It was the summer of 2007 and I felt deeply frustrated about my day job.
It wasn’t that it was such a bad job. I was just fed up with the daily commute, working in an office, and the constant interruptions.
I was SO ENVIOUS of people who could work from home every day. That’s what I wanted more than anything. I wanted to work from home. I wanted more autonomy.
And I desperately needed more time and space so that I could work on my side hustle.
I thought my only option was to quit my day job. But I wasn’t ready then. Not at all. (I ended up leaving my day job the following January).
Then I found out that I could negotiate a work from home agreement with my boss. The very idea floored me. I didn’t even think it was possible.
Me? Work from home? They’d never allow that!
And I was right. But not because there was a rule against working from home. It was because I had never asked to work from home!
The fact is, I commuted 30-minutes one way so that I could remote desktop into a computer almost 2000 miles away in Denver, CO.
Why drive 30-minutes just so I can work off a computer 2000 miles away? Why can’t I do that from my own kitchen?
It was time to make my case for why I should work from home.
Now I wish I could say that I thought up this strategy all by myself. Truth is, I was in the middle of reading The 4-Hour Workweek by Tim Ferris. In the book, he outlines a step-by-step process for negotiating a work from home agreement.
I read it and it was simple. It was elegant. It was logical. I’d try it.
So here’s what I did:
I called in sick, but I assured my boss that I would work from home. I did. I called in sick the next day, too. Again, I told my boss that while I was really feeling under the weather, I’d still attend the morning conference call and get some work done.
I showed up to work after being out for two days. I wasn’t behind. All my projects were humming along smoothly.
Yes, I felt SO guilty about lying. But I was going to test this experiment fully.
I let a day or two pass, then came the gutsy moment. I asked my boss if I could speak with him for 5 minutes.
That afternoon, we met in a tiny conference room. My heart pounded. What if he said “no”?
And just who do I think I am asking to work from home when absolutely nobody else on my team, let alone the entire building, works from home. The managers don’t work from home. People more senior than I was didn’t work from home.
I explained to him that despite being sick, I found that I was more productive working from home. I told him that without the distractions of the office, I was more focused and productive.
With my heart pounding, I asked the question. “Would you mind if I worked from home two days next week?”
I laugh now when I remember this meeting, because I literally memorized the scripted dialogue that Tim Ferris wrote in his book about this exact scenario. I was literally doing it “by the book”.
My boss thought for a moment and said, “sure”.
That was it. I had permission to work from home two days per week!
And I did. He had me install an instant messaging app on my laptop, but the following week, I worked two days from home and it was glorious!
I kissed my wife goodbye as she got in her car to drive to the very same building 30 minutes away (we both worked for the same company). Instead of getting in the car and making the same commute, I had a solid 45 minutes before I even needed to be at work!
I couldn’t believe that a stupidly simple strategy written in a book worked so well in real life. In MY life.
That went on for a couple months. I’d show up to the office on Mondays, work from home on Tuesdays and Wednesdays, then back to the office on Thursdays and Fridays.
The goal was to ask for a third day, then a fourth, working from home, until it made no sense whatsoever to have me come in just one day per week. Full time working from home was my goal.
I never got there because a couple of my coworkers noticed that I was working from home, and I think my boss saw this as a slippery slope. (He can’t be the only one of his time in the office!)
So ultimately, he ended the deal, but by that time, I had finished The 4-Hour Work Week book and was well on my way to getting the guts to give my two weeks notice.
And I did – right before Christmas. My last day at that job was January 18, 2008. I haven’t had a day job since.
So the main takeaways of my experience is this:
If you somehow have never read The 4-Hour Work Week, it’s time you read it.
Don’t think that you can’t ask for incredible benefits that you think are impossible, or that you don’t deserve. Too often, we give ourselves an automatic “no”, but we never asked for permission in the first place.
There are some major benefits to working from home. You’ll feel more rested, focused, and free. And if you have a side hustle, you’ll have more time to work on it because you can reclaim your commute time and lunch break.
So if you are thinking about asking if you can work from home, do it. The worse they can say is “no”. And they just might say “yes”.
Have you done this before? If so, post a comment and share your experience with negotiating a work from home agreement.
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