The key to freedom? 🏖️ Constraints

Hey, hey!

I’m gearing up for my 16-hour flight home from Cape Town to Atlanta. 

Call me crazy, but I love long-haul flights. There’s something about just sitting in one spot for hours on end and staring out the window that gets me all pensive and daydreamy. 

So what am I currently pondering? Lately, it’s been all about how adding constraints to your life actually gives you more freedom. 

Let’s dive in.

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.

Want More Freedom? Add Constraints

Before I started living a nomadic lifestyle, I always daydreamed about living a life abroad and having complete freedom.

But once I got there, I realized that being such a “free spirit” is really just a one-way ticket to being flat-out broke.

How do I know this? Because that’s exactly what happened to me. 

First, I got the remote job that I wanted and took off traveling. But not long after, I started finding it difficult to manage my work while also exploring a new country. TLDR; I was spending money like there was no tomorrow. 

Credit card companies LOVED me.

It took a year of being fully location-independent for me to realize that being successful in this lifestyle means having the foresight, willpower, and motivation to create an insane amount of constraints for yourself. 

Because (believe it or not) these constraints end up leading to a lot of good things, like:

• Fostering greater creativity

• Allowing ideas to flow more freely

• Supporting a healthy work-life balance (for me, this means knowing when it’s time to disconnect)

• Getting all your freelance work done on time—without getting stressed

Let me explain.

1. Constraints make you more creative, not less

Sorry to be the one to tell you this, but there’s no such thing as writer's block. 

Your standards are just too high.

This is good news. Because the next time you’re feeling stuck on a creative project, or you’re too scared to create a TikTok promoting your business, or whatever the thing is, you can use this trick: Come up with the first step, and then lower your standards.

For example, when I first came up with the idea to start SiteSee, I sat down on a Saturday to build the website … and it was the most overwhelming experience of my life.

I felt like I was walking straight into a void. I was totally lost on where to start.

If I could go back and relive this experience, I would add in some constraints. For example, I would tell younger Kelsey: 

• Today: Give yourself just two hours to write your brand mission and make a list of all the companies you eventually want to work with. 

• Tomorrow: Buy the domain.

• The next day: Write the content for the about page.

Adding in these constraints and breaking things down into smaller, bite-sized pieces keeps your creative minions in check. 

When you don’t build in constraints, then you start to feel overwhelmed—and all your creativity evaporates.

Which brings me to my next point…

2. Constraints keep you sane

I don’t know about you, but for me, the hardest part about working remotely is actually stopping working when the workday is over.

With a normal 9-to-5 job, you leave the office and start commuting home, which signals to both your body and your brain that work is over for the day. But when you work remotely, this line between professional you and after-work you becomes blurred. 

The fix? Bake in a ritual that tells your mind and body that it’s time to stop working. 

You can start by filling in this sentence: “At [insert time] my workday is over, and I’ll know this by doing [insert activity].”

For example, some of my friends only work at coffee shops or coworking centers. When they leave those spaces, it’s a clear signal that the time for work is over.

Personally, I’ve been working from home more often—so what’s my signal? I either take a shower or go for a walk. 

Not only does this physically move me away from my laptop, but it also starts to transition my nervous system from the sympathetic mode to the parasympathetic mode. Translation: It tells my brain and body that it’s OK to chill out and start to relax now that work is over.

You can go one step further by creating barriers between your professional life and your personal to help solidify these constraints. 

For example, if you find that clients are constantly hitting you up on Slack when your workday is over, then uninstall the Slack app from your phone.

In many ways, working remotely has become a subtle art in knowing how and when to protect your peace while living in a constantly plugged-in world. 

3. Constraints hold you accountable

Struggling to finish a freelance task? Then write the first paragraph. Can’t write the first paragraph? Just write one sentence. 

Breaking things down into smaller chunks helps you keep moving forward—even if it’s just inch by inch.

All too often, we find ourselves down the rabbit hole of future events, constantly fixating on what could be, should be, or would be. In the end, we never take that first step forward, and we just keep kicking the can further down the road. 

Setting up constraints helps us get out of our heads and actually do something. 

Here are a few examples of what that looks like:

• Format constraints: Adhering to predetermined formats, such as word counts. You start writing an article and set the goal at 500 words down. Remember that no one is going to see this draft, so just get the 500 words down and then take it from there. 

• Time constraints: Set a strict time limit to complete a task or project. You set a timer for 30 minutes to focus on a work deliverable. In those 30 minutes, you’re not “allowed” to do ANYTHING but work on that task. 

• Technology constraints: Limit the use of certain technologies or software. You turn off your phone for one hour and see how much progress you can make. (This one is my favorite.) 

Above all, remember that if you’re feeling restless or stuck, there’s likely nothing majorly wrong. It just means you haven’t set up constraints that work for you. 

With practice, you'll eventually discover the constraints that best align with your unique working style.

Gear Check🧳

A water shoe that doesn’t make you cringe? Turns out, it can be done.

I used to think it was impossible … But then found these water shoes from Crosskix. 

With summer in full swing in Cape Town, I've been frequenting the beach quite a bit, exploring the nearby tidal pools, and going for cold plunges at Saunders Beach. And these shoes have quickly become my go-to. Not only are they suitable for water activities, but they're comfortable enough (and stylish enough) for workouts. Whether you're into water sports or simply enjoy leisurely walks by the beach, I wholeheartedly recommend these shoes.

Airport Reads🗞️

• On the hunt for a remote job? IMHO, the Remote Source newsletter is one of the best out there for getting access to up-to-date job openings for fully remote positions. 

• This weekend, my closest friend is tying the knot. Instead of purchasing a dress in South Africa and dealing with the hassle of transporting it back and forth to the States, I opted for a rental—and it was super easy. Via Rent the Runway, I sent five dresses to my parents’ house so I can have a mini pre-wedding fashion show of my own and pick out my favorite for the big day. 

• United Airlines, American Airlines, JetBlue Airways, and other airlines are raising their baggage fees. Boo. Yet another reason why you should travel with just a lightweight carry-on.🧳

Last Thing✨

Thanks for being here! Before we part ways, I wanted to share a quote I’m meditating on as I head back to the States and take some time away from work:

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

Onwards,

Kelsey

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