Roth IRA Challenge: Monetize Money and Passions

I am absolutely loving this guest series! Today, I introduce you to another blogger-friend of mine, Penny from She Picks Up Pennies. Penny and her husband took the Roth IRA Challenge together and successfully funded two Roth IRAs with side hustle income! Check out how they did it:

Last year, we put one-third of our net income towards debt. We don’t have loans. We don’t have consumer debt. But we have a whopper of a mortgage. As committed as we are to paying off our mortgage early, another key ingredient of financial independence has to do with retirement security. My husband and I are both teachers. We put just under 10% of our salary toward our respective pensions. But given the current–and, seemingly, eternal–budget crisis in our state, neither of us is really certain what will be waiting for us when we retire. As a result, fully funding both of our Roth IRAs is a goal we are determined to fulfill each year. But with our aggressive debt repayment goals, we decided to do a little side hustle action to max out our retirement savings. When it comes to making extra cash, my husband and I have learned one thing really well over the past year: monetize your passions and talents.

The Jock – $7000

My husband truly is a man of many talents, many of which converge on athletics. Not only is he an incredible athlete, he has the patience of a saint. He’s the perfect coach. In fact, he’s such a wonderful coach, he’s been asked to coach multiple sports throughout the school year. Last year, he oversaw two interscholastic teams: a soccer team and a volleyball team. He also sponsored intramurals that were open to younger students.

Since he coaches middle school students, many of these kids have never actually played the sport before, at least not competitively. That’s where the patience comes in. He has to keep the handful of students busy who have taken private lessons or played on travel teams, while helping the students who are still figuring out the different between a layup and a free throw.

His patience and athletic prowess paid off. In fact, he made over $7000 last year. That seems incredible — and it is! — but calculating the hourly payout is a bit of a reality check. Intramurals alone requires thirty meetings for an hour and a half each session, not to mention the time practicing, playing in games, and traveling for his interscholastic sports. This side hustle does make for a much longer work day, but since he’s so passionate about it, I’m glad he coaches. And I certainly know he is.

The Book Nerd – $5000

The coordination gods smile down upon my husband, whereas they mostly laugh at me. Seriously, I trip over flat surfaces on a semi-regular basis, and I think my track coach in high school was incredibly relieved when I fell down two flights of stairs and had to sit out the remainder of the season. In short, it wouldn’t be fair to anyone if I took a coaching position.

I do, however, sponsor a literary review and supervise a study club. Because books? That’s my jam. Last year, I earned a $1200 stipend for the literary magazine. I’ll early slightly more this year, because the stipend increases every year of experience. While I don’t know that I’ve gotten better across the board, I now have students writing about the latte factor and other financial matters, so I’m calling that a win.

In addition to the stipend, I earn an hourly wage for sponsoring the study club. I work primarily with special education students, so we are funded through special grant monies. I don’t know that the funding will always be available for this, but I plan to take advantage of it for as long as I can. I work with between 15-20 students for an hour at a time for a rate of $20 an hour. I know could earn a lot more through private tutoring, but these students’ families could never afford that. Plus, I work with them for free after school the other three days a week! With a somewhat irregular schedule, I netted about $800 last year. Altogether, this extra work scored me an extra $2000 last school year.

Because I’m a glutton for punishment I love teaching, I also teach summer school for six weeks in the summer. I only work four hours a day, there is minimal grading, and there are no standardized tests. It’s such a breath of fresh air. It also nets me $3000 before taxes. Overall, capitalizing on my talents and my passions helped me net an extra $5000 last year.

The Shopaholic – $870

If you follow my blog at all, you know that even though I don’t have consumer debt, I practically majored in overconsumption for most of my life. I brought many things to our marriage, including over 100 pairs of shoes and several dozen designer handbags. It was a problem. While I’ll never recover the money I spent shopping, I am trying to figure out how to make back as much as I can. Last year, I made money reselling in two different ways: I listed items on Craigslist and a local subdivision version of it and I took items to resale shops like New Uses, Plato’s Closet, and Clothes Mentor. When it was all said and done, I made $870.86 last year (Yes, I kept a spreadsheet. Of course). My hope is that I’ll make even more money this year, now that I’ve started using Poshmark, an online selling app that pays more generously than my local consignment stores and has a significantly lower creep-factor than Craigslist.

Monetize Your Talents

While I’m fairly certain our side hustles will continue to evolve over the years, I do know that we’ll always go back to the same guiding principle: monetize your passions and talents. The money is nice. The money will help lay the foundational for our financial independence. But we want to enjoy our time now since it’s all we know we have for certain. For us, future financial independence isn’t worth more than our current days. So while we continue to hustle, we’ll also continue to enjoy ourselves.

Roth IRA Picks Up Pennies


Are You a Saver or a Spender? The Why.


How Much We Spend


  1. Thanks for sharing this, Maggie! I’m so glad I took the challenge. We are already running some numbers and planning some summer side hustling to make sure we can do this again for 2016!

    • MaggieBanks

      Thanks so much for participating! I am loving collecting all these stories about successful hustling! Very motivating!

  2. Great job Penny! I love how your monetizing hobbies – making the side hustles so much more enjoyable. I’m still working on how to do that too. My mom and I are planning to make some crafts to sell at a fair during the holidays, so that’s a start. As a former coach myself, I can definitely attest to the very low hourly rate . . . but there are other benefits 🙂

    • MaggieBanks

      Monetizing hobbies is definitely awesome advice! Now to analyze my hobbies…

    • Oooh! I hope you’ll blog more about crafting. Have you considered Etsy? I’ve heard mixed reviews, but I do have one friend who has been quite successful with seasonal craft fairs and Etsy in between 🙂

  3. Great share, Maggie.And great job, Penny. You and your spouse are smart to have found side hustles that you enjoy, to bring in money. I’m still scratching my head about how much clothing and how many pairs of shoes you must have started with. And by the way, I’m not questioning the costs. I’m just not that great at shopping. I don’t think I could accumulate that many things that I actually like and want to wear.

    • MaggieBanks

      I’m a terrible shopper! Every time I leave Alaska, I realize just how much I don’t have a clue!

    • Mrs. Groovy, you don’t even want to know! I’ll post the shoe photo one day when I get around to full fess-up on the blog. Part of it is that I was trained to take care of everything and never part with nice things. Looking back, I think the idea was good. I’m glad I treasured my things. But learning the concept of “enough” definitely would have helped! I still blame Cher Horowitz in Clueless 😉

      • MaggieBanks

        LOVE Clueless! And wish that computer program at the beginning was a real thing! Pick my outfits, please!

  4. I need to figure out some of those clothing resale options — I’ve always just donated everything. Or, rather, I needed to figure out those clothing resale things a few years ago — now I’m down to nothing good to resell since I’ve gotten rid of everything I don’t wear, and the stuff I do wear I wear to death. 🙂 Congrats on finding so many ways to hustle for funds! xoxo to you both.

    • MaggieBanks

      Donating is so much easier! I have a small pile of stuff to sell on ebay and, ugh, it would be so much easier to just donate it. But money! 🙂

  5. Thank you so much for sharing! Reading about other people’s side hustles is very motivating. Thanks to a handful of blogs, I started my own side hustle of accounting/tax services (I’m a CPA) and it has been awesome. It’s wonderful to make money doing something that you enjoy. I look forward to following your future success!

    • MaggieBanks

      I would love for you to take the Roth IRA Challenge! When you’re ready to write about it, let me know!

      • That would be amazing! Thank you. 🙂 I’m in my first year of this side hustle game, but I hope I can make you proud at years end!

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