How I've landed (almost) every online job
3 min read

How I've landed (almost) every online job

Every meaningful working relationship I've created to date has been the result of a cold email or cold DM.

Before I had any experience working online whatsoever, it was sending cold DMs on vBulletin forums that opened the door for me to forge a career without any degrees or certifications.

Cold outreach can change your life by creating friendships, landing jobs, or simply receiving advice. There are few low-hanging fruit opportunities with this much upside. I'm realizing as I write this that I'm not doing enough proactive cold outreach.

I can't tell you whether my cold outreach technique is good or not, but it has landed me incredible working opportunities and connected me with amazing people who would have never known who I was otherwise.

This is how I approach personal cold outreach.

I don't try to influence or persuade. My objective is to present myself and my situation as authentically as possible. The recipient is free to decide whether or not they want to get involved once all the facts are on the table.

I completely avoid candy coating. I want to be as honest as possible by clearly expressing what I need from them, why I want it, and what's in it for them.

I explain why I'm contacting them instead of somebody else. This separates my message from spray and pray spammers who don't show a personal interest. It makes clear that they have a unique ability to help me.

I share how the opportunity fits into my bigger picture. Explaining how I will benefit from their help, and where exactly it will take me, helps paint a picture of the positive impact they can have on my life, if they decide to give me a chance.

I explain why they will benefit from helping or hiring me. Successful people (usually) love to help people hungry to succeed. If you're hungry and you can build a strong case as to why they would benefit from hiring you, everybody wins.

Your success rate on cold emails is dependent on your ability to authentically present yourself, meaningfully connect with the recipient, and craft convincing win-win situations.

I have likely sent less than 50 cold emails in my lifetime—and I'm conflicted about this. More outreach would lead to more opportunities. But I kind of like having this skill, which sometimes feels like a superpower, in my back pocket for only the opportunities I really, really want.

From day 1 of working online, I've been paid to write. I understand the concept of cold outreach may be more intimidating for those without a writing background.

Your message needs to standout if you want a positive response. If you don't have the writing ability to standout via email or DM, you need to get creative and/or work harder to capture attention.

I've been lucky enough not to need to resort to the more creative tactics, so I'll save my thoughts on those until I try them for myself.

I'll end this post with what I believe to be the best reason to do cold outreach: landing your dream remote job.

This is the advice I give most often to friends toying with the idea of getting a (new) remote job:

  • Make a list of 3-5 people or companies you'd love to work for
  • Find out how you can help them by looking at their past job postings
  • Craft a convincing case on why you're the perfect person for the job

If you're not qualified, ask them if that's even an issue first. Ambition can sometimes make up for lack of experience.

If your lack of experience turns out to be a dealbreaker, share with them a 90 day gameplan you're going to follow to become drastically more qualified. Then ask them if your gameplan is missing anything important.

Execute the gameplan and email them again in 90 days or less.

The jobs/gigs/clients you will land by being proactive on cold outreach like this are 100x more rewarding than the stale opportunities you'll find on remote job boards.

And that's how I've created a career, with zero qualifications, out of cold outreach and working hard.