Hey portfolio pather,

We’ve featured many amazing people over the years, but today we have our first-ever guest post from fellow portfolio pather, Chris Ming.

Let’s dive right in.

Today, in 10 minutes or less, you’ll learn:

• 🕰️ Why remote work is a gateway to taking the portfolio path

• 🧠 How to use AI tools to automate research, source leads, and craft winning applications

• 🎯 A proven 6-step strategy that helped clients go from zero interviews to multiple offers

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💼 Landing Remote Jobs in 2025 (Using AI) | Chris Ming

The first 6 years of my tech career were spent in SF offices.

While I feel grateful for building in-person relationships in my 20’s, it wasn’t until I moved to Singapore and COVID lockdowns hit shortly after, that I realized the power of remote work.

I built a remote product team that spanned Singapore, US, Indonesia, Philippines, and Vietnam. I discovered how much leverage I could get on my time not needing to commute 1-2 hours (let alone fly across countries).

Fast forward to 2 years ago, I connected with Chris Ming through Linkedin DMs.

We quickly bonded over expat life (he lived in Dublin then).

Since then, I’ve gotten to know him through our recurring masterminds.

In particular, I have been impressed with how he’s built his remote career—navigating the same transitions that many professionals in our community are currently pursuing. And now, his insights have also helped many professionals accelerate their remote job transitions.

Without further ado, enter Chris:

Chris Ming is the founder of RemoteLifeOS, where he teaches people how to land remote jobs using his 6-step strategy & the latest AI tools. His experience at Clay, Persefoni, Reforge, Noom, and I Will Teach has shaped his remote job search strategy, which he's tested while living in Europe and across the US. He lives with his family in Philadelphia. You can connect with him on Linkedin.

My biggest fear? Waking up to realize I traded my best years—the years my kids needed me most—for a promotion.

That's the Old Career Deal: Climb the ladder, get promoted, and (fingers crossed!) someday you gain more freedom.

But there's a New Career Deal: Build flexibility on your own terms—through remote work and multiple income streams.

In my experience, remote work makes a portfolio career possible.

It gives you time back, which turns into leverage to create your own portfolio path 🙂 

As someone who's been working remotely for 10+ years and coaching dozens of successful remote job transitions (many going from zero interviews to multiple offers), I've also seen what works and what doesn't.

So find your favorite Taylor Swift album on Spotify (mine's "Reputation"), put it on in the background, and let's dive in!

Remote Job Landscape is More Competitive in 2025

Companies are pulling back remote offerings, with LinkedIn reporting a 57% drop in fully remote job postings from their peak.

Yet, these dwindling opportunities still attract over half of all job applications.

So is pursuing remote work even worth it anymore?

Absolutely. But the old “spray-and-pray” approach no longer works.

You need a better strategy that acknowledges the new reality of remote work in 2025.

One of my clients came to me after months of sending applications into the void. She'd been doing everything "by the book" but getting zero responses.

After implementing the system below, she landed four interviews within four weeks and a job offer within another few weeks.

Here are 6 strategies I recommend to earn the freedom to work remotely (and how to supercharge your search with AI):

1/ Start With Companies, Not Open Roles 🔍

The best roles are rarely listed. You have to start with companies you believe in, not just job boards.

👉 Do this: Use a tool like Perplexity to find companies by industry and stage.

✍️ Use this prompt:

Once you have your list, start researching each one (more on that below).

Save the ones that align with your values, product interests, or mission.

2/ Do Deep Research 🧠

Research is the secret sauce.

This applies to every stage in your job search funnel, but it starts with company research.

👉 Do this: Use Perplexity or Manus to get smart, structured intel on a company's priorities.

✍️ Use this prompt: