One of the challenges will be overcoming the fears of quitting a 9-to-5 job and becoming a digital nomad.
Ten years ago, I left my secure, well-paid job of 24 years to become a digital nomad. It was one of the best decisions I’ve ever made, but I’d be lying if I said I didn’t have fears. If you’re considering quitting your 9-to-5 job and are scared, let me reassure you: you are not alone.
Quitting your job to travel and work remotely sounds like a dream. That’s what I thought, too, and the moment I got serious in my planning, the fears showed up. Fear can hold you back and stop you from making life-changing decisions.
Create a Vision Board
In this post, I share my fears and how I dealt with them. One idea that worked for me was to create a vision board, which I put on my bedroom wall so it was the first thing I saw every morning.
Print out images of what you want life to look like, including places you’d like to live, apartments you’d love to rent, tourist attractions you want to visit, and food you’d like to eat.
This sounds stupid, but it works when fear takes over. Look at the board and imagine what your life will be like when you overcome your fears. Let me first go through my biggest fears.
The Fear of Financial Instability
I was paid the same salary on the same day every month.
Relying on unpredictable freelancing work felt very scary. I remember lying awake one-night thinking, “What if I can’t earn enough? What if my savings run out? What if I find no clients?”
These fears are real and valid questions to ask yourself in this situation. You’re not being paranoid or overthinking. You’re thinking like someone responsible, and that’s actually a strength.
Read this post about how to make money as a digital nomad because freelancing isn’t the only option open to you!
The Fear of Loneliness
One of the hardest things about leaving a job isn’t the work.
It’s the people. You may not love your job, but chances are, you’ve got routines, colleagues, and casual connections that make you feel connected.
You lose all of that when you become a digital nomad. That’s not easy. Keeping yourself motivated and productive when working alone can be difficult, and finding a work routine that works for you takes time.
I’ve had moments abroad where I felt truly alone, surrounded by strangers, unable to speak the language, and missing family. Loneliness is a real part of this life, especially in the beginning.
It doesn’t last forever, though, because you gain the courage to talk to people, and it’s so easy to make new friends when you’re living in new countries because people are genuinely interested in getting to know you because of the type of life you lead.
The Fear of the Unknown
When you quit your 9-to-5 to become a digital nomad, you’re not just quitting a job; you’re stepping into a world where you’ll have to figure everything out as you travel.
I had no idea how to get a SIM card in South Korea or how to navigate the train network in Japan, but you learn. Step by step, you figure it out.
I remember walking into a restaurant in Tokyo and looking bewildered, trying to figure out how it all worked as the conveyor belt sent delicious-looking sushi around the room.
When I arrived in Medan, Indonesia, I had to figure out how to get from the city to Lake Toba the next morning. It was either a 13-hour bus journey or an 8-hour taxi ride back then.
The unknown doesn’t stay unknown forever, and what once felt scary becomes second nature.
Fear of Making Life-Changing Decisions
At 50, you’ve likely built a life with structure, routine, and responsibilities. The idea of “starting again” in a completely new way, learning remote work, navigating foreign countries, and adjusting to a different pace can feel overwhelming. A quiet voice often says, “That kind of life is for younger people.”
Here’s the truth: starting at 50 doesn’t mean you’re inexperienced; you’re well-equipped. You’ve got decades of real-world problem-solving, emotional resilience, and a clear sense of what you want and don’t want.
That’s a huge advantage.
Fear of a Lack of Long-term Security
At this stage in life, you’re not just thinking about next year; you’re thinking 10 or 20 years ahead.
There’s a very understandable fear that choosing a flexible, remote lifestyle now could jeopardize your financial future later. Many worry: “Will I still be able to retire comfortably?” or “Am I trading security for short-term freedom?”
These fears are essential to address with careful planning, like keeping up with savings, investing wisely, and choosing destinations that let your money go further, but they shouldn’t stop you from living now.
My retirement looks much more comfortable because I decided to quit living in England and become a digital nomad.
This fear haunted me the most: What if I woke up and wished I hadn’t quit my secure job with an excellent pension? What if I miss my old life, routines, friends, and home? What if this dream turns out to be a mistake?
The Fear of Regret
These are fair questions, but here’s the truth: I’ve had hard days, but not once, not for a moment have I regretted trying. The real regret would’ve been staying in a life that no longer fit because I was scared to try something new.
When I am in my 80s, I want to look back and not have a lifetime of regrets. I want to be proud of the life that I built for myself and believe me, as I type this for you today, I have goosebumps because I did it, I got through these fears, and you can too.
How I Handled the Fear (You Can Too!)
Now, let’s talk about what helped me overcome the fear instead of letting it stop me. Fear isn’t something you eliminate; it’s something you work with. You still live with fear because you continuously live outside your comfort zone. You aren’t living according to societal norms, so of course, fear will appear when you are least expecting it to.
Build a Financial Cushion
One of the best things I did was clear debt and save before I left. I saved the equivalent of six months’ salary to cover my expenses while I got used to remote work. I also built some freelance clients before quitting my full-time job, so I wasn’t starting from zero.
You don’t need to be rich to live this life, but having a bit of a buffer gives you peace of mind and options. This financial cushion gave me the confidence to quit my 9-to-5 job and start living the digital nomad lifestyle. Without the savings, I would have struggled, and stress would have spoilt the entire experience.
Slow Travel is the Only Way
You see so many digital nomads moving from place to place quickly. At the start, I spent a few days in Kuala Lumpur, then flew to Bangkok, and then to Chiang Mai a few days later.
Not only is this exhausting, but it also means you’re spending more money on your travels. The best way to travel is slow. I learned quickly that spending 30-90 days in one city or country is the best strategy.
Many benefits will help you deal with your fears:
- Save more money and plan for retirement.
- Spend quality time experiencing what it’s like to live in those places.
- Easier to make friends when you’re in places longer, which deals with the issue of feeling isolated and lonely.
- Fewer travel hassles like flight cancellations and unexpected problems that don’t occur because you’re in one place.
Exhaustion is a real problem for digital nomads, especially when they work 7-8 hours a day and want time to explore where they live. Slow travel helps with this, as you can have more days to relax in your apartment and chill in coffee shops.
Become a Financial Planner
I talked about creating a financial cushion to deal with the initial fear of quitting your 9-to-5 job, but this doesn’t stop when you jump on the plane and set off on your first adventure. You must continuously plan for the future, budget, and manage your finances while traveling.
You’re taking care of your future and retirement plans by saving money in savings accounts and shares. When you’re in your 50s, considering when you will retire is crucial.
I will write about financial planning in a future blog post, but I know that many fears about retirement and the future can be remedied by having a plan to save a percentage of your monthly income.
Redefine Who You Are
My life before I became a digital nomad was very materialistic. I hate this the most. You felt you had to compete with work colleagues, friends, and family by proving you’re doing good in life by buying expensive TVs, computers, cars, and honestly crap that you do not need to be happy.
I started to have a minimalist mindset and still do to this day.
I bought a 46L backpack and traveled only with the essentials: my laptop, a camera, clothes, and a mobile phone. I never checked in any luggage; it was just one bag, and I was traveling the world.
Being a minimalist is a very liberating experience, making my life easier. I never had to worry about an airline losing my baggage because it was always on me. Living this way makes you realize you can survive with just the essentials.
Becoming a minimalist helped me deal with many fears around fears of the unknown while traveling as a digital nomad.
Find Your Community
For me, it was YouTube and Instagram. Over the years, I have met so many amazing people. You don’t have to be a content creator to make friends. You can join sites like Meetup, which lists events based on location and interest.
Over the years, I have participated in photography walks and food events and met many interesting people.
Working in coffee shops or co-working spaces is another great way to meet new people. Finding your community online and offline will help you overcome loneliness when traveling and working solo.
Have a “Worst-Case” Plan
Some might see this as having a negative mindset, but writing out my worst-case scenarios was one of the most freeing things I ever did. Doing this task was one of the biggest factors that gave me the confidence to quit my 9-to-5 job and travel the world.
So, you quit your comfortable office job, travel, hate the experience, and cannot find a remote job? You return home and live with parents or friends for a few months while you find a new job and a place to live.
Is this really the end of the world?
Sure, your pride might be dented, but at least you took action, right? You won’t be 80 years old and regret not making the effort.
Write down all your fears and consider the worst-case scenario if you were to take action and everything went wrong.
You will find that most fears vanish just by reading this blog post and doing this exercise.
Fears of Quitting a 9-to-5 Job and Becoming a Digital Nomad
Looking back, I’m so thankful I didn’t let fear decide for me. Yes, I was scared, with sweaty hands, and I was overthinking everything.
Truthfully, even now, I still get nervous before landing somewhere new, but over the past ten years, I’ve built a life around freedom, something I once thought was out of reach.
I’ve saved so much more money than I did living full-time in one place. I’ve made friends I would’ve never met and challenged myself in ways my old routine never could.
I feel more alive, more capable, and more me than ever, and all of it started with one choice: I said yes—even though I was scared.