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.

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.

Homework:

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?