I recently moved from a management position at an established digital agency to become a freelancer, working remotely for a variety of agencies across the continent. I traded my 45-minute commute to the office for the benefits of working from home; the stability of a 9-to-5 for the uncertainty of contract work.

It was a jarring transition with a steep learning curve, to say the least. Perhaps it might not have been so bad if I was developer or something, but as a project manager — a job that is all about communication and relationships — it proved pretty daunting.

Rather than face the darkness alone, I called up a few friends — Robert Jolly, Mark Fromson, and Natalie Semczuk — to shed some light on the challenges they’ve encountered with remote freelance PMing and how they dealt with them. We came up with five big ones:

1. Challenge: Working at home can be isolating and distracting.
   Response: The first step is the same that all remote workers need to tackle: have the right setup. Create a dedicated office space to help promote a work mindset every day, and make sure you have a good headset and reliable internet. Get comfortable using current industry-favorite communication tools like Slack, Google Hangouts, and/or Skype.
2. Challenge: Leading teams remotely is much harder than in person.
   Response: You’re going to need to work harder to build relationships, starting right at the kickoff. Set expectations up front about who is responsible for what and how you prefer to communicate (see below). From there, get to know team members on a personal level through chat or voice/video meetings whenever possible. Mark took this one step further and bought iTunes gift cards for team members who really delivered.
3. Challenge: Each project introduces new tools and processes.
   Response: Robert’s observation on this is that we have to be chameleons: always adapting to new sets of processes and tools. This means that in addition to standard PM skills, experience with a variety of project management and communication tools is now almost a job requirement. If you don’t know it, expect to learn it.
4. Challenge: Communicating remotely is different and more difficult.
   Response: Gone are the casual conversations at someone’s desk. Everything has to be very intentionally (over-)communicated — to everyone. Unless you’re told otherwise, CC anyone who might be at all interested on your project emails. Not sure if that person needs to be at that meeting? Invite them anyway (set to optional). On the flip side, make sure you’re easy to contact. Something Natalie does is to reach out even if nothing is going on, just to let people know she’s available.
5. Challenge: Freelancers always have to be looking for that next gig.
   Response: Landing that next project is all about your connections. Develop your personal network and use word of mouth to let people know what you’re doing and when you’re available. This isn’t a common way of doing project management, so expect some pushback from companies that aren’t quite ready yet. Finally, remember that doing good work will lead to repeat work.

We don’t have it all figured out yet, but together we’re getting closer. Is anyone else out there doing it? What challenges have you faced? What advice do you have?

Companion content:

book: Remote by Jason Fried
link: Local Solo
song: Beastie Boys – Remote Control