About the Remote Job Course Guy

Hey — my name’s Rob! 

I’ve worked remotely for the past two years and landed three full-time remote jobs during that time. Yes, my churn rate has been high for many reasons (explained below), but now I have a tested approach for finding and landing remote jobs. On this site I share that approach with you, and the tools and templates needed to make it work.

A brief history of my remote work experience follows. It includes the mistakes I’ve made from hastily accepting remote job opportunities in the past. Please take them with more than a grain of salt!

To distill everything below into a few sentences: The perks of a working remotely don’t outweigh the satisfaction of working with a company you care about. That said, working remotely does open up some amazing opportunities. (For me this was traveling.) So, if you get an offer from a remote company that’s mediocre and a non-remote company that’s awesome, go with the latter — unless you have an explicit reason for working remotely and that reason will outweigh the misery of working for a company you don’t give a damn about.

A brief history of my remote job experience

My first remote job actually started off as an office job. After the initial company I was with got acquired in mid-2016, I convinced the new company to let me work remotely. At this time I was interested in driving up and down the east coast and living in different cities. I was able to convince my manager to let me work remotely because I had proved my value over the years.

After a few months in of working remotely, the work became unbearable. The vision of the new company didn’t align with my values and people I respected resigned. There also wasn’t a remote work culture in place. I was often left out of team conversations which made me feel like a lone freelancer. This got the better of me so I left and started looking for other remote jobs.

Lessons learned: Only work remotely for a company with a remote work culture in place. And don’t be afraid to resign and look for new opportunities.

My second remote job was a full-time contracting job for a SaaS startup. It was an employee management tool that let employers see what employees were working on through time tracking and screenshots. I took the job because it was readily offered to me and I needed some money to start my worldly travels.

Three months in, I lost all motivation because I didn’t care about what the company was building. In fact, the product went against some of my values. It promoted micromanagement and encouraged employers to be okay hiring people they didn’t trust. (They could rely on the time tracker to hold employees accountable.)

Lessons learned: Only work remotely for a company you actually give a shit about. And be weary of contract jobs that don’t come with any benefits.

My third remote job was a full-time employee position with a publishing startup. The startup was located in San Francisco and I accepted the opportunity while traveling in Europe. My hours became 2pm to 10pm instead of my preferred working schedule of 9am to 5pm. For me this wasn’t sustainable. I’m an early morning guy.

There were also some micromanagement issues here and hours upon hours wasted on aimless conference calls (morale killers). While the company was cool, I just couldn’t hack my way around the inefficiencies and time zone differences. Upon resigning from this remote job in mid 2017 I completed my worldly travels and joined a company in Boston.

Lessons learned: Don’t work remotely for a company with a schedule that interferes with your sleeping patterns and social life.

My last full-time job was an office job in Boston that I joined in late 2017. The pay was great, the benefits were good, the office was nice, and I had a fancy new loft in East Cambridge. But being in a bitter-cold climate and not really caring about what the company was building made me miserable. (Yes, I made the same mistake I made with my second remote job.)

In full transparency, at this point in my career working remotely isn’t as important to me as it was two years ago. What’s more important is working for a company I give a damn about. But for those of you set on working remotely, you’re in luck…

In 2017 I needed to master the art of getting interviews with remote companies in order to fund my excursions around the world. And even though the remote jobs I landed didn’t work out, I came away with a template for landing them. And now I share it with you.

Happy hunting! ✌