🦅 6 Strategies to Earn Your Freedom to Work Remotely

Hello there 😎 

My main focus in 2025 is helping as many people land their next remote role as possible. If that's your goal too, you're in the right place. Stay subscribed and keep reading - we've got a lot planned.

Becoming valuable at work is the best way to unlock the freedom to work from anywhere. When you're indispensable, you can write your own ticket.

Here's what you'll learn today:

• 🎯 How to stand out in a crowded remote job market

• 🚧 3 common pitfalls that hold people back

• ⚡️ 6 proven strategies to become irreplaceable at work

…and more!

Let’s jump in.

🤫 My friend ignored his company's RTO mandate

This is at a BIG agency. One of the biggest.

95% of the company got herded back to their offices.

My friend?

He’s crushing targets from his home office by the mountains.

His secret?

Being so damn good they can't say no.

🎯 Being In-Demand Matters

Here's the truth about remote work: you can earn it through leverage. And leverage comes from being indispensable to your company.

(Should you "have" to earn it? No. I believe most people should have the option if the work allows for it. I’m just saying that being invaluable gives you the power to make it happen.)

When you become invaluable, you can negotiate:

• Pay: Command higher salaries

• Projects: Choose work that excites you

• Location: Work from anywhere you want

The equation is simple:

Solve big problems + Drive measurable results = Freedom to dictate your terms.

Companies will bend their policies for people they can't afford to lose.

💪 How to Become Valuable at Work (So You Can Work Remotely)

When it comes to land remote opportunities, too many people chase things that don’t matter:

• Upskilling with general “remote skills” (like what? Slack?)

• Prioritizing learning tools instead of demonstrating their results

• Scrapping for limited remote opportunities without positioning themselves as a must-hire.

In short: they wind up blending in instead of standing out.

In today’s job market, that’s a losing strategy.

Here are 6 strategies to become valuable at work so you can work remotely:

1/ Become the Go-To Expert

Lean into a specialty. Depth trumps breadth in today's market.

When you narrow your focus from being a "full-stack developer" to a "React performance optimization expert," you move from being good at many things to being exceptional at one thing.

You want to become the undeniable expert of X at your company.

My friend Vic wrote a great guide on how to learn better.

2/ Work at Smaller Companies

At smaller companies and startups, you’ll have more chances to deliver big results. You (and your work) contributions are more visible.

The work you do is directly felt on the bottom line. What you build and how you interact with customers will:

• Make the company money

• Save the company money

• Save the company time

And others will notice.

This visibility often translates into more flexibility in how and where you work.

The rigid policies of big corporations (like RTO) just don’t work the same way at smaller companies.

Smaller teams tend to prioritize results over rules.

My first 8 years at remote-first companies were all small companies. These years were intense and hard. But it was worth it.

3/ Build Your Reputation

Your reputation IS your workplace currency.

It’s more than the work you produce. It’s about consistently being recognized for excellence.

This is important. I’m going to double-down:

Optics—how others perceive you—is a necessary ingredient.

Delivering quality work, hitting deadlines, and solving tough problems builds a track record that outshines any resume.

Over time, this reputation becomes your golden ticket to flexibility and new opportunities.

4/ Get Things Done Fast

There’s an expression that gets thrown around: slow is fast.

Like many work ironies, this applies at the senior executive leader level. But if you’re mid-career, or you’re an IC…

Fast is fast.

When you complete projects faster than expected—and do so without cutting corners—you’re showing your team they can rely on you to drive results.

This is about working smarter and mastering execution. It’s NOT about rushing.

5/ Know Your Company Inside and Out

Every organization has its own unwritten rules and ways of working. Understanding these nuances is like unlocking a secret playbook—it gives you a competitive edge.

You have to:

• Know who makes key decisions, e.g. Head of Product needs to approve all feature changes, while the Engineering Lead has final say on technical implementation approaches

• Learn how different leaders like to work, e.g. one executive might prefer detailed written proposals, another doesn’t read and relies on quick, informal stand-ups

• Understand what matters most to your teammates, e.g. who wants to give early feedback? Who wants detailed documentation? Who expects to be recognized for any contribution, no matter how small?

Every organization has a unique culture. I loved the culture at Reforge because I helped build it. Then, I went to Noom and struggled to adjust—even though the people were smart and nice.

6/ Build Relationships That Open Doors

Strong relationships are career rocket fuel.

When key stakeholders trust your judgment and see the value you deliver, they'll fight to keep you—including advocating for remote work arrangements.

I've seen this play out countless times: a manager advocating for their direct report to work from another state or a CEO making a special exception for their right-hand person who wants to work abroad.

• Invest in your remote relationships

• Schedule regular coffee chats to connect beyond work topics.

• Share resources or insights with teammates before they ask.

• Celebrate others’ achievements publicly

• Be the teammate everyone knows will follow through on commitments.

💫 The Bottom Line

Seniority, circumstance, and luck all play a role in who “gets” to work remotely.

But demand is the great lever—and fortunately, this is where you have the most control.

If you can solve problems faster, smarter, or better than anyone else, companies will bend policies for you.

That’s a wrap. See you next week 👋

🤝 3 ways I can help you with remote work: