🧑‍💻 Meandering careers

How to navigate a pathless career, why degrees soon won't matter, and how the workweek is evolving.

Hey Insiders,

Happy Friday! Careers and the way we work is changing fast. As we speak we are in the middle of a reset in our relationship with jobs, as a reader of this newsletter you know that, but the majority of people don’t!

Today’s email is all about how careers are changing, and how companies are adjusting to continue attracting top talent.

In 3min 50sec we cover:

  • 🧭 How to navigate a meandering career

  • 📄 Ripping the “paper ceiling”

  • 📅 Evolved workweek era

Let’s dive in!


Praise for the Meandering Career

There’s an existing narrative that if you want to build a successful career you need to mind your resume.

It should make sense and show a clear progression.

As Simone Stolzoff, the author of The Good Enough Job, writes for Every, your resume should be “free from breaks, twists, and turns.”

This may have served workers in the 90s, but it’s not the reality anymore.

Today, two-thirds of workers don’t feel engaged by their work, so perhaps exactly in this environment is the time to question why we do the jobs that we do.

A non-traditional work path can be difficult…

Most Americans asked about why they don’t try it mentioned things like health insurance, savings, and promotions. All are valid, especially health care, but the world is changing.

If you’re interested in pursuing a non-traditional path, Stolzoff has two pieces of advice:

  1. Trust your curiosity: You don’t need a 10-year career plan or to reverse engineer other people’s careers. Instead, lean into what you’re naturally interested in. That internal compass is more useful than anyone else’s advice.

  2. Find the others: Paul Millerd, author of The Pathless Path, points out that one of the reasons so few people take the non-traditional route is that it’s quieter. People in positions of power have a vested interest to highlight the life of excellent sheep. But when you find other people who are also pursuing a non-traditional path you will have more confidence to do so yourself.

Are you interested in a Non-Traditional Career?

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Companies are dropping degree requirements, but they still have no idea how to hire without them

The filtering of potential employees based on the absence of a Bachelor’s Degree is what’s known as the “paper ceiling”.

But more large companies, from Kellogg’s, General Motors, and Bank of America, to the US government are removing the requirement for a 4-year degree.

That’s just step one though, it turns out that without a 4-year degree, hiring managers actually have no idea how to judge talent or hire. It’s not how they’re currently being trained.

There are new protocols being tested and promoted at the moment such as LERs (Learning and Employment Records) that serve as a sort of “digital wallet” of skills and experiences gained through work, volunteer positions, training, and traditional education.

The nonprofit Education Design Lab has designed a program for “micro-credentialing” which provides certifications for soft skills.

In addition, Salesforce runs a micro-credentialing program for its products that can be used to level up sales skills with or without education.

Above all, however, companies need to change their culture. No amount of training programs and certifications will fix the problem if companies internally don’t remove the biases to degrees.


What is an ‘evolved workweek’?

Post-COVID the traditional workweek is no longer the universal blueprint it once was.

Companies of all sizes are experimenting with different evolved workweek structures such as:

  • four-day workweeks

  • compressed-hour weeks

  • summer Fridays

  • WFA and hybrid models

  • extra PTO terms and others

This is all in an attempt to retain top talent that has more access to opportunity thanks to remote work, and to try and curb burnout.

Not everyone is on board though. One of the key challenges is that many in management (coming from an old-school background) aren’t keen on the idea.

Another pain point comes from figuring out if everyone should be off at the same time. Some organizations may have to stagger time or days off depending on the nature of some roles.

No matter what, companies that employ an evolved workweek stand to win. 80% of job seekers on ZipRecruiter said they prefer roles with a four-day workweek.


  • 🇸🇬 Heading to Singapore? Check out this list of the best coliving spaces in the Garden City

  • 🏠 From office to apartment. I’ve written about office conversions in the past, but here’s a great NerdWallet piece that explains how we ended up with so many offices in the first place, and why just creating more housing won’t solve the problem.

  • 🏕️ Remote work cabins. A new crop of startups has popped up offering “work cabins” that allow you to escape the city, and enjoy nature, without losing internet.

  • 🎟️ 132,000 Golden Visas. A new report found that over 130K people received golden visas to the EU between 2011 and 2019. Will these programs increase thanks to remote work, or has the “golden age” of the golden visa passed?

  • 🤝 Fighting loneliness with community. Loneliness is the main problem faced by digital nomads, but new community models and leaders are rising up to solve it.


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. (👋 I’ll be there)

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.


Looking for a job that’s not just remote, but that you can work from anywhere in the world? We’ve done the heavy lifting for you. Check out these awesome WFA positions 👇

That’s it for today! Thanks for starting your day with Remote Insider, let me know what you thought of today’s email, and make sure to comment if there’s anything you want us to cover in future emails 👇

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Have a great weekend and we’ll see you on Monday!

Cheers 🍻

Today’s email was written by Mitko Karshovski