What is a Portfolio Career? [#48]

In investment 101, you learn that you need to diversify your investments by building a portfolio. Having all eggs in one basket isn’t enough. 

But we don’t do this with our biggest and most important investment: our career. 

Despite the need to diversify in everything else, our career is supposed to be the opposite: work for one employer in one job, doing one specific thing. 

This creates dependency. When you lose your job, it feels like you lose everything. And in order to avoid the potential feeling of losing everything, sometimes you go above and beyond your natural boundaries. For a business that’s not even yours. 

Growing up, we’ve been told to get a stable job. But what is a stable job really?

If you work for the government or big corporate in countries like Germany or France, where employment law heavily favors the employee and it’s basically impossible to fire someone at a certain company size, then yes - you might have a “stable” (albeit boring) job. (But not even those are safe: Infineon laid off 1400 employees in August, several 100 of them in Germany.)

Any privately held company that tells you that your job is “safe” is full of shit.

It’s not safe.

Between 2022 and today, there have been >570k layoffs in tech companies according to layoffs.fyi. Major German tech companies like Lilium, previously hailed as the messiah of Germany’s economic future, are going bankrupt. 

In an economic environment that’s prone to change more rapidly than ever, with major geopolitical events happening on a yearly basis, job safety simply isn’t predictable. 

Your full-time job isn’t safe. 

And you gotta do something about it - by diversifying your career. 

Enter: The Portfolio Career. 

“A portfolio career looks like having multiple sets of experiences and skill sets at the same time, and diversifying your learning, knowledge, networks, and growth tracks. It broadens your surface area for 'getting lucky', or for stumbling upon exciting and interesting opportunities. It reminds you that the world is large, and there are many more ways than one to build a life for yourself.” Mallory Contois

Sounds cool, doesn’t it?

Let’s dig. 

This is the first part of an (at least) 4-part email series, published over the next weeks about the topic of the Portfolio Career. The deeper I went in my research, the more I felt that I had to say - and that wouldn’t fit into one newsletter. Also, some have asked for shorter, more concise newsletters. Here you go. :) 

Chapter 1: What is a Portfolio Career?

Chapter 2: How do you build a Portfolio Career?

Chapter 3: The Three Stages of Multipreneurship

Chapter 4: How I’m currently building mine

Chapter 5 - X: TBD (also depends on your feedback!) 

Today, let’s explore the concept of a Portfolio Career. 

Chapter 1: What is a Portfolio Career? 

A Portfolio Career is a generalist’s paradise, where you get to do several things at the same time - often, but not always, unrelated ones. In addition to the definition above, a Portfolio Career also allows you to diversify your income streams. 

In the past, you’d rely on your full-time job for your income. 

In the future, you might still have a full-time job, but will freelance on the side, build digital products, or have a small business you run on weekends. Pair this with smart investments, and losing your full-time job will start looking like an opportunity, not a threat. 

(Especially in countries like Germany, being fired is one of the best things that could possibly happen to you if you’re early in your career. It means that the government finances your costs of living for up to a year, giving you the freedom to explore.) 

That peace of mind is - of course - much easier to have when you already have a diversified career. Which you will build step-by-step. 

Traditional Work vs. Portfolio Work

Besides diversifying your income, a Portfolio Career offers a ton of other benefits: 

1. You get to work for yourself: instead of being tied to one employer, you are now tied to several - which gives you leverage over the clients you work with. Instead of being stuck in a toxic client relationship, you can get out, because you have more streams of income. 
2. You get to work remotely: depending on your archetype (which I’ll explain below), you likely work remotely. Imagine commuting to three different jobs every day - that’d take up way too much time. 
3. Every day is different: while the days might be structured in a similar manner, the things you do during your work blocks will differ immensely. Which, as generalists, we love. 
4. It allows you to design your life the way you want it to be. We work to live, we don’t live to work. 

Let’s create our own definition: a Portfolio Career … 

• Includes different income streams
• Allows you to work in different functions and/or industries 
• Gives you control over your own time
• Allows you to work at your pace 

And most of all, a Portfolio Career allows you to be uniquely you, unifying your different skillsets and interests into one career that only you can do. 

(Which builds a competitive moat - it’s impossible for others to beat you at being you.)

Treat your career like you’d treat your investment portfolio.

Diversify it. 

But how? 

There are different ways to do this - depending on your Archetype. 

Archetypes

Portfolio Careers can be broken down into 5 Archetypes: 

• Freelance Specialists: go heavy on one or two core skills and then market them to different audiences, usually working with more than just one organization
• Fractional Executives: part-time work in multiple organizations, mostly in leadership roles 
• Side Hustlers: work full-time in a “stable” job with freelance/entrepreneurial work on the side
• Serial Specialists: go all-in on one topic for a finite period of time, then pick the next one and go all-in on that. The previous topic might yield long tail income streams after if you monetize them well (eg. I don’t do any international expansion anymore, yet still make some money with writing and consulting on it). 
• Multipreneurs: build a portfolio of companies at the same time.

One of the first choices you’ll have to make is which type of Portfolio Career you want to pursue right now. You can always change paths later: you might start out as a freelance specialist, and become a fractional executive later - or a side hustler might eventually turn into a multipreneur. 

Now, these Archetypes give you a rough idea of where you want to look. But the lines between them are blurry. So while I believe it’s good to be able to put yourself into one “bucket”, I do like Anna MacKenzie’s take on what a portfolio career can be: 

“To me, a portfolio career can be made up of many things:

• A part time job (eg. working 3 days a week for a company)
• A part time business (eg. working 3 days a week for your own company)
• A done-for-you service (eg. contracting, consulting)
• A done-with-you offer (eg. coaching, mentoring, advising)
• A do-it-yourself offer (eg. a digital product, online course)
• Creative work (eg. writing, podcasting, Tiktok-ing, playing music)
• Giving back (eg. volunteering, pro-bono work)
• A mix of any or all of the above”

Mix and match, and see what works for you. 

Why now? 

Why should you start a portfolio career right now? 

I believe the future belongs to generalists. The pace of technological development accelerates year by year. What seemed impossible five years ago is reality today, and what might have been a valuable specialization five years ago is now more and more obsolete (eg. Software Engineering). 

In Range: How Generalists Triumph in a Specialized World, David Epstein argues that generalists thrive in “wicked” environments:

“In wicked domains, the rules of the game are often unclear or incomplete, there may or may not be repetitive patterns and they may not be obvious, and feedback is often delayed, inaccurate, or both.” 

The world of future is a “wicked” environment. The rules aren’t clear. We don’t know what comes next. The problems that we’ll face will be problems that we’ve never seen before. 

In contrast, “kind” environments are characterized by immediate feedback and clear, repetitive patterns - so if you’ve solved a problem in that environment before, you will be able to do so again.

Chess is a good example: there is a finite number of possibilities, and by studying the game and specializing hardcore, you will eventually find success. That chess skill just won’t help you anywhere else in life. 

Specialists thrive in kind environments. Generalists thrive in wicked environments.

The world of the future is a wicked environment, and it will require the ability to adapt quickly, solve problems, and think critically. 

The best way to become a generalist is to do more than one thing. 

Like, in a Portfolio Career. 

Next week, I’ll send out Chapter 2: How to build your Portfolio Career. 

Stay tuned - and if you haven’t subscribed yet for some reason, now would be a good time to do so :). 

Question for you: 

Having read this post - which other questions would you like me to answer in this series? 

PS: A few more resources on building a Portfolio Career:

• Nikita Khandwala’s Portfolio Career Playbook
• Anna MacKenzie’s “WTF is a portfolio career?” 
• “The Future of Careers” by Ben Legg