Finding the Courage to Go Through With It

By Sean Ogle •  Updated: 08/27/09 •  6 min read

This was one of the last post I wrote before leaving my job in late 2009. Looking back, I think of this post as a pivotal moment in both my career, and my life as a whole. I was wrestling with so many emotions, and I truly didn’t think I’d actually have the courage to go through with it.

I left this post completely unedited, as I think it’s important to the back story of Location Rebel. I also think there’s a chance you may resonate if you’re going through something similar in your own life.

-Sean Ogle, February 2022


We all have something in our lives that we want to do yet haven’t done.  There is that one thing that we continue to make excuses for and will never make any progress unless we embrace a shift in thinking.  For me, this thing is traveling abroad.  For the last few years, and the last few months in particular I have had a strong urge to spend time traveling, and experience things outside of the tiny little town of Portland.  However, I obviously haven’t much of that.  What is holding me back?  I’m not getting any younger, and the time couldn’t  be better for me to go see what the world has to offer.

I am slowly coming the the realization that there is no perfect time, and there never will be.

That is something I have heard over and over again through the years, yet it hasn’t really sunk in until now.  I find myself constantly saying “when this happens” or “after I do this” about my life.  If  I am constantly waiting for other things to happen, or to find the perfect time, I am NEVER GOING ANYWHERE.  It is frustrating, because there obviously are things in life that are important.  There are events and people that mean something to you that you don’t want to disappoint.  Yet at the same time, if you are staying in an unsatisfying situation because of that, something isn’t right.

I have finally reached a point where I am done putting things off.  I am sick of waiting for the right time.  I can plan to my heart’s content, but there are still certain variables that will never change.  I just need to take action and see where the result takes me.  One thing I am confident of, is that I won’t regret it.  The only thing I would regret is not doing all of the things I have set out to do in my life.

One thing that has proved very useful in this quest of mine is to repeatedly ask myself one simple question:

What is the worst that can happen?

What is the absolute worst-case scenario?  And you know what, every time I ask myself that, the result is something that really isn’t that bad.  If you are in the same situation where you have something you want to do, or a change you want to make, I urge you to ask yourself that question; and to do it honestly.  I bet the answer will be surprising.  Even professors of lifestyle design can occasionally get caught up in traditional thinking.  That you are supposed to do things the way society wants you to.   However, by looking at the reality of your life, you will see that you don’t have to be traditional, you don’t have to do things the way everyone else does.

So, lets say I decide to move to the Caribbean, learn how to sail, then travel on through Central America, and then on to the World Cup in South Africa.  What is the worst-case scenario?  Hmmm, I spend all my money, can’t get a job when I come home/fail at building my own business, and have to move back in with my parents.  What is the likelihood of that happening?  Probably not very high.  I like to think I am more resourceful than that.  If that does happen, is it really all that bad?  Sure it’s not ideal, but it isn’t that bad.  Would all of the experiences I had along the way make it worth it.  I can’t say for sure, but I am betting yes.

Now that isn’t necessarily my plan, but it is something I have considered, and it makes a great illustration of my point.  Let’s look at another situation. Maybe you are stuck in a job you don’t like.

If you quit right now, what is the worst that will happen? Answer: whatever it is, its not as bad as you think it will be.

I think often about what my life would be like, if I dropped everything that is currently going on, and devoted the next 2 years of my life to my bucket list.  Would I be able to do it?  Financially? emotionally? What is the worst that can happen?  I don’t know, but part of me is willing to find out.  Hell, just making that decision alone crosses of #31 (although I think that one is getting crossed off soon regardless of what I decide to do).

On Saturday I am going to attempt to cross off #16: Climb a Mountain.  I am totally stoked for it.  The South Sister is the third tallest peak in Oregon, and the hike is 5.5 miles to the top with a 5,000 ft elevation gain.  I have heard everything from, “oh it’s easy”, to “it was 8 hours of absolute hell.”  So we’ll see what happens!  Either way, it is good to feel like I am making progress.

This is what awaits me on Saturday...

This is what awaits me on Saturday…

If you take one thing from this post, I hope that you realize that whatever it is you have been waiting to do, the consequences of not doing it are far worse than what may happen if you actually go through with it.  If you aren’t taking conscious steps towards the things you want to do in life, then you need to reevaluate what you are doing.

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
Learn How to Make Your First $1,000 Freelance Writing (in 30 Days or Less)

Join over 40,000 people who have taken our 6 part freelance writing course. Sign up below and let’s do this together.

By entering your email address you agree to receive emails from Location Rebel. We'll respect your privacy and you can unsubscribe at any time.

Keep Reading

16 comments on "Finding the Courage to Go Through With It"

  1. “If you aren’t taking conscious steps towards the things you want to do in life, then you need to reevaluate what you are doing.”

    That is so simple, yet so profound.

    Wish you the best for your climb on Saturday. Eight hours of hell can easily be wiped out by one minute of bliss. 🙂 Go do it!


    1. Sean says:

      @Rasheed, That is what I am banking on! But it is the first thing in a few months that has actually been a planned out accomplishment, so I am looking forward to it.

      @JD Yeah plane tickets can be expensive, but if you can find a creative way to get one cheap, your destination could be a lot less expensive than the place you are currently living. I know you were interested in Rio, and while it is less expensive than here, I know the Real has gotten stronger towards the dollar, making things a little more expensive there. You could probably get a one way flight to some place in Central America however for under $500, and living expenses there would be way low. Anyways, just some thoughts if you are still thinking of going location independent

  2. I’ve also been learning this and I think I’m at a point where I have the mindset to go through with it but I lack any financial stability whatsoever. My focus now is on building a business that can sustain my lifestyle. I wish it was possible to do the things I want to do while being broke, but plane tickets are expensive.

    Great post Sean. This makes me want to make my own list just to remind myself what I’m working for!

  3. Ross says:

    I think I read it first on Chris Guillebeau’s site, but the best thing I’ve ever heard about starting things is:

    Ready, Fire, Aim.

    Don’t research it to do death. Do a bit of prelim and then figure as you go. You will never know as much as you know after you do it.

    As for the mountain climbing, be careful. It gets addictive. Hiking boots turn into runners or a mountain bike or snowshoes and then you’ve got an obsession on your hands 😉

  4. I wish you the best, it takes gusto to get perspective and start making moves toward a big decision. There’s a different tactic to it then squeezing out productivity in a work day or something like that. I’ve used this little mental trick to help push me onward to big goals…make the smallest move and ignore the other parts….for now.

    Sure, moving the the Carribean and learning how to sale, or run an internet business from a coconut tree bungalow sounds crazy…but don’t start with that…start with…hmm what airport would I fly into? or even a step down from that…put on a calendar when to look up cheap living there. It’s such a small step, but builds subconscious commitment to the idea. I found myself helping teach English in a spanish camp this summer by simply e-mailing my friends about learning more Espanol. I knew I wanted to travel abroad again, but committing to it and where was where my mental floofy aversion came in. Take the smallest step now, use my best friend the calendar and honor it!

  5. Karen says:

    I love how my blogging friend write articles that need to read at exactly the right moments 🙂

    I really need to get another job… just for more income, and not necessarily something I love. And, it scares me. I don’t want to leave the comfort or security of my current position, although I know i deserve better. I don’t want to have to work a job I hate in a cubicle. But, I know it’s the right next move, although it scares me for so many reasons…

    Thanks for the good thoughts… I needed to think about what is the worst possible scenario? It’s never as bad as we think it’ll be.

    And, it’s fun seeing you cross things off your list! 🙂

  6. Jenny says:

    Great post Sean! I’ve been thinking about quitting my job and doing some travelling myself. I have it all planned out and yet the last step, the quitting-my-job part, still really scares me. Thanks for sharing your thoughts, I will start thinking about whats the worst that could happen.

    Have fun climbing that mountain on Saturday!

  7. Nate says:

    Sean, we are on the same page once again. All this week there’s been this thought that keeps coming back to me. “There is never going to be a perfect time.” I was excited to see that it was written in this post!

    I really like everything you said here, and good luck with your hike. Looks like a great time.

    Hope all is well.

  8. Sophia says:

    Two quotes come to mind when I read your post. “If we are facing in the right direction, all we have to do is to keep walking.” ~ Ancient Buddhist expression. And, “Courage does not always roar. Sometimes, it is the quiet voice at the end of the day saying, “I will try again tomorrow.” I don’t know who said that one, but it ties in nicely I think with all you’re talking about, goals, fears, accomplishments. One note, do not mess around with “What’s the worse that can happen?” when climbing a mountain. Be smart about it, be prepared, above all, HAVE FUN! I’ll be looking forward to your post about it 😉

  9. Elisa says:

    I’m coming upon that crossroads right now. I know things aren’t where I want them, and I keep trying to “plan” and “mend” and “prepare.” Someone explained it to me like this: There’s no perfect time to have a child. Something will always come up. Sure, you can plan a bit, but there is so much beyond your control it’s never “just right.” Yet the moment you see of that new child/experience/business/life you realize that all the scary, unplanned insanity was SO worth it. Good luck climbing your mountains. 🙂

  10. We regret the things that we didn’t do more than the things that we did do and went wrong.

    No regrets is the proper way of living.

    There are no mistakes.

  11. Kaitlin M says:

    I know what you’re saying, you can get so focused on the somedays, that years later you look back and go what the hell happened?
    Or even worse like you mentioned you plan everything down to the last detail and then pack it away, it’s so silly sometimes.
    Thanks for the great article and good luck with the mountain – remember don’t try and run once you get to the top!

  12. Payman says:

    Hey Sean, Payman here.
    Found out about your site through your postcast interview about living in Thailand from another site. Loved and it and I have literally been devouring all the awesome articles on it for the past few days. I can relate tremendously to all you went through as I am going through it all myself at this very moment. My release date is October 28, 2010 as that’s the date I’ll be flying to Bangkok for a 3 months mini retirement. I’m scared yet very excited at the same time about all this new adventure.

    Thanks for putting and sharing an awesome site with the rest of us, like minded who want to live life on our terms. Btw, was wondering if I can post this article of yours on my blog once it’s ready as I was about to write something similar but after reading your article, it’s perfect, you put into words exactly my thoughts. 🙂

    Anyways, if you’re in Bkk between end of October to mid Feb, I’d love to meet you and other like minded entrepreneurs, to pick your brains as that’ll be my first time in Thailand/Asia. Oh and drinks on me.



Comments are closed.