Keeping Your Job While Taking a Family Road Trip

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Now that the plans of our long trip are out, I’ve been getting some questions from family and friends. A question from my Grandma is illustrative: “So how can you take off six weeks and keep your job?” Well, let’s talk about some of the details. The honest is that you can’t start with a six-week trip – just as you can’t start out by deciding to drop everything and go full time, and you can’t even start with something as simple as working remotely one day a week. It starts before that.

Start with your dream. What do you want to do with your life? Your job is a tool that’s going to give you the free time and the funds to live your dream. Your job is going to give you the freedom to live your life. But to get there, you’re going to have to have a vision of where you want to go, and the guts to manage your job.

Don’t be a slave to your job.┬áThis may sound obvious, but is the important first step. If your job owns you, you remote career opportunities won’t have the time or energy to manage it. You need to be the “boss” of your job. Set limits on your job. If you’ve got a job that’s impossible to manage, consider whether you can afford to keep it; you’re sacrificing your dream to keep this job. Is it a fair trade?

Get organized. Both at work, and at home, start getting organized. This will help you better manage your job, and will also assist you in advancing your dream. A couple of good places to start with a couple of books I can’t recommend enough: The 4-Hour Workweek and Getting Things Done. You’ll find yourself getting more productive at work and at home, and setting yourself up well for the next step:

Work remotely. With your newfound organization and productivity skills, raise the possibility of working remotely – either occasionally or on a regular schedule. For example, if you’ve got an appointment at school at 3:00, consider arranging a day to work remotely, on the theory that you can start a bit earlier, and end a bit later, than if you’re commuting in to the office. If you know it’s going to snow tomorrow, arrange to work at home on a terrible commute day. Try appealing to your boss’s “green”side: working from home one or two days a month reduces your carbon footprint! You get the picture; you’re working your way into a regular, recurring remote work day – one or two days per week.

Be effective when working remotely. Don’t give anyone reason to believe you’re “working” remotely (with air quotes.) Be sure to answer the phone when it rings. Try to have a rapid response to emails and instant messages. Ideally, forward your desk phone at work to your mobile phone or office phone at home. What you’re aiming for is that nobody notices any difference when you’re in the office, and when you’re at home. When you’ve accomplished this, you can move on to the final step.

Achieve the dream. Work on a road trip. Work from a vacation home for a week or two. Start small and gradually work your way up. Each time, exceed expectations, and continue to massage your job into what you want it to be – the tool that you use to take off on your next great adventure.

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