Wins and Losses Series: Justin from Saving Sherpa – “I turn denial into fuel and it worked out beautifully”

Wins and Losses Series: Justin from Saving Sherpa - "I turn denial into fuel and it worked out beautifully"

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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


(Photo courtesy of Justin Montemarano)


This week we have: Justin from Saving Sherpa!


Justin shares with us some difficult and joyful moments in his life, but the thing that I took out of his post below is that we can all learn from the way Justin handles adversity. The guy is a rockstar and I’m glad to have him here today! Take it away, Justin:


Wins and Losses Series: Justin from Saving Sherpa - "I turn denial into fuel and it worked out beautifully"



Worst Moment #1 – He Was Almost Home




It was right at the end of April and my Granddad was found where he’d be most of the year until the frost started to move in. Sitting on top of his blue tractor. He was just yards away from the house I spent the summers in. The house where I learned my first money lessons.


In that house, he would go through his stacks and stacks of tiny 3”x5” spiral notepads where he could tell you exactly how many bushels of peas he sold on a given day a decade prior. He would ask me riddles such as “Would you take $1M or a penny that doubled every day for a month?”. He would also beat me at checkers over and over again.


It’s where I learned my first lessons about business and doing right by your customers which I learned the hard way after selling a man a watermelon I was certain was ripe but was awfully green when he cut it open.


I learned so many things… And all of these build up to what I learned and why I learned so much from that terrible spring day. My grandfather, the kindest and hardest working man I’ve ever met. And that day he was making his route down the side of the highway on that blue tractor, in transit from a bush hogging job like he had done so many times before, and then it happened.


His tractor was struck by a car which threw it into a spin and the shock caused him to die of a heart attack


He was in good health, he was active, he was happy, he was my hero, my mentor, and now, he was gone.


His funeral was scheduled for a few days later in early June. I, however, wouldn’t be a pallbearer, a speaker, or even in attendance. See I was in Air Force ROTC and in between my sophomore and junior year where I had to go to my form of boot camp (called field training) which I was assigned to from June 3 to July 3, 2010.


I stood there in the halls getting screamed at for not having the perfect dimensions on my folded undershirts and tried to keep my broken self together. I couldn’t comfort my family, I couldn’t say goodbye, I couldn’t say any last words, my career took that from me.


So what did I really learn from all this?


I learned how precious life was. I learned how little was promised. I learned that no matter how great a life can seem, it can be flipped upside down in a moment’s notice.


But I also learned something a little brighter. I came to truly realize how powerful these small actions that my grandfather had taken were on me. I keep that with me always when I’m writing and when I’m trying to explain to people concepts on my site such as Can Money Buy Happiness or How  Much Would You Save If Life Was Short.


My story will probably never spread the nation and that’s ok. Just go out there and teach people how to better their lives and realize that it really doesn’t take much to make a huge impact on someone’s life. I’m so passionate about it because if I can help one person avoid letting their profession rob them of even one major event, then it was all worth it.



Worst Moment #2 – I Finally Had It All



I had just graduated college and commissioned into the United States Air Force as a Second Lieutenant. Becoming many firsts in my family in the process. I had just moved to my top choice location, Colorado Springs, I was making close to $50k after taxes which was more money than I knew what to do with, and it couldn’t have been worse.


I found myself in a depression for the first time in my life


I was always happy and energetic, the jokester of the group. That was all gone now. Why was I in such a dark place when everything seemed perfect?


The truth was that I had always had goals. There had always been a destination that seemed so far away but that I was hell-bent on achieving. But now I was just working. On top of that, I was working 1100 miles from every person I knew or loved and the Air Force saw it best to start this journey days before Christmas.


I had taken for granted the big moments like Christmas, birthdays, and  Mother’s & Father’s day. But I had also taken for granted the small moments.


See in my hometown, people rarely moved away.


You could go down to the local grocery store and see at least five people you knew every single time. I thought it was annoying at the time, and now all I wanted was to walk in Gardner’s Supermarket and have someone ask me about me and my family.


I’m an engineer, I solve problems, but this dark place I was in was a problem I didn’t even know how to begin unwrapping. But then after a few weeks, I started having clarity and 90% of what drives my fuel to financial independence was unknowingly uncovered in solving my current situation.


I knew I needed happiness in the worst way if I was going to survive this thing. So what made me happy? That’s a question I don’t think we spend enough time on as a society. That list was family (1100 miles away), friends (1100 miles away), obtaining goals (current list complete), and helping people.


There it was, there was my answer. I decided if I couldn’t be happy, I would help others until hopefully, their joy wore off on me.


So I went to my church and I asked for every outreach and mission team’s information. I begin to hear about this orphanage in Mexico and how the team would be heading down in a few weeks. Someone mentioned how much I’d probably like it and that I should keep it in mind for next year because all the members plan and fundraise for a year leading up to it and like I said, I only had a couple weeks and there weren’t any beds left.


I didn’t have a year. I wasn’t sure what I would look like if I didn’t solve my current situation in a year. I thought about it for mere seconds and knew what I had to do. I went to the leader and explained how badly I wanted to go. I wrote a check for the full amount and agreed to sleep on the floor under the kitchen table.


I learned so clearly that money was a tool to my happiness but that I would never draw happiness from it directly. That riches and success in the eyes of society were not what I would chase but instead the path to the greatest happiness.


On your path in life and certainly your path to financial independence you must have purpose. You must save with purpose. You must spend with purpose. You cannot be naive enough to think you will amass some great wealth and everything will fall into place.


If you try that, you will either lose motivation before you reach your goals or you’ll reach your goals and find yourself as empty as you began. Be purposeful.


Wow… that was a lot of words on two little prompts. Now as we step through the best moments you’ll see a little more succinct description. That’s just a factor of my personality. I learn and am motivated much more by loss and failure than I am success. I take setbacks and denial as motivation to be better and honestly at times to give those who doubt me nightmares for as long as possible.


That may not sound 100% healthy but you need to understand what motivates you. Where do you find your fuel from? Take all that raw emotion and do something useful with it. Make yourself and those around you better with it. Ok, now some lighter subjects.



Best Moment #1 – The acceptance letter


I was a junior in high school and after having zero stress about what I’d do next, I realized that I should probably start looking into college sooner than later. No one in my family had graduated from college so I didn’t have a lot of insight on how it all worked.


When I say that I mean I didn’t know how you applied, where you lived, how to buy books…literally no idea. I went to my “guidance counselor”, and I used quotes for a reason, to ask how I could go straight to a University.


That may not seem like much of an ask for a lot of people but in my hometown, everyone went to the community college 15 miles down the road first. You didn’t just go straight to a University.


I wanted to skip the community college because I was afraid I’d sink roots in, get complacent, and never leave


So I go ask that simple question about going straight to a University and I got the best advice I’ve ever gotten.


When I say “best” I do not mean that it was sound advice. What I do mean is that the advice would ensure my success going forward. So what did he say to me that was so inspiring?


“If you want to go to college and put your parents in debt for the rest of their lives, I won’t be a part of it”


Wow….On one hand, he was right because I didn’t have a penny in a college fund but the fact that he had no belief in me and just discounted the notion, well that made me angry. And as I mention before, I turn denial into fuel and it worked out beautifully.


I went on to take the ACT seven times in order to gain high enough scores to fully pay for my tuition. I then got a full ride scholarship from the Air Force that included housing and a stipend.


All in all, I cleared a couple thousand dollars after expenses every single semester. That advice, or lack thereof, gave me so much motivation.


It’s important for us to not dwell on failures and setbacks but also to learn from them. Promise yourself you will come out stronger. Turn their laughter into disbelief. Failure is the greatest teacher. 



Best Moment #2 – The main event


This final one is a little less philosophical but still important to me. It all started on a cold Colorado night just a few days after I had moved there with a spitting snow coming down.


As I mentioned in the loss section, at this point I had no friends at all after moving across the country from Mississippi but there was a UFC fight on that I just had to see. It was Anderson Silva, the king of Mixed Martial Arts.


So I make the trek downtown and I’m able to find one empty folding chair up against a wall at Gasoline Alley down on Tejon St. That chair would change the course of my life even if it took me a while to see.


What made this chair so important was the fact that next to it was sitting another guy who was the same age, arrived in town the same time, and was also an Air Force officer like me.


What were the chances of that? We would go on to become very close friends and roommates. Through meeting him, I would meet another great friend and Air Force officer.


He would then invite over one of his college friends to the house one night and there I would find my now girlfriend of over three years. All of this because of a chair I sat in.


Picking the right chair is not the moral of the story though. The lesson here is to take action even if you’re not comfortable. Even if you feel out of place.


I felt so awkward walking in there by myself as these groups of friends were all having such a good time. I felt like a loser trekking down there with no friends. But I knew that the only way to change my situation was to get out and meet people.



I hope you enjoyed getting to peek into my life. I take pride in being transparent because I believe being an open and honest example is the most powerful way to influence others. If you want to continue following along on my journey, please come check out my blog where every month I give you a behind the scenes look at my life and the real numbers behind my 70% savings rate. So head on over to and see what you think and be on the lookout for my new podcast project that will be coming soon called The FI Show.



Reader’s Input


I absolutely love Justin’s approach to turning doubt or denial into motivation, then success. His attitude is one that we can all learn from! I also want to thank you, Justin, for your service. Without people like you, we can’t live the lives we do today – thank you.


What about you, readers? What lessons did you take away from Justin’s stories? We’ll be monitoring in the comments below!


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 Comment

  1. Spectacularly told stories. I feel like I read part of a novel and know the character all the better. Those two hard lessons are eye opening and really have you connect with the reader. I’m thankful you saw how to develop purpose in life beyond just amassing wealth. The wealth comes from finding purpose, the independence comes from finding purpose in the way that means the most to you without having to worry about how it affects you or your loved ones financially.

    Really a great read to to follow Thanksgiving. Thanks for sharing your story.

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