You know that feeling when a scary idea pops into your head, but it brings along just enough excitement so that you don’t immediately shout “Go away scary thought. I will never, in a million years, make you happen!” Yeah. We all have those moments, right? The ones where a thought quietly slips into our mental periphery and dances around hoping to catch our attention. An idea that makes us a little afraid but also intrigued at the possibilities should we elect to pursue it.

I had that happen recently about something I had never before dedicated a single moment of brainpower to. But once I turned my attention to the seed of the idea and invited it to flourish in my imagination, well, here I am. On the threshold of taking a new chance and, hopefully, changing my life. Again. In a small way, this time. Or maybe bigger than I imagine.

But before we begin, some confessions…

First, I am vain. Maybe not in an outwardly observable way these days (island heat and humidity have beaten me down, down, down). But I do give a lot of thought to my appearance. I suspect most women do. Otherwise, I wouldn’t be reading a best-selling memoir right now that focuses exclusively on the concept of body self-loathing.

Second, once I hit my 40s, I started taking great pride (see vanity statement above) in people exclaiming “you don’t look ____” when I reveal my age. A number I’ve never tried to hide, by the way. After all, getting older is a non-guaranteed privilege. But still…it is a confidence boost to hear people tell me I look younger than I am. Especially as I hit the fifth-decade mark last year.

How I’ve spent the past 2.5 decades of my life.

But part of what keeps me younger-looking (besides the kitesurfing, I suspect), is that I’m a slave to coloring my hair. I have been ever since noticing those first silver strands in my late 20s. Aside from the utter unfairness of turning gray before I even celebrated my first milestone birthday (21 doesn’t count), I didn’t think twice about rushing to my stylist to banish those gray locks from my naturally chocolate brown strands. It was just what I was supposed to do. And for more than two decades, I carried on this routine. Never thinking for a hot second there was an alternative.

Even when I moved to the Caribbean, one of my first priorities was finding the island’s best colorist. And as I colored my hair a few days before I left the US, I had approximately three more weeks to find this hair magician. Nevermind housing or a job, I had priorities, people! I needed to find the person here with the magic chemicals and crafty fingers who could aid my denial about my real hair color (whatever that is…I’ve sort of forgotten over the years). Whether I actually styled my hair was irrelevant. It. Could. Not. Be. Gray!!!

Thankfully, I found a superbly talented Dutch wonder woman, and she’s been my go-to ever since. She’s seen me through some important milestones – a wedding (mine) and a 50th birthday (also mine…eek!). Of course, she also helps me with the more mundane semi-monthly appointments (I tend to be a little – ok, a lot – more lax about my root touch-ups here than when I lived stateside). She’s done her best to keep my hair looking fab.

But as much as I love her, I no longer want to see her on a monthly basis. In other words, I want to stop being a slave to my tresses. At least when it comes to coloring them. For a couple reasons. One being time. I’m starting to hate sitting in the chair waiting, waiting, waiting for the color to process. I’m getting selfish with my time as I get older. Another is money. I’m not a DIY colorist. At all. If I consider how much I’ve shelled out at salons in my attempts to cover the gray over the past few decades, well…I don’t really want to consider that.

But perhaps the biggest reason is that all that chemical covering isn’t exactly healthy for my long hair. Especially because I spend copious amounts of time playing in salt water under the harsh Caribbean sun. The ends of my hair are not happy campers, and I can’t really blame them. I don’t nurture them as I should between salon visits. Far from having the lush, healthy sun-kissed beach hair of my dreams, my ends more closely resemble the bristles of a well-used broom. (Yes, I can disguise the damage with a good blow-out or gallons of product, but who has time for that…did I mention the humidity here?)

A broom or the ends of my hair?

So after recently being introduced to the Instagram account of a woman who can only be described as insanely inspiring for the “go gray” movement, I made the decision to say fuck it and restore my hair to its natural color – whatever that turned out to be. Thinking I was being all cutting-edge about this, imagine my surprise when I discovered that “going gray” is a trend that started long before I discovered it. Turns out there are a multitude of YouTube channels, Instagram accounts and blogs dedicated to this very thing. I’ve become obsessed! And a little worried that by time mine grows out, the look won’t be on point anymore. Story of my life in the islands.

Suffice it to say there is no information shortage on the pros and cons of embracing your gray. Nor a lack of tutorials on strategies for surviving the transition. Cutting it all off. Leaving it long and embracing the demarcation line. Coloring your processed strands to “match” your base color and the gray. Covering up the outgrowth with temporary chalks or sprays. Wearing hats for, say, two years. I’ve done a lot of research in the past few weeks. Turns out, there are as many options to get through the transition as there are shades of gray.

I’d like to claim that I’m a woman who pays no attention to her appearance (and some who know me only from the island may indeed believe this is true) and that this will be a simple transition. But I’m not (I’m vain, remember?) and it won’t be (nothing worthwhile ever is).

Which is why I now find myself constantly wondering if I have the courage to really do this. Will I have the strength and willpower to handle the bad hair days (and there will be many, many, many according to all that I’ve read)?

The beach girl’s ultimate gray hair inspo pic.
Photo: @annikavonholdt (Instagram)

If I decide to keep some version of my long hair, do I have the stamina and self-assurance to look in the mirror each morning and see the unfortunate middle state that exists after you toss the dye but before your colored hair is gone completely? If I choose the super short route, will my identity as a beachy, surf chick disappear along with my familiar and comforting long locks? I can’t think of too many kitesurfing women I know with a cropped do. Even fewer with long, flowing silver strands (my hoped-for final outcome).

But it’s not all doom and gloom, people. Interwoven among all these fearful questions is a building sense of excitement at the change. After all, I’ve seen the “after” images of women who have gone before me on this quest. And many, many, many of them look ah-mazing!

But it isn’t just the “after” that excites me. I’ve always been willing to make drastic changes in all aspects of my life. (Exhibit One: My move to the Caribbean.) So the prospect of an unpredictable journey is exciting, too! Plus, hiding out on an island where nobody puts too, too much effort into their appearance is the perfect place to make this transition. Lucky me!

This is where the “going gray” journey begins.

So how will I approach this transition? At the moment, I’m leaning towards a dramatically shorter ‘do to start. After all, my long locks are damaged beyond repair anyway, so starting fresh doesn’t mean sacrificing perfect hair. But then again, maybe not. I haven’t had short hair since high school when I impulsively showed up at a scheduled hair trim appointment and proclaimed “cut it ALL off!” A decision I immediately regretted. Unfortunately, my senior pictures were taken a few weeks after, leaving me with a permanent reminder of what my impulsive nature is capable of. But then again, maybe I will like having short hair now. Maybe I’ll find a wash-and-go style that tolerates the humidity and my lifestyle more?

Today, I cannot say. The only thing I do know is that I’m taking this journey one baby step at a time. For the moment, making the decision seems like enough. And I’m not sure if I will occasionally write about it here or if it will be more of a behind-the-scenes change. I first considered not mentioning it at all, but then realized the Adventures of Island Girl’s motto is ‘take a chance, change your life.’ And this seems like something that qualifies as a taking a chance. So why wouldn’t I share it here? Especially if it helps someone who might be on the fence about reacquainting herself with her silver strands. We can go through this journey (and commiserate) together!

Plus, since I started doing the Ask an Island Girl videos, I realized there may be some confusion if I went from a woman with long highlighted hair in one video to someone sporting a spiky, platinum pixie cut in the next. Not saying that is going to be my transition strategy, but you never know. After all, I did mention that I’m rather impulsive, right?

All I can say is…stay tuned. And if you have any “going gray” strategies or stories to share, I’d love to hear them!

Perfect for pinning.

Got questions? Want to know more about island life? Thinking about making a big life change (whether that includes an island or not)? I’d love to hear from you. Check out this post or send your thoughts to hello@theadventuresofislandgirl.com and let’s connect.

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