Nomad guilt 💔

Create your own work schedule. Take Zoom calls with your feet in the sand. Live like a king in a country with a low cost of living. Afternoon naps. 

These are just some of the many often-advertised perks of being a location-independent professional. 

But there’s one big downside that most people prefer not to talk about: guilt. 

When you decide to build your life around travel, you’re inevitably going to end up missing out on a lot of things going on back home. 

• Birthdays

• Graduations

• Family reunions

• Bachelorette parties

• Baby showers

The list goes on and on. And this doesn’t even include the quieter, more nuanced moments you’re probably missing, like watching your niece and nephew grow up or seeing your parents slow down into retirement.

Missing out on these moments is hard. And sad. And sometimes lonely. 

But there are ways to alleviate these guilty feelings. It’s all about learning how to involve your friends and family in your location-independent life—without sacrificing your freedom or your sense of adventure.

Let’s explore. 

Hey, this is Kelsey, and you’re reading the SiteSee newsletter. Think of me as your Big Sis when it comes to travel, inspiring you to keep going places. You can expect an email from me every Friday filled with nomad stories, tips for living a location-independent lifestyle, and the gear to get you there.

Travel Story: Nomad Guilt

First, let me say how incredibly blessed and grateful I feel that I get to even be in the situation of missing home.

I was born in the US; I consult for US-based companies; and I charge US prices. I recognize that being in this position is just one of the many lotteries I’ve won in life. 

That said, I believe that the guilt associated with living a location-independent life (and thus missing out on events back home) is important and complex in its own right and deserves some recognition.

After all, guilt is a powerful emotion—one that I’ve felt plenty of after all my years of living on the road. Many times, I’ve had to remind myself that there’s nothing wrong with wanting to live a life that’s different from that of your friends’ and family’s—it means you have to find different ways to connect with them. 

Since leaving home and embracing location-independent living, I’ve found three strategies that have worked to help me cope with the guilt AND bring my friends and family along on my journeys.

1. Share your travels beyond your Instagram posts

One of the things I cherish about writing this newsletter (other than fostering connections with fellow enthusiasts of this lifestyle and refining my writing skills) is that it keeps my family informed and updated.

I can guarantee that if only one person opens my email this week, it’ll be my Dad. 🫶

In fact, he’ll often send me a WhatsApp message with his thoughts on this week’s email, or he’ll forward me other newsletters with travel topics that he thinks might be a good fit for a future email. 

Obviously, you don’t have to start a newsletter just to keep your friends and family updated on your travels and your life (although that would be cool!). 

If newsletters aren’t your thing, worry not. There are other easy ways to keep your peeps in the loop, like:

• Forming designated WhatsApp groups (one for your family and one for your closest friends). Every now and then, share photos or short videos with them to keep them updated on your activities.

• Scheduling a 30-minute window in your week to send voice notes to the closest people in your life with a quick recap on what you did that week.

• Creating a shared album on your iPhone and adding photos of your recent excursions. (This one’s easy-peasy because they’ll automatically get a notification every time you add something.)

And if you want to go above and beyond, you can find things that remind you of certain people back home—and then let them know! 

For instance, my friends enjoy hosting game nights. During a trip to South Africa last year, I discovered Unstable Unicorns and became enamored with it. I shared a camping photo of me playing the game and sent them their own version so they could join in.

When in doubt, just post some photos on Instagram and/or Facebook. The Boomers will love it.

2. Send small surprises via Amazon

You know what’s nice?

Getting Amazon packages delivered to your door.

You know what’s even better?

Getting surprise Amazon packages delivered to your door.

I love to surprise my friends and family with little gifts, either for their birthdays or just because I was thinking of them. 

My go-to surprise gift? Inward by Yung Pueblo. 

There are so many amazing, beautiful poems in this little book. When I send a copy to a loved one, I usually like to find a poem that reminds me of them, write the page number in the gift notes, and ask them to let me know what they think of it. 

Remember, you don’t have to spend a lot of money. Just sending small, physical gifts goes a long way to remind your loved ones that you’re still there with them in spirit—even if you can’t be there in person. 

3. Remember it’s about being self-focused (not selfish)

Some days, no matter what I do, I’m plagued with guilt and a sense of homesickness.

To be honest, it’s something I still struggle with myself. But this is my best advice: let yourself feel it out. 

Don’t try to run away from your feelings. So if you’re feeling sad, then let it out with some tears. 

After all, we’re all only human. 

Also, I find it helps to remind myself of why I chose this location-independent lifestyle in the first place. 

So take a moment: Look deep inside of you. Is it because you have a desire to explore? To see the world? To step out of your comfort zone? 

You might be familiar with the expression: “You must fill your own cup before you can pour into others.”

Well, for us nomads and location-independent professionals, fulfilling this desire to explore and see the world is how we fill up our cups.

So the best thing you can do in this life to fill your cup is to continue traveling and doing what makes you happy. Because when you do what makes you happy, you become magnetic. And when you’re magnetic, you inspire those around you. 

My therapist calls this “being self-focused. Not selfish.” And I gotta say, I love it.

At the end of the day, we have to remember that the sting of being far from home is just that: a sting. Let yourself feel it fully. Go for a walk. Journal it out. Sit in the park and watch the clouds go by. 

And then share that feeling with the people you love. No matter what the update is, they’ll be happy to hear from you.

Gear Check🧳

The other day, I was buying a new wetsuit at a local dive shop here in Cape Town, and I stumbled on these fun sandals. 

Let me tell you: They’re beyond comfortable. Like, next-level comfortable. But what really captured my heart is the company’s mission.  

SoulShooz uses neoprene scraps and surplus fabrics from nearby factories to make these vibrant, cozy sandals. What's more, they're dedicated to employing individuals from marginalized communities in Johannesburg and Durban, contributing to sustainable job opportunities for South Africa's youth—a group that’s currently grappling with a 32% unemployment rate.

Airport Reads🗞️

• Seeking a one-of-a-kind adventure travel experience? Enter, AdventureFix. They curate the top expeditions from remote places around the world (like abseiling caves in Australia to see canyons filled with glow worms). You can sign up for their weekly newsletter here.

• I've reignited my interest in the Stuff You Should Know podcast. Whenever I start feeling burnt out from business or personal development podcasts, these episodes are always a breath of fresh air; they’re entertaining, easy to listen to, and cover a wide range of topics.

• This LA Times article on how to tap into your inner child and act more like you did when you were a kid.

Last Thing✨

Thanks for being here! Before we part ways, I thought I’d leave you with this quote:

Have a wonderful weekend, I’ll see you here next week. 💫

Onwards,

Kelsey

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