Want To Work Remotely? How To Ask The Tough Questions

Not my pretty face, but the cleavage is similar...

About a year ago, I accepted an on-site, part-time position at YourTango, despite misgivings about resuming the dreaded NJ-NYC commute I had left behind several years before.

I was desperate, though. I needed some regular income to supplement the other work I was doing, and I was also badly in need of some quasi-regular human contact. Happily, I ended up enjoying my work at YourTango so much that the commute didn’t seem so bad. Plus, I loved the people I was working with.

Still, it eventually began to wear me out. It ate up my time. It was expensive. And, after almost a year of doing it, I began to resent it.

So at the tail end of September, I requested a new, remote working arrangement and, several weeks later, they approved it. Now, I work with my three cats laying in a semicircle around me. I sleep in a little bit more. I dabble in yoga and take daily walks. I have extra time to work on my other projects and extra time to make plans with… well… other human beings. Once again, I feel like I’ve achieved a healthy balance.

Maybe some of you are a little bit like me. Maybe you have full-time jobs, and squeeze in your freelance work in the evenings and on weekends. Or perhaps, like me, you have a part-time gig, and have to commute in to an office. Maybe you often think to yourself, man, I could totally do this job from home, and it would totally free up some extra time for my personal projects! But you’re afraid to ask permission.

How do you go about proposing such a fan-flippin’-tastic work arrangement to your big-time scary boss?*

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