Wins and Losses Series: Scott at Making Momentum – “Did the Risk Pay Off? Hell Yes”

Wins and Losses Series: Scott from Making Momentum - "Did the Risk Pay Off? Hell Yes" #finance #mistakes #lessons #learning #personaldevelopment

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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: Scott from Making Momentum!


I was stoked to see that Scott had volunteered to write for the Wins and Losses Series. His blog is packed full of actionable content for those of us trying to do more, save more, or just be better (and so much more than that). He’s a guy that’s blowing up in the blogging world and I know that big success is ahead for him. More than that, we’ve struck up a bit of a virtual friendship over the past couple of months. I’m thrilled to have him so let’s get to it!




Hello MikedUp Blog readers!


My name is Scott from Making Momentum, a blog focused on taking control of your money and life. From the basics of personal finance and money management to productivity and life hacks, the goal is to provide actionable advice and resources to keep you moving forward.


In the grand scheme of things, I’d say I’ve lived a pretty enjoyable and rewarding life to date. In large part that’s due to my family and growing up in a “traditional” middle-class Canadian manner on the west coast of BC.


I’ve avoided any truly crippling financial mistakes, had only minor health issues, slipped up a few times (once majorly) and remained “up” with only some brief moments of being too deep in my own head or hard on myself. All in all, the wins and losses I’ve had seem vanilla to me in comparison to what others have to deal with.


For me personally, I know the best is still ahead and also expect life’s biggest challenges are yet to come.


With that said…




Taking A Risk Has Given Me The Greatest Returns


The greatest decision I’ve ever made in my life carried quite the risk.


I packed up everything I had and moved across the country to a city I’d never been to in order to pursue my dream job.


This was in my early 20’s.


Every single person I knew was now 4,000+ kilometers away. I had only a carry-on, a suitcase and two Rubbermaid Tupperware containers to shuttle anything I’d ever owned across most of Canada. I’d never been to Toronto or Ontario for that matter until those wheels hit the ground.


I stepped off the plane and was now calling this new place “home”. There wouldn’t be a familiar face no matter what street I walked down. My support system was gone. The routine and comforts I’d developed from living 20+ years in the same general area were gone.


I’d taken a low-paying, entry-level position in my dream industry. I placed a bet on myself that it would pay off financially and intrinsically.


It was a risk


I could’ve ended up broke and lonely in an unfamiliar place at a time when I was supposed to be prospering and building the foundation for my future. Or had to pack everything back up and return back to BC a failure.


Thankfully, since landing on that runway 6+ years ago the entire journey of my life was forever changed.


I landed my dream job, increased my income by over 83% in the last 2.5 years alone and have had amazing growth personally and professionally. I met new people, saw new places, learned so many life lessons and broke free from the comforts of everything I’d ever known.


Was I nervous? Yes. Could the decision to leave everything I knew behind have gone terribly wrong? Yes. Do I still miss my friends and family? Yes.


Did the risk pay off? Hell yes!


Wins and Losses Series: Scott from Making Momentum - "Did the Risk Pay Off? Hell Yes" #finance #mistakes #lessons #learning #personaldevelopment


Taking that risk allowed me to find the most amazing, beautiful person I could ever have hoped for. This risk and bet on myself introduced me to the woman of my dreams.


The key takeaways I have reflecting on this:



  • Embrace The Uncertainty: your true character will often shine through in moments of risk, uncertainty and desperation. Sometimes you just need to trust your intuition and gut if it’s telling you to “jump”…lean in and place a bet on yourself.




  • Believe In Yourself: it sounds so hokey typing that out. But it’s so true. A healthy self-belief can do amazing things and position you to accomplish your goals. I’ve used this confidence and self-belief to grow my professional standing and income, start new entrepreneurial ventures and reach various goals.




  • Life Is A Wild Journey: there is a beginning and an endpoint (I think). However, everything in between is, for the most part, entirely up to you. Control and the ability to have the freedom to make choices shouldn’t be overlooked.



Win The Morning, Win The Day


This wasn’t exactly one specific moment in my life but more so a course correction and drastic shift after a slow, downward trajectory had started.


The excitement of landing my dream job in the career field I moved across the country to chase slowly had slowly started to fade. Not because of the work I was doing or lack of appreciation that I had for doing something that I loved.


I was becoming increasingly lazier outside my 8-6 career work. My broader life goals, fitness efforts and relationships had started to suffer because of this.


There was a growing lack of discipline and focus on my physical and mental health


My alarm clock in the morning was being pushed later each day. I’d roll out of bed and shuffle off to work. By the time I got home, I was burnt out and stressed with no energy left to take care of my health, give my amazing girlfriend the attention she needed or have the brainpower to pursue my entrepreneurial inspirations.


I was slipping down the slope quickly.


Thanks to seeing Tim Ferriss reference “Win the morning, win the day” and highlight countless successful entrepreneurs and leaders morning routines, I decided to make a commitment.


A drastic change.


Moving forward I would now wake up at 5AM every day.


That was 28 months ago and I’ve woken up at 5AM approx. 97% of days since then.


The outcome? I’ve made over $20,000 extra in side hustle income in the morning to help fast-track my student loan debt repayment, rededicated myself to reaching my fitness peak of younger years and shifted my entire life trajectory.


My personal and professional relationships have all benefited in some way. And most importantly, I’m happier and healthier.

Does this work for everyone? Of course not. We’re all unique with a specific set of circumstances and lifestyle. Waking up at 5AM works for me and has truly changed my life.


The key takeaways I have reflecting on this:



  • Commitment: Change takes commitment, dedication and a relentless want to better your situation. The first couple weeks were tough but slowly a continual commitment to doing this unlocked a new sense of energy, passion and purpose. Stay committed, embrace the suck and build the necessary habits to accomplish whatever it is you want to. A half-hearted effort will give you a half-hearted return.




  • Learn From Others By Testing: Often stubbornness and skepticism can misdirect what could be a blueprint for success or inspiration. Tim Ferriss making reference to these various morning routine aficionados gave me a framework to test and learn from. If waking up at 5AM didn’t work for me, at least I’d know and could try something else.





“Put Your Hands Up, Interlock Your Fingers On The Back Of Your Head And Walk Backwards”


The red and blue from those lights is still burnt in my memory.


So is the sound on my parents’ voices when I called to explain the situation. Disappointment, confusion and just general sadness was the vibe.


I was 21 years old and had lived a wild, adventurous life from 17-21 without really getting a reality check. All while excelling athletically and academically.


I had it pretty good across the board


I won’t get into the specifics of what actions got me into that situation or what exactly happened.


However, that chin check from reality was exactly what I needed. Not serious enough of a situation that my future career, ability to travel or life, in general, will be overly constrained due to legalities but enough of a shock to realize it was time to mature and that I had been granted a mulligan.


Young and dumb is an easy way to excuse myself but that would be passing the buck and diverting taking responsibility.


I lost the respect and trust of my parents. Embarrassed my family since we knew many of the police families in our town. Plus felt a ton of shame and self-hatred in the immediate future following.


The key takeaways I have reflecting on this:



  • Thanks For The Fun: the wild days were done immediately. Partying and any potential for trouble ended at 21. I said “thanks for the fun” and put that in the rearview. Never again will I put myself in a situation to potentially cripple my future and all I’ve worked for.




  • Honesty, Ethics & Good Natured: plain and simple, those 3 characteristics are now what I value most in myself and people around me. I focus on being a better version of myself, seek out good people and don’t have time for anyone outside the realm of what I’d consider a good person.




  • Long Term Outlook: this moment of clarity and reality check really helped me shift my focus from the short-term, immediate gains to the long-term, bigger picture of this crazy thing called life. I have to take responsibility for my actions and every decision I make.   



The Doldrums Of Being A Financial Dullard


This loss isn’t a single catastrophic moment but almost a death by a million paper cuts.


Bless my parents for helping me understand the necessity of hard work, pushing yourself and chasing what you want (minus my lapse in judgment above). Unfortunately, I decided to ignore the bulk of the money lessons they attempted to instill in me throughout my childhood and teenage years.


By the time I had access to my own money through the various jobs I worked, I was beyond reprise. Not to mention once I got my hands on a credit card and had entered post-secondary education with some building student loan debt.


This series of stupid money mistakes from my late teens into my early 20’s created a weight around my ankles by the time I was able to finally even reach the starting line of bettering my financial situation.


Below are just some examples of financial illiteracy in my younger years:


  • Paid for my last semester of undergrad with a credit card to avoid more student loans then carried that balance well after graduating only paying the minimums
  • Didn’t apply for the dozens of scholarships available to me that could’ve helped offset a healthy portion of my tuition
  • Stopped checking my credit card balance due to financial depression and had gone over my limit by 30%
  • Didn’t ask my parents or other adults in my life for financial advice due to misplaced pride and embarrassment
  • Avoided hitting the max % of my company’s RPP match (401k) due to the weight of my student loans and credit card debt creating a want to avoid anything related to finance
  • Decided vacations and entertainment were more important from age 22-26 instead of reaping the market gains or purchasing an investment property in the Vancouver and Toronto booms
  • Developed a consumer mindset and spent over $10,000++ on so much “stuff” that is now nowhere to be seen in my life after being boxed up and ended up who knows where or thrown away


Clearly, these are all first world problems and in the grand scheme of life, not too crushing. However, the combined power of being a financial dullard has taken six figures off my potential net worth at this present day and likely required me to work an extra handful of years to prepare for an ideal early retirement.


As I’ve mentioned multiple times here, I’ve had it pretty good in life. But it’s still a loss and negatively impacted my life in a multitude of ways not only financially. The stress and angst that financial strain brings when it comes to student loans, credit card debt and continually being behind the 8-ball when some of your contemporaries are zooming past you can be a troublesome thought process.


Thankfully, I can now push these aside as learning experiences. I was young and finding my way through life. Plus some of the money I spent a little recklessly also provided me with amazing experiences, adventures and memories that will be with me for the rest of my life.


The key takeaways I have reflecting on this:


1) Spread Financial Literacy: Luckily, I saw the light and put mastering my money at the forefront of my priorities. It’s part of the reason I started Making Momentum, I can relate to being stupid with money earlier in life and then having to work to better it. I now try to pay it forward by sharing financial advice, resources (like these 30+ personal finance podcasts), tips (such as these 89+ personal finance tips) and tools for the “everyday person”.


2) Working Harder And Developing An Abundance Mindset To Offset Losses: the losses incurred from being financially illiterate didn’t bankrupt me or ruin me. But they did put an anchor on bettering my financial situation. That weight is still felt to this day. Because of that, I’ve developed an abundance mindset and have actively looked to grow my professional income, pursue entrepreneurial opportunities and continually look to create a prosperous financial situation however possible.



Check out the complete Wins and Losses Series Here


Reader’s Input


I absolutely love this series, and what Scott has done above. I think we can all relate to making our share of mistakes and achieving some success in life. That’s great and all – but the most important part is taking lessons (good or bad) from those experiences and applying them to your life. Can you relate to the lessons that Scott has learned? Let us know 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. Thanks for giving the opportunity to share Mike! I love what you’ve created here on your site and with this new Wins & Losses series.

    Can’t wait to see the next features and dive into the takeaways those experiences have had for others.


    1. Scott,

      Thanks so much for volunteering your time and some of your past. It’s because of you and the others awesome posts that this Wins and Losses Series has turned out so well! Thanks again and happy Friday, Sir!

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