Wins and Losses Series: My Early Retirement Journey – “I’m still a work in progress. Everyone is.”

Wins and Losses Series: Ellie from My Early Retirement Journey - "I’m still a work in progress. Everyone is."

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Hi, Team!


Welcome to another edition of MikedUp Blog’s Wins and Losses Series, where we interview a generous participant about 4 of the best and worst moments of their life. The point? To learn from the past so that we can improve in the future!


If you’re interested in participating in the Wins and Losses Series, please send me a note here (you don’t have to be a blogger to participate!)



Check out the complete Wins and Losses Series Here


This week we have: My Early Retirement Journey (MERJ)!


MERJ is a single 30-something actively trying to leave the workforce on her own terms and figure out what exactly to do with her life. She writes a great blog over at My Early Retirement Journey and I’m stoked to share a small portion of her story with you here today! Take it away, MERJ:



Wins and Losses Series: Ellie from My Early Retirement Journey - "I’m still a work in progress. Everyone is."



When Mike invited me to add my story to this series, I made a short list of things about which to write. Surprisingly the losses were easier to come up with than the wins. Maybe because we remember pain so vividly. Or maybe because the losses hurt so much and seem to touch more aspects of our life.


I wanted to write about something that was worthwhile to readers and honest. Part of the trouble was I didn’t really know what I learned from some of my losses other than sometimes life sucks but you carry on anyway. When I read some more from the series I realized I didn’t have to go that deep (as I wont to do).


In fact some of the losses that came to mind I decided might just be too heartbreaking for the average person to relate to and might take me to a place that would take longer to come out from than I needed right now. That being said, I was able to whittle away my list to two wins and two losses which are honest, real, and relevant to who and where I am right now. I blog over at My Early Retirement Journey, where I like to say I put the personal in personal finance. So my story here reflects that.


#1 Win Getting into college


This one was the first thing that came to mind. It is most easily my first tangible and relatable win. I technically got into college when I was 16 years old because I applied early decision and got in during the Fall semester of my junior year. Prior to this, my biggest academic win was winning the school spelling bee in 8th grade.


To earn the application fee for the college entrance exam, I had to do chores around town and subsequently applied to college using a fee waiver. So when the big envelope was waiting for me one crisp autumn evening in 2000 (wow, can’t believe that was 18 years ago already), I just knew I had made it!


I just knew my life was going to change and be exponentially better


It felt like everything in my life was leading me up to this point. I had always been cheered on by my teachers and family because I was a good student and made good grades. I pretty much knew college was in my future, but I didn’t really have any college prep until it was time to apply for college. By then I began to wonder how I really stacked up with the rest of America.


An acceptance letter from the #8 school in the country (at that time) showed that I was somebody. I just felt so invincible. Even though, as you’ll see later, this win quickly became a loss, just recalling the memory makes me feel really good.




Applying yourself and seeing your efforts rewarded is an unforgettable high. I recommend it!


#1 Loss Having to quit college


So I started college in the summer of 2001 ready to take on the world. I was done with my small town and its small town views. I was going to Fancy U! I was going to be educated with people from all over the country and even different parts of the world. Together, I was sure we were going to change the world!


I got through my summer classes and school was everything I thought it’d be with just a whiff of – this might be a little bit harder than I thought. Fall rolled around. My family helped move me into the dorms. I had a mini fridge and a bunk bed and a new roommate from North Carolina. One of my friends even had a laptop and a cell phone!


Then I found out my financial aid fell through and I couldn’t stay


I thought I was going to combust from the inside. I’ve written about this in private quite a few times but don’t often share this story orally. At this point it doesn’t matter as much, but when it was happening my whole world folded in on me. I was suffocating from the inside so no one could see. Over Fall Break when everybody left for home, I quietly packed up my stuff. My brother picked me up in the middle of the afternoon as if it were any other day. But it was really the day my life ended.




I was afraid of a pithy takeaway but worse than that is no takeaway.


Sometimes life just doesn’t even give you lemons. The universe was fresh out that day. I’d love to say all these wonderful things happened after I left my dream school, but there’s nothing I can think of really. The only thing I can think of from a faith perspective is maybe, just maybe I was saved from something really horrible at Fancy U that I haven’t been made aware of yet. I highly doubt it at this point though. What I can tell you is this – spending your time in the aftermath of heartbreak searching for meaning definitely leaves you eternally frustrated. So… don’t do that. Don’t spend your time searching for meaning in what is probably just a sucky situation.


#2 Win Getting into college…again


Yes, friends, a few years later I eventually graduated from college incognito and without ceremony. I decided to try my hand at Fancy U2 for graduate school. This time the single girl got into the #2 school in the nation at the time! And even though she couldn’t really afford it, she went anyway! Hence the beginning of my massive student loan debt.


Maybe this is actually a loss? But at the moment it felt really good. It felt redemptive. I felt like I was getting a second chance to again set the world ablaze.


As you can see by the fact that in my spare time I overshare my life on a personal finance blog, ablaze the world I did not set.


Nonetheless, I felt drawn to the opportunity. I was determined to make myself matter and right the wrong I felt was done to me the first time I tried to go to college. I got a degree in teaching that I didn’t end up using. Coincidentally enough, a few of my classmates did go on to make noteworthy impact in their individual communities. I was not so empowered. Mostly I was tired. The degree was enough because it felt like it just took so much to get there.




Sometimes in life, you do get a second chance but maybe you don’t really need it. Don’t let the win be the end of your journey!


#2 Loss- Loss of self


Somewhere along my struggle journey, I lost my self. I was trying so hard to recreate the past the way I had envisioned it I forgot to develop myself. It was a classic tale of revisionist her-story. I wanted to be the girl that graduated from a fancy school because that was something no one would be able to take away from me.


While I don’t regret this goal, I perhaps approached it in a slightly maniacal way. Twice I couldn’t afford it, but I refused to let that stand in my way. Now that I know more about personal finance and now that I know that the actual degree-granting institution seldom matters and if so, only in few very particular circumstances for even less amount of time than you originally think, I think I did eventually get it right the third time around. Sort of. But that’s a different story for a different day.


Summarily, I was chasing a ghost from my past and I spent all my energy doing it. I didn’t develop another part of my personality. I got that part wrong. I think it’s why I make such sharp turns now – I don’t want to get stuck on another 18-year journey chasing ghosts. I still don’t always get it right but I will say journaling and now blogging help in so far as they serve as mini reflection points.




Sometimes you can just get it wrong. Twice.


Hopefully, nobody dies. On the bright side, life is really, really, really, long (contrary to popular belief). So you can give yourself other chances to get it right. These days when I’ve been beaten down or just not quite sure of myself or what to do next, I just ask myself what is the next best choice. It’s served me well so far. But if you’re wondering, no, it doesn’t always work and no, you don’t always have the most ideal outcome. But it’s a quick go-to and gets me out of the stagnancy of indecision when I need it most.


Ultimately, what I want readers to take away from my story is I don’t have all the answers and I’m still a work in progress. Everyone is.




Reader’s Input


MERJ – I know you didn’t ask for my opinion… But: When you wrote that, “Sometimes life just doesn’t give you lemons…” I couldn’t help but say – “PREACH!!” It’s so true. Life hardly ever works out according to plan… But the heartache and pain that you had to go through after your dream situation at your dream school fell through probably had a lot to do with making you the person you are today. And I know that we only know each other through a few emails and the blogs we write – but from what I can tell – you’re a pretty awesome person. Maybe the takeaways from that turmoil are a little more nuanced and not so obvious? At any rate – I thoroughly enjoyed your contribution to this series. Thank you so much!


What do you say, readers? Let us know what stuck out to you in the comments section below and we’ll keep this conversation going!


Thanks for reading!


If you’re interested in discovering a better version of yourself – whether with fitness, finance, or family – then subscribe below to MikedUp Blog’s FREE newsletter and let’s improve together!


I’m glad you’re here. Thanks again and talk soon!


– Mike
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  1. And to Mike, thank you for your thoughtful comment. You’re probably right about the nuanced takeaways. Sometimes I do feel really lucky. Sometimes I just wonder how my life might’ve been different…

    Thank you again for including me in this! Looking back is hard to do sometimes!

  2. Really liked this post – very personal and emotional and gives those of us who follow MERJ more of her back story. Absolutely raw honesty. Sometimes there are reasons why things don’t work out, however painful they are at the moment. Keep on the FIRE path.

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