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.
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