Portfolio Careers: The Future of Work

What is a Portfolio Career

In the same way that an investor builds a diversified portfolio of investments, a Portfolio Careerist (someone who builds a Portfolio Career) “invests” in different income streams de-risking their financial well-being.

Portfolio Careers can take many shapes:

• a full-time job coupled with a side hustle

• one or two long-term clients with a product on the side

• a main job with side freelancing offers in the same industry

There are a hundred different ways to construct a Portfolio Career, but the main idea is that you are not reliant on a single employer.

Instead your “career” is actually a portfolio of jobs, services, and/or products.

From Company Man to Portfolio Careerist

In the 1950s the concept of a company man, someone who works at the same company their entire career, ascending the ladder, until retiring with the gift of a golden watch, was common.

However, over the last 50 years, we have seen this slowly disappear.

A 2016 poll found that 40% of Baby Boomers stayed with the same employer for more than 20 years.

This changed dramatically with Gen X and even more so with Millennials who on average changed jobs every 2.75 years.

And Gen Z workers are expected to job hop even more!

Specialization makes sense in a stable economy with relatively slow technological developments.

You know that your job will exist because you know there won’t be dramatic technological changes in the next 20 years.

But today we live in a world of incredibly fast changes where new positions are popping up every year and others are being rendered unnecessary.

According to Zippia, today in the US alone there are over 27,000 social media managers.

This profession didn’t exist 15 years ago!

Portfolio Careers are a natural continuation of these long-term changes.

20-year jobs turn into 2-year jobs which turn into 6-month contracts.

Enjoying this so far? Consider sharing it with someone you think will also like it👇

Benefits of a Portfolio Career

At the beginning of the year, we saw massive layoffs in the tech space.

According to estimates by TechCrunch in the first half of 2023 over 224,000 workers were laid off. 

That’s nearly a quarter of a million people who went to bed one night with a well-paying job and woke up the next day without an income!

However, if they had a Portfolio Career, they wouldn’t have gone to zero.

Here are a few other benefits of a Portfolio Career:

📉 Reduce risk

As I illustrated in the above scenario, having a single source of income makes you fragile.

Conventional advice would call a 9 to 5 job “safe” or “stable”, but if you were to ask any of the 200K+ people laid off this year I don’t think they would agree.

Don’t get me wrong, full-time jobs can provide stability in some cases, but you shouldn’t put all your eggs in one basket.

👀 Expand work options

In her TEDx Talk, Dorie Clark, a Duke adjunct business professor, author, and career coach provides several examples of people who used their career portfolios to land new higher paying jobs.

For example, there is Lenny who was a nurse but became interested in coding and outside of his regular work developed several apps.

When his hospital manager learned of this they promoted Lenny to the social media manager of the hospital, later promoting him again to the overall Head of Communications.

Portfolio Careerists are able to learn new skills on their own time and combine them in unique ways that open them up to job options that may not have existed for them before.

💰 Increase financial leverage

The online business world is in love with the idea of passive income.

But I’m in love with Highly Leveraged Income.

Doesn’t sound as sexy, but it’s just as powerful and much more attainable for 99% of people…

Let me ask you this, would you trade $2000 per month in passive income for 5 hours a month of work at a rate of $1000 per hour - a total of $5000?

Most sane people would!

As a Portfolio Careerist, you can take the skills you’ve developed at your 9 to 5 and freelance them, doubling your hourly rate.

After a year of freelancing that skill, you can start consulting or coaching doubling your rate again.

Perhaps a year after that, you can launch a cohort course where you take a few clients at a time doubling that rate a 3rd time… although in this final scenario, you can likely more than double your rate.

Following this simple example, we can see how:

• $50 per hour salary becomes $100 per hour freelancing

• which then becomes $200 per hour coaching and consulting

• before doubling again to $400 per hour in a cohort setting

By doing this you could reduce your actual work hours while making the same income as when you started…

Or stack all of these to maximize your income!

Downsides of a Portfolio Career

Portfolio Careers have a lot of benefits, but they do carry some negatives you need to be aware of before getting started down this path…

🚀 You will need to be more “productive”

In most cases, a full-time job can make life simple and easy.

You can clock in and clock out and don’t have to think about much else.

Studies even show that full-time employees really only work 3 hours per day on their actual job and the rest is spent on secondary activities.

A Portfolio Career will require you to be far more focused and productive.

📅 Self-management

As a Portfolio Careerist, you won’t have a manager to control your time which you will have to take into your own hands.

This is obviously also a positive since you have complete control of your day, but you will need to have a lot more self-control over how you spend your time.

🏥 Taxes and insurance

Portfolio Careerists are technically self-employed so you will also have to take care of your own taxes.

You will need to track your income and make sure that you’re setting aside enough for taxes.

Eventually hiring a fractional bookkeeper can help here.

Perhaps the biggest pain for Portfolio Careerists is health insurance.

This is mostly reserved for US citizens where health insurance isn’t nationalized but connected to an employer.

Self-employed health insurance is pretty straightforward to figure out but it will cost you.

No Career Portfolio, No Han Solo

In his fantastic book The Formula: The Universal Laws of Success, physicist and network scientist Albert-László Barabási shares that according to their research, a person’s chances of success in a given field are directly correlated with their output.

Meaning the longer you try, the higher the chance you succeed.

For the baseball fans reading, the more swings at bat you take, the higher the chances that you will eventually hit a home run.

This brings up a great story I once heard about actor Harrison Ford.

Ford moved out to LA in the hopes of becoming an actor in the mid-60s and found it incredibly difficult to break through.

He didn’t want to quit but he had to find a way to earn money.

At the time he was already married and had 2 young kids…

So he taught himself carpentry!

While many actors came and went, Ford was able to stay in the game longer because he had an income from his carpentry work.

A few years in he ended up doing some carpentry work for several writers and directors, one of whom then introduced him to George Lucas.

Lucas took a liking to Ford and brought him in to read lines with actors auditioning for roles in Star Wars, but fell in love with his portrayal of Han Solo and gave him the part.

It was Harrison Ford’s first main role and led to future franchises like Indiana Jones and solidified him as one of Hollywood’s leading actors.

None of this would have been possible if Harrison Ford hadn’t adopted a Portfolio Career approach.

By using carpentry to pay the bills and support his family, Ford was able to use the rest of his free time to continue going to auditions, mastering his craft, and building relationships in Hollywood.

He didn’t succeed because he was a standout actor but because he was able to outlast everyone else.

A Portfolio Career can provide you with the same opportunity!

The first or second income streams you build as part of your portfolio may not be the home runs you’re dreaming of, but they can keep you in the game until you eventually hit it out of the park.

📝 MITKO’S JOURNAL

In this section, I share things I’m working on at the moment, interesting things that I have stumbled across, or anything else that’s on my mind that I think you will find value in.

🏢 Kowloon City. The most densely populated place in history was Kowloon City on the outskirts of Hong Kong. Before being torn down in the 90s it housed over 33,000 people in just 6.5 acres. For comparison, NYC’s East Village, the most densely populated area in the US, is home to 44,000 people on 250 acres. This is how Kowloon City came to be.

🧘 Ro. I recently listened to Lana Blakely on Ali Abdaal’s podcast where she discussed the concept of Ro. It’s a word shared among all 3 Scandinavian countries and despite not having an exact translation in English it describes a sense of tranquility, calm, and peacefulness. Lana talks about how in Sweden people try to “find Ro” in everyday life.

👋 Personal Branding. While researching several topics for this newsletter, from Portfolio Careers and the future of work to the creator economy, I continue to find just how powerful personal brands can be. You don’t have to be a famous person to have a personal brand, in fact, you already have one. It’s what people say about you when you’re not there! But when harnessed it can help you land a dream job, increase your rates, or get recognized as a thought leader.

💸 $10,000 Tasks. A few years ago Khe Hy gained notoriety for his concept of $10K per hour work - the process of identifying your highest priority tasks, those that really move the needle, and committing small amounts of time towards them every day. The idea isn’t that you should get paid $10K per hour while doing those tasks, but that when done, they will continue to pay dividends. As we inch closer to the end of the year, what are the $10K tasks you need to work on to make 2023 the most successful year to date?

📆 UPCOMING EVENTS:

Aug 28-31: NomadEire [📍Tralee, Kerry County, Ireland] - Wide-ranging discussion on all things related to nomadic life along with skill sharing, business coaching, and celebration of what Ireland can offer digital nomads.

Sept 28 - Oct 1: Nomadness Fest [📍Louisville, Kentucky, US] - A festival for travelers of color and their allies. 30+ speakers covering topics such as branding, business, domestic travel, effects of over-tourism, and much more.

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.

Dec 7-13: Nomad Island Fest [📍 Madeira, Portugal] - Learn from world-class industry experts on topics like mindset, marketing, tech, wealth & health.