A Modern-Day Nomad’s Guide: How to Leave Everything Behind and Start Over

by Anne Dorko

I want to start over. I need a new life. I want to go somewhere far away.

You’ve reached a major turning point in your life. For one reason or another, you want to say goodbye to your old life and start a new chapter. This is not a decision to be made lightly, but at this point I’ll assume you already know it’s what you want. Trust me, I’ve been there.

Making this kind of change is never easy. But you can help mitigate your anxiety with some good old-fashioned preparation.

So, how do I start over?

I have gone through many huge life changes, all of which required leaving behind an old lifestyle and embracing a new one.

You know what I think? It’s kind of like being a spy. When I was a kid, I thought being a spy would be pretty neat, so in a way I’ve kind of achieved that.

Here’s what I’ve learned from my own experiences of starting a new life:

Inspect and Strategize Your Resources

If you’re able to be flexible, you can still go far while having little to your name. The worst aspect is taking inventory and accepting whatever that is.

A box, bicycle, two instruments, and a few miscellaneous items.

It’s not always a lot.

Knowing what you have available to you will help you to make this work to your favor. Remember the spy analogy? Spies are known for their ability to get in and out of any situation. How do they do this? They know what they have, what they don’t, and how to use their resources creatively to get what they want.

Here’s my personal checklist for this:

1. The Monthly Budget

Money is the source of all stress.

Visa, loan, application, <your example here> denied? 98% of the time you didn’t have enough money.

Despite what they say, money can help you buy happiness. It helps you feel secure in the simple things like eating and sleeping with a roof over your head.

Start by counting up all your assets to see how long your cash would last you as you currently live without any more income. Then, try to see how far you could stretch it to make it last as long as possible. Think of it as a mental exercise. Which expenses do you absolutely need? Which ones can you get rid of? Perhaps your cell phone is a must-have item, but your daily cup of Starbucks can go.

Afterwards, ask yourself how you can start increasing your monthly income in this new life of yours.

2. The Skills

Your skills are an asset.

Can you write? Draw? Photograph? Organize? Bathe pets? Clean a house? Make beds? Program iOS apps?

Write down all your skills, big and small. Whatever you can do, you should consider it an asset. Work can be traded for accommodation, food, and money. These are all important to your future.

Don’t sell yourself short. Just because you don’t have a college education doesn’t mean you’re not worth being paid for a job. Write it all down.

These are the things you have at your disposal to make more money down the line.

Have a skill you don’t know yet, but really want to add to your repertoire? I recommend going all out and use the obsessive learning technique I love to talk about so much. (That’s more of a pirate thing though.)

3. The Debts

There is an astonishing amount of personal debt, and it can be incredibly stressful to deal with.

List your debts in order from smallest to biggest. Research the legal rights you still have if you are unable to pay any of them. Are your debts deferrable? Is there a liable asset of yours that they can seize?

Know your rights.

Paying down your debts is your fastest route to financial freedom. My recommendation in your new life is to live on minimal expenses, dedicating every last penny to getting rid of your debts, snowball style. That means paying off your smaller debts first and then worry about the big ones.

Plan for Best Case, Worst Case Scenarios

One of my biggest fears is that everything is going to go dreadfully wrong.

That’s why, at any given point, I have two or three wildly different plans for what I’ll do if something goes sideways.

Here’s a few examples from my own life:

Backup Plan: Visa Application Edition

Talk about international intrigue! Adventure! I’m currently applying for a visa to stay in Germany.

Cologne Germany Bridge

Of course, there’s no guarantee it will work out the way I hoped. To deal with this, I have two alternative plans to follow in the event my long term visa application is rejected.

Plan 1: I can either fly onward and hop my way around the world, spending a measly $350/mo on flights and still be home to visit family for Christmas.

Plan 2: If that doesn’t work, I can fly directly back to the States, move to a cheap city and pick up work while I save up for the next big adventure.

Backup Plan: Bicycle Tour Edition

Last year, I planned an insane solo bicycle tour from San Diego to Salt Lake City. There were a lot of unknown variables. Any grand plan will – it’s inevitable. Plans are just guesses, anyways.

The questions about the viability of my trip piled up.

Could I make it in time to start my summer job? Could I survive at all, since I’m normally a total couch potato? What if something went terribly wrong?

Before heading off, I researched every possible backup plan for transportation. Every step of the way, I knew the closest shuttle or bus system that could take care of me. I made sure that my friend picking me up at the end could drive down a little farther south to meet me, in case I wasn’t where I expected to be by the end.

Anne Dorko selfie

Spoiler alert: I totally made it!

What’s Your Backup Plan?

When you leave everything behind, you also leave behind comfort and predictability.

A spy is ready for every situation, good or bad. It involves a lot of thinking on your feet and practicing the art of devising creative escape routes.

Think out the worst-case scenarios, such as:

  • Your new job lets you go
  • Your house burns down in flames
  • The airline loses all your things
  • Your visa doesn’t get approved
  • The bicycle you’re living on falls to pieces

What will you do if something like that happens? Where will you go? Who will you turn to?

This is the point where most people panic. That’s a completely normal initial reaction. But the truth of the matter is, sometimes this stuff happens. Panic about it for a minute now, and then take a step back to think through a rational second plan of action.

Think outside the box! As they say, when one door closes, another opens. Or maybe it’s time to climb out the window.

Maybe you can pursue an entirely different career. Or you can volunteer on a WWOOFing farm. Teaching English in South Korea sounds like fun. Seriously, get crazy with it. Having a wild alternative to turn to has a strangely calming effect. There is so much to do out there in the world. It’s a huge place.

By the way, are you keeping backups of your important documents? If your vital paperwork is destroyed or stolen, caches and digital backups can do you a lot of good.

In any case, taking the time to dream out completely different courses of action helps in a couple of ways:

  1. You don’t feel boxed in by your immediate circumstances. There are always alternatives.
  2. You’ve already created rational courses of action to tackle unpredictable situations.

Backup plans help to take out the element of surprise and risk. That said, don’t let your fears get the best of you. The point is to be prepared in case of emergency, but don’t let these concerns dictate your life!

Use your backup plan as a safety net to ease the anxiety, and then let it be.

Choose How to Commemorate Your Things

Letting go of stuff is hard. We create a deep emotional identity in our belongings. When you’re new to the practice, it’s especially difficult.

But when it’s time to move forward and leave your old life behind, you have to learn to let belongings go. In my opinion, there’s a reason every society is steeped in rituals. Rituals help us cope with what is outside of our control.

In the same way I recommend you create a ritual to deal with letting your belongings go.

It doesn’t need to involve an altar or idol, but pick out a few methodical steps to walk through before making your way to the dumpster or donation center.

Here’s one of my own rituals:

  1. Take a moment with the item. Look over it, think about the times and memories associated with it.
  2. Write down anything that really stands out. Describe the item in textured detail. Chronicle your favorite story. Talk about how it came into your possession. Mark down why it feels so important.
  3. Take a digital photo.
  4. Put it in a special, clean trash bag before throwing it away or donating it.

Evaluate What Home Means to You

The idea of home is an evasive one.

Is home a physical location? A feeling? A person? I believe there are many definitions and types of emotional homes, much in the same way we have different physical homes. However, it’s not a question you ever ask yourself until you move away from… home. Whatever that means to you.

Sometimes it

Sometimes it’s just having a decent bed to sleep on.

Much like our belongings, home plays a lot into our identities. When you live somewhere else and are surrounded by new culture and different ideas, you change. Not necessarily for better or worse, but a new version of you will emerge.

You may never pin down what home means to you, but knowing that we all search for it helps to cope with the weird feelings you get.

The best part is if you begin to identify what little pieces feel like home for you, you can learn to put them back together wherever you are in the world. Because even adventurous spies get homesick sometimes.

Learn to Appreciate Family


The people who raised you, grew up with you, were there for you in your times of need.

When you leave everything behind, it can also mean you’re leaving everyone behind. Whatever your reasons are for starting a new life, leaving behind everyone you know can be a very lonely experience.

This is where the idea of a rogue spy goes sideways. Being a lone wolf isn’t all it’s cracked up to be.

Feeling alone and rejected is not healthy for us as humans. Just because you’re moving on in the world does not mean you should ever feel this way.

Starting over often comes with sudden clarity as to who your real family is. In some cases, you needed a fresh start to get away from bad relationships. When you can, hold onto those you left behind – you don’t need to completely start over. In any case, family doesn’t need to be blood related, and you do need to create a support system for yourself wherever you wind up.

Thankfully you can keep in touch with the friends and family you already have via services like Skype, WhatsApp, Facebook, and email.

And sometimes, they come to visit you in your new home.

And sometimes, they come to visit you in your new home.

But what about the people around you after the move? Being able to meet up with other people to talk, love, and play with is also important. In your new life, it’s useful to learn how to form new friends. Start by exploring your new city and meeting people.

In the end, don’t forget about the people you grew up with and the people who will miss you. At the same time, keep an open mind and heart for the new souls you’ll meet as you move on.

What Does This All Mean?

Starting over is a practice in introspection. You will be forced to re-evaluate your beliefs, actions, and behaviors. Who are you when you are stripped bare of your usual environment? How do you behave when left to your own devices when no one you know is watching you?

There’s no one right way to leave everything you know behind and start over new. However, a few things are certain.

When you take the time to:

  • Evaluate your resources,
  • prepare for worst case scenarios,
  • ask yourself what home means to you, and
  • value the relationships in your life.

You’ll be much better prepared to tackle the new life ahead of you. Kind of like a badass spy.

Have you ever had to start over fresh? What helped you get through the change?

Are you about to go through a big life change right now? What questions do you still have about the process?

Photo credits: Anne Dorko

First published June 17, 2016

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