19 in 2019: Money Milestones and More

19 Milestones from 2019

I’m going to stop singing (OK, fine, I am just making up words like everyone else) Auld Lang Syne long enough to round up 19 highlights from 2019. 

Creating this list did exactly what I hoped it would. It reminded me that there were so many more highlights than I had space for on my list. Even though this wasn’t an easy year to muscle through, there are so many moments and milestones that are special to me. 

Here’s a short recap of some things that stand out the most to me before we move in 2020.


I landed on my feet at my full-time gig. 

OK, maybe I didn’t exactly stick the landing, but I feel like I have at least one foot on the ground most days. After a really rough school year last year, I found out that I was changing grade levels and content areas. I moved back to a grade level I used to teach and absolutely love (both then and now!), but to say it’s been easy would not be true.

I’m finally getting paid closer to what I’m worth.

I worked tirelessly to double my teaching salary. But in true educational bureaucratic fashion, I haven’t been paid for all of my work yet. Two years after my National Board certification, I’m finally getting that stipend. It’ll take a full additional calendar year to get credit for all of my graduate hours, though. Still, forward motion is something. 

I quit tutoring entirely.

This one is bittersweet. For over a decade, tutoring has been a passion project. Working one-on-one with students who need extra support or want to be challenged is fun and rewarding and engaging. It’s hard work that is so fulfilling. But in recent years, there’s been a shift in how families out here view tutoring. They seem to want things to happen on an as-needed basis, filling in gaps before tests and working around other commitments. Now that I’m juggling three schedules instead of one, it just got to be too hard to accommodate last-minute requests. Plus, I couldn’t very well have my husband make sacrifices to make more time for us and then do the opposite.

RELATED POST: When It’s Time to Choose Time Over Money

Freelancing continues to be a dream. 

I can honestly say that I appreciate and respect all of the people I work for and with. This year, I got to explore writing in a few additional niches, plus I got to pick up more ghostwriting and editing. In addition to continuing to be part of the best team on the Internet at Women Who Money, I also am constantly alternating between typing and pinching myself that both FinCon and Choose FI have let me work for them, too, this year. I also have a handful of additional clients who are doing amazing things in personal finance and other spaces. It’s so fantastic to work for them and cheer them on at the same time. 2020 is going to a big year and I am here for it!

Blogging is still a hobby.

I really wanted to hang up my blog about halfway through the year. The feeling didn’t really subside either. It just felt like one more thing that I was adding to my plate, and I wasn’t sure I wanted to keep going. Instead, I took a complete gamble and wrote a post at the beginning of December much akin to how I used to write: for me and for me alone. I’m still not sure how it happened, but that single post pulled in more traffic than my little site has even experienced in a single day by thousands and thousands. And so many of the comments made me weep. It was Internet kismet, I think. 


Our mortgage dipped into five figures.

Earlier in the year, we crossed the threshold from six-figure to five. It felt like such a huge moment when I reminded myself that I took out a loan for over $200,000 (by myself!) only six years earlier when I was just 26 years old. 

RELATED POST: Smashing 6 Figures of Debt & Learning From What Doesn’t Apply to Me

We paid over $30,000 toward our mortgage principal in a single year.

I heeded the advice of the sage commenters who reminded me to not play too fast and loose with the money I was itching to spend. We made one last sizable mortgage payment for the year, and brought our balance down to just under $90k. That means we put over $30,000 toward the principal of our mortgage this year. 

That would be like putting every penny of my 2010 take-home pay toward our debt payoff goal! 

Our Roth IRAs are maxed out early again. 

I really value comments on my blog. Not just because I think the wisdom is great for other readers, but because it helps me so much. Like, literally, plan my life for me, OK? Dovetailing from the mortgage milestone, I also listened when people said to prioritize investing. We maxed out our Roths earlier in the year and plan to give ourselves a healthy head start once the calendar turns. 

Our son’s 529 is finally picking up steam.

My blog has been more or less mum on HP’s 529. I try hard to avoid telling stories that aren’t mine, so it feels odd to share his financials (even though I know full well it’s our money!). But the truth is, our 529 was in bad shape simply due to the timing of his birth. We were in the red for months, and now that over two years have passed, we are finally seeing real growth on our investment. 

We let ourselves spend a bit more. 

It’s true. Time to scrap the frugality blog and start over. Call it lifestyle inflation, call it necessity, call it an utter lack of willpower. Whatever you want to label it, we are allowing ourselves to spend a bit more. Whether it’s weekly treats to make Mondays more palatable or beefing up our grocery budget some, we are spending more. And it feels better than OK. It feels good. 

Family & Friends

We put ourselves and our son first.

My husband gave up two out of three seasons of coaching, and I stepped away from some opportunities at work. I’ve also let go of some freelancing work that was interfering with boundaries. The most notable thing we did, though, as a small family was to actually book a getaway for a long weekend right before Christmas. That actually meant skipping out on smaller celebrations on both sides of our family. But we had three uninterrupted days with our son, and we came back three more days of non-stop family parties. It felt like the perfect balance. 

I showed up for people. 

This has been a hard year. In fact, it’s been one of the hardest years that I’ve had since I started this blog. My in-laws experienced death, illness, and divorce in their families. Friends and coworkers (who are my friends, too!) went through hardships. And I struggled. My initial reaction was to throw myself into my work as much as possible as a way to mask my grief. But a combination of writing, Internet friends, and real-life conversations made me realize that the truest gift I can give anyone is to show up for them. And I think I did that this year time and time again.

RELATED POST: The Importance of Showing Up 

Our list of travels grew.

I’m a pretty big fan of cultivating roots instead of growing wings. But I do like to travel, too. This year, we got to do a bunch of it. We road tripped throughout Canada for nearly two weeks. Plus, we went to DC (#FinCon19!) and New Orleans. We also spent a bunch of time with my parents at their cottage in Wisconsin. 

We gave more.

There’s nothing record breaking about our charitable giving. But I am so proud to say that it’s the budget category that we grew the most this year. If we are going to inflate our lifestyle in other ways, this feels like an important balance. 


I took more naps.

I wish I could say I feel refreshed, but I don’t. I’m working on it! The remarkable thing is that I actually allowed myself to do this. It’s a small step toward showing myself the kindness I deserve. Plus, I figure getting more sleep is much more cost effective than buying the La Mer eye cream that I keep, errr, eyeing. 

RELATED POST: I Put Down My Badge of Busy and Took A Nap Instead

I took more risks. 

I attended FinCon again, giving me the chance to meet more people and reconnect with others. A short time later, I actually had the chance to speak at Tanja’s Cents Positive retreat in Chicago. Truthfully, I still can’t actually believe she invited me to do that! Both those experiences motivated me to say yes to more opportunities that I’ve wanted and empowered me to say no to more things that don’t deserve me. It turns out, I like a more confident me! 

My goals feel more like me. 

I never really know where I fit in the blogging world. As a result, it always feels like I’m swapping clothes with roommates like I did in college. Too big, too small, and oh, that is so definitely not something I would ever buy. This year, though, it felt like we had a direction that felt good to us as a family. What else matters?  

Failure found me. 

I fell off the decluttering train hard. I also didn’t prioritize myself as much as I wanted. The good news is, I see how I failed and am starting to take small steps back toward my goals. 

I stayed grateful. 

I would be lying if I said I loved all of 2019. There were moments that felt like mountaintops, but there were weeks where it felt like I was plummeting to the other side of the Earth. Of course, now that I have enough perspective to look back on the year as a whole, I can see it more for what it was. I didn’t want or need everything that happened, but I tried to stay grateful through it all. I am thankful for the good times and appreciative of the people who made the bad times a little less awful. I’m not sure I could ever ask for more. 

So Tell Me…What was a highlight for you in 2019?

PS – I’m wishing you all the best for 2020! I’ll see you back on the blog next week. 


  1. My favorite highlights for me were the times spent with you and HP in Wisconsin and DC! You’re among my favorite people on the planet, and I’m glad you haven’t quit the blog yet!
    Congratulations on the wins and for finding such better balance for you and your family!

  2. I keep thinking that I just SURVIVED 2019. I didn’t do anything notable or achieve anything particularly worthy of highlighting. But I survived on my terms: we saved, invested, traveled, cared for family and showed up for those who were hurting *every* *single* *day*.

    Then I realize, no wonder I didn’t have time for anything else. I was keeping myself and my family healthy and seriously supporting my extended family who is going through some seriously tough times right now.

    I would really like to start doing some freelancing this year but I’m not positive I have the bandwidth for it as we’re still doing this support thing.

  3. Penny! What a beautiful, reflective post. Congratulations on the mortgage payment, personal goals and taking more naps. Big believer in naps over here 😀

    For me … standout moment of 2019 was definitely quitting my job. Other than that … Because my husband and I knew there’d be big career shifts for both of this year, we intentionally set out to have the MOST fun summer. More boating when I should’ve been blogging. More beach when I should’ve been cleaning. More naps when I should’ve been meal prepping. And now that the big shifts have hit, I’m so, so glad we had this summer to really make the most of being young and in love and in Charleston. I’ll treasure it <3 sending you all the good vibes for 2020!

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