one thing I've learned is that the hardest part of an unconventional career usually isn't the day-to-day work - it's figuring out how to grow without a predefined path.

Success in unconventional careers requires an enormous amount of self-direction. You need to be both the employee and the manager, both the worker and the career counselor.

In Part I of this series, I walked through how I decided to leave academia. In this piece, I want to share what I've learned about making an unconventional path “work”. I think this is the guide I wish I had when I started exploring the world of unconventional careers.

I'm fortunate that my current role with the Ali Abdaal team has great professional development guidance - many of the strategies I'll share below were actually inspired by practices and experiences at work.

But even with good structure, I've noticed that many in unconventional careers grapple with similar challenges:

• How do you measure progress when there's no clear promotion ladder?

• How do you make sure you're developing the right skills when no one's telling you what to learn?

• How do you build value that translates beyond your current role?

These questions require more than just self-motivation. They require something else. Let's call it “Career Agency”, which is a bundle of different attributes:

• The ability to create and prioritize your own to-do list when no one's telling you what needs doing

• The skill to identify and say no to things that don't serve your goals

• The capacity to see things from your employer's or client's perspective

• The ability to solve problems without creating new ones

• The judgment to know when to take initiative and when to seek guidance

Before we dive into specific strategies, let's chat about what makes unconventional careers different.

The Trade-Off: Conventional vs. Unconventional Careers

At its core, the difference between conventional and unconventional career paths comes down to a tradeoff between risks and expected returns. You’re essentially choosing between different risk-return profiles for your human capital.

Kinda bad picture showing what I mean by the risk-reward variation

A conventional career typically gives you

(1) Clear progression timelines

• McKinsey consultant: analyst → associate → associate manager → engagement manager → associate partner → partner (this is probably the same for other big consultancy firms)

• Doctor in the UK National Health Service (NHS): foundation year training → junior doctor → specialist training → consultant

• Academia: PhD → postdoc → assistant prof → associate prof → full professor

• You get the idea.

(2) Predictable returns

• You work a fixed number of hours per week and get a certain amount of money in your bank account.

(3) Low variance in outcomes

• You enter a decent earning floor but there’s a somewhat fixed ceiling in most conventional careers (though, of course, the ceiling varies across industries - from low 6 figures as an NHS doctor to 7 figures as an investment banker)

Getting your foot into McKinsey isn't easy. Becoming a doctor isn’t easy.

More often than not, it requires the foundation of a good university, good grades, and a fair degree of conscientiousness to pursue those paths.

But once you’re in, everything becomes pretty structured. As long as your performance is average or above, you can predict your career trajectory with surprising accuracy.

So investing in a conventional career is like putting money in the S&P 500 index fund. You might face the occasional market crash (like 2008's ~40% drop), just as you might face redundancy. But on average, you sort of know with reasonable certainty what you’re getting.

Let’s turn to unconventional careers. I'm not sure if there's a definition of “unconventional” career even though this term is being used more and more.

It feels like 'unconventional' careers are defined by the lack of structure or a clear career path. Think of freelance web designers, freelance writers, software engineers turned startup founders, discord community managers, online fitness coaches, doulas, game testers:

(1) There’s no pre-defined path and clear promotion timelines

• Say you're an online fitness coach, there's no predetermined job title that you'll progress into in a year.

(2) The returns aren’t always predictable

• Say you're a freelance web designer, there might be weeks where you're spending 40 hours a week trying to get clients (earning $0) and other weeks where you spend 20 hours making a website that gets you $5000.

(3) There’s a high variance in outcomes

• Say you’re a startup founder. There’s a 90% chance your startup will fail. But if you do make it to the top 10% of 1%, you will have an amount of wealth that most people struggle to comprehend the magnitude of.

These differences suggest that one way to make an unconventional job 'work' for you is to reduce the risk and increase the potential rewards that come with it.

Sometimes this is down to luck. But I think there are 3 core things that anyone in an “unconventional” career can do to tilt the risk-reward profile in our favor.

(1) Be Strategic About Skill Development

I love this blog post by author and cartoonist Scott Adam (creator of the Dilbert comic strip). He writes:

If you want an average successful life, it doesn’t take much planning. Just stay out of trouble, go to school, and apply for jobs you might like. But if you want something extraordinary, you have two paths:

(1) Become the best at one specific thing.

(2) Become very good (top 25%) at two or more things.

The first strategy is difficult to the point of near impossibility. Few people will ever play in the NBA or make a platinum album. I don’t recommend anyone even try.

The second strategy is fairly easy. Everyone has at least a few areas in which they could be in the top 25% with some effort. In my case, I can draw better than most people, but I’m hardly an artist. And I’m not any funnier than the average standup comedian who never makes it big, but I’m funnier than most people.

Traditional careers are much more like path (1) than path (2). The skills you need to progress are usually pretty clear. A software developer needs to be really good at coding and problem-solving. A lawyer needs to be excellent at reading and writing contracts. A doctor needs to have comprehensive medical expertise. In my case in academia, I needed to get really really good in the field of research I was doing and publish in top journals.

In unconventional careers, the skills you need to stand out can be more varied. A startup founder needs to have the right mix of entrepreneurial zest, problem-solving skills, and social swagger. A freelance designer/writer needs to be good not only at the thing they're doing for their clients (making websites, writing), they also need to be good at marketing and getting clients.

When I transitioned to the unconventional path, I made the mistake of following path (1). I wanted to become a really really good researcher-writer, primarily focusing on just the craft of synthesizing complex info in a digestible, engaging way through words. This was the wrong strategy. While I still want to develop those skills, I realize that my comparative advantage lies in pairing two skills: strong research/writing abilities paired with project management and strategy skills.

The flexibility of unconventional careers creates an incredible opportunity to strategically select projects to build a unique combination of skills that suit your current situation. Instead of waiting for years to move up the ladder, you can exercise “high-level” skills from the start - strategic decision-making, agency and execution, coordinating and managing complex projects.

So, I guess what I wish I knew earlier is this: Get clear on which two areas where you're going to aim to be in the top 25%. Then claim those areas. Make yourself rare and invaluable by combining two or more “pretty goods” until no one else has your mix.

(2) Write Your Job Description

This might sound a bit odd, but it's incredibly useful - especially in unstructured environments like startups or freelance work. When I work with freelance clients, I always write up a scope of work. Initially, I did this mainly to avoid confusion about responsibilities, but it's become a powerful tool for clarifying how I add value.

Your job description should outline:

• Core tasks/roles that you're responsible for doing (which part(s) of the workflow do you own and when do you hand off to someone else?)

• How often do you do those tasks (daily? weekly? monthly?)

• Key metrics or outcomes you're responsible for (ideally, these are quantitative metrics that you can put a number on - e.g. revenue)

In a corporate job, you have clear markers of progress - performance reviews, promotions, and salary bands. So, where possible, for an unconventional job, you want to write your description so that the roles, responsibilities, and key metrics potentially become signals of progress to signal you're growing in value.

Will the key metrics allow you to say that you've increased the company’s key outcome from X to Y? Will it increase your chances of getting a referral from a satisfied client? Will it increase your chances of receiving compelling job offers (even if you don't accept them)?

Even if you never show this job description to anyone else, it helps sharpen your thinking about what you're actually offering to the market. It's a way of making your skills more tangible and measurable.

Oh, also: When you're writing this up, it's really important to make it about your employer/client - not about you! Think of your employer or client as someone who's hired you to solve specific problems. Your job description should show precisely how you can solve these problems with minimal fuss and maximum impact.

(3) Maximize Your Network Surface Area

One advantage of unconventional careers is that hierarchies tend to be flatter. As a relatively junior person, you might find yourself working directly with founders or the equivalent of C-suit execs. These interactions are golden opportunities and you should make use of them.

I think there are two main mistakes when it comes to maximizing your network surface area:

(a) not doing enough of it (I fall into this category) (b) not doing it in the right way

When it comes to not doing enough of it, the problem is simple. In my case, it's not making the network. It's not following up with people I've met who might turn out to be future collaborators. It's not reaching out to interesting people for virtual coffees. It's the lazy mentality of “eh, people will reach out if it's really that important” rather than the active mentality of “I need to put in effort to actually meet people.”

When it comes to not doing it the right way, the main mistake (and turn off) is approaching networking with the mentality of “what can I get?” rather than “what can I give?”. If you focus on what you want to get rather than lead with what you want to give, a LinkedIn connection will stay a connection (or even just stay a request) rather than flourish into a real relationship.

To be quite honest, I hate the word networking. But if I think about it in terms of giving value by helping someone else solve a problem they might be facing, it becomes a little more palatable.

Last year, I connected with someone in a similar field - not with any specific goal in mind, but simply to share insights about what we’re working on. Six months later, when they were starting a new project, they reached out to me first for consultation work. Even though I didn’t have the capacity to take it on, this is an opportunity that wouldn't have existed through traditional job-seeking channels.

Ultimately, you need to become excellent at self-direction

Career agency isn’t something we’re born with - especially not when traditional, conventional careers are the norm. But it can be developed over time.

The goal isn't to replicate the structure of a conventional career. It's to create enough structure to ensure you're growing while maintaining the flexibility that drew you to an unconventional path in the first place.

In many ways, succeeding in an unconventional career is about becoming excellent at self-direction. It's more challenging in some ways, but it also offers the freedom to shape your career in ways that would never be possible on a more traditional path.

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You got this.

Ines

If you enjoyed this, you might also want to check out…

• Why I left academia to work for a YouTuber - Part 1 of this series

• Your Job vs Your Calling - A piece about why your job doesn’t have to be your calling

• oops, I’m co-dependent on AI - A piece about how to (and how not to) use AI