How to Fight Off the Glory Days

By Sean Ogle •  Updated: 03/10/22 •  5 min read

I recently read this post again for the first time in nearly twelve years. (It was originally published in August of 2010).

It was fascinating to reflect back on, as it was originally written just two weeks after I’d returned from my big stint in Thailand. I was terrified of the fact that in that moment, I felt like maybe I’d peaked. Maybe that Thailand trip would be the best time of my life. Those would be the glory days.

It feels good to look back and show my 25-year-old self, that at least to this point, I have not settled.

I didn’t do much editing to the original post, because it represents a different frame of mind than where I am now – and I think it’s beneficial for people who aren’t as far along in their journey to see this.

Here’s a video I shot reflecting back on the concept of the glory days, and how quite frankly, they terrify me.

How to Avoid the Glory Days

A while back Chris Guillebeau had a post entitled “Glory Days” which really had a bit of a profound impact on me.  He pointed out that, everywhere you look there are people who still rely on their past accomplishments, rather than working hard to create more.  It’s like the 70-year-old man who won a state football championship when he was 17 – and still talks about it on a regular basis.

I don’t want to be that person.

This concept is fresh in my mind after reading Chris’ new book “The Art of Non-Conformity”, where he discusses the topic of the glory days again.

I found myself thinking really hard about how the idea of glory days comes into play in my life.  The last time I read his initial post I was in the middle of my Thailand adventures and was like “ah, this doesn’t apply to me! I’m living the dream!” Well, I’m not in Thailand anymore.

I read this latest chapter from a public transit train in Portland. Hmmm, how things have changed.

So what does this mean?  Will my time in Southeast Asia forever be known as my glory days?

Hell no.

We all go through certain phases in our life.  Some are more dedicated towards work, while others are more aimed at play. When in work mode you have to realize that you’re doing it towards an end.  For some, it’s a comfortable retirement a few decades down the road.  For me, and others like me, it’s a life of adventure and freedom – not just six months of it.

Lately, I’ve spent a fair amount of time in front of my computer (ok, I always do), but it’s hard not to sometimes feel like the good days are over! I begin to wonder if this is what the rest of my life will be like?  The easy approach would be to say, “yep it is.”

But when was the easy way ever the best way?

If you aren’t consciously making an effort to live the life you want, then you won’t be.  Simple as that.  I knew when  I arrived back in Portland that it was going to be way too easy to fall back into old routines and habits.

Yet, I refuse to let that happen, because that’s exactly what I was trying to avoid when I left in the first place. I know that the work I’m doing now is inevitably going to give me the flexibility that I crave and ultimately should make me a lot of money in the process.

Rather than settle for the glory days, or even the glory years, I want a glory life.

I want to look back and know that I accomplished everything I set out to, I saw everything I wanted to see, and that I didn’t ever, ever, settle for easy. Easy just isn’t worth it when there is such an awesome life out there that is hard.

Ryan Martin and Sean Ogle swimming in Thailand

Ryan and I living the glory life in Thailand earlier this year.

Yesterday I talked to my buddy Ryan for the first time in months when he called me from Cairo.

He’s been traveling for 7 months, money is starting to run a little low, and he wanted to know how he could start working for himself to sustain the lifestyle he wanted.

Now there’s a guy who’s going to have a glory life.  In half a year of travel, he has more good stories than most people will have in their entire life.  That’s the kind of life I want. One worth talking about, writing about, and more importantly, reading about.

So today you should think about your glory days. Have they already passed?  Still to come? Or are you dedicating yourself to live a glory life?  It may be hard work, but it’s not difficult.

If that football trophy is looking a little dusty by now, it may be time to think about replacing it with something else…

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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14 comments on "How to Fight Off the Glory Days"

  1. David Walsh says:

    LOVE it Ogle. It’s damn easy to throw back to the past when everything was golden, but that’s primarily because we’re deletion creatures and have this amazing way of forgetting all but the best of times in hindsight.

    Reminds me of this post I just came across from Derek Sivers:

    To assume you’re below average is to admit you’re a beginner. It puts you in student mind. It keeps your focus on present practice and future possibilities, and away from any past accomplishments. Most people are so worried about looking good that they never do anything great. Most people are so worried about doing something great that they never do anything at all.

    … that said, the more epic one’s life and decisions (e.g., the life and decisions of Sean Ogle) – the more you’re constantly challenged to up your game and shake off the past, rather than rest on it.

    I feel a self-attributed quote coming on. Yeah, here it comes… wait for it…

    Your glory days are the days you own – the days not mandated and directed by another’s pursuit of his own glory days.

    Solid post.

  2. Deborah Fike says:

    I never thought about “glory days” versus a “glory life,” but that’s a beautiful way to put it. Don’t get me wrong…I do enjoy nostalgia and there are things I will always miss about the past. I love what my past because it includes people and memories that I love. But I hope I can always look forward to something bigger, something that adds to my glory life. 🙂

  3. Nate says:

    A very eye opening concept. It just really comes down to whether you are willing to settle and be ok with circumstances that aren’t really ideal, because it’s easy. You’re right on. I prefer the harder (but more interesting) road as well.

  4. “I want a glory life.”

    Awesomely put.

  5. Brett says:

    Hey Sean,

    This is a glorious post. I haven’t even begun my glory days yet – I’ve been slowly biding my time over the past few years – but when they come, I hope my candle keeps burning and they never stop coming to me. I want to make every day I live into a glory day, through discipline, hard work, and artistry, because that’s what it takes.

    Off the top of my head, this is how you make every day into a glory day, and your life truly glorious: each day you live, do something new, exciting and scary, so you truly feel alive. Switch it up. Never get too comfortable. Always be having new adventures, new mountains to climb and conquer.

    Love what you’re doing here, Sean. Keep keepin’ it real 🙂

  6. Lach says:

    I know what you mean about coming back home. After an extended period of adventuring, it can feel a bit surreal to come back to the “real world”. The place is familiar, but in a strange way still feels totally alien because you’ve long ago grown out of your old life there. It’s great that you’ve decided to create your life on purpose, but I was curious about why you associate the awesome life with the hard path. To me, the opposite of the “easy path” isn’t necessarily the “hard path”. It’s just a different path. One you choose consciously rather than accepting by default. It’s mindset that decides whether its hard or not. What’s your view?

    1. Sean says:

      @Walsh Glad to see you’ve surfaced! I like that point about your glory days being the days you own. If you make a conscious effort to own all your days and make the most of them, you will be just fine. Lets catch up soon, been way too long.

      @Deborah The idea of a glory life just kind of came out as I started writing the post, but I really like the concept!

      @Nate Well it sounds like you are on the right path too bud. Walking across America is definitely hard and definitely living on purpose – cant wait to follow your adventure.

      @Joel Thanks man, lets setup that time to Skype soon!

      @Brett I definitely respect the person who knows their best days are yet to come and is working hard to pursue that. I think that is an excellent criteria for living a “glory life” if you keep doing exciting and scary stuff, you may be uncomfortable at times, but that is way better than the other option.

      @Lach Thanks for this comment Lach. The reason I referred to it as the hard path isn’t necessarily because the work itself is harder or more difficult, but rather it’t the idea of going against the grain which is more difficult. I’m sitting here while all of my friends are getting bonuses, raises, promotions etc. and making a fraction of their income. Many of my friends, while supportive, don’t really get what I’m doing. Many of desk jobs or variations of them, and to do something completely different than all of them is hard. I know its going to pay off in the long term, and hell, I’m having more fun than them in the short term, but it can be difficult to keep that in perspective when everyone around you is taking a different path. Does that make sense?

  7. Lach says:

    @Sean Totally. Well said.

  8. Walter says:

    It is the habit of the mind to cling into the past and if we are not aware of this then we won’t be able to see what’s ahead. Every moment is an opportunity to make something new or something extraordinary. Life is too short to waste our time over things that have already passed. The possibilities are endless once we explore forward. 🙂

  9. Brad Chaffee says:

    This is a great post Sean! It really gets one focused on their future rather than their past. The past is to remember but the future is to behold.

    The first thing I thought about when I started reading this post, besides my own glory days, was the old TV show Married With Children. Al Bundy works in a shoe store and lives vicariously only through his high school football years! As you watch the show and laugh at the character you start to realize that’s all he’s got. It makes for a hilarious TV show but a lousy existence.

    Like you, I want to have the glory life. That really can mean so many different things to so many people. We’re thinking about moving to Europe for a year to add to our adventure. 🙂

  10. Complacency is evil. Mediocrity worse. Live awesome. Live adventure. Live life.

    “You’re lucky you got to travel when you were young, because now you have to be serious, settle down, focus, and put in your time.” The glory days are ingrained into the fabric of the way we were brought up. It’s a soothing way of thinking compared to the alternative of that gut wrenching feeling of recognizing living mediocrity.

    Ahhh, now living the glory life. Now that is refreshing and cool.

  11. Hugh says:

    I love your term “glory life”. I turn 30 in 2 weeks and I’ve been working on my list of goals for my next decade. Thinking about it in relation to this post, I have a ton of glory days behind me, but I know that the next decade will bring even more. Instead of getting all down about turning 30, I’m fired up!

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