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The Ultimate Guide to Measuring Your Progress While Living the Digital Nomad Lifestyle

How many potential or existing digital nomads out there are wondering if this lifestyle is right for you? We realize there are plenty of articles out there about the successful digital nomad, the “after” to the “before.” If you are wondering if you will ever reach that point, we invite you to read this article to guide you on how to track your progress. Learning how to track this will help you realistically weigh the pros and cons of the digital nomad lifestyle as well as help you grasp where you might be in the process of success and your personal and business growth.

The digital nomad mindset for growth requires a balance of work and travel, adventure, energy maintenance, self-awareness, remote working, business savvy and growth, and a constant desire to learn, among other things. On paper, this can be quite overwhelming. You have lots of questions. How do you tackle all this? How do you know when to throw in the towel? How can you tell if you are reaching your goals?

This article will provide you strategies for how to evaluate your progress especially when the going gets tough, how to understand your growth as a person when it comes to new experiences, and criteria for success for entrepreneurs and freelancers.

Becoming a digital nomad requires a lot of planning – Digital Nomad Explorer

The Truth About Becoming a Digital Nomad

As a preface, we want to provide you the most accurate understanding of what it takes to be a digital nomad. Before you begin to track your growth, it is wise to know if the lifestyle is something you are willing to adapt to, because it does require some work and a certain mindset to be successful. Like we’ve previously said in other articles, it requires balance.

Many people think a digital nomad decides one day to up and leave their corporate job and buy a one- way plane ticket to the nearest beach. Although this is what movies might make it out to be, this is a highly simplified image of what goes into the decision making prior to making the jump. As epic as we wish it would be to quit that pesky job, you are stuck in and never look back, and this decision cannot be made impulsively during a moment of burn out. It is neither responsible nor sustainable.

With that same token, one cannot be too uptight when it comes to planning the digital nomad lifestyle. If too much planning is involved, the digital nomad might get bogged down with so many details that they crack due to overwhelming pressure. Or worse, they might psych themselves out so much to the point that they give up on the idea altogether, not even allowing themselves to try. When choosing to abandon a 9-5 work schedule for the freedom of the digital nomad lifestyle, many details are involved in transitioning as comfortable as possible. These details must be acknowledged without becoming a cause of fear or anxiety. It is a tough path to walk because there will be things you cannot prepare for, no matter how ready you feel. However, balanced preparation will help you be better equipped to face these inevitable setbacks with more ease than if you were going into the experience completely blind.

There are some basics you can begin to focus on to prepare you for the lifestyle and to use as starting points from which you can then measure your growth. These basics can help act as a foundation.

As a digital nomad, one of the key basics to get into place is to grow your income – Digital Nomad Explorer

The Basics


Income is everything when starting as a digital nomad. Before you venture out, you need a safety net. We know the “unknown” of the nomadic lifestyle might be alluring for some, but it is not something to mess around with, because you could get yourself into a dangerous position with a complete lack of preparation. Have a steady source of income set up and begin cutting back your expenses. You will have to learn how to cut out many comforts and slim your lifestyle down to just the necessities. It will make things easier to move around as well as keep your purse strings tight. If you can prepare for this a few months in advance before you entirely become nomadic, you will be ready to do it for real.

Your income needs to either come from a remote salary, freelance work, previous investments or retirement funds, or even savings. These base funds are pivotal in case of emergency. If you have to fly back home, you don’t want to be stranded.


Having a flexible attitude will help ease the tiny stresses of the nomadic lifestyle. The entire reason you are probably choosing to be a nomad is to leave the standard corporate American lifestyle for something new. With that, you need to prepare yourself to expect the unexpected, and learn how to have a thick skin. Don’t take things too personally because it will be tough at some points, especially in different countries with different cultures. If you can push past initial discomforts of not knowing what you are doing right away and realize it’s fine to make mistakes as you go, you’ll start to look at every new opportunity, good or bad, as a stepping stone for your next career move.

We hate to break it to you, but if you can’t handle a little discomfort now and then, this lifestyle is probably not suited for you. The structure of 9-5 jobs can be nice in that it helps you map out your day, but as a nomad, you’ll need to get comfortable with the idea of each day being a little bit different. Start saying yes to things that might not be right in your wheelhouse because they will often provide valuable business lessons you can apply. Furthermore, there is nothing quite like the confidence you’ll feel when you’ve begun to conquer a new environment and a different culture. The independence and empowerment should be enough to keep you pushing forward, but that euphoria is often on the other side of a severe circumstance or fearful moment.

Business progress has many variables to measure – Digital Nomad Explorer

Every person you meet as a digital nomad should be viewed as a valuable resource. Don’t think you are too good or not good enough to connect with different creators. They might help you make connections that propel you forward or help you realize a new business strategy you hadn’t tried before. You are more likely going to get useful information out of these people if you can, in turn, exude patience, confidence, and empathy. It will also help you work across cultural differences, a hugely important skill to have when you are a nomad.


Find a community in some way. Finding people you connect to is not necessarily the hard part but having the courage to enter into an environment full of strangers is- but it’s a necessary first step. If you can find community in other freelancers and co-working spaces, or find community in a sports league, a book club, a group of adventure buddies, locals, etc. your experience will be more joyful than when spent alone. Every person, no matter what, strives for community and human connection. The nomadic lifestyle has the potential to get lonely if you don’t put yourself out there enough. You’ll grow as a person as you widen your circle of peers and friends and bounce ideas and values off one another. It is always comforting to know you will have a local community to fall back on if things are particularly tricky and you can’t handle them by yourself.

Remember your “why”

Remembering your “why” is the last piece you need before you can begin to measure growth because it is the factor that all of your growth is ultimately measured. If you don’t know the “why” behind choosing to be a digital nomad, or you are not as truthful with yourself on all the reasons for your “why,” then you will hinder your growth in the years to come. Many people enter into the digital nomad lifestyle because it can provide them travel. Traveling is romantic, awe-inspiring, and captivating in many ways, but it cannot be the only reason you want to become a nomad. Before you can jump in, calibrate yourself both mentally, physically, and spiritually. These factors can help you become as grounded as possible in your reason for your new life, which will help you see, in comparison to this level of stability, if you are straying away from that feeling or if you are meeting or exceeding this potential.

Measure the your progress of your startup – Digital Nomad Explorer

Measuring Progress with Your Business or Startup

The “why” behind your nomadic lifestyle choice is your baseline measure of success. From there, you need to start your measurement process by setting tangible business goals. To do so, you need to create a business plan, grounded in the questions, “am I controlling my fate?” and “does this align with my why?” It requires a deep-level understanding of what your business purpose is at the core. We recommend getting your business plan set in stone before you move to a different location because new places can be quite inspiring, constantly stirring new ideas. It is not all bad, but it can be distracting when it comes to your business plan. If you all of a sudden shift your focus away from your original method because of a new location and the ideas it sparks in you, you risk muddling up your original vision. Simplification is critical when creating this lifestyle for yourself and working smarter and not harder. If there are too many moving parts to nail down, the chances that you succeed all on your own become smaller. Start with small, everyday achievable goals and begin to build up from there.

After you have your “why” set in place, it is essential to see if your skills are right for your “why.” Sometimes, the vision is there, but our ability to execute is not realistic to our strengths or weaknesses. Some self-awareness is vital here, as you have to understand what you as a single creator can bring to the table of your business, and if you are missing a key piece of expertise, it might be valuable to seek out someone who can bring that key strength into your business. It’s essential to understand your value proposition to the world. Hold yourself accountable for your work output, be self-disciplined, and be okay with performing smaller, less exciting (but necessary) tasks to keep your business afloat.

Once you get a clear understanding of your goals, they should be at the forefront of your mind. Begin by writing them down in a journal, and then check back in with them in a consistent time frame. For some, this means a check in every week, month, quarter, or year. Regardless, make sure these goals are written down and tangible because those with creative minds can just as easily forget a great idea as soon as they come up with a new one.

Begin looking into paid apps and services that can help you schedule your own social media posts at the right time of the day based on your time zone. Many apps help you schedule your posts ahead of time so that you can focus more of your time on creating more and more content.

Business analytics are a great to way to measure your business progress – Digital Nomad Explorer

Make sure you are also looking at business analytics. Google Business and Facebook Business are both great tools. You can see precisely what demographics clicked on content and how long the landing time on a page was. Did they read it or did they get bored and click out? These stats are small but all vitally important to the overall health of your business. Be warned. You need to have a bit of a thick skin when looking at these statistics. Sometimes they might tell you that whatever you’re currently outputting is not working. Unfortunately, they probably won’t give you the “why” answer because they focus on just the numbers. You might have to do a deeper dive and have regular brainstorming sessions after compiling data to break down what might be working and what might not be based on a week’s worth of results.

As you check in regularly, conduct some form of self-assessment and objectively review your progress. It can be difficult when you are examining yourself, so consider bringing in third-party focus groups who can give you unbiased feedback on something you’ve created and whether or not it resonated with them. As painful as it might be to hear sometimes, honesty keeps you in check and somewhat removed from your work, which is both pivotal and beneficial when you are alone, living and breathing your work all the time. You might conduct incentivized focus groups to understand better the language of an article you wrote, and if it hit the target audiences you hoped, the design layout of your website or promotional materials, or the effectiveness of your social media strategy. Try to get feedback for more than one area of your business, because sometimes it just takes a small shift in one aspect that can have a significant effect on the entirety of your plan.

Make sure you are working- a lot. Sometimes we get so overwhelmed with the amount that needs to be done, that we only knock-off simple, shallow tasks on our to-do lists. It can make you feel that sense of productivity and accomplishment, but won’t get you anywhere until the deep dive work is completed. So, make a real dent in your to-do lists, and keep old lists to see what was achieved vs. what you just wrote down to keep yourself feeling busy. Don’t overschedule yourself each day, or else you will feel too anxious to sit down and do anything. Instead, break up your workload into small, doable chunks that you have little to no excuse not to get done daily. It might be helpful to come up with a master list of goals and necessities for your business growth, but then allocate those tasks by dispersing them to yourself and those you might outsource to get them completed over a timeline you create.

Another vital thing to remember is making sure you are sticking to a budget that is allowing some form of income to come in, even when you are building your business. Get comfortable with Excel spreadsheets so you can go back and track your spending, calculate your profit margins, and see where you might have slipped up in the past to prevent those mistakes from happening in the future.

Measure your personal growth as a digital nomadDigital Nomad Explorer

Measuring How Much You Are Growing as a Person

Ultimately, the point of becoming a digital nomad is to escape a restrictive work life cycle that does not provide you real joy and purpose, on top of the desire to travel and move around freely while making your passion your life’s work. You have chosen this lifestyle to challenge yourself, to seek something new and fresh and exciting every day instead of getting stuck in a rat race of life. You know as a digital nomad, you made the active choice to make a lifestyle for yourself instead of being managed by someone else. The sooner you can embrace the discomfort that comes with such a shift in lifestyle and lean into that for personal growth, the better off you will be to enjoy the “unknown” the lifestyle might bring.

Your bank account might not be entirely as secure as it might have been in your steadier job, but you have replaced that security with passion, which can provide a different kind of success. Instead of using money as the only measure of growth, it is essential to reflect on how far you have come as an individual. Are you happier and more content waking up in the morning knowing you get to do what you love, lead your schedule, and live in the places you’ve only dreamed of vacationing to before? Then you are already off to a good start!

Start looking to your change in feelings as a valid measure of growth the same way you might look at money or sales growth. A great way to do this, and we’ve mentioned this in our article about energy maintenance and balance, is journaling. You can do this in whatever way you please. If you love to sit down at the beginning or end of the day and reflect by diving into pages of writing, go for it. If you know you might not be able to commit to such a task every day, try bullet-point journaling. Just jot down a few bullet points about how you feel that day personally, how successful or unsuccessful your work output was, what your goals are moving forward if you’ve accomplished any new goals, and what you think you need to improve on.

Sometimes, when we are in the thick of a transition in our lives, it is tough to tell if we have grown at all, especially if you are a digital nomad living alone. You don’t have an outside party to tell you what they might be observing, which can be good in that it can get rid of naysayers or negative influences, but it can also be difficult if you are stuck in a negative mindset when the going gets tough. You have to rely on yourself to pick yourself up and dust yourself off!

If you can’t be introspective enough to realize how far you have come from your starting point and can only focus on mistakes made in the present moment, you’re going to feel constant discouragement. You might have a long way to go in creating the digital nomad lifestyle you dream of, but it’s comforting to know that you likely started even smaller and can grow much further. So much of how you continue to grow is how you choose to look at life. If you’re a digital nomad, you need to be an optimist.

Another form of journaling that is great for focusing on optimism is gratitude journaling. When the going gets tough or your mental health feels like its slipping because of loneliness, write down three things each day, you are grateful. These habits take a bit of discipline and consistency, but we promise they will help you learn to look at the glass half full when you need it most. Consistent practice will begin to carry over into all aspects of your life and again, will make you sweat the small stuff just a little less.

Capture the growth mindsetDigital Nomad Explorer

The Growth Mindset

One crucial mindset to have is continued progress over perfection in everything. At the very basis of this article is the understanding that as a digital nomad just starting out, you cannot expect perfection. It’s great to set the bar high for yourself, but if you set the bar too high and aren’t making the mark when you start, you will only feel discouraged. It’s just like trying to lose weight, for example. You can’t start with a complete lifestyle overhaul overnight and expect long-term success. If you over-exercise and cut out all unhealthy foods altogether, the chances of that lasting long term are low because you are going to burn yourself out, and one little mistake will make you feel like you’ve completely fallen off the wagon.

The same can be said for starting your new digital nomad lifestyle. If you expect yourself to have all your ducks in a row from the first day you begin and every moving part pinned down entirely, it’s going to feel too overwhelming to tackle all at once. Instead of trying to start everything from scratch right away, give yourself time to ease into the lifestyle and space for trial-and-error to see what does and doesn’t work for you.

You might be thinking, “well isn’t this a waste of time?” No. The sooner you understand that these trial-and-error periods are an investment of your time, the easier this mindset will be to adopt and follow. Giving yourself a bit of a grace period to really figure things out might not necessarily get your business growth started as quickly as possible, but it is going to be more beneficial in the long-term because you will have made mistakes and learned what not to do, while also finding out outstanding strategies for what does work. If you can learn sooner rather than later that you will make small mistakes along the way, but you don’t need to sweat those little mistakes, then you are going to put yourself in an advantageous position. It will help you learn how to be flexible, understand the ebbs and flow of starting a new business or nomad lifestyle, and will help you feel less inclined to give up when the going gets tough.

How do you measure the intangibles of growth on your digital nomad journey? Digital Nomad Explorer

Measuring Progress on the Intangibles

To complement your growth mindset, try having a gratitude mindset as well. This mindset focuses on measuring your success through intangibles such as intellectual growth, following your intuition, and growing in your values with a focus on being grateful for each lesson. It’s hard to put a metric on this type of growth, but it is arguably the most exciting transformation that can take place as a digital nomad. Again, journaling is our top recommendation when understanding the thought process behind the lifestyle shifts; you will feel like a digital nomad. Most of these shifts will occur internally and without others noticing. They are something only the digital nomad can feel within themselves.

Reaching the point where you realize you are living the life of your dreams makes it all worth it, but make sure you are sticking to your values, whatever those may be. Listening to your gut on whether or not a business decision feels right is the best way to strengthen that connection with your moral compass. It’s like a muscle, and the more you work it out, the easier it becomes to handle more difficult tasks in the future. The growth you might feel as a person in terms of the capabilities of your mind and soul are worth the initial struggle because your confidence will soar as you realize the power of your intuition.

Final Thoughts

Ultimately, happiness is an essential factor in this equation. Your gut feeling may be telling you that the digital nomad lifestyle makes you significantly happier than your previous life. Look deeper, and you find it is because it provides you freedom of movement, the ability to fill your time with other hobbies and interests, and the ability to see the real purpose in your life’s work. By these accounts, then you are growing, and you should feel grateful you are experiencing a joy that others struggle to find. If you start to see that you are no longer working to live and survive, but you are living to work and thrive and enjoy the thrill of learning new things, you can confidently say you’ve experienced intangible growth.