Six months ago, I left a comfortable, secure job that provided a good income with excellent benefits that included low-cost health coverage and nearly five weeks of paid vacation annually. Plus, it was in New York City, arguably the excitement capital of the world.
While I can’t say everything is perfect now – or that I am making more than just a fraction of my former income yet – what I can say is I don’t miss going into an office every day. I have yet to experience any lingering regrets about my decision.

Photo by Jeff Ballinger (iPhone 5s)
If there is one essential lesson to share, it’s this: you must be equipped for failure. Not the complete and utter sort, but stuff will happen that you cannot anticipate. Plans will fall apart. Promises will disintegrate. Other stuff will happen that you will interpret as making you to change your path or – hopefully not – convincing you to give up and look for another full-time office job.
New opportunities will also arise to alter your plans, but you may not recognize them for what they are if you allow yourself to wear blinders out of disappointment about the plans that disintegrated.
Don’t forget that plans are for the future. Reality is now. If you find that you can’t adjust when plans fail – and some of them will – perhaps the safe, warm cocoon of the cubicle really is for you after all.
Naturally, I did not take my own advice here initially.
My decision to leave New York City was a culmination of months of planning. I had countless discussions with my wife, Mary Schiller, about how to make the transition from working in an office to working remotely. Up until now, I have always had salaried or hourly jobs with the perceived security of knowing how much I was bringing home each week. Millions of people thrown out of work in recent decades can attest to just how secure such work actually is.
I even hired a life coach, who was very helpful in focusing my efforts and recognizing my marketable talents. I highly recommend Lydia Lee, who created Screw the Cubicle to help people achieve their dreams outside a traditional office. She is living her dream in Bali and coaching people online and on the small Indonesian island.
My plans – really our plans, with my wife – to work from home took a new course before we’d even settled on a direction. The terminal illness of my father sped up my departure, as I felt the need to spend some time with him before his condition deteriorated. Even that changed when I was out in California for 10 weeks, when his condition improved a bit, enabling me to return to my wife and home in New York to pursue some new plans and ideas.
In fact, I’ve tried to stop referring to them as plans. I still find myself making them, but the word “hopes” seems more appropriate, as in “I hope it turns out this way, but if it doesn’t that’s OK. I’ll just figure out what to do next if it comes down another way.” I don’t even bother writing down the details. I just write out the basics at most, such as “I want to work from home some time in the next 12 months.” Too much detail leads to unnecessary expectations, which I’m learning are redundant.
I try my best to limit my expectations, eliminate them or just expect the worst. This keeps disappointment at bay. More importantly, it allows my mind to remain in the present, a place where I can take action.
For example, I adjusted the timing of my departure from New York after my former boss did not approve my proposal to telecommute. This would have allowed me to relocate temporarily to my father’s place in California while keeping my job and, more importantly, steady income. Not that I expected my boss to say yes. In fact, I expected the opposite and my boss former obliged.
In addition, I knew that the only official policy on telecommuting at Columbia University is that it is left up to the individual work units. This is pretty much the same as discouraging it.
I maintain no hard feelings. Honestly. My friends and colleagues were more upset than I was at this decision. However, it did reinforce an important lesson about the perils of harboring expectations of other people.
My experiences the past six months have only reinforced that lesson…over and over again. A few months after I left my job, something else happened – or didn’t happen, as the case may be – that I had never envisioned rose up to alter my plans and present new opportunities.