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┬áthis 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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