All The Things I Messed Up And Didn't Optimize This Year

The other day, I finally got around to finalizing my taxes for 2023. If you’re wondering why I’m filing my taxes so late, it’s because I got a tax extension back in April. I always file for an extension since I never get a tax refund anymore (so there’s no urgency for me to file) and I like giving myself more time to organize my stuff.

I’ve been writing about money and financial independence for 8 years now, and during that time, I’ve spent an inordinate amount of time trying to optimize my finances. Unfortunately, even with the extra time I gave myself to file my taxes, a combination of being overwhelmed with family duties, some disorganization, and a little bit of laziness meant that I messed up fairly badly this year, forgetting to do a bunch of stuff I usually do and leaving money on the table as a result.

It happens though. So if you’re ever feeling bad about not doing everything perfectly, you can look at all the stuff I didn’t do this year and maybe feel a bit better about what you may not have done.

Forgot To Do A Backdoor Roth IRA

This was definitely my worst mistake for the year.

My wife and I have been taking advantage of the Backdoor Roth IRA for many years now since our income is too high to contribute to a regular Roth IRA. If you aren’t familiar with the Backdoor Roth IRA, it’s a way you can contribute to a Roth IRA even if your income is too high for a normal Roth IRA. There’s more that goes into a Backdoor Roth IRA than I can go into with this post, but essentially, what you do is make a nondeductible contribution to a traditional IRA, then immediately roll over your contribution to a Roth IRA. By doing this, you’re able to contribute to a Roth IRA, even if your income is too high to directly contribute to one.

Taking advantage of the Backdoor Roth IRA is important because it allows me to put thousands of dollars each year into a tax-advantaged account. That money can grow tax-free and I can withdraw the money tax-free as well. For last year, the contribution limit was $6,500 per person (if under 50). That means my wife and I could have contributed $13,000 total to our Roth IRAs as a Backdoor Roth IRA contribution.

The deadline for making this contribution, however, was the regular tax filing deadline and not the tax extension deadline. That means I needed to make this contribution back in April 2024, which I completely forgot to do.

It’s a fairly expensive mistake to make too. $13,000 invested in a Roth IRA could grow to around $50,000 in 20 years and to $98,000 in 30 years. As you can see, that’s a lot of tax-free income I left on the table due to my forgetfulness. It won’t ruin me by any means, but it does hurt to lose out on that much potential money.

Over 30 years, $13,000 invested in a Roth IRA could grow to over $98,000. That’s That’s potentially $85,000 of tax-free growth I can never get back.

Didn’t Max Out My 529 Tax Deduction

Another minor thing I forgot to do was max out my state 529 plan tax deduction. As a quick background, a 529 plan is a tax-advantaged account that provides tax-free growth if used for qualified educational expenses – usually college tuition for most people. In many ways, a 529 Plan is like a Roth IRA where you contribute to it using after-tax money and can then withdraw the money tax-free later.

Depending on which state you live in, contributing to a 529 plan could also qualify you for a state tax deduction. I live in Minnesota, which gives households up to a $3,000 state tax deduction for 529 plan contributions to any state’s 529 plan (i.e. I don’t have to contribute to the Minnesota 529 plan to qualify for the state tax deduction). In this case, I contribute to the New York 529 plan since I find that plan easy to use, it uses Vanguard funds, and most importantly, it has low fees (just 0.12% expense ratio as of when I write this).

For some reason, I only ended up contributing $2,800 to my 529 plan last year, which really makes no sense. It’s not a huge deal that I didn’t get to that max of $3,000, but as someone who likes to optimize everything, seeing that I randomly forgot to contribute an extra $200 for no particular reason hurts. At a minimum, I should always be contributing at least $250 per month to a 529 plan so I can maximize that state tax deduction (I’ve since gone ahead and updated my auto-contributions to be $250 per month).

Did A Terrible Job Keeping Track Of My Expenses

A big advantage of being a business owner is that a lot of your everyday expenses can qualify as business expenses, allowing you to reduce your taxable income and essentially pay for things using pre-tax income. There are a lot of things I already pay for that can qualify as a business expense. Things like my phone and internet or the bike maintenance I do on my bikes are good examples of things I’m already paying for that can qualify as business expenses. Even going out to eat can qualify as a business expense since I’m usually going out to lunch with my business partner.

The catch, of course, is that you need to actually track these expenses. And this is where I’ve been really bad lately because I’ve been doing an awful job of tracking my potential business expenses. As a result, at the end of the year, I’m always underreporting my expenses because I’ve simply forgotten what I spent money on.

This is something I need to work on improving because by not reporting all of my expenses, I’m for sure leaving money on the table. Even if I’m worried about stretching what is a business expense, I can’t even consider whether to include it if I never tracked it in the first place.

Final Thoughts

We’re still in October as I write this, which means I have plenty of time to optimize things this year. For contributions to tax-advantaged accounts, it’s important to think about when the contributions need to be made. It’ll either be by the end of the calendar year or by the tax filing deadline. But you have to pay attention because even if you get an extension, the deadline might still be with the original tax filing deadline and not the extension deadline.

As we head into these last two months of the year, I have time to at least make sure I don’t miss out on some of these easy things I missed last year. With my 529 Plan, I noticed I was coming up short again on the contributions, so I changed it so it’ll at least hit $3,000 in contributions by the end of the year.

For the Backdoor Roth IRA contributions, I’m planning to make my contribution soon after I write this. I’ve always been 1 year behind, where I make my contribution for the previous year in the current year (i.e. I’d normally make my 2024 Backdoor Roth IRA contribution at the beginning of 2025). I’m planning to get on track and make my contribution for the current year in the same year, just to simplify my thinking a bit.

So yeah, as much as I’d like to optimize everything, I don’t always do it. And this past year was probably my worst year when it came to optimizing things because I was so busy and forgetful.

It’s not the end of the world, but if I can optimize my finances, I’d rather do that.

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More Recommended Ebike/Scooters

Check out these other ebikes and scooters I've reviewed:

Urban Arrow Ebike – Last year, I made one of the largest purchases I’ve ever made – I bought a $9,000 electric cargo bike from Urban Arrow. In my Urban Arrow review, I will discuss what it is and why I decided to buy this bike, as well as discuss how impactful a bike like this can be on your journey to financial independence.
Troxus Explorer Step-Thru Ebike – The Troxus Explorer Step-Thru is a fat-tire ebike that I’ve had the pleasure of riding for a while now. It has amazing power, great looks, and awesome range. If you’re looking for a great fat-tire ebike that offers a lot for the price, the Troxus Explorer Step-Thru is definitely one for you to consider. Check out my Troxus Explorer Step-Thru Review.
Hovsco HovBeta Ebike – The HovBeta is a folding ebike with great specs and a lot of interesting features, and importantly, it’s sold at a good price point. I’ve had a blast commuting with it and using it to do deliveries with DoorDash, Uber Eats, and Grubhub. Check out my Hovsco HovBeta Ebike Review.
Vanpowers Manidae Ebike – The Vanpowers Manidae is a fat tire ebike that I’ve been riding as my primary winter commuting bike and have also been using it to do food delivery with apps like DoorDash, Uber Eats, and Grubhub. After clocking in a decent number of miles with this ebike, I wanted to write a post sharing what my experience with the Vanpowers Manidae ebike has been like. Check out my Vanpowers Manidae Review.
Sohamo S3 Step-Thru Folding EBike Review – A Great Value Folding Ebike – The Sohamo S3 Step-Thru Folding Ebike is an entry-level folding ebike that offers a lot of value for the price point. I’ve been riding the Sohamo S3 for a while now, putting the bike through its paces, and I have to say, this bike has exceeded all of my expectations. Check out my Sohamo Review.
KBO Flip Ebike – The KBO Flip is an excellent bike. I’ve had a great time riding it and think it’s a versatile bike that can be used for a lot of purposes and can fit a variety of lifestyles. It’s worked out great for me as a general commuter bike and as a food delivery bike. Check out my KBO Flip Review.
Hiboy P7 Commuter Ebike – The Hiboy P7 is an excellent electric commuter bike that’s offered at an affordable price point. The range and speed of this bike are both very good, so you won’t have any trouble getting anywhere you need to go with it. As a food delivery vehicle, this is also good – with how much range it offers, you’ll be able to work all day on a single charge. Check out my Hiboy P7 Commuter Electric Bike Review.
Himiway Escape Ebike – The Himiway Escape is an interesting bike for anyone looking for a moped-style ebike. If you’re a gig economy worker, the Himiway Escape is particularly interesting and it’s possible to think of it as an investment, especially if you can opt to do deliveries with the Himiway versus using a car. It’s not cheap, but you can definitely make your money back when you compare the mileage you’ll put on your car versus using an ebike. Check out my Himiway Escape Bike Review.
Espin Sport Ebike – The Espin Sport is a good ebike for someone who is looking for an ebike that feels and rides more like a regular bike. There are many ebikes that are really only bikes in name. In reality, they’re basically electric mopeds. The Espin Sport, by contrast, is a bike you could probably ride without the battery and you’d feel like you’re just riding a regular bike. Check out my Espin Sport Review.
Varla Eagle One Scooter – The Varla Eagle One is an excellent scooter that can make sense for a lot of people. It can work as a primary mode of transportation. You can use it to work on gig economy apps like DoorDash, Uber Eats, and Grubhub. And it can also be a recreational vehicle if you’d prefer to use it for that. Check out my Varla Eagle One Review.
Varla Falcon Scooter – The Varla Falcon is an excellent scooter that offers a good amount of power at a lower price point compared to more powerful scooters. It’s not exactly an entry-level scooter, nor is it a high-powered scooter. I think it fits somewhere in-between those two categories – an intermediate scooter if I had to give it a category. Check out my Varla Falcon Review.
Hiboy S2 Scooter – The Hiboy S2 is an excellent entry-level commuter scooter that's perfect for someone looking to save some money in transportation costs and improve their commute. Check out my Hiboy S2 Review.
Hiboy S2R Scooter – The Hiboy S2R is one of the more interesting electric scooters I’ve been able to test out. It’s not a high-powered scooter, but for an everyday transport option, it’s very useful, especially given some of the unique features that it has. Indeed, for the price, the Hiboy S2R might be the best value scooter I’ve used. Check out my Hiboy S2R Review.
Fucare H3 Scooter – The Fucare H3 is a fun scooter and I’ve enjoyed testing it out. For a daily commuter or quick trips or errands, the Fucare H3 is probably the scooter I’ll use. It’s portable and easy to maneuver, so it’s just easier to take on the road when I need it. Check out my Fucare H3 Scooter Review.

More Recommended Investing App Bonuses

For additional investing app bonuses, be sure to check out the ones below:

M1 Finance ($100) – This is a great robo-advisor that has no fees and allows you to create a customized portfolio based on your risk tolerance. You also get $100 for opening an account. Check out my M1 Finance Referral Bonus – Step-By-Step Guide.
SoFi Invest ($25) – SoFi Invest is an easy brokerage account bonus that you can earn with just a few minutes of work. Use my SoFi Invest referral link, fund your SoFi Invest brokerage account with just $10 and you’ll get $25 of free stock. I also have a step-by-step guide for the SoFi Invest referral bonus.
Webull (20 free stock shares) – Webull's current promotion gives you 20 free shares valued between $3-$3,000 each if you open an account using my referral link. Here’s a guide I wrote about how to earn your free shares using Webull.
Moomoo (15 free stocks) – Moomoo is a free investing app currently offering 2 different referral bonuses if you open an account using a referral link. Read my Moomoo referral bonus guide for more information.
Robinhood (1 free stock) – Robinhood gives you a free stock valued between $2.50-$225 if you open an account using my referral link.
Public (1 free stock) - Public gives you a free stock valued between $3-$70 if you open an account using my referral link.

More Recommended Bank Account Bonuses

If you’re looking for more easy bank bonuses, check out the below options. These bonuses are all easy to earn and have no fees or minimum balance requirements to worry about.

Upgrade ($200) – Upgrade is a free checking account that’s currently offering a $200 referral bonus if you open an account and complete a direct deposit. These bonus terms are easy to meet, so it’s well worth doing this bonus as soon as you can. Here’s a post I wrote with more details: Upgrade $200 Referral Bonus – Step By Step Directions.
Ally Bank ($100) – Of all the banks out there, Ally is, without a doubt, my favorite. At the moment, Ally is offering $100 to customers who open an eligible Ally account and meet the requirements. Here are the step-by-step directions to earn your Ally Bank referral bonus.
Fairwinds Credit Union ($175) – Fairwinds Credit Union is offering a referral bonus for users that sign up using a referral link. Fairwinds has no fees or minimum balance, so this is a particularly easy bonus to earn. Since this is a smaller credit union, my gut instinct tells me this offer won’t be around long, so if you’re in a position to meet the bonus requirements, grab this bonus before it’s gone. Here is my step-by-step guide on how to earn your Fairwinds Credit Union bonus.
Chime ($100) - Chime is a free bank account that offers a referral bonus if you use a referral link and complete a direct deposit of $200 or more. In practice, any ACH transfer into this account triggers the bonus. This bonus is easy to earn and posts instantly, so you’ll know if you met the requirements as soon as you move money into the account. I wrote a step-by-step guide on how to earn your Chime referral bonus that I recommend you check out.
US Bank Business ($900) – This is a fairly easy bank bonus to earn, since there are no direct deposit requirements. In addition, you can open the Silver Business Checking account, which comes with no monthly fees. Check out how to earn this big bonus here.
GO2Bank ($50) - GO2Bank is an easy bank bonus that I recommend people take advantage of if they have an easy way of meeting the direct deposit requirement. I like that it’s easy to open the account and that the bonus pays out quickly. Check out my step-by-step guide on how to earn your GO2Bank $50 referral bonus.
Current ($50) – Current is a free fintech bank that’s offering new users a $50 referral bonus after signing up for an account using a referral link. Current is an easy bonus to earn and also gives you access to three savings accounts that pay you 4% interest on up to $2,000. That means you can put away up to $6,000 earning 4% interest. That’s very good and makes Current an account I recommend to everyone. Check out my step-by-step guide on how to earn your Current Bank bonus.
Novo Bank ($40) - Novo bank is a free business checking account that’s currently offering a $40 bonus if you open a Novo business checking account using a referral link. In addition to being a good bank bonus, Novo is also a good business checking account. It has no monthly fees or minimum balance requirements and operates a good app and website. Indeed, it’s the business checking account I currently use for this blog. Check out my post on how to easily open a Novo account.
Varo ($25) – Varo is a free fintech banking app similar to Chime or Current. It’s currently offering a $25 bonus to new users that open a new Varo account with a referral link. The bonus for this bank is very easy to meet, all you need to do is spend $20 within 30 days of opening your Varo account. Check out my step-by-step guide to learn how to earn this bonus.

Kevin is an attorney and the blogger behind Financial Panther, a blog about personal finance, travel hacking, and side hustling using the gig economy. He paid off $87,000 worth of student loans in just 2.5 years by choosing not to live like a big shot lawyer.

Kevin is passionate about earning money using the gig economy and you can see all the ways he makes extra income every month in his side hustle reports.

Kevin is also big on using the latest fintech apps to improve his finances. Some of Kevin's favorite fintech apps include:

SoFi Money. A really good checking account with absolutely no fees. You'll get a $25 referral bonus if you open a SoFi Money account with a referral link, and an additional $300 if you complete a direct deposit.
5% Savings Accounts. I'm currently getting 5.24% interest on my savings through a company called Raisin. Opening a Raisin account takes minutes to complete, it's free, and all of your funds are FDIC-insured. I explain how it works, why I'm now using it to store my emergency fund and any other cash savings I have, and why I recommend everyone check it out in this review.
US Bank Business. US Bank is currently offering new business customers a $900 signup bonus after opening a new account and meeting certain requirements.
M1 Finance. This is a great robo-advisor that has no fees and allows you to create a customized portfolio based on your risk tolerance. You also get $100 for opening an account.
Empower. One of best free apps you can use to monitor your portfolio and track your net worth. This is one of the apps I use to track my financial accounts.

Feel free to send Kevin a message here.