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.
    : 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


Natalie is a freelance and consulting digital project manager working with small, remote-based agencies on client-based projects, project management practices and internal processes. Outside of work, Natalie drinks too much coffee and runs a blog called catphotosfrommymom.com.

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Mark specializes in digital project management, functional analysis, user experience and information architecture. With more than 15 years of experience, he has played roles in over 400 projects for over 150 clients at top interactive agencies in the US and Canada. As if project management wasn't exciting enough, Mark is also an avid surfer, trapeze artist, and former professional high diver.

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For over 15 years, Robert has worked on web projects with clients from non-profit, government, higher education, small business, start-up, and enterprise organizations. At Happy Cog, Robert helped lead projects for the likes of Thomson-Reuters, Zappos, and Georgetown University. Robert also has a long passionate relationship with Waffle House, and makes it a point to visit whenever the opportunity presents itself.

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Carson has been doing the digital project management thing for over a decade now, and still loves every minute. After hours, Carson listens to music no one else likes, plays hockey poorly, and co-runs the DPM Edmonton Meetup.

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  1. Hello,

    Thanks for the article on remote project management. I’ve been working remotely for a global software company for years, and these challenges are very real! The isolation piece is definitely the hardest for me.

    I wanted to reach out because I am looking to transition out of my current company and into another remote position. I’m wondering if there would be an opportunity to speak with you about remote PM work and any suggestions that you may have regarding networking. Is that possible? Here is my LinkedIn profile:


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