#6: Working From Anywhere with Phil Montero

Phil Montero of Montero Consulting specializes in educating and training people and organizations about all things telework, mobile offices, remote-work arrangements, virtual teams, and working from anywhere. He blogs about these things regularly at TheAnywhereOffice.com and also runs YouCanWorkFromAnywhere.com.

Phil was gracious enough to join us and talk about the topic of working anywhere as it relates to freelancers. How can we build trust with clients we may never meet face to face? What are some ways we can ensure success when we work in virtual teams with other freelancers? What effect does technology have on the shift from employee to freelancer? And is that shift here to stay?

This was our longest episode by far and a very engaging conversation all-around. You’ll definitely learn a few things from this one.

Mentioned in this episode:

This episode’s soundtrack:

Check out the tight vocal harmonies of the Fleet Foxes and their new album Helplessness Blues.

Opening clip: “Helplessness Blues”
Closing track: “Lorelai”


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  1. Really enjoyed the show lads. Phil was a great guest.

    I work in a shared studio space, but as a new(ish) Dad it’s nice to be have the freedom to work from home when it’s required. I’ve definitely noticed a trend in the past few years towards clients relying less on face to face meetings, though as Phil mentioned in the show there are some old school clients who always seem to want to do everything face-to-face. But I’ve found that working remotely has no negative impact on my client relationships, or project management.

    Cloud based apps (Dropbox, Passpack, Apollo, Slimtimer, Google Calendar) and IMAP email mean my work and important data is accessible all the time, so moving from home to the office is no drama.

    • Brian

      Thanks Jonathan! It’s all about the cloud… I spent a few hours yesterday syncing my calendar across mac – mac – iphone – ipad. The anywhere office is complete :)

  2. Brian

    I should have mentioned this during the episode, but this Ted talk from Jason Fried, “Why work doesn’t happen at work” is a great take on this conversation:


  3. Hey guys (and fellow freelance jammers) – thanks so much for having me on the show – it was a blast!

    I really love all the information you are providing for freelancers and the resources you share are excellent.

    Keep up the good work!


  4. Martin Lundell

    Great stuff! I found myself updating my delicious account often with all the webapps you were discussing.

  5. A little late to the party with my comments, but just wanted to say 2 quick things:

    1. The New Small is a great book, definitely worth checking out.

    2. Phil Montero’s comments about the value of working from home and being able to spend more time with his family were excellent. I did the NJ-to-manhattan commute that Phil’s father did, and I cringe at the thought of how many hours of my life was spent in crowded NJ Transit busses sitting in Route 3 traffic over just a few years. I’ve had the privilege of working from home since last summer and spending time with my son, and it is definitely priceless. I wouldn’t trade this for anything.

    Great show, guys. Keep up the good work!

    • Brian


      I used to do the NYC commute as well. It’s rough, especially when there are subways involved (which have no internet connection!!) – BC

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