Why Professionals Are Afraid to Update Their Headshots

We refresh our wardrobes and update our LinkedIn skills obsessively, yet cling to decade-old headshots taken on Waikiki Beach like security blankets. What are Honolulu’s professionals really hiding from?

Last month at a networking event in downtown Honolulu, I was searching for a potential business contact. Their LinkedIn profile showed someone with sun-kissed hair against a backdrop of Diamond Head, looking fresh and energized. When they approached me, though, they had an extra 20 years, 40 pounds, and significantly less of that beachy glow. The tropical sunset behind them in their photo? From an iPhone that didn’t even have portrait mode yet.

This type of temporal whiplash has become endemic in the professional scene. As a journalist covering the islands’ business community, I’ve been ambushed by outdated headshots more times than I care to remember. I’ll arrange to meet someone at Morning Brew Coffee or Arvo, armed with their professional profile pic taken at Lanikai Beach, only to realize the person waving at me bears only a passing resemblance to their official image.

Is this because professionals in Honolulu can’t afford a new photoshoot? Hardly. Our islands are blessed with incredible natural lighting, world-class beaches as backdrops, and talented local photographers who specialize in professional headshots. Yet walk into any business mixer from Kakaako to Kailua, and you’ll meet people whose profile pictures are clearly from the pre-pandemic era – or earlier.

The irony is particularly acute here in Hawaii. We live in one of the most photographed places on Earth. Tourists snap millions of pictures daily. Our Instagram feeds overflow with pristine beach shots and golden-hour selfies at Makapu’u. Yet when it comes to our professional headshots, we freeze in time like ancient lava flows.

Before I get too high-handed, though, I should admit my own sins. Yes, I used the same LinkedIn profile picture – taken at Ala Moana Beach Park with that perfect late-afternoon Honolulu light – for seven years. When I finally updated it, someone commented, “Oh, you got a new hairstyle!” Reader, I had not changed my hairstyle. I had changed my face. Time had changed my face, the way time rather insists on doing, even in paradise.

So what’s actually going on here? Part of it, I suspect, is simple vanity dressed up as practicality. That shot from 2015 at Kahala Beach really was rather spectacular, wasn’t it? The trade winds were perfect. Our skin looked camera-ready and we appeared ten pounds lighter. “It still looks like me,” we tell ourselves, squinting a bit at our current reflection. “Essentially.”

Here’s the uncomfortable truth: when it comes to representing ourselves professionally, we prefer comfortable fiction to uncomfortable fact. We choose the image that makes us feel like we’re still that fresh-faced transplant who just moved to the islands, or that youthful local who graduated from UH Manoa a decade ago. We criticize influencers for presenting idealized versions of themselves, but we’re doing the same thing – just with less Facetune and more time travel.

The situation becomes almost comical at industry events. Look around any professional gathering in Honolulu – at the Hawaii Convention Center, Bishop Street offices, or even casual meetups in Chinatown – and you’ll see a room full of people who look distinctly different from their online personas. We’ve created a collective delusion, an emperor’s new clothes situation where everyone pretends not to notice that no one looks like their profile pictures anymore.

Time for a Honolulu Headshot Reality Check

So maybe it’s time we all took a good, hard look at our professional profiles. Not to obsess over every new line, grey hair, or sun spot (we live in Hawaii, after all – some weathering is inevitable). But to ask ourselves: would I recognize this person at Aloha Tower Marketplace? At a conference room in downtown Honolulu? At a coffee meeting in Kailua?

If the answer’s no, it’s time to update. Schedule that session with a local Honolulu photographer. Find a spot with good natural light – we have plenty of that here. Maybe choose somewhere meaningful: your favorite beach, a spot with a view of the Koolaus, or even just a clean professional setup in town.

Your colleagues, clients, and network deserve to know who’s actually turning up to that meeting. Even if – especially if – that person looks a bit more lived-in than they used to. Even if their face now tells the story of years spent building a career in paradise.

After all, there’s something beautifully honest about showing up as exactly who you are, right now, in this moment. And if there’s anywhere we should embrace authenticity, it’s here in Hawaii, where the natural beauty around us reminds us daily that real is always more compelling than filtered.

Ready to update your professional image? Hawaii Headshot Photos offers professional headshots, from beach settings to urban backdrops. Contact us for info to book a session!