The Back Story

Today (Christmas, 2013) our family of seven shared a Christmas meal around a small table in a rented vacation home.  I am grateful to be with all of our adult children before heading out to Australia (our first stop in 2014) and to be wearing shorts on Christmas day.

Still, I feel a bit unsettled — and although none of our children mentioned it today, I’m sure I’m not alone in that feeling.  It seems like just yesterday that we were gathered around the family table in our Virginia home celebrating Christmas 2012.  The tree twinkled, the fire crackled and the house smelled of pine needles and Christmas cookies. I wrapped endless presents, my husband (the chef) cranked out endless meals, and our crazy brood battled over endless games of Trivial Pursuit.

We didn’t know then that it would be our last Christmas in that house (the house I swore I would never leave).  We would have laughed if you had told us that by Christmas 2013, strangers would be sitting around our family table — and, in fact, enjoying much of the rest of our furniture (all sold in an estate sale). We were blissfully unaware that 2013 would come roaring in and kick some butt.

So, how did it all happen? How did we go from a 7500 square foot house to one suitcase each plus a bike and a set of golf clubs?

It all started on a freezing-ass cold, February morning. I was sitting in our kitchen with my husband, drinking coffee and staring out the window as a steady, icy rain fell.  Cold weather always makes me cranky, but on this particular morning I was also plagued by a growing sense of foreboding about my company.

I’ve had my own business for many years and was pretty successful with it for a long time.  But, in 2010, I made a serious misstep with a flagship software product.  I failed to get outside funding for the product and now, in 2013, our closest competitor was flush with cash after two rounds of investment.  We simply couldn’t keep pace.  The stress of it all was keeping me up at night — and perhaps more importantly, causing me to question my entire professional life.   I’m not ready to retire (and really can’t afford to given my tastes and lifestyle), but at the same time, I began to realize that I no longer had the level of desire necessary to make my product succeed, or even to continue with my business.  The naked truth was that I loathed my working life, which consisted of long hours behind a desk doing work that had stopped being fun (or even mildly interesting) many years ago.

As we stared out into the rain that February morning, we suddenly began to have a conversation that thousands of couples have probably had in the middle of a nasty winter punctuated by troubles at work.

“We could cash out and go someplace warm.”
“Sell the house?”
“What would the kids say?”
“Live a simpler life…work less, play more.”

It was a silly conversation that might have simply ended right there at the kitchen table, never to be spoken of again.  But, week after week, we kept returning to the idea of a grand escape from winter and from a stressful and unsatisfying work life.  And each time we talked about it, the plan began to unfold in sharper relief:

“What would we do with all our stuff?  The cars, the furniture…”
“We could store it.  No, let’s just sell it.”
“Where would we go?”
“Spain?  We’ve always loved Spain.”
“What about all the places we haven’t seen yet? Let’s make a list.”

And so it went.  We continued to fantasize about our escape while winter droned on relentlessly and I kept beating my head against the wall at work.

What pushed us over the edge?  When did we stop talking and start acting like the fantasy was real?  Hard to say. In all fairness, it was probably more than one thing.

The first, and most significant event was the terrible news that a dear and cherished friend of many years had been diagnosed with Stage 4 cancer.  As we struggled to make sense of this awful reality, those *silly* conversations about making our escape to a simpler life in warmer climes seemed less like crazy talk and more like an imperative.More signs appeared as spring came on.  A young entrepreneur in California wrote an article about Zombie companies that helped me realize that I was “doubling down” on a losing proposition with my product.  My husband began to notice an elderly man at the nursing home where his mother lives. Each night the man visited his wife, bringing along a stack of travel brochures — grand plans for a retirement that never happened thanks to early Alzheimer’s disease.

By early May we had reached our tipping point. We put the house up for sale and I began preparing to shut down my company. At that point, we didn’t have much of a plan. We knew that we wanted to travel (a long-time passion) and we had some destinations in mind, but nothing was definite. We assumed that getting rid of the house would take some time, but within a few weeks, we were scrambling to get rid of all the stuff and move out within 30 days.

Today, barely 6 months after that fateful conversation, we are finishing out a transition phase that allowed us to spend Christmas with our children, plan the first leg of our journey, and complete the process of closing out my company. We are beginning to consider ourselves officially — and most days joyfully — gypsies (except perhaps for Christmas day, which was admittedly weird).

That’s it. That’s our story. Or perhaps the beginning of our story. Stay tuned.


  1. Stacy says

    One of my favorite questions to ask clients is, “What would you do if you had no fear?”. Something changes in them when they think about this ~ they dream bigger and play with ideas that light them up.
    You and Len felt the fear and went directly towards it – where the best stuff is found. I LOVE this chapter of yours! It reminds me to play bigger in my own world.

    Love and cheers (not necessarily in that order).

  2. Charlotte Ashley says

    We are so delighted to hear you are coming to stay in the cottage, after reading all about you I am so excited! What a brave thing to do, I hope your having the time of your life and we can’t wait to meet you.

    Best wishes,
    Charlotte and Roy Ashley.

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