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My father in-law, Ron was one of the most generous, kindest men I’ll ever know.  The sad part is, I never had the privilege of meeting him.  Even sadder.  He died on my birthday a year before I met my husband Nathan.  At 51, a heart attack shortened the life of an incredible man and he never made it to retirement.

Three years ago, I watched retirement advance on my mother much earlier than we all expected.  It wasn’t a choice.  Suddenly my mom became a fraction of herself riddled with paranoia and confusion. In the span of 3 months, she seemed to age over 20 years.  Unfortunately for a year, no one could properly diagnose it so she suffered.  We all suffered.*

Through these circumstances, I learned a valuable lesson:  Life is not guaranteed.  You could wake up one day and on the next, you have no tomorrow.  Or you could wake up tomorrow and suddenly be a fraction of what you were yesterday.  Now, I really hate to be a drag, but this is a reality.  It doesn’t have to be our reality, but it could be.

Question: Do you really want to risk your dreams betting on a tomorrow that’s not guaranteed?  I know I don’t.  Why should any of us when we really don’t have to?   

One of my dreams was travelling the world, visiting tropical places and because I simply can’t stand the cold, at the end of every winter, I’d say to Nathan, “OK this is the last winter, I’m spending in Canada, next year, we’re going somewhere warm.” But each winter, where did we find ourselves?  In Canada.  Sure, we’d take a trip to Florida each year to visit Nathan’s mom, but it was hardly the type of Snowbird life I had envisioned.

From time to time, I would think about Ron and I would ask Nathan about other male members of his family secretly wishing that he wouldn’t suffer the same fate.  I knew their lifestyle and eating habits were vastly different, Nathan made sure of it.   He plays basketball 3-4 times a week, he eats healthy and he loves what he does.  He’s designed his work in a way that minimizes stress.  Caring that much about his health and valuing a balance between work and play was sadly a lesson he learned from his father’s death, not his life.  But it’s one of the main reasons why we started to take our dreaming seriously.

Big life lesson 2 in this area was my mom.  I think I naively always thought my mom would work until her death bed.   I probably imagined my life would be the same too.  It’s not so much that I was a workaholic, I just found work fulfilling.  I had the opportunity to help people live out their dreams and visions and I was passionate about that.  I just wasn’t exercising the same passion to live out my own.

But then watching my mom go through some really tough battles with her health, I realized, if I don’t take my dreams seriously, no one will.  Your work isn’t going to put itself on hold and sometimes your health isn’t going to wait for you to decide – sickness can just show up unannounced.  Anyways because of these things my desire to retire early went from dreams to plans.

And it was easy, so easy, I almost wanted to smack myself for not starting earlier LOL.

Here’s the steps I took:

Step 1.  Decide.

Armed with life’s harsh experiences mentioned above, I knew waiting for tomorrow was no longer an option.  So last year, we didn’t just say, “This was going to be the last year…”, we picked the place – Thailand and set some dates.

Step 2. Devise a plan

The next step was getting the money.  Aside from finding time, this is probably the other biggest potential hiccup.  Thankfully for us, time wasn’t much of an issue.  Working from home and running our own Internet-based business meant we could be very flexible.   Our office could pretty much be anywhere we could find a stable Internet connection.  We use it to connect with our team and clients everyday from Canada so why not anywhere else?

So, back to the money.  Moving from dreaming to planning was a crucial part in my achieving.  When I started to get serious, old ideas and new opportunities started to find us.  Suddenly, I remembered a saving game a friend and I played to help fund our trip to Florida many years ago.  Instead we paid for everything in cash and any coins we received as change  went towards our Florida fund.  So Nate & I  decided to do the same thing and sock away all our change and any monetary gifts we received.

Now mind you a trip to Florida and a trip to Thailand are vastly different in price, especially flying from Detroit (the closest airport to our location), so we were going to need to ante-up to make it.  In comes opportunity – Airbnb!  I won’t give you all the backstory, you can learn more about it here.  But after using Airbnb to book accommodations for a business trip in Chicago, we figured why not try it ourselves.  Nathan’s host shared an interesting story about how she pretty much covered the monthly rent for her downtown condo using this awesome service at $1400/mo that meant we should be able to easily make enough for the trip.  And that we did!  Booking odd weekends and holidays, 4 night stays here and there, within less than 6 months we saved enough for 2 return tickets not to mention the quaint condo we booked on Airbnb for our one month Snowbird test run – Thai style!  

Step 3.  Don’t get discouraged by setbacks

I know this all probably sounds too good to be true and you know what – it was.  Even though the end was great everything didn’t go as planned, but even that cloud had a silver lining.  During those months we were saving, one of the big projects we had scheduled to work on hit a massive delay.  This proceeded to throw off our cashflow so our emergency savings followed by our travel fund took a hit.  It could have been an emotional nightmare, but it wasn’t.  And I was really thankful because if we didn’t have it, we may have resorted to credit cards as a backup or took on a lot of extra work, or jobs we weren’t interested in, but we didn’t have to.  The funds were replenished as the project came together and we started to get a flurry of activity on Airbnb too.  And let me not forget my husband’s genius plan inspired by Ramit Sethi to get a TD Travel Visa.  We’ve been using it to process our regular monthly payments both business and personal.  And within only a couple of months of using the cards (including their introductory bonus) we managed to accumulate $600 in travel dollars that we’ll be applying to the airline tickets – booya!

Everything is set and now my only concern is…whether I’ll come back!


Step 4.  Go!


Sa-wat-dee ka:)

Hi I’m Sherice, I wanted to be a snowbird before 40. I wondered, “What’s the point of waiting to travel the world and do work I love?” Today, with my husband, Nathan, we run thriving businesses from the comfort of our own laptops. We spend 6 months a year in Thailand, travel frequently — and spend the rest of our time at home in Canada — at least that’s the plan for now, who knows what the future will bring ;).