Fear of Failure

Why You Should Travel Despite Your Fear Of Failure

Derek Perspectives 104 Comments

Fear of Failure

I know it’s scary. I know you’re worried. I know you’re ready to change your life and start traveling but no matter how badly you want it to happen, you just can’t take that first step. You try, and you try hard, but you just can’t get that one nagging question out of your head, that one question that stops you from walking out the door. That question is…

“What if I fail?”

Yes, what if you fail? Well, I’m here to tell you that you very well might fail. You might not achieve your goals. You might start traveling, quickly spend all of your money and be forced to return home, broke and without a plan.

That’s just how life goes sometimes.

However, I’m also here to tell you that if you do fail at first, who cares? So you have to return home and get a job. That’s certainly not the worst thing in the world, especially when you’ll have had some incredible travel experiences to look back on. And besides, you can always save up some more money and try again.

I’ve failed. In fact, I fail all the time. Whether it’s failing to find a way to follow through with some of my travel plans, spending months working hard on new projects only to watch those projects fizzle and vanish or failing to achieve many of the goals I set for myself each year, failure is a part of my life.

And I’m quite certain that failure is a part of many people’s lives, if not most.

Of course, even though we all fail from time to time, the thought of potential failure is still not easy to digest, especially whenever we are thinking about making such a drastic lifestyle change as the one involved with long-term travel or whenever we are thinking about doing anything that goes against what we’ve been taught is ‘normal’.

And that is why so many of us give up on our goals…we are simply unable to get beyond that fear.

But that’s the problem. If we allow our fear of failure to stop us from trying new things and to keep us from jumping into the unknown, many of our wildest dreams and most of our biggest goals shall be left unachieved. At the end of life, there we shall be, repeating a long list of regrets over and over again in our minds.

Being scared is not a valid reason to stay at home when our hearts and souls are telling us that we should be experiencing every corner of the world first-hand.

We all worry, we all fail. We’re all human in the end.

The difference is that some people say, “Well, I might fail. Screw it, here I go!” and then take that leap towards their goals despite their fear. And some people, upon failing, take a deep breath, stand up straight and try again.

These are the kind of people who eventually succeed, the kind of people who recognize that worry and failure are a part of life, the kind of people who don’t let that fact stop them from making the most out of their short time on this planet.

Which kind of person are you?

Are you letting your fear stop you from traveling? For those who did take the leap, was it worth it?

Since 1999 I've been traveling and living around the world nonstop. Sign up below for personal stories, real advice and useful updates from my adventures. Only good stuff, no nonsense.

Are you ready to earn money and travel?

How to Work on a Cruise Ship and Travel eBooksClick above and get started!

Comments 104

  1. Ashley

    Hi Earl I may be writing this a little to late but I have so many worries about traveling. The anxiety and excitement to travel outweighs it. I’m currently in a contract that will be ending in the next few months. I am planning to start selling everything after the holidays and finally take off. I plan all the timet however like you said things never go according to plan. Any websites you can share that help you earn bucks on the road? Any advice you can give me. I honestly only have 5000 saved up to start my adventures. Should I wait?

    1. Wandering Earl

      Hey Ashley – There really aren’t any guaranteed ways of earning money while on the road. In fact, working while moving around is quite difficult since you need to figure out how to enjoy your travels and get your work done at the same time. Of course, if you have a skill that you can turn into a freelance gig or you want to teach English or get a working holiday visa for Australia or NZ, there are options. You might want to read this post:


  2. dags

    It sure is worth it! Thanks Earl for your posts and sharing your experiences with us all. I recently took the leap of faith and sold everything i had for some genuine travel time to see the world.
    I feel and look better, my outlook has changed from negative to ‘absolutely-positively-awesome’ and meeting like-minded people on the road just makes the decision to jump that first hurdle so much better!
    just do it!


  3. Pingback: Conquer your Fears | S'door is Open

  4. Pingback: Travel Inspiration of the week - foodandphotosrtw.com

  5. SB

    Ciao Paolo! A me, è capitato più meno la stessa cosa… ancora sogno di altri paesi quindi, per forza (o fortuna) devo viaggiare da sola, di nuovo…sennò rimango a casa per sempre 🙂 Mi sono resa conto che, per me, un viaggio di 4-10 settimane è ottimo, e mi basta, forse c’e l’hai tu un limite così pure.

    In English: Hi Paulo! The same thing happened to me… I still think about travelling to other places so I have to force myself to travel… if not, I’d stay at home forever! I realised, that for me, a trip of 4-10 weeks is perfect… any more than that and I’d get fed up, maybe for you it’s the same thing?

  6. Pingback: On seizing opportunities | Journey Count

  7. hannah

    Hi there,
    I often find myself day dreaming and constantly thinking about traveling, I want to backpack so much! I just worry that its only ever going to be a dream, as I think money holds me back!

  8. Paolo

    Hi Earl,

    I have just bought my ticket home. I planned to travel for a year, maybe more. I had planned (not much, perhaps just dreamed) that I would travel around the world without flying. I left my hometown in Italy and mostly hitchhiked for over 6000KM, and in 2 months I made it to Georgia where I am now. The adventures have been incredible, and I have enough resources to go on for many more months. The memories will stay and they will be very happy ones.

    But I can’t say I’m happy, I often feel genuinely lost and depressed. I think I have cried everyday for the past 3 weeks. Buying a ticket home is my failure and right now I can’t really cope with it. I would love to try again one day but I’m scared I will fail again. That my insecurities will get the best of me again. That my fear of loneliness will crush me into deciding that home is where I should be, safe with friends and family. And now that I know that I have failed, it will take time before I will muster the courage to leave again.

    It’s so strange because I know I have accomplished so much in just 2 months, but I often felt my head was elsewhere.
    I know there is no right or wrong way to travel, but I know that the right thing now for me is accept failure and go home.

    1. Wandering Earl

      Hey Paolo – First, don’t look at your situation as a failure. You wanted to travel, you traveled and as you said yourself, you have some incredible memories and experiences that will always stay with you. That certainly is not a failure at all! And trust me, long term travel is not for everyone but the only way to find out if it is for you is to try, which is exactly what you did.

      With that said, I can offer this advice in case you do attempt such a trip again. Have a purpose. If you don’t have a purpose while traveling, it is much easier to be come lost and depressed while out there. And the purpose doesn’t have to be anything grand…it could be learning a language, meditating, studying the history of a particular region, sampling a certain cuisine, biking or hiking, etc. Any kind of focus will make a big difference as you will have a specific goal every day when you wake up…without this goal, travel is often not as exciting as many think.

  9. jessica

    hey earl, i just found your website today online and i think i’m literally reading every article you’ve written thus far (great blog btw). going along with this ‘fear’ notion… this is why i haven’t taken the step yet. i worry about everything. (i was going to expand on that thought but there’s no point because i literally do worry about everything.) but in regards to this: what is my first step? (which might sound stupid and i apologize) but i’ve researched everything, looked at plane tickets constantly, googled every awesome looking forest/ ocean/ cliff etc and i think i’m almost getting unmotivated by all the ‘research.’ i guess my question is… help!

    1. Wandering Earl

      Hey Jessica – I know the feeling and the best thing to do is stop researching. It won’t help at this point. You just need to choose your first destination (when you close your eyes and think of travel, which destination gets you the most excited?) and book your ticket. Then, book the first three nights of accommodation at a hostel and that’s it. Get there, meet people and let the adventure begin…it will all be much, much easier than you can possibly imagine at this point and the more research you do, the more unnecessary confusion it will cause!

  10. shane

    I want to travel permanently but I am torn between two lives and still can not find the answer. We returned from a 6 month adventure across 32 countries and that is what i want to do. But i also have a great career at home that pays well and supports my other loves, sustainable living and permaculture. My wife and I have a brought a lovely peace of land and are close to building on it. So how do I mix the two lifestyles together? I would love to hear your opinion. Thank you for your time.

    1. Wandering Earl

      Hey Shane – Thanks for the comment and it’s tough to mix it all together. You seem content with your career and building on your land so that obviously makes it tough to travel. Travel requires some freedom that a stable career often eliminates. With that said, you can always try to get a little more freedom at work and to work remotely for certain periods of time if your position/boss allows it. This might allow you to go overseas for a few months per year. Just an idea, one that many people are turning to in order to combine their careers and travel.

  11. Pingback: Fear of Failure Prevents Success | counselorssoapbox

  12. Pingback: Ten MOST Influential Bloggers - Travel 'n' Wellness

  13. Sara W

    I definitely want to travel when I get older. It would be amazing to see the world and meet tons of people. I don’t think any failure could possibly compare to all the wonders that you can see. I will probably be terrified when I start travelling, but I will do it anyway.

  14. sharad @ tiger safari india


    This is something us Indians have always been wary about. Risk-averse to the core, travelling for days, as a backpacker, has never been a cup of tea for us.

    This generation though is bucking the trend. They are constantly edgy and travel is a way out for them to push this edginess of them. They are venturing out for prolonged periods of time and this augurs well because they come back a responsible soul with greater clarity in their thought process.

    So yes, they are not worried about failure anymore.

  15. Kristin of Be My Travel Muse

    I took the leap in September. So far, yes, I have watched my savings dwindle as I’ve worked on supporting myself on the road, but, I knew that would happen. I knew I was leaving a cozy, but unfulfilling and boring life behind and jumping into the unknown. Worth it? Every day. Would I go back home? I never plan to. The most common question before I left for my trip was, “what will you do when it’s over?” I always thought whatever the next step in my life should be, it would come to me on the road. I still believe that. There’s no failure where following your dreams are concerned. Money isn’t a measure of success, if you ask me. Traveling really opens ones eyes up to that fact.

  16. Stephen S.

    Couldn’t agree more! I actually look forward to my failures (Which happen often). They knock me back to reality and teach me some valuable lesson. Not just lessons about life, but lessons about myself.

Leave a Reply to jessica Cancel reply

Your email address will not be published. Required fields are marked *