I quit my job to travel and work remotely 5 years ago — here’s what I wish I knew before

Stephanie Smolders
Stephanie Smolders recommends saving as much as possible before starting a digital nomad lifestyle.

  • Stephanie Smolders is a marketing and business coach, writer, and digital nomad.
  • She and her partner have been traveling the world full time and working remotely since 2016.
  • If they were to start over, Smolders says they’d bulk up on savings and be more flexible with travel plans.
  • See more stories on Insider’s business page.

It may sound idyllic to be a remote worker and log onto your computer from anywhere in the world.

It is, but after five years of working remotely as a digital nomad, there are definitely a few things I wish I’d known beforehand.

In 2016, I quit my teaching job and started traveling full-time and working remotely with my partner, Peter. Our fair share of mistakes have taught us a lot. If we were to start over again, this is what we would do differently.

1. You get what you pay for

Save yourself endless frustration and energy by not always going for the cheapest option. At first, we tried hard to save extra cash, whether on software and tools we needed for work, flights and accommodation, or even restaurant visits. We’d spend hours figuring out how to save an extra $20 a month on a software that was supposed to save us time. 

In most cases, we’d discover that we needed the premium or paid plan after all, could have used that extra storage, or should have paid for a flexible flight ticket. The amount of time we spent trying to be frugal was not worth the couple hundred dollars we saved. Now, when we think we need something, we get it and save ourselves on time.

2. The lifestyle will cost more than you think

On the road, things rarely go as planned. A general rule of thumb we’ve learned is that your estimated lifestyle costs 25% more than you think and planning takes double the time. Overestimate your budget and your timing so you save yourself guilt-tripping later on. We now calculate 25% more in our budget because it’s hard to estimate your daily spending in a new country. 

3. Take a break and enjoy

Doha 2017 Stephanie Smolders
Smolders in Doha, Qatar in 2017.

In the first three years, despite traveling to over 40 countries, we rarely explored or took a day off. We started a marketing company and wanted to provide the best service to our clients, so we hardly even took weekends off. 

Looking back, we missed a lot of the beauty of traveling and connecting with a new country and culture. Despite the tropical locations, if you’re working as a digital nomad you’re not  always on vacation, so never taking a real break will be unhealthy and unsustainable in the long run. 

Now, we take at least a week-long break every three months. It keeps us motivated and productive. Even when you live in paradise, if you’re working full-time you still need a few days off every couple of months to recharge. 

4. Don’t skip out on insurance  

Working remotely and traveling comes with a lot of risks. Not knowing the culture or local regulations can make it difficult to find a hospital, who to ask for help when you get into an accident, or what to do if your property get stolen or lost. 

As a preventative measure, we knew it was important to get travel and health insurance tailored to digital nomads that understand the lifestyle. For health insurance, we use Safety Wing Nomad Insurance and are covered with our Revolut Metal plan for all travel-related incidents and theft.

5. Remain flexible at all times

Stephanie Smolders' partner Peter working from a hotel while on their travels.
Smolders and her partner Peter working from a hotel while on their travels.

On two occasions we decided to change our travel plans completely but our flights and accommodation were already paid for. We hadn’t paid for flexible options so we ended up losing our money, about $2,500. This isn’t a situation you can afford often. 

The best thing about remote work is the flexibility to go to places you want to be. When you sign a lease for a villa for six months but want to move after two, you’re in trouble. Twice, we lost money due to ending a house lease early. Negotiate flexible contracts for your housing, buy changeable flight tickets, and don’t commit to a long stay before you’ve seen a place in person. 

6. Bulk up your savings

As mentioned before, things always cost more than you think. When working as a freelancer or starting your own business as we did, it’s great to know you have a buffer and at least a year’s worth of runway. 

At the start, we didn’t always hit our income goals, and during the first few years, we had periods when we went way over our calculated budgets and as a result, had to make decisions that damaged our business’s ability to grow. With a bigger buffer, we could have hired better support earlier or afforded a bad quarter without putting the business at risk. In hindsight, we would probably have waited six months to a year longer to save up a year’s worth of expenses before starting our digital nomad journey. 

This article originally published September 6, 2021.

Read the original article on Business Insider