forks in the road the cookbook

Download the Free ebook now!

Buy us a beer

  1. Quick facts
  • Total days on the road: 586
  • Currently in: USA
  • Miles Driven: 36821
  • Countries Visited: 17
  • Days Camping: 389
  • Days Indoors: 202

   See all the stats here!

  1. Get Updates via Email

Delivered by FeedBurner

How to be a Successful Telecommuter

Written by Jared on March 20, 2011

To find success as a telecommuter you must go above and beyond your employer’s expectations. Prove that you can be more successful when working away from the office. Then use the trust you’ve gained to further your professional goals.

Be prepared to work extra hours in the beginning. Not having to commute or take a company lunch break means that you should have extra time on your hands. Use that time to deal with the new logistical challenges of telecommuting so that you can exceed your employer’s expectations with the work you’re assigned. Make use of your new flexibility and find ways to work smarter.

The most challenging aspect of telecommuting is the reduction of communication between yourself and your boss and colleagues. You can find yourself out of the loop pretty quickly. Spend time establishing new communication strategies that help keep you informed of what’s happening at work. For example: dial into meetings, chat with your colleagues over the phone or online, setup weekly progress report meetings and make use of online collaborative tools.

Stay Connected

The first major hurdle encountered by many telecommuters is figuring out how to handle day to day communication. To be successful, you must quickly adapt to your remote workplace. In addition to changing your work behavior, you also have to help your boss and colleagues adapt to the situation. Make this process as easy as possible for them, so they stay positive about your new role as a telecommuter.

The hardest part of telecommuting for many is losing human contact and growing slowly out of touch with your workplace. You miss a lot not being at the office, mostly small stuff, but it adds up over time. Water cooler chat, the informal meeting that happens right after a meeting, group announcements, etc. You lose the social atmosphere of a work environment. There is no way to completely solve this problem (aside from going in to work) but there is much you can do to maintain your connection with your employer and colleagues.

  • Make sure your boss and colleagues know your work schedule and how they can contact you at all times.
  • Emphasize voice communication over written. The human element tends to be missing from emails.
  • Schedule reoccurring conference calls to discuss your work. More frequent in the beginning.
  • Recruit colleagues who work on-site to help keep you in the loop. It helps to have a chat at least daily with people you work closely with. It doesn’t have to be formal, just frequent.
  • Make more meetings virtual. Promote the use of web and/or video conferencing that allow you to be more involved with the discussion.
  • Find ways to move your work online. This will give immediate visibility to your employer, and will make it easier for your colleagues to collaborate with you.
  • Use tools like online messaging to make yourself immediately available.

Build Trust

The ability to continue telecommuting and add flexibility to your lifestyle depends upon the relationship you build with your employer and colleagues. If your boss is happy with the progress you make while telecommuting, you’ll have leverage to continue your new lifestyle and perhaps to increase (or decrease) the amount of time you spend working remotely. Continuing to build upon your success as a telecommuter will allow you to achieve the goal of becoming completely location independent.

Building trust is easy. Do your job better and faster than expected. Set conservative expectations and strive to exceed them. In other words: under promise and over deliver. Use the flexibility of your remote workplace to find ways to work smarter and faster. Being removed from the distractions of a shared work environment and not wasting time on a commute should make this simple.

Maintaining the trust of your employer requires you to be on time and available during your work hours. Fulfill your telecommuting proposal by being where you say you’ll be and working during the hours you’ve agreed to.

Always be conscious of how and when people expect to be able to communicate with you and do everything possible to maintain those channels of communication. If your boss or colleague calls, or sends you an email, be available and respond immediately.

Keep your employer and colleagues aware of any changes to your schedule. Your availability will inevitably change, real life tends to get in the way of work from time to time. It’s very important that you immediately notify everyone who may need to contact you when there are changes to your availability or means of communication. If you know ahead of time that you won’t be available, give people plenty of warning and send out an additional reminder just before you disconnect.

Up the Ante

Once you’ve gained the trust of your employer and demonstrated that you are an effective (and hopefully overachieving) telecommuter, it’s time to raise the stakes and take another step in the direction of becoming location independent.

You’ll probably need to go through a renegotiation process with your employer several times to reach your final goal. Have these steps mapped out and set goals for each. As an example, here are steps you may consider taking:

  1. Work from home one day a week.
  2. Work from home 3+ days a week.
  3. Work off site (but not from home).
  4. Work from home full time.
  5. Work and travel for several short (1-2) week trips.
  6. Work and travel for longer trips (4+ weeks).
  7. Reduce the hours you work, if necessary.

Consider asking for fewer hours if you don’t see yourself maintaining a full time job and wish to travel long term. Experiences gained on shorter trips will tell you if this is necessary. We have found it very difficult (and unnecessary) to combine long term travel and full time work. You ultimately end up planning your travels around your work schedule instead of the opposite. This may be fine, provided your focus is on your career rather than travel.

Knowing when to propose a change to your telecommuting proposal is tricky business. You’ll have to gauge for yourself when the best opportunity arises. It gets easier as you build trust, so considering aligning your renegotiation with significant successes. Just finished a big project ahead of schedule? Saved your company a bunch of money? Succeeded after taking on a lot of new responsibilities? These are the times you should act.


Tyler Straub
#1 Tyler Straub 2014-03-22 11:16
I've started to telecommute and travel, first in South America. I'm here in Cartagena hoping to glean some incite from experienced travelers doing something similar to what I'm doing, but so far after 4 or 5 pages of reading, this all seems to boil down to use common sense. Maybe I'm looking looking in the wrong areas, but where is the parts about getting extra smartphones/hot spots and how to charge them in each place, how much it costs... ect. I heard Ecuador just got 4g, but it's only in a couple cities. That would be useful.

This content has been locked. You can no longer post any comment.