Workcation Hawaii

Workcation - is this the new family vacation?

Workcation - how to extend your vacation time!

When I’m thinking about an experience, in business or in life, I always ask myself, “Would you do it again?”  Would I go have dinner at that new Mexican restaurant?  Would I buy another pair of jeans just like the ones I have?  Would I keep doing what I’m doing knowing what I did and what I have to do?

Last year I had this grand idea of taking a month long ‘workcation’ to some new place.  My wife and son could play all summer and I could work remotely and play with them in the evenings, weekends and on my days off.  Heck, I work at a company that strives on connecting people and making them more productive wherever that person may be working.  Sounds good.

Now, it seemed a bit odd as I developed this plan.  No one really did this at work.  I’ve never done anything like this – our family never had, but in the back of my mind I had this nagging thought – “I want my kid to grow up with experiences.”

Right after our son was born I started a personal blog.  It was my place to write about experiences.  Writing + experiences = goodness.  Life comes along and new things sweep me away, but I still think about it.  “Experiences”.  They matter.  They imprint memories, lessons and emotions.  #thatislife

So, we planned this trip.  Initially, I wanted to go to Barcelona.  It’s sunny, it has beaches, and I loved the Spanish people the one time I travelled there.  Sounds great – but luckily for me, I have a very thoughtful wife.  Spanish + 18 month old + working dad = challenging.  (In hindsight, I’d also add for me the time zone change from my necessary working hours would be very challenging.)  After a conversation, we decided Hawaii.  Maui, Kauai?   Talking to some knowledgeable folks, searching websites for the right location (A/C, pool, close to beach, 2 bedrooms) we found a great place = Kaanapali, Maui.

Now, I’m NOT going to take you through all the stuff we did (or didn’t do), there are enough guidebooks and websites for that.  But, here are the Top 5 Reasons to Take a Workcation.

1. Just Do It

First thing to understand, I’m not a risk taker or someone that pushes the envelope.  After high school I went on a backpacking adventure through Europe for a month – my buddy planned it.  I followed him.  I’ve worked in the same industry since I was 16 years old.  I drive a Honda.  If you have something in your mind that seems exciting and has value to what you want to do in your life = just do it.  For me, the experience for myself, my wife, my kid to spend an entire month in Hawaii is worth this – so we did this.

2. Define the Rules & Guidelines

“Are you ‘really’ going to work in Hawaii?”  If I had $5 for every time someone asked me that, I could pay for all my condo-made mai tais!  Dang it – next time.

I’m thankful that at work and at home with the wife I was able to set some clear expectations on my work schedule – since we’d never done this before.  At work I had multiple conversations about ‘what to expect’ and when I was in Hawaii I continued to remember those talks and deliver on those expectations.  I worked Monday - Wednesday and had Thursday - Sunday for play.  My wife even commented I was working more than usual!  #rolloutofbed2work

Set clear expectations with work, specifically your manager, so you can fully enjoy your time when you are away.

3. Money Is An Object, Spend It On What You Want

Money is meant to be spent and you should spend it on what you want.  Constantly, I have to remind my wife that, “Yes, you should go do that” or “Yes, go buy that.”  Don’t go in debt, but we work hard to earn it, we should spend it on what we want.  If there’s that ‘one thing’ you’re thinking about and you can’t stop thinking about it, and the main blocker is money, then do it.  You’ll find ways to minimize the impact and the investment in the experience will be worth it.  We rented our house on Airbnb.  We flew to Maui on airline miles.  We knew a guy in the mafia that got us a good deal on airline miles.  (okay, not really.)  We bought food & liquor at Costco.  Really, it’s manageable, it’s possible.  #proof

4. People Are Good

We rented our house to a family from China that lived in our town for 10 years and they come back every summer to visit friends.  I met them when they ‘moved in’ to our house – lovely.  Funny, energetic.  Our rental in Maui is from a couple from California – very attentive and thoughtful.  The folks we’ve met at various beaches, pools, restaurants, etc. – so friendly.  The Alaska Airlines stewardesses, Westin Hotel bartenders, condo neighbors, Kaanapali Golf Courses attendants, and the countless people we met because we have a social butterfly for a 1.5-year-old – thank you!  You are all good and lovely.  That’s what life and travelling is about.

5. You Learn New Things About Yourself and Those Around You

I might run more – and golf more.  My wife might try golfing.  I might do more pushups.  Our son doesn’t like dragon fruit.  I have a new love for scratch mai tais. (Only one other hotel/bar had a comparable mai tia #sheraton.) Dodge Chargers drive like boats.  Airbnb +1.  Acai bowls are delicious.  My kid learned how to say things like boat, hat and mai tai.  Okay, not mai tai.  Geckos are awesome, until you get one that sleeps in your rental car.  The ocean is beautiful and strong.  So is my wife.  Grandparents are a grandkid’s best friend.  Home is where the heart is and experiences will last forever.