Almost Fearless

Turning Your Job Digital: Day 3 of 30w30d

This post is part of 30 Ways in 30 days to Redesign Your Life and Travel the World. This series seeks to give you the practical, real world steps you need to take to get from wherever you are, to exactly where you want to be– traveling the world and living the lifestyle you want.


30 ways in 30 days, digital nomad, work wirelessly, around the world trips

If you can swing it, getting your boss to let you work remotely can be a great way to travel the world. It’s not as rare as you might think, either. In my former corporate life, I managed almost completely virtual teams. Even when a team member was based in the same office as me, it wasn’t unusual for one of us to be working from home. My own boss lived in another state.

If you’re not lucky enough to work in an environment with an established remote employee program, you may still be able to convince your boss to work outside of the office. To determine if you’re a good candidate, check these four conditions:

1. You don’t need to physically interact with machinery, customers or venders to complete your work (for example, a PC technician, nurse or sales rep would not be a good fit).

2. The company already has the hardware (like speaker phones) and/or software (like video conferencing or teleconferencing service) and you’ve seen them in use within your department (even if it wasn’t specifically for a remote employee). Also be sure to check that you can access everything you can at work.  Can you check email and voicemail from home?  Can you log into your companies network?  Download files?  Use work-related software?

3. You have a laptop for your job already, or some people in your company have one. If you think you’ll be able to buy your own and use if for work purposes, it’s going to really depend on the IT Security policies at your company. Any sizable company should have a problem with business info on a personal PC. Also, keep in mind that your boss may have to budget for it a year in advance.

4. You are a trusted and valued employee. If you’ve just gotten written up for being late or missing assignments, it’s highly unlikely a boss will trust you to work even more independently.

  • Do you meet all four conditions? Then it may be worth approaching your boss about working remotely.

How to Broach Going Digital

This is a case where you’ll want to be very sensitive to your companies culture. If you get a “no” it can be hard to come back from that. Use your gut instinct, but here are some ways to approach it:

The Litmus Test

1. Let your boss know that you have an appointment at your house one morning next week, that you need to wait for. Reassure him that you’ll bring your laptop home and keep working as you wait. (This is better than faking sick and working from home, as you might make the wrong impression– like kiss up).

Goes well? Continue on…

2. Schedule a meeting with your boss and ask him directly about the ability to work from home. You’ll want to be prepared with how you’ll stay in contact, a back up plan, how they will keep track of your assignments and a communication plan. But your bosses first question is going to be, “why?”. You want to keep this simple and objection free. Good and true reasons like, “I am sick of the commute” are often easier to swallow than “I’d like to backpack across Central America”. While both may be true, your boss isn’t ready for the latter yet. They are concerned that you’ll keep doing the work and won’t make them regret the decision. Leave your big travel plans out of it, for now.

Goes well? Continue on…

3. Your boss probably said something along the lines of, “let me think about it” or “I’ll have to check with HR”. Now is the time to give him a little air, and work your butt off being the superstar that you are. In two weeks, pop into the office and casually mention that you “just finished XYZ awesomeness, oh and by the way is there any update on the work remotely thing?” Be persistent but friendly, work hard and be productive, but don’t be surprised if your boss drags his feet. It may take a few months to get an answer, in the meantime, start forming your backup plan.

The I’m Gonna Quit

This one is uber-risky. It’s a quick way to find out how valued you are– or are not.

1. Schedule an appointment with your boss. Let her know that you’ve received an offer to work at another company. You really don’t want to take it, but it’s working 100% remotely, which is something that is very appealing to you. You would love to stay where you are– but it’s just so hard to pass that up. Is there any way that they could accommodate you? Be prepared to have information on how this would work if they did let you. The decision will come fast, and it may mean goodbye.

The Big Fat Lie

Well the last one was a lie, but that’s a business lie, which doesn’t count, right? This one is lying about your personal life. Not for the weak stomached.

1. Craft an elaborate lie about possibly, maybe having to move just beyond what would be reasonable to drive. Maybe your spouse got a new job? Try not to say your mom’s sick, that’s just immoral.

2. Schedule an appt with your boss. Set out your very compelling dilemma and ask them to help you figure out how to make this work. Perhaps suggesting something absurd like working 80 hours one week and zero the next as you fly between cities. Then it comes to you… could you, would it be possible, to work from home?

Goes well? Hug your boss and try to keep your story straight.

The Truth

This one worked for my husband, don’t underestimate it.

1. Schedule an appointment with your boss or just send an email. Ask if you can work remotely, because you’d like to travel to X. Assure them that you’ll be able to complete the work and you understand that for any reason they could let you go if they weren’t happy. If you’ve worked remotely before, mention it. Then sit back and wait. In my husband’s case they made him sign a letter saying he’d still do his job. If they ask for that, do it! It’s no more protection than what they already have.

Other Tips:

  • If you can’t get a “yes” from any of these methods, then you can always to ask to do it on a trial basis.  Try 1 day a week for 90 days.  Then work you butt off in that time to prove how easy it will be for your boss.
  • I mentioned this above, but be prepared to answer their objections.  How will it work for meetings?  What if you need to see the client?  How will they get in touch with you?  Will you pay for your own phone line?  Do you have high speed internet at home?  What about sensitive information on your laptop?
  • If you’re not considered a rock star in your office right now, you might want to take some time earning that designation before you approach your boss.  Have a list of your accomplishments ready if you need to justify why you deserve this “perk”
  • I specifically didn’t mention how to go from working remotely to traveling the world in this post.  One step at a time.  If your boss does bite, you’ll want to spend sometime working out the kinks from your home, before you hit the road.
  • A word about honesty… I would suggest you go the honesty route, but I’ve included the other options, because, hey sometimes they work.  I’ve personally seen people negotiate nearly 100% remote working based on some “personal situation” when it was absolutely not allowed for anyone else.  Is it fair?  No, but your boss is human.  They want to help.  And if you don’t like your job, and will probably quit anyway but wouldn’t mind squeezing a year or two of remote work out of them, then you might not feel very bad about painting an inaccurate picture of your home situation.
  • Be aware that change in managers can mean that your work remotely agreement is revoked.  Always have a backup plan.


1. Have you turned your job digital? What worked? What didn’t? Share in the comments…

2. If you don’t think you’re current job will be able to be converted, don’t despair, we’ll be discussing other options later in the month.

Additional Reading:

Challenging Telework Myths

Tools and Tips

How Much Does Your Commute Really Cost You? Calculate It… Then Kill It?

Christine Gilbert

I’ve been dragging my husband around the world since 2008 always with the promise that, “Yes, Drew there will definitely be hammocks there.”



  • As of Tuesday, I officially had “the talk” with my boss (good timing with this 30w30d blog!). I currently am a 2 day a week at the office, 3 days at home employee. Until January, I was full-time home, but after a merger, we made the decision to move everyone to a more part-time telecommuting situation. Hence, my case was relatively simple to put together, but still thought it good to share.

    I sat down with my boss over lunch to have a “life discussion” as I termed it. I basically told him that I see this as a good time in my career to take some time off to travel and go back to school. I also emphasized the bad economy and our workload lightness to portray my situation as a possible solution to easing the billability burden a bit (I work in consulting) on the company. Although I’m using grad school as a crutch more than anything right now, I do have plans to go back eventually, just not sure how near in the future that will happen (probably depends on when I run out of money!)

    But I recommend to anyone in the 20-30 age bracket to use this. My boss was incredible receptive (after all, when I come back in 5 years with me PHD, I’m more valuable to them as well) and lobbing 9 months of travel time to the front of my pending September 2010 school start date not only gives me a security blanket but also allowed me to parlay a smaller workload (10-20 hours a week) and 100% mobility. So far, success! Thanks Christine!

  • My day job was 100% in office. My coworker and I shared a tiny, cold, dark office with no natural light so we asked if we could work from home from time to time. Went well, then we asked to do it Tues/Thurs. Also went well. When we ran out of space at the office, they asked if we would work from home full-time for several months until we move to a new space. Now that the new office will be ready in a month or so, we want to keep working at home! I love the flexibility, and we use Skype for inter-office communication. It’s nice to be able to do what I want.

    However, it’s tempting to stray from the computer. There are so many distractions, and it’s hard to be in a cool place “traveling” when you are tethered to the computer all day. It isn’t so bad if your boss let’s you do flex time, so you could work a few hours, go explore a few hours, then work again at night. But if you have an 8-5 job, it can difficult when you just want to be out exploring a new place. Also, you start to feel a bit disconnected from your coworkers and work environment. We go in for on-site meetings once a week which keeps me feeling a bit connected, though if I’m abroad, that won’t be possible. It’s very doable and a great idea to work remotely while traveling, though if I had the choice, I would rather do it on a part-time basis so I had more time to really enjoy the traveling.

  • I’ve really enjoyed your first three posts in this series, especially the second part on how to improve our relationship with money – and saving (something I’ve found difficult in the past and am constantly working on).

    By the way, I know this is a bit late but, congrats! Traveling with kids is one of the best things there is. You’ll have a lot to look forward to!
    .-= Erica´s last blog ..Top 3 Chocolatiers at =-.

  • I have more of a question than anything else. I’ve broached the topic of taking Friday off with my boss and he was receptive to it, but here’s my … circumstance. I deem it that because I see it very much as an advantage, but perhaps for taking 2-3 days to work from home, it might seem a bit of a disadvantage.

    I live next door to work. I mean literally, my window faces my office window. I’m an IT Support and Administration professional. So, to my question, is it even worth it to try to ask for more days remote?…I essentially have all the advantages and freedom I would have if I was working from home anyway. I can take allotted breaks for errands when needed, I run next door for anything thats needs physical presence, otherwise, just like mentioned in the post, being the rockstar at work that I hopefully am, I blend my full day to be fully available to work, and also to alternate life and business pursuits (cooking, haircuts, web design, freelance client calls, etc.)….so…am I stuck, or fortunate?
    .-= Robert´s last blog ..Life Designed | 70 days in, What have I done?! =-.

  • Robert,

    I took a look at your blog to see a bit more about what your goals are… From your about page:

    “become a speed reader, train in Jeet Kune Do, pay 6 months rent in advance, own a company, visit China…”

    Based on what you’ve described you’re in a perfect position to do this, and I wouldn’t change a thing. You can build your freelance work up into a strong consulting business, with the extra income you’ll easily get ahead on rent and afford a trip to China and with the flexibility you can pursue your other interests like Jeet Kune Do and speed reading.

    For your website partner, Brandon, who wants to: “learn Spanish, learn to play the piano, leave country in 6 months” this kind of situation might not be ideal. He’ll want something he can take on the road with him and being office bound 4 days a week, even if it’s incredibly flexible, isn’t going to get him overseas.

    Ultimately, I think there is no “right way” to approach redesigning your life. It has to be purpose-driven and the changes should move you forward. Sounds like your situation is giving you just that, even if it’s not 100% remote. After all, the goal isn’t 100% remote, the goal is flexibility to do what we want.

  • I tried all of this (before I read the article), and in the end just had to quit. For my boss, it was more important that no one else in the team decided to follow my footsteps and also work “location independent”. So he couldn’t justify allowing it to happen.

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