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4 Tactics For Becoming an Unconventional Tourist

The following is a guest post. My love of unconventional travel started when I was 12 years old. My dad had decided that, of all the ways to spend Christmas, we should go on a cycling tour around Cuba. And so we did it. We figured out how to...

I Hate Hair: Reasons Why Shaving Your Head Skyrockets Confidence

Welcome to #DifferentLifeStories, where Without Boxes is sharing how people are living differently right now in the real world. Enter Aron James: Hair loss is something that happens to our grandfathers. It is the sign of the wisdom that comes with old age; a rite of...

How to Be a Solo-Female Hiker: Put One Foot in Front of the Other

Welcome to #DifferentLifeStories, where Without Boxes shares how people are living differently right now in the real world. Enter Hayley Turner (a.k.a. Little Foot): I can still remember everything about that day, from waking up and walking 12 miles by noon, the dogs...

Do You Really “Find Yourself” When You Travel?

"I know this sounds cliché, but I have to ask—do you really 'find yourself' when you travel?" the girl asked me. Her young friend crouched next to my table, gently stroking the cats as they slept. Café Neko is a small coffee shop in Vienna that allows cats to wander...

When Not Everything Goes as Planned, It Still Goes: A Story About Finding Your Passion

Welcome to #DifferentLifeStories, where Without Boxes is sharing how people are living differently right now in the real world. Enter Jen: As a kid, I was told that I was lucky that I already knew what I wanted to do with my life. From age four, I knew I wanted to be...

The Digital Nomad’s Roadmap – A Complete Guide: Successfully Live, Work, and Travel Anywhere

So you wanna be a digital nomad. I’m not surprised: the future is bright for freelancers and location independent workers. Statistics show 40% of Americans will be contingent workers by 2020. That’s a lot of potential for digital nomads! Yet there’s no hands-on guide...

Limitations: Why the 9–5 Job Doesn’t Need To Stop You

Over the years I’ve had a number of conversations with people who talk about cool things they want to do, see, or make. A lot of these conversations end with “Well, I’d love to do it, but unfortunately I have XYZ,” and many times those XYZs are very valid limitations...

Stealing Second Base: From Side Gig to Self Employed Full Time

Welcome to #DifferentLifeStories, where Without Boxes is sharing how people are living differently right now in the real world. Enter Katherine Stimson: “You can’t steal second base with one foot still on first.” In the spring of 2010, a Facebook ad posted by a total...

Dreams Are Like Pirate Treasure: Hard to Find, But Worth the Risk

All dreams start somewhere and typically, no matter the size of the overall dream, most dreams start small. Let’s say yours is to feel better at work every day. You focus on sitting up straight in week one. Week two finds you taking a 10-minute walk at lunchtime. Week...

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

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? Let us know your stories and worries for the future in the comments below.

Photo credits: Seriously Inspired




  1. Avatar

    Great insight , we all most likely think this way however are afraid to take that first step . 15 years ago I started over , now my children have all grown on to their lives I’m thinking of doing it again , I’ve started looking into the right now deeper and the future further . Your story was mind opening and very helpful , I believe the lesion here is plan multiple senaireos for different situations . And research where and how you will make those plans become fruitful then go back over them very carefully , find the weak spots and fortify them .
    Mostly have faith in yourself .

    • Anne Dorko

      Hi Michael – I’m glad you found this insightful! Having multiple backup plans is absolutely essential, I think, for this kind of lifestyle. And some faith in yourself is good, too 😉

  2. Avatar

    This is pure greatness and in every way did this give me the knowledge I need to truly “Leave everything behind and start over”

  3. Avatar

    Love this and the whole concept behind it. My wife and I feel like everything is crumbling around us and are desperate for change. We want to go somewhere new and naturally inspiring to us and not start from square one again in a place we have no desire to be. Not sure where to start, but blogs like these definitely help us with insight on what to expect, how we might feel, hope that it is possible and direction on how one might accomplish climbing out of what seems like a very deep hole at the moment. Needed that, so thank you.

    • Anne Dorko

      Hi Dan, thanks for commenting! I wish you and your wife the best as you seek out the next big adventure. I’ve definitely been a few deep holes myself, and I’ve only gotten through those times by sticking it out and pushing forward anyways. There’s never any guarantees but you have a far better chance by staying flexible, creative, and optimistic in the face of everything. You got this!!

  4. Avatar

    I am so ready to do this just have to take the leap of faith.

    • Anne Dorko

      You can do this! Be sure you get to know yourself well enough to choose the right direction, take the time to set yourself up for success, keep an open mind, and go. Don’t sit on these steps, walk up them and get to the next one. You don’t need faith so much as action – if anything, have faith in your capability to make things happen.

  5. Avatar

    I agree with the article. I’m at that point in life where I’ve been married, divorced, raised my boys in their childhood home (it’s up for sale now) and just refuse to be controlled by significant other. I can work anywhere but the job growth is booming in CO in my field and not so in PA. So, once my house sells, I’ve decided to move back home (CO) from PA. Call it a midlife crisis, but I’m yearning for change. It’ll be interesting, but one step at a time. I have family in CO and my kids can come visit. I’d love to be there for my dad when he needs help; the one whose been there for me.

    • Kat Franchino

      Thanks for reading Kate! We like to look at those quarter and mid-life crises as amazing opportunities. Keep us posted!

  6. Avatar

    Excellent article ❤️

  7. Avatar

    Currently my SO and I are contemplating starting over with new jobs in a new city. She is fearless and ready to go. I want to be fearless so badly but I am my own worst enemy. The “what ifs” keep playing in my head and I can’t get them to stop. Your article was insightful.. Thank you.

    • Anne Dorko

      Hi Mary, thanks so much for visiting us here! It is so brave of you to be considering this with your SO. Especially given your nervousness, I am sure she appreciates your willingness to consider taking the leap with her. And it is so often we are our own worst enemies, right?? There will be a lot of “what ifs” that are negative, but remember that there are limitless positive “what ifs” on the other side as well. Remember, you are not in this alone, either.

      I wish you two the best of luck as you move forward. As our space mom (Carrie Fisher) once said, “Stay afraid, but do it anyway. What’s important is the action. You don’t have to wait to be confident. Just do it and eventually the confidence will follow.”

      Feel free to come drop a comment here again or send us something in the contact form to keep us updated or ask questions!!

  8. Avatar

    I would do this, but I’ve too l much debt and yet not a lot to show for it, i do not have any real saleable skills and am dyspraxic and slow to learn, I;d be fired from even a bar job. my skills are too weird and small scale for survival and I am not a team person. And I am old. Cannot drive, rubbish with tech But hell, I think I’ll give it a try anyway. i heard about an American woman working as an artist’s model in Paris in 2017- sounded great.

    Thanks- sorry for rambling on

  9. Avatar

    You probably know that you are wise, but I must say it: your clarity of mind and approach to reality is admirable. I am on the younger end of elderly, have no assets, sole person that is family has discarded me, and, I won’t have a place to live within two months – although it will be too cold in the house to stay, anyway. What identifies “home” for me, other than other humans, are my books and paintings, and things I’ve picked up on many adventures-by-default. I have no living friends.

    Your recommendation to write about objects, and photograph them, is, again, very wise. It made me think about what it would be like to engage in that activity. Photographs? Perhaps. But everything before now, leads up to my being discarded. Pleasant memories now seem unreal – false. So, I think that taking what I can carry and put in my car, and leaving all this detritus for the discarder to deal with is the best thing I can do.

    There will be no plan B. There isn’t that option. I don’t for one second delude myself that things can’t get very bad, very fast, including the possibility, the very real possibility of being homeless. On the other hand, if I get ill here, or on the road, that wouldn’t make a difference. I can’t stay here without heat and other repairs – I rent from the discarder. Still, having a home base has only been the case for ten years, and, it is hell when you don’t.

    I hope that people reading this understand that it is hell if you do not have a plan B… if there isn’t somewhere you know, without question that you can go to for shelter, and, if you are fortunate, (or just lead a normalish life), someone who will welcome your presence.

    Anyway, you’re one wise gal, and as one who has dropped most and moved many times, (but not solo), your writing has helped to further face the realities ahead.

  10. Avatar

    You are such an inspiration. I have plans to leave it all behind this summer and move to California. I’m 30 and have never lived outside of my home state, and am scared but at the same time so ready for a complete change. I feel like I have no true friends here. I’m really hoping that things will go better for me in CA.

  11. Avatar

    Thank you for this very insightful article. I have been planning to start a new life in a new city and this helps a lot in making my plans for the future.

  12. Avatar

    I think it’s going to be harder for me because I have 3 children. I want more than anything to leave the state I’m in but I seriously have no idea how to go about it. This article definitely gave me some insight but I definitely have to do more research. Thank you for sharing your journey and tips with us!

  13. Avatar

    Loved your article Anne! Thanks for your insight! Especially the part when you say one loses the meaning of home. That is exactly what has happened to me. I left everything behind a year go and have come back to pick up the pieces left (mostly material things) so I’m sorting out my life (my stuff) and find myself so attached to these material things that I don’t know how to manage it. I am not very effective on knowing what I should keep or discard, I procrastinate. I get confused. Don’t know where to start… could go on. I hate to be so attached. I’m aware of it and let it take a toll on me. I am very stressed!! Wish you the best on your journey around the world!

  14. Avatar

    My community wants me to move away from them

  15. Avatar

    Anne, thank you for sharing your experiences and providing tips to the rest of us. After wanting to leave my home state (VA) for as long as I can remember, I finally made the decision to move to WI and made it a reality over the summer. I never felt that I would stay here but knew I was meant to go and try it out. I’ve realized so much about myself over the months I’ve been here and have decided it’s time to try Plan B, Portland, OR. WI was never an ideal place but my boyfriend was here and I wanted to see if we could make it work.

    I’ve been dreaming of going to Portland for a few years and now it feels like a good time. I want to go out on my own and prove to myself that I can handle whatever obstacles come to pass. That said, I sincerely appreciate your advice and already feel a bit better with my decision. Here’s hoping I know what I’m capable of and can handle the solo adventure. 😨

  16. Avatar

    Hey Anne! Thank you so much for making this post. I really needed to read this today. Everything you stated here resonates with me at this time of my life. I just became 100% debt free as of last week and it is the last huge weight I needed off of me to truly consider making a change I feel my mind, body, and soul have desperately craved for awhile now. I have been doing lots of research and hunting for advice on how to make these types of changes and I have to say yours is the most unique and grounding. I especially appreciate that you address merging the need for personal freedom with reality because it is so easy to get lost in the dreaming stage!

  17. Avatar

    Thank you. I’m still trying to decide if I should do this. I have. Fiancé who I’d want to take with me and I don’t think he’d protest. But I’m worried it may not be the right thing for us.

  18. Avatar

    I am living in California after breaking my fiancé broke things of in Chicago. I still love her so much and I think she still the one. I’m having a weird feeling that I should move to Wyoming. It was great feeling to start with. It was cause my brother started asking for money for me to stay and I was barely keeping a float with money already. So the whole Wyoming feeling came up. I packed everything up and was ready to go. I didn’t have much but then I had a panic like I wasn’t gonna be able to do it out there. Then i unpacked everything and said I was would think it over and make sure I’m ready to make the move. But right now I’m still having the feeling I’m gonna regret not doing it because I feel this is the way to get back the girl I love. But then I have the feeling it’s easier to stay here and work my way to make some more money and the I could work my career from here and I will talk to her and just make it work that way. I don’t know what to do


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