💻 Break Into Remote Work: Your 6-Step Playbook

Hello, Connectors 😎

Today in 5 minutes or less, you’ll learn the six steps to break into remote-friendly roles or industries, even when traditional paths seem closed off.

Plus, the best links and resources on remote work. You'll learn:

• ⚓️ Remote work's real advantage: deep work 

• 🤑 The paradox of happiness and pay in remote work

• 💻️ How remote work is changing the productivity game

Let’s jump in:

💻 Break Into Remote Work: Your 6-Step Playbook

You want to break into remote work. Or a new role, or a new industry.

But to break in, you need experience.

From the outside, it can seem impossible to break in. Typical blockers: 

• I never worked in a related industry

• I have the wrong degree

• I’m not tech-savvy

You can do it, too. 

The biggest mistake people make is trying to solve this via resume optimization. 

Solving this with only resume tweaks and narrative changes is difficult. There are a few other strategies you can deploy. My favorite?

Let’s dive into how you land that first experience. 

1/ Leverage the Bannister effect

On May 6, 1954, at a meet in Oxford, Roger Bannister ran a 3 minute, 59.4 seconds mile. 

Before that, a sub-4-minute mile was thought impossible.

46 days later, John Landy ran a 3 minute, 57.9 seconds mile. 

Fortunately for us, we barely have to break a sweat to find people who solved the Experience Catch-22. We just need LinkedIn. 

Let’s say you’re interested in breaking into product management, but you don’t have PM experience. Work backward to leverage the Bannister effect and see how others landed the role:

1. Search LinkedIn. You’re looking for people with the role “product manager”. (Replace product manager with whatever role you’re targeting.)

2. Profile surf. Find these LinkedIn profiles. Profile surf for an hour, and you'll find at least five paths to your goal. Search for people with your current role, your desired role, and anyone who’s previously worked at any companies you worked at.

3. Reach out. Ask them how they did it.

Why reach out?

To hear it directly from them. The gold is in the details. After you know it’s possible, the next step is uncovering the how.

Here’s a script I’ve used in these situations:

You only need to see it done once to take your career in an “impossible” direction.

2/ Find startups and small, early-stage companies

You’re learning how others have done it. 

In parallel, start searching for opportunities at small, early-stage companies. 

There are a ton of benefits of going early, but in particular: 

1. Many are open to remote work

2. And you get to wear a lot of hats

When I joined Reforge in 2017, we were a remote team of 5. I got to wear all the hats: content creation, content operations, customer support, program operations, marketing, product. 

It was the best tech education I could have asked for. I saw how each function worked. I built intimate knowledge of all the nooks and crannies of each role, nuances no one volunteers in a JD. 

Get in with an early-stage company, add value, and you’ll “earn” whatever title you desire.

So what are you looking for in early-stage companies? 

• Areas you have domain expertise

• Areas you're passionate about

• Where you can add value

Where else to look for such opportunities?

Start with the “big” startup job boards. 

• Y-Combinator

• Hacker News

• AngelList

• BuiltIn

From there, diversify with LinkedIn, Reddit, and X.

(Don't worry if the company doesn’t have a good-fit open role. You won't be applying through some job portal.)

3/ Do deep research

This is where people make the biggest mistake: they misunderstand what I mean by deep research. Here’s what it looks like: 

• Read 30 company tweets

• Read 10 company blog posts

• Study 7 employee LinkedIn profiles

• Watch 5 interviews with the CEO

• Listen to 3 industry podcasts

I’ve invested months into research before sending a single cold email to an author. 

I read everything they wrote. Not just his books. Every unproduced TV script. His short stories. His play adaptation of his own short story. The adaptations by other writers of his work.

Is this hard? Yes. That’s why it’s valuable. 

That's because you're playing a different game. This is chess, not checkers. 

4/ Reach out to founders

Reach out has two simple steps: 

1. Get their attention (covered here)

2. Send them a message (covered in the next step) 

How do you get a founder’s attention? 

First, find out where their attention is focused.

• Email (use hunter.io)

• LinkedIn

• Twitter

• Instagram

Figure out where they spend time and be there. Your goal is to get around the gatekeeper and go straight to the decision-maker.

Really can’t find the founder’s email? No problem: work your way down the chain of command and repeat. Look for the C-suite, VPs, and then department heads. 

Always start at the top. It's better to get passed down vs. passed up.

5/ Pitch a high-value, no-risk short-term project

You got their attention.

Now, you need to send a message. 

You’re sending a cold email. So you need to bring value fast. 

In these situations, what’s worked for me is pitching a high-value, no-risk short-term project. 

That’s a lot of hyphens. Let’s break it down: 

• High-value. You solve a real problem, earn money, or save them time

• No-risk. Your project should be free (financial risk) and require no oversight from them (time risk) 

• Short-term. There should be a clear “end” to the project. 

What project should you pitch? It should be directly related to the role you’re trying to add to your resume. For example: 

How you present yourself and this project matters a lot. Here’s a template that’s worked for me:

6/ Land the title, get the experience

Once they’ve accepted your pitch, it’s about execution. 

Remember: the output needs to be high-value. You need to deliver without any input from them. And you need to deliver on time. 

In other words, you need to keep your promise.

If you keep your promise, you can expect at least one of these outcomes: 

1. You’ll be able to honestly and ethically add that coveted title to your resume

2. You’ll have a new reference who can speak for your work and get you new leads

3. You’ll get an offer to stay on and continue your work 

And once you get that first title under your belt, you’re off to the races. 

Conclusion

By following these six steps, you can beat the “Experience Catch-22' challenge and start building the remote work career you want. 

Happy hunting.

🧭 Want to Land Multiple Remote Job Offers?

The second cohort of the Land A Remote Job launches soon.

Click here to learn more.

Details at a glance:

• Goal: Land an awesome remote job for a life with more freedom and autonomy

• You get: The full program with lessons & videos, group coaching, office hours calls, direct feedback from me, accountability, a personalized resume review, a personalized cover letter review, and more

• Land A Remote Job program: The end-to-end system I use to land my remote roles, exactly what I teach my clients.

• Group coaching: Direct feedback from me on your toughest questions, support and accountability from your peers, office hours calls (over Zoom)

• When/where: The program starts in late February. Office hours are on 3/6, 3/20, 4/3, 4/17. All video calls, time TBD but likely 8-9pm EST.

• My promise: If you keep putting in the work, I'll keep working with you until you land a remote job

Click here to learn more.

That’s a wrap. See you next week 👋

🤝 3 ways I can help you with remote work: