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🧑‍💻 Types of Portfolio Careers (Which one is right for you?)

Portfolio Careers can be broken down into two different camps: Parallel and Synergic, which one is right for you?

Hey Insiders!

Last month I wrote about the growing popularity of Portfolio Careers and why they’re such a powerful force in our changing economy.

Over the last year, I’ve likely studied hundreds of people who have developed such portfolio careers

But not all portfolios are the same, in fact, they can be divided into 2 camps:

  • Parallel

  • Synergic

In the next 3min 18sec, you will learn the differences between the two so you can decide which type of portfolio career is right for you.

Let’s dive in 👇

Parallel vs Synergic Portfolio Careers: Which One Is Right For You?

What is a Portfolio Career

Before we dive into the different types of portfolio careers I thought it might be prudent to quickly remind you what a portfolio career is

Portfolio Career: when a person monetizes their skills through multiple streams of income rather than a single full-time job. This can include side hustles, multiple part-time jobs, and freelancing.”

If you want to read more about what a portfolio career is and revisit my original article on the topic, you can read it here.

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Parallel Portfolio Career

People who have a Parallel Portfolio have two or more sources of income that do not cross over with each other, but instead run parallel to each other.

Often times these people are multipotentialites who have developed a wide range of skills.

Parallel Portfolio Careers allow people to scratch multiple “itches” and often include income streams that have no relation between them, for example:

  • An accountant who sells handmade jewelry online

  • A music teacher who is a personal trainer on the side

  • A lawyer who has built a large social media following around travel and runs group travel trips

A Parallel Portfolio allows people to explore multiple interests, but it can limit the growth of all parts of the portfolio since they do not build off each other.

They lack synergy…

You can think of it like trying to push 2 large stones up a mountain.

There’s nothing wrong with this, however, it’s a downside you should be aware of before you decide to head down this path.

On the flip side, a Parallel Portfolio has the great advantage of giving you truly diversified income.

If you work in an industry that becomes heavily impacted by some technological development in the future, then you won’t be as impacted as others in your field since you have an income stream in a completely separate field.


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Synergic Portfolio Career

Like a Parallel Portfolio, a Synergic Portfolio is made up of two or more income streams, but in a Synergic Portfolio these income streams are aligned and build off each other.

People who build Synergic Portfolios can also identify as multipotentialites but they focus their energy on the interests that play off each other, instead of dividing up their energy between two unrelated interests.

If we were to take the examples from the previous section and recreate them as Synergic Portfolios they could look something like this:

  • An accountant who sells accounting courses for new business owners

  • A music teacher who tutors people in learning a new instrument online

  • A lawyer who has built up a social media following by covering newsworthy trials and helps people understand how to protect themselves with the law.

The last example in particular has gained a lot of traction over the last 3 years:

It boils down to creating a personal brand in the industry you already work in.

This not only allows you to build a new income stream by selling products or consulting to your new audience, but it will likely help you in your “day job” as well

We can imagine that the lawyer in the example probably picked up a few new clients for his practice from his social media following.

A great real-world example of a Synergic Portfolio is my friend Chase Warrington who is the Head of Remote at Doist but also runs the About Abroad podcast where he interviews remote workers, digital nomads, and expats.

Another example is Nischa, a UK-based accountant and investment banker who has quickly built a YouTube channel with over 634K subscribers where she teaches people about personal finance from an accountant’s perspective.

A Note on Skill Sharing

Looking at these two Portfolio Career options, one thing you may have thought of is how skill sharing impacts their branching.

You could make the argument that even if you have a Parallel Portfolio, you can apply something you learned from one endeavor to the other without them crossing over.

For example, if you’re a salesperson by trade and sell handmade jewelry on the side, your sales skills will undoubtedly help you with your jewelry side hustle.

This is certainly true and some amount of skill sharing will always occur even in a purely Parallel Portfolio, however, that doesn’t mean they have synergy - they don’t build off each other!

If you are a great software salesperson, that experience does not bring credibility to your jewelry business.

On the other hand, if you are an accomplished investment banker your accolades and accomplishments bring you more credibility with your YouTube audience who you sell courses to (Nischa).

On the flip side, your large audience provides you with leverage in your day job where other investment bankers know of you and may end up doing business with you.

That’s the key difference between a Parallel and Synergic Portfolio, even though some skill sharing will always occur between endeavors in a Parallel Portfolio, those endeavors do not have synergy and do not build off each other.


One of my goals for Q4 is to run our very first Remote Insider/WFM training! Based on conversations with some of you guys over the last 6 months I have a few ideas, but…

I’d love for you to play a bigger part in selecting what training we actually run!

Here are the trainings we’re considering creating, which are you most interested in 👇

⚙️ You OS: Personal management for remote workers and solopreneurs. Learn the secrets of the most productive knowledge workers, build your own second brain, and establish systems for continued success!

🔥 You INC: Building a personal brand for the 99%. You don't have to be famous to have a personal brand, and this training will teach you how to create and grow your micro personal brand to help you land your dream job or create a side hustle centered around you.

🚀 Career Transitions: Are you interested in changing jobs or industries? This training will teach you the blueprint you need to execute a career shift and set you up for lasting success, a skill that will become more and more important in our constantly changing economy.

🗂️ Portfolio Career Launch: Does the idea of working on one thing bother you? This training will teach you how to build and grow your very own Portfolio Career and establish an antifragile income stream.

Which of these topics are you most interested in?

Pick the training that you'd be most interested in attending. What you guys choose will have a lot of sway on which training we actually produce.

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Sept 30: DNCH [📍Bern, Switzerland + Virtual] - Learn about location-independent life and meet like-minded people interested in the digital nomad lifestyle.

Oct 9-15: The Nomad World [📍Albufeira, Portugal] - Transformative experience for digital nomads and remote workers from across the globe. A mix of expert talks, hands-on workshops, and beach-side fun, aimed at celebrating freedom, connection, and personal growth.

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That’s it for today!

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Cheers 🍻

Today’s email was written by Mitko Karshovski