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Christopher Guest Post: She Picks Up Pennies

Happy Thanksgiving, friends!

I’ve got a special guest on this special day, a gal that is thankful that you stopped by today to let her share a bit about herself and her story. She’s also grateful when she sees money just lying there on the sidewalk. It doesn’t matter the denomination. She Picks up Pennies.

“Penny” is an award-winning blogger, school teacher, and all around good person. We met briefly at FinCon17 but regrettably failed to cross paths this year. If we had, I’ll be she would have let me drink from her coveted Plutus Award.

Taking a purposeful approach to her finances, she and her husband are working towards financial independence on both fronts: increasing income and decreasing expenses. They also pick up spare change, apparently.

Hopefully, they don’t encounter any of those jerks who superglue change to the sidewalk so they can have a good laugh from their perch inside the store where they work.

Penny’s been featured here before in The Sunday Best, and I’m proud to host her here on a bigger stage.



Christopher Guest Post: She Picks Up Pennies


What in the world is a Christopher Guest Post?


Inspired by Nigel Tufnel, the character portrayed by Christopher Guest in Spinal Tap, I took Mr. 1500’s ten questions, and amped them up to eleven.


If you’re not familiar with the scene, take 50 seconds to watch this video and enjoy the dialog between Nigel and Rob Reiner.


I decided I’d start a Q&A of my own. Not satisfied with just ten questions, “this one goes to eleven”. Just like Nigel’s amplifiers.



What do you do (or did you do) for a living? What do you like best about your job? If you were a physician, what type of a physician do you think you would be? Why?


I am a full-time middle school teacher. My favorite thing about my job is that I get paid to do what I love. No two days are the same, and there’s nothing like watching something click for the first time. Plus, my students are hilarious and compassionate. Young people are going to change the world, and it is so energizing to be reminded of that each day.

I found my AP Biology class to be so fascinating (and I aced it!). I got through the fetal pig. I got through the cat. But I couldn’t bring myself to go on the field trip to observe an autopsy. All things considered, I’m pretty certain that the only type of physician I would be is a terrible one. That being said, I spend as much time in my professional learning as possible reading up on neuroscience. The brain is remarkable, and learning about learning is imperative. I wish teachers had more opportunities to do so.


[PoF: I sometimes struggle to deal with two kids at a time. I can’t imagine closer to 30 at once. And with all those hormones coursing through their veins and confusing their developing brains, I can imagine middle school teaching can be especially challenging. You seem to handle it all quite well.

I’ll give you neurologist rather than neurosurgeon. The neurologist only sees the outside of our bodies and nervous systems.]


Describe your blog and tell us why your blog would appeal to a physician seeking FIRE in eleven sentences.


My blog chronicles my journey to live and spend more purposefully. We are on the hunt for financial freedom as two teachers raising our young son. In addition to side hustling and selling all of my clutter (I owned well over 200 pairs of shoes!), we are also working on maximizing our income in a field that doesn’t have the best reputation for doing anything right when it comes to money.

Beyond that, though, my blog helps me explore my why.

Frugality and minimalism aren’t my favorite words, and true practitioners of either would probably be offended by the association. Instead, I’m trying to build habits surrounding purposeful spending and consumption to allow me to save more, invest more, give more, and have a more positive impact on the world.

If you are struggling to pare down or turn away from consumerism, boy, can I relate. I don’t have all the answers. I’m not sure I have any answer. But I’ve got stories, I’ve got honesty, and I have a whole bunch of frugally awkward moments. If you’d like to be challenged in your thinking or would enjoy a laugh on your own journey for financial freedom, swing by!


[PoF: Trying to figure out if I’ve owned 200 pairs of shoes throughout my entire life. I suppose with the various sizes of wrestling shoes, football cleats, running shoes, dress shoes, etc… it’s possible. 

I love your honesty. Being relatable will help you really connect with people, and you do that very well.]



What inspired you to start a blog of your own? Was there a particular event you remember that made you feel your blog had arrived? Any big plans for your blog in the future?


I spent a long time lurking in the personal finance world, but it took something else to get me to actually start writing. My grandma was the most tenacious person I knew, and when she died, I was left with this incredible sadness. Though she never made a fortune (she lived and died in poverty), she made the lives of others rich beyond measure. She aced purposeful living, and I wanted to write to push myself to do the same.

Last year, I was nominated for a Plutus Award, and this year, I was nominated for THREE. As if that wasn’t surreal enough, I actually won for Best Frugality Blog. The Frugalwoods won last year so this is a BIG DEAL.

My only future plans for this blog are to try to continue to chronicle my journey as authentically as possible. To me, that means continuing to build a relationship with my readers. I enjoy sharing my story, but the best part of blogging is hearing the stories (and advice and money wins!) of others.


[PoF: You’re crushing this blogging thing, Penny. I’ve been fortunate to receive a couple nominations myself, but the only Plutus Award I’ve gotten my hands on belonged to Liz, the Chief Mom Officer. She was kind enough to let me drink from the plastic grail.]


Plutus Award Beer


Give me eleven posts you think Physician on FIRE readers might want to read.


  1. Why I Pick Up Pennies: A Manifesto of Sorts – This is why I blog in a nutshell.
  2. My Passion is My Work – I disagree with the popular take that you follow your passion only after you’re FI/FIRE. That just isn’t for me.
  3. To the Teacher Whose Broken Bookcase Post Went Viral – Burnout is real. Here’s how I address it.
  4. Here’s to Strong Women: The End of the Financial Damsel in Distress – This post is sassy. It takes on the talking heads of personal finance and explains why it’s time to flip the script.
  5. You Don’t Have to Give But You Absolutely Should – I don’t have a big net worth. I don’t have a cushy job. But I do have the ability to make an impact with my dollars. So do you.
  6. Teacher Talk: I Doubled My Salary – Maximizing my income is one way that I am working my passion and pursuing financial freedom at the same time.
  7. Frugally Awesome…or Awkward – I wasn’t always thrifty. I’m still not always thrifty. But one of my favorite things about learning to be more purposeful with my dollars is the absurd reactions that I get from family, friends, coworkers, and random strangers at the grocery store who stop me when I’m buying clearance produce. This post is one of an entire series.
  8. If I Were Rich, Where Would I Be? – “Oh, dear. Bread and beer. If I were rich, I wouldn’t be here.” Where would you be if money were no object?
  9. Changing the Conversation About Privilege – The word privilege gets volleyed around a lot. Acknowledge, don’t apologize is my take on it.
  10. I Spent $700 on a Pair of Shoes and I’d Do It Again – Buying shoes, literally hundreds of pairs of shoes, is what brought me to my personal finance watershed moment. But my Jimmy Choos? I’d buy those over and over again.
  11. How Frugality Doesn’t Paint the Whole Picture – Frugality is important to me. Purposeful spending is important to me. But my success? Yeah. Frugality isn’t the whole picture. Not even close.


[PoF: Frugally awkward… I’ve been there! I don’t have to be frugal, but I still am. I don’t have to give, but I still do. Some days I love my job; other days the burnout is real.

It seems we’ve got quite a bit in common. Except for the Jimmy Choos. I would not choose those. I’m more of an Asics guy.]


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At what age are you most likely to retire (or at what age did you retire) from full-time work? What are you doing to help realize your retirement target?


The retirement system in the state of Illinois is complicated. Actually, anything related to money in the state of Illinois is complicated. Currently, I’m entitled to a full pension at the age of 57, and I can apply up two years of sick days to retire sooner. We are hoping to hit FI by our (late) 40s, though, that remains to be seen, and we aren’t banking on our pensions.

I work hard to be the very best teacher that I can be. Though my job is fairly secure, the education market is very volatile. Finding ways to be my best and give my students my very best is the greatest form of job security that I can think of.

So we are working on doing well with jobs we love and maximizing our income in those jobs. In addition to that, I do a lot of side hustling. I freelance, ghostwrite, and copy edit. I also do some virtual assistant work.


[PoF: You’re smart not to count on an Illinois pension. I don’t know if there’s another state pension so woefully underfunded. With the side hustles you’re developing, I think you’ll be just fine whether or not that pension is ever realized.]


What does an ideal retirement look like for you? What will you do with your time when full-time work is in your rearview mirror?


I actually can’t imagine myself leaving the classroom, at least not for long stretches of time. There is a literacy initiative in Mexico called Hekab Be Biblioteca that I absolutely fell in love with on a vacation. If I ever left the classroom, I would love to find ways to support literacy initiatives stateside and globally.

I also hope to have more time with family and friends. Reading, writing, gardening, kayaking, and pursuing other hobbies of mine are important to me. Travel is important to me. But I am much more inclined to cultivate roots than try to grow wings.


[PoF: It almost sounds like you’ve got that whole “find a job you love and you’ll never work another day in your life” thing going on. But I know some days are tougher than others.

The Mexican “open road community library” initiative sounds fantastic. Our family spent some time in Mexican classrooms a year ago, but as pupils, not teachers.]


I’ll give you eleven sentences to dish out advice to a young physician. Any and all advice is welcome. We talk about personal finance, so money is fair game, but if you have advice on being a better doctor, a better parent / spouse / friend / human, we’re all ears.


This goes against common personal finance wisdom, but that’s kind of my jam. It’s OK to love what you do. In fact, it is essential that this world has people who live and work their passions. If that happens to be you, enjoy every second of it. You don’t owe anyone any justification or explanation.

And remember to take care of yourself, too. Find ways to fight burnout. We need to keep good doctors (and nurses and teachers and firefighters, the list goes on!) in the profession as long as we can.

Take time to celebrate small wins. Come up with other metrics besides money that you can use to measure your success and check in on your own happiness. And since you likely don’t hear it enough, thank you for what you do!


[PoF: I’m trying not to feel a tinge of guilt for helping physicians and other professionals transition out of their chosen professions decades earlier than their counterparts if they so choose. It’s not working.]


You’ve got eleven days to visit anyplace in the world with an $11,000 budget. Where do you go and what do you do?


There are so many places that I would love to visit. A big vacation budget with a short amount of time is tricky! There’s that balancing act between doing all the things (and spending all the money!) and really savoring what you’re experiencing, right?

I suppose I would say Costa Rica. We went a few years back before we became parents, and I think it would be awesome to return in a few years when our son is older. It’s the only vacation that I’ve taken to date where I really felt like I have to go back to see and explore more. I would also love to visit Nicaragua this time. And Panama. Hmm.


[PoF: You might need more than eleven days, but in Central America your money goes a bit further, so I’ll bet you could swing it. My wife and I visited Costa Rica about five years ago and we’re likely headed back next spring with our kids. They’ll love seeing monkeys in the wild!]



Name eleven beverages you enjoy. You can be as general or specific as you like.


I don’t drink beer. I can’t believe that didn’t disqualify me from participating in this series, tbh.

Chai. Chai lattes. Genmaicha (brown rice tea). Green tea. Any tea really. Hot cocoa in the winter (which is half of the year in the Midwest). Water. Gin and tonic. Rum and Diet. The last two count as four so I’m stopping here.


[PoF: Who let this no-beer-drinkin’, tea freak into this place? Have we no standards?!?

Actually, I’ve hosted numerous guests here in this series who don’t drink alcohol at all. They seem to be among the more productive bloggers I know, too, a fact that makes perfect sense to me. Even I’ve been known to take a break from time to time.

I’ll have a G&T ready for you the next time you stop by this here bar.]


Now, eleven foods.


Sushi. Deep dish pizza. Caprese salad. Veggie burrito bowls at Chipotle. Guacamole. Homegrown veggies. Homemade bread. Pasta. Ice cream. Gelato. Dark chocolate.


[PoF: A good mix of healthy and hearty foods there. Not as much meat as this midwest boy likes, but I could live on that diet for a while.]


How did you first learn about PhysicianonFIRE.com? What one piece of advice do you have for me?


I started following you on Twitter, and I was so captivated by your story, your blogging success, and especially your charitable giving. Keep being you! You share invaluable information and you challenge people to look beyond themselves and their own lives when it comes to money. That’s the good stuff, PoF!


[PoF: Penny, thank you so much for taking the time to share more of your story, your advice, and the excellent selections from your site with us today. 

Have a great Thanksgiving weekend, don’t go wild on Black Friday (not that I thought you would, and keep inspiring others with your words.

Readers, be sure to get to know Penny a little better on her own site: She Picks Up Pennies.]


I've got my 2 acres of non-leveraged, crop-producing, cashflowing farmland via AcreTrader. Get yours.


Interested in hearing how other top personal finance bloggers have answered these questions? Check out additional Christopher Guest Posts from many of the top personal finance bloggers:


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5 thoughts on “Christopher Guest Post: She Picks Up Pennies”

  1. Love this!! I didn’t know about the 200 pairs of shoes- I bet it was a beautiful collection! I love shoes myself especially Cole Haan shoes. My shoes these days that I actually wear are all comfy flats after being a mom, lol.

  2. Subscribe to get more great content like this, an awesome spreadsheet, and more!
  3. You just had to drop a Chipotle reference, didn’t you!? Good getting to know you a bit better, Penny.

    I’ve had the pleasure of meeting the entire PoF clan and hope to on end day meet you IRL as well.

  4. Oh another Chicago deep dish fan =) it’s the food of Gods.

    “Travel is important to me. But I am much more inclined to cultivate roots than try to grow wings.”

    I heard that line from Adventure Rich once about roots vs wings. Are you two still in contact with each other?

    I’m more of a roots person too. A lil jealous of people with wings and thirst for adventure esp when I can’t make it out of bed in the morning =p

    • Ha! Oh, Lily. Deep dish pizza is the best! I reached out to Mrs AR a little while back. I’m still hoping to hear from her!


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