Digital Nomad Milestones: A Guide To Measuring Your Success

digital nomad milestones

I’d like to think of digital nomadism as one big life project. And in every project, there must be some sort of measure of success to tell you that you are moving in the right direction, and to show you how far you’ve come. For these reasons, I’ve made a list of digital nomad milestones.

Some of them are personal milestones I’ve surpassed, but I’ve delved into the specifics depending on what type of digital nomad you are. The digital nomad milestones accomplished by a freelancer in their first year on the road will be very different to an entrepreneur or a remote worker, for example.

Of course, you may have a different set of milestones all on your own. That’s totally understandable! You are your own person. Ultimately, the point of keeping a list of digital nomad milestones is to stay on track and celebrate each milestone ticked off!

Milestone 1 – The Game Plan

digital nomad milestones

How many times have I told you about the importance of having a game plan? There’s no nice way of saying this, but you’re a fool if you don’t have one on this road to digital nomadism. As I have spoken about in my How To Become A Digital Nomad guide, you’ve gotta save tons, you’ve gotta work harder than ever, and you’ve gotta map out your game plan and contingency plan!

This takes an awful lot of time. Therefore, being armed with a game plan is well considered a milestone!

Milestone 2 – Bye, Homeland!

digital nomad milestones

This is a milestone of mixed emotions. I still get a lump in my throat when I think about the moment I quit my job, sold all my belongings (that did not fit in my luggage), and said goodbye to my friends and family. As I like to think, it’s not goodbye just “see you soon.”

Let the emotions flow—the sadness and the excitement. At this point, there’s no turning back now! No more fucking around as you count the days to finally stepping foot on that plane. It takes a shitload of courage, but you’ve made it this far.

A quick pro tip? You might wanna have some quick retreat and time for yourself before stepping on that plane. The road leading up to this day would be tiring AF, so it’s best to take a quick break to get mentally refreshed for the next challenge of your life.

Milestone 3 – Settling In

digital nomad milestones

If you’ve devised a kick-ass game plan, then chances are, at this point, you’re ready to move into your new home (for the next few days or so!). From my experience, I already pre-booked an apartment for a month through Airbnb before my flight out of Switzerland. This saved me a lot of time and spared me the hassle of wandering around, looking for a place to stay temporarily.

After a smooth moving in, you’re ready to be out and about! It’s understandable that you’ll want to tick off the top tourist spots on your things-to-do, but the real milestone here is the effort you’ve put in to immerse yourself in the local culture. Isn’t that the fun part of becoming a digital nomad?

Don’t limit your circle to expats! The moment you meet your first few local friends or drinking buddies, learn a few sentences, and pick up on a few cultural norms—you’ve earned yourself a new digital nomad milestone! These things are all part of engaging yourself to your new community which will make your digital nomad lifestyle all the more fulfilling!

What makes digital nomads different from tourists and travelers is that we don’t come to see and do, we come to live. With digital nomadism being a fairly new phenomenon, it is the responsibility of us, pioneers, to set the standards. We must prove that we don’t move around solely to find the cheapest cost of living, rather to experience the world and enjoy the company of those who inhabit it.

That sounded quite profound! Now, onto the specific digital nomad milestones!

Digital Nomad Milestones for Freelancers

If you are a freelancer, then you know that sweet feeling of victory from each new client or new project! A new gig is a milestone in its own right. They even refer to projects as milestones on UpWork!

Milestones for freelancers come in thick and fast compared to remote workers and entrepreneurs, but this doesn’t make them any less hard worked for.

Booking your first job

digital nomad milestones

If you are indeed a well-prepared digital nomad, then at this point, you’ll have already a regular client base before you even hit the road. I remember when I was seeking my first job as a freelancer, I felt like the search was never-ending (it took me days, or even weeks!). It was such an uphill struggle!

Let me tell you this: The first project is the hardest. Although an uphill struggle, I can assure you you’ll find a snowball effect soon after. Well, only if you’re fucking awesome which I know you will be!

Once you’ve got that first job secured, give yourself a hearty pat on the back!

Getting your first feedback

digital nomad milestones

Reading your first lot of feedback can be daunting and a bit unnerving! I’ll tell you now; it may be constructive more than it’s complimentary. But this is a good thing! By knowing what you can improve on, you can seriously up your game time and time again until you’re one of the best and most sought-after freelancers in your niche.

Creating your own website

digital nomad milestones

Many freelancers start out using PeoplePerHour and UpWork, which are both great. Although neither of these sites allows you to take work off the platform, what you can do is to refer new clients and potential clients that you find organically to your own website. Once they award you with their project, you keep 100% of the fees rather than giving a percentage away to the platform.

Setting up your website takes time and a bit of money.  However, it not only makes you look more established and professional, but it also doubles your chances of being found digitally.

Digital Nomad Milestones for Remote Workers

Arguably, remote workers have the toughest start in the digital nomad world. However, it’s a small price to pay for the job security it brings.

Negotiating your contract

digital nomad milestones

Perhaps you’re keeping your same job but taking it remotely, or perhaps you’ve got yourself a whole new job that allows you to work remotely. Regardless of this semantics, you’ve gotta make sure your contact works for you.

This is really tough because not all employers are open to the idea of remote work. And if they are, be prepared to compromise in order to make the move. That said, some bosses are absolute heroes and offer kick-ass remote working contracts, so you may just get lucky!

Finding the work-life balance

digital nomad milestones

Work-life balance is different for everyone. But this hits hard for remote workers because their work hours are still dictated by their employers. This means that if you’re a remote worker, being able to build a routine that works for you is a sweet achievement!

With flights to catch and new friends to make, as well as working a 40-hour week, finding balance can be hard work. The relief that comes with the realization of nailing the right groove is well-darn-deserved.

Digital Nomad Milestones for Entrepreneurs

It’s a little trickier to find a fit-for-all digital nomad milestones for entrepreneurs given that different individuals tackle different paths across different industries. Let me try, though!

Going live

digital nomad milestones

Whether the time from idea to product was long or short, it matters not. What matters is going live. Being digital nomads, work as entrepreneurs know it is all online. So, there is a stage when all ideas, ramblings, and wanderings come together into one place and go live online.

Much like when I launched this blog. It was the most nerve-racking moment of all, but when you can sit back with a cold beer and see your business go live—the fruit of your labor—life couldn’t be much sweeter!

Earning your first profit

digital nomad milestones

Being the risk-taker that you are, you already expect not getting a profit in your first few months, or even years, of operation. You will, however, be able to forecast when money will finally start coming in. If it does happen, rejoice! I was wrong earlier—life couldn’t be much sweeter when you actually start getting cash! This is the realization that you’re self-sufficient and have made an impact on the world of commerce forever.

Getting your first endorsement

digital nomad milestones

Whatever product or service you are offering, your first endorsement is a big deal! It affirms that you are good at what you’re doing and that your business is a viable solution in your niche.

Remember, being an entrepreneur and digital nomad is all about blowing your own trumpet in the most humble of ways. Make sure you share this endorsement far and wide to let your broader community know that you’re kicking ass!

These are just some of the digital nomad milestones to tick off. Everyone’s success is different, so your list may be different than what I’ve provided here. And if you don’t have one yet, I hope this inspires you to make one for yourself. This is a helpful way for you to appreciate better how far you’ve come on your journey as a digital nomad.

My key bit of advice? Don’t put a time limit on achieving them. Although having time-bound goals is integral to success, there is a lot to be said for going with the flow and seeing what the universe sends your way.

Be prepared to jostle your milestones around to accommodate the unexpected. Be patient but be keen. Be on the lookout for opportunities to reach your milestones, for opportunities are everywhere if you should only be open to seeing them.

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