Entrepreneurship/ Freelancing/ Wellness/ Workplace

My #WorkFromWherever Experiment


On my own from a fairly early age, I’ve always prided myself in the ability to “out work” just about anyone.

Whether it was college sports, my doctoral exams, a coveted internship, or running my own business, I always worked long and hard.

Assessing the quality of my work and its effects on my health and well-being was not something I was accustomed to.

Maybe I lacked self-awareness.

Maybe I lacked understanding.

Maybe I just didn’t know any better.  

For the past few years, I watched in awe as many of my entrepreneurial colleagues have let their office lease expire, converted their established business model to a virtual one, and packed their bags for an international excursion.

“Wow” I thought, “I could never do that.”

But I wanted to – bad.

So I started taking an inventory of-sorts, cost-benefit analysis of all my “work stuff”, and was quite amazed at the results.

Postmortem on Hannah’s career to-date revealed that I’d wasted hundreds of hours in ineffective meetings, thrown away money for a “real” office, and filled any and every extra hour of my day with some stupid bit of busywork, all under the guise of “working hard”.

I suppose, unconsciously, I reasoned all my work “invested” over the past few years would set my career up for sustainable success. You know, the rolling in the dough, no more workdays, retire at 30  kind.

But it hadn’t.   

Equipped with an experienced mentor, strong Wi-Fi connection, and extensively highlighted version of Tim Ferris’ “The 4-Hour Workweek”, I embraced decided to embrace the “work from where ever” mentality with full gusto.

I was (finally) free to do “all the things” I needed to do as a primary caregiver, wanted to do as an adventurous spirit, and free to let my business soar beyond the constraints of a physical location.

The Experiment

Truth be told, working remotely has been awkward at times (they don’t exactly cover this work modality in Business school). I’ve had to adapt new ways to stay organized and stand behind my commitment to avoid time wasters like the endless stream of e-mail.

Some have criticized my new working style as “not really working”. The naysayers are also typically chronically single, unhealthy, and downright miserable despite making “good money” at a “normal job”, so their criticisms carry very little weight in my present psyche.

Have you seen the Hyundai Tucson commercial that poses the culturally relevant question of, “Since when did leaving work on time become an act of courage?” Here it is: https://youtu.be/G14SwPSgjbU .

When did it?

When technology – an innovation that was supposed to make our lives a lot easier – “revolutionized” the 9-to-5 into 24/7?

When the Great Recession hit and we were losing our jobs, our retirement accounts, and our houses?

Or maybe it was more subtle of a cultural change, sparked by national events but embraced by the eager beavers – the ambitious professionals (like myself…and probably you, if you’re reading this blog) – that were determined to move up socio-economic classes regardless of the “investment” (aka: long hours, worry lines, broken relationships, etc.).

The Hyundai Tucson commercial became a sort of religious-like mantle for me, on my #workfromwherever journey.

And after unsuccessfully asking the question above (When…?), I found myself asking a better question: “Does leaving work on time have to take an act of courage? Or should it always just be the norm?”

The Results

Since starting the experiment turned sold-out lifestyle, I’ve learned a lot about myself over the past few weeks:

  1. I used to work for work’s sake. Now I only work when work will make me money. What about all those pesky business housekeeping duties – paying bills, invoicing, graphic design, editing, etc. Outsource, baby.
  2. My previous self was secretly looking for someone to notice my 14 hour days and applaud my efforts and make me feel valued – it never happened. I’ve learned to provide internal validation for myself and ignore majority of external everything (still a work in progress, but we’re baby stepping).
  3. I’ve missed out on a lot of great things over the past few years as a self-admitted workaholic. Working remotely has forced me to cut out all the unnecessary BS and be there for those important things in life – like the people, the causes, and the communities I love.
  4. Pareto’s 80/20 Rule has new meaning, when every two to four weeks, I comb through my client list and make cuts accordingly. Super high maintenance? Not contributing to my profit margin? Consistently late on settling accounts? Sayonara, my “friend” – go try the consulting company down the road…
  5. I enjoy things again. Who knew working all the time could be a total joy bummer (okay, lots of us “know” we just don’t live like we know.  My new working mindset has provided me with opportunities to enhance my well-being (self-care, anyone?). I’m currently working on my Reiki Master certificate, spending more time with my beloved horses, and training for my first competitive running event in years.

Transitioning my career to a remote one has been challenging (and terrifying) but totally worth it.

Like all working environments, working remotely has its ups and downs, but it’s proven to be just the right mix of challenging and empowering for the current season in my life. Who knows, maybe it’ll stick around as the working style of the future.

For more tips and tricks on how to work remotely, check out my blog posts on business automation and telecommuting.  Maybe you’ll decide to cut the cord and join the millions of entrepreneurs on this journey toward freedom.

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