Michael D. Watkins’ famous book, The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter outlines important steps you can take to succeed in a new job in your first 90 days. Moving from the hustle and bustle of Washington, DC to a small rock in the eastern Caribbean, I thought I’d deploy his tactics to help myself acclimate to my new island life. It sounded good in theory – here’s how it has worked out for me so far…


Change your Mindset

Gone are boring black suits, business cards, Uber, and LinkedIn profiles. Instead, we spent 6 hours opening a bank account, 2 days getting a driver’s license, and 4 days clearing our personal items through Customs. Comparing island adventures to how things happen at “home” is wasted breath. This is our new reality and we’re trying our best to navigate it with grace and humor.


Accelerate Learning

I succumbed to a rookie mistake early in our rock existence… On Thursday, there were lovely chicken breasts at the market. I, however, didn’t plan on cooking chicken until Sunday. I naively thought I’d get them later. Well, as any experienced rock dweller will tell you – if you see it, buy it.  Little did I know, we were headed into a holiday weekend and chicken (and milk for that matter) would be unavailable across my rock for the next 5 days. Note to self:  Don’t make this mistake again.


Make a Suitable Strategy

After four unsuccessful trips in pursuit of a driver’s license, we decided not to return at the “appointed” time but to simply wait – and wait. We patiently stood in the lobby awaiting the return of the very busy inspector. Eventually, our patience paid off and we proudly emerged with a local driver’s license. We’re learning that patience may be the most important island strategy.


moving to an island container shipping Anguilla

Four weeks after leaving Virginia, our container arrived.

Secure Early Wins

Moving to a rock is not all beach days and rum punches. Finding a place to get a simple haircut was a challenge – especially after having the same person cut my hair for 10 years before our move. There are an abundance of barbershops, but I wasn’t finding lots of options for middle-aged women outside the expensive resorts. Enter: the island network. It took recommendations from 2 people until I was accepted as a new client, but this has been a huge win for personal grooming standards and island gossip.


Negotiate Success

The post office is perhaps the biggest test of patience (second only to the bank) on our rock. On a recent visit, I found myself stuck in a bureaucratic loop based on a well-intentioned t-shirt my sister added as “padding” to a shipment. After explaining I did not have a receipt, know the value, or necessarily even want the aforementioned shirt, they took pity on me and found a way to make the paperwork align between the shipper and Customs. Success!


Build the Dream Team

Trying to maintain a home on a rock is a constant battle – salt and rust seem to appear overnight. Our dream team consists of an amazing housekeeper and a series of other important players to help with rock dwelling – pest control, water delivery, handyman, gardener, and pool maintenance. Hubby serves as bartender most days and occasionally fills the role of pool boy, but it’s good to keep a professional on call.


Keep your Balance

Balance comes in many forms. I’ve sought to improve my balance with new attempts at kayaking and a stand-up paddle-boarding. Working remotely also requires balance since hubs is now fully retired. I try to balance time between rock exploration, scavenger hunts (i.e. basic grocery shopping), and work in a way that keeps everyone happy – including myself.


Help Everyone Else with the Transition

The first 90 days have been full of challenges. But instead of focusing on these, my Facebook page is filled with beach scenes, sunsets, and happy days. If anyone tells me they are considering a radical move to their rock of choice, I’d enthusiastically tell them to do it. There will be frustration, but the clear seas, friendly locals, and starry nights are worth it. And hopefully my own learnings, which I’ve shared here, will also help others in their own newbie days on a rock.


sunglasses with palm trees

This doesn’t suck.


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What do you think is essential for newbies to learn and/or accept in their first 90 days on a rock?

Written By:

Current Rock of Residence:


Island Girl Since:


Originally Hails From:

Springfield, Ohio

As a former flight attendant, Kim loves to travel. Married to an Army officer, they spent 15 years moving around the U.S. to various military bases before landing in Washington, D.C. In 2005, she left the increasingly “not-so-friendly” skies for work with a medical specialty society. She and her husband always felt a pull towards the Caribbean and visited often over the years.

In 2015, they discovered Anguilla and slowly started unwinding from life in the United States to pursue their dream of living in the Caribbean. After selling their home, storing 20 boxes in her sister’s basement, and holding a crazy estate sale, Kim and her husband shipped a container with their remaining belongings to Anguilla to experience life on a rock. She still considers herself an island newbie and looks forward to years of adventures in paradise.

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