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Financial Regrets and the Idea of “Failure”.

Rell Simon
8 min readJun 18, 2023

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I watched a recent Money Guy live stream on YouTube where the hosts tried out viral gadgets seen on Amazon and TikTok to gauge their effectiveness. An under-the-desk treadmill, and cat holder backpack (amongst other things) were reviewed. The episode later featured general Q&A from their subscribers. One person asked about the hosts’ biggest financial regrets and mistakes. Rebecca mentioned not saving into her 401K until near the end of her tenure at a previous job. Bo Hanson mentioned managing every single dollar of the finances in the first year of his marriage without consulting with his wife as one unit. As such, these are real-life mistakes and fumbles that we may encounter in life. This made me ponder over my financial mistakes since graduating from college in 2010. It’s 2023, and I have been in the adult workforce for 13 years now. I am humble and acknowledge that I am not perfect. I have my demons just like you do. It’s the mistakes, regrets, and failures that we hope to gain wisdom from. Here, I’ll share some of my financial mistakes. I’ll also examine quote from an NBA player that was topic of interest during the 2023 playoffs.

#1: Overextending myself and foolishly accepting financial offers.

When I graduated college (shout out to Drew University, Class of 2010), the only debt I had in my name was student loans. When I moved into my first apartment in 2012, I had at least 1 credit card. In 2013, I foolishly took out a $5,000 personal loan from Discover because I was not managing my income correctly. I was over my skis in managing rent and bills, and living a bachelor lifestyle. I paid off the Discover Loan in 2016. In 2017 I amassed a total of 5 credit cards. I took advantage of 0% APR offers to transfer balances between cards to manage my payments. I ask myself now what in the Hell was I doing during that period? My credit has always been good to excellent, but that doesn’t matter. I got sucked into offers, and using what i refer to as “shadow money” (money that is not really of my own). The banks siphoned away my earned income due to interest on balances. I advise you, to never take out a personal loans or credit offers, especially when you are unstable financial ground. (Side Note: If you own a business, taking out a business loan is okay as long as you realize that all debts become due). When you are NOT generating enough income, you will fall into the trap of overextending yourself and looking for bailouts. When you ARE generating enough income, you can still fall into the trap of overextending yourself and looking for bailouts.

#2: Settling for the Minimum.

I have been debt free since 2021. If I could change the hands of time — I would have completed that much sooner. For reference , my payoff range is from May 2010 (date of graduation) to March 2021 (debt-free date), so 11 years). I would have preferred 2018 or 2019 as my target date. My point is that when my Sallie Mae/Navient Loans and private school loans were due, I would pay them on time. Monthly and quarterly as instructed. I never missed student loan or credit card payments, but I would always pay the minimum. Do y’all remember looking at those loan letters with the terms and estimated payoff dates? I don’t remember my exact, but for example, estimated payoff is 2032. 2035, 2041, etc. The banks and services will weasel you into setting for the minimum with no issues. Interest on all your debts will accrue. During my debt payoff journey, I wised up and worked to pay off the debt in substantial chunks. The 2nd job and staying frugal helped immensely. My advice to you is to accelerate whatever you have outstanding. Now, the inverse of that is saving. I may not be saving enough right now as i should. People who practice the FIRE movement save 60–90 of their incomes. They have no life, and no immediate need for possessions & experiences in the present moment. Everything will all play out on the back end for them. Im not saying you practice FIRE (nor would I), but the intent here is clear. If we think we are saving enough, we’re likely not. Accelerate saving and investing just the same as paying off all those bad debts. Don’t settle for the minimum; always settle for the maximum.

#3 Not Investing (and Saving) Sooner (and Smarter).

My Roth IRA had lay dormant for years while I paid down my debt. While this is okay (since debt payoff is a return on investment), I should have taken advantage of my earlier years to educate myself on how investing works. I did contribute to my employer-provided TSP account, but the funds allocated all to the One type of fund instead of into multiple. For reference, there are different types of funds within a TSP you can allocate your money towards. Timing is everything because my fund would have grown substantially had I made a few tweaks before 2017. Dave Ramsey and the internet taught me how to allocate funds — not my employer. Or rather, I may not have taken advantage of the financial workshops offered at my job. The first few years of being hired, who thinks of attending a “retirement planning seminar/workshop”? The power of compounding interest is at its strongest during your younger years. Referring back to the Money Guy Show, they have resources on their website to help you see the numbers and visualize your future. One of there deliverables a wealth multiplier, a chart that shows the worth of a single dollar is from your current age until 65. $1 for a 20-year-old is worth $88, for a 30-year-old it’s $23, a 35-year-old is $12, and for a 40-year-old, only $7. Here is where I stand in 2023: I would need to save and invest $606 a month to be a millionaire by age 65. Thankfully I have the income and savings to make possibly keep on track. Yet, if was only 10 years younger, less effort would be required (only $184 a month). The pressure mounts with each passing day to reach goals that may not be on our minds at the moment. Again I credit and source the data from moneyguy.com, a resource I truly enjoy. Average return on investments are typically between 8–10%. Throughout the history of the US stock market, there have been dips due to (2008 market crash, 2020 pandemic, inflation, other instances), but has historically remained steady. Investing early and often is to your benefit.

The beautiful thing about being a contributor to this financial space is allowing room to reflect. To grow from mistakes and help others benefit through proper education & awareness. Now, lets talk about this word called “failure”.

Giannis Antetokounmpo — Power Forward for the Milwaukee Bucks. 2x MVP, 1x NBA Champion and Finals MVP. Nicknamed “THE GREEK FREAK”. This young man is a professional on and off the court. His on-the-court play, family and community work is stellar. In the 2023 NBA playoffs, the Bucks lost in the first round 4–1 to the Miami Heat. On April 26, 2023, In the postgame interview presser, he was asked if this season was a failure. He responded:

“Oh, my god. You asked me the same question last year, Eric … okay? Do you get a promotion every year? In your job? No, right? So every year you work is a failure? Yes or no? No. Every year you work, you work towards something, towards a goal — which is to get a promotion, to be able to take care of your family, provide a house for them, or take care of your parents. You work towards a goal — it’s not a failure. It’s steps to success. I don’t want to make it personal. There’s always steps to it. Michael Jordan played 15 years, won six championships. The other nine years was a failure? That’s what you’re telling me. I’m asking you a question, yes or no? Exactly. So why you ask me that question? It’s the wrong question.”

“There’s no failure in sports. There’s good days, bad days, so days you are able to be successful — some days you’re not. Some days it’s your turn, some days it’s not your turn. That’s what sports is about. You don’t always win — so other people are going to win, simple as that. We’re going to come back next year, try to be better, try to build good habits , try to play better. Not having 10 days straight of playing bad basketball, and hopefully we can win a championship. So 50 years from 1970–2021 that we didn’t win a championship, it was 50 years of failure? No, it was not. It was steps to it. We were able to win one, hopefully we’re able to win another one.”

The reporter asked if the season was a failure & I agree with Giannis’ stance. This was the wrong question to ask as the season was no failure. They won over 50 games this season and were the #1 seed in the Eastern Conference. The only failure is that they did not win the championship this year. The team has won a title recently in 2021. The NFL’s Detroit Lions haven’t won a playoff game since I was 3 years old in 1991. As i mentioned earlier, the Denver Nuggets won this year after being an active franchise for 47 years. That doesn’t mean either franchise were complete failures. Detroit has had nice Drafts along the past 3 years and have the tools to make progress not that the NFC North division appears to be wide open. Going back to Giannis, he has already accomplished what many stars in the league, past and present, can only dream of. The NBA on TNT crew broke down that interview — with Charles Barkley regretting not winning a title (which is often the opening salvo many of his detractors use when questioning his greatness), but he does not discredit that from his hall of fame legacy. He was on the 1992 Dream Team and won the Gold medal in the Olympics. Michael Jordan has six titles — but also had 9 seasons with no title. He is still referred to as the GOAT by some.

Failure is based on perspective and personal views. Some athletes never win a title but may have invested and saved their money wisely to have a fruitful post-life career. Or they may dabble into other ventures later in life. Other athletes may have mishandled their finances and are in difficult shape — but should never give up hope. In 2017 I felt like a failure after a difficult breakup and the weight of debt crushing me. Those roadblocks did not define who I am. They did not overshadow the work I’ve put in to become better every single day. Giannis realizes the brevity of the situation; life is ever-flowing and changing. We’re all human, go through the motions in life, and do the best every day to improve. In terms of finances, if you never get out of debt at all- THAT is a failure. If it takes you 5, 10, 15, or 20 years to become debt free, that is a success. The endpoint is the ultimate reward after “X” amount of time spent. It took the Bucks 50 years to win another title. After the win, you move on and reload until you get back to the apex. When you pay off your debt, start saving more. When you start saving more, start investing more. When you start investing more, look for ways to develop your business, family legacy, and community. Keep going and going and live life not under the lens of failure, but within the circle of success.

Disclaimer: I am not a professional financial advisor and this article is opinion-based. Always do your due diligence and seek a professional for guidance.

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Rell Simon

Laurel “Rell” Simon is an artist, podcaster & writer from Washington, DC. Graduate of Drew University. Debt Free on 03/19/21. Site: https://linktr.ee/rellsimon