A Project Reborn

Hello friends,

Two years ago, I wrote the first post for what I hoped would be an interesting project focused on helping educators on their path to financial stability. At the time, I had a bare-bones website, a newly purchased domain name, and a podcast that existed mostly as an idea. So I guess that was something? I’m now reworking my old content for Substack and bringing it to what I hope will become a larger audience.

Project Origins

Although my interest in helping others with personal finance might have seemed to take off suddenly in the months before I started, there’s a bit more to the story than that. Rather than a sudden start, I think it is an example of compounding in real life. Things start slowly: you learn about topics, you find resources, you make connections, and it all builds on itself. Eventually those isolated ideas start to connect and intersect with each other, and you start to recognize this thing had been brewing on the back burner.

In that first post, I said I wasn’t planning to let the project grow exponentially. I thought linear growth might be manageable, and I’ve kept to that goal. Maybe even exceeded it in some cases. In addition to short-form content, I’ve dabbled with a podcast, built some free browser-based tools, and done a variety of presentations. I’m now shifting to Phase 2 of the project, which I call Compounding With Interest, where I hope to do more one-on-one handbook chats with teachers, give presentations to Western Wisconsin districts, and complete a research study on Wisconsin teachers’ financial literacy and well-being.

What I Spend Time On

• Making useful content

• Celebrating teachers, teaching, and education

• Holding space for other educators, their experiences, and their stories

That list hasn’t changed.

What are the aims of this project?

• Build relationships and foster a supportive community for educators.

• Identify and discuss resources and tools useful for personal finance.

• Think through strategies and approaches for different financial topics.

• Share my perspective on education, teaching, and learning.

Two principles have become more explicit over time:

• This project is informational, not prescriptive. There are many reasonable financial paths for educators, and my goal is to help you understand your options, not to tell you which one to pick.

• My goal is conflict-free personal finance education, not personal financial gain. I’m not interested in selling books or charging for subscriptions.

What do I mean by “educator”?

I think of educators as all the different folks working in schools: classroom teachers, aides, staff, and administrators. We have different roles, but we’re all focused on the shared mission of teaching and learning.

Who is this for, and what do I assume?

When I work through examples, I have to make some assumptions about the finances of the people in them. Those choices are guided by the core audience: early- and mid-career educators working in K–12 schools in Wisconsin. In my examples, I typically assume:

• Age: 24–44

• Salary: $45–60K

• Student loans: $35K

• Monthly expenses: $3–4K

Educators in higher education, people in similar retirement systems, couples, folks with more debt, and folks with kids can also benefit from the ideas here, even when the numbers don’t match exactly.

What topics will I focus on?

Personal finance weaves in and out of so many things. Sure, there’s math, but there’s also psychology, philosophy, and humanity. It connects to beliefs about who we are, how we want to live, and how we work in relationship with others. The topic list has grown since that first post, and I still welcome suggestions.

What about the timeline?

When I started in June 2024, I planned to review the project after one year and decide whether to keep going or set it down. I kept going. The work helped me learn more, and conversations with educators kept confirming the need. The financial climate of the last two years has only strengthened my dedication to this project. New writing, podcast episodes, and tools now live here on Substack. The original blog posts remain available at personalfinanceeducators.com, and I’m reworking the foundational ones for this space.

Just who are you?

You can read more about me on the About page. I’d describe myself as a knowledgeable other inside the education space. If you’re an educator, I’m on a similar journey to yours, but it’s probably different. Maybe I’m farther down the road (maybe not). Maybe I’m taking a different path, using a different vehicle, with different companions. We’re all on a personal finance journey, and our choice is to either turn inward and walk alone or turn outward and help each other. I’m extending a hand, hoping it can help you.

~Josh

New here? The New Here page has a short reading list to help you get oriented.

This post is for educational purposes only and is not individual financial advice. If you have questions or topic ideas, reach out at josh@personalfinanceforeducators.com.

What is TLP?

TLP is a relatively new program. It was created by Wisconsin Act 55 in 2015 with a follow-up act later that same year refining some of the details around eligible work locations. The goal of the program is to incentivize teaching in specific areas of Wisconsin.

TLP works by giving loans to Wisconsin resident undergrads working toward teacher licensure. The money is a loan that has the potential to be forgiven in pieces if you teach in the right place.

• Who’s eligible: Wisconsin residents, sophomores through seniors, enrolled at least half-time at a participating UW System school or a nonprofit private college in Wisconsin.

• GPA requirement: 3.0 or higher on a 4.0 scale

• How much: Students can receive up to $10,000 per year (max $30,000 total)

To be eligible for a loan, you have to be licensed in a discipline the U.S. Department of Education has identified as a teacher shortage area for Wisconsin. As of right now (September 2026), that includes:

• Standard Disciplines: English as a Second Language, Bilingual Education, Foreign Languages, Mathematics, Music, Reading, Sciences, Library Media

• Special Education: Cognitive Disabilities, Cross Categorical, Deaf and Hard of Hearing, Early Childhood-Special Education, Emotional/Behavioral Disorders, Learning Disabilities, School Speech and Language Disabilities, Visual Disabilities

• Career and Technical Education: Agriculture, Business Education, Family and Consumer Education, Marketing Education, Technology Education

This list changes from year to year, so check the current shortage-area list before you count on a specific discipline qualifying.

Where you have to teach

In order to qualify for loan forgiveness, you have to teach full-time after graduation in one of the following places:

1. The city of Milwaukee. Anywhere within city limits qualifies, not just a specific county.

2. A county that the statute defines as “rural.” HEAB publishes a specific list and map of which counties qualify. I’ve generated a version of the map below.

The current list of rural counties is:

Adams, Ashland, Barron, Bayfield, Buffalo, Burnett, Clark, Columbia, Crawford, Door, Dunn, Florence, Forest, Grant, Green, Green Lake, Iowa, Iron, Jackson, Juneau, Kewaunee, Lafayette, Langlade, Lincoln, Manitowoc, Marinette, Marquette, Menominee, Monroe, Oneida, Pepin, Polk, Portage, Price, Richland, Rusk, Sauk, Sawyer, Shawano, Taylor, Trempealeau, Vilas, Washburn, Waupaca, Waushara, Wood

If you meet all the criteria, 25% of your loan will be forgiven for each year you teach in an eligible location. Thus, meeting the criteria for four years will result in forgiveness of the entire TLP loan. If you don’t meet the criteria in a given year, that portion gets repaid instead, at 5% interest.

For folks who are already planning to teach in Milwaukee or one of the “rural” districts, TLP is close to free money. However, if you’re not sure where you’ll end up teaching, it’s probably worth thinking through before you take the loan. That said, the current federal Direct Loan rate for undergraduates is 6.52% so TLP’s 5% fallback rate is meaningfully better than federal loans. That doesn’t mean it is automatically better than every private option, which depends on your credit, but for an undergrad without established credit, I think TLP's worst-case 5% is probably better than anything they'd qualify for privately.

If the mention of loan forgiveness jogs a memory of programs like Teacher Loan Forgiveness or Public Service Loan Forgiveness, you should know that TLP is a different animal, both in how it operates (state level), how quickly it forgives loans (as fast as four years), and in the fact that it puts money in your hands while you’re still in school rather than forgiving a loan you’ve already been repaying. I plan to discuss federal loan forgiveness options in a future post.

How to Apply

TLP doesn’t have an application you fill out yourself, but you do need to file the FAFSA, since HEAB uses it to help confirm eligibility. Beyond that, the process runs through your school:

1. Tell your financial aid office you’re interested. Applicants apply through the financial aid office at a participating Wisconsin institution, not directly through HEAB.

2. Your financial aid administrator designates you, based on the eligibility criteria above, and offers you the loan.

3. The school submits your paperwork to HEAB. Once HEAB receives and approves the completed documents, the loan is disbursed directly to your school, not to you personally.

4. You repeat the process each year you want to draw on the loan again, up to the $30,000 lifetime cap.

One thing to note, funding is limited. So, being eligible and applying doesn’t guarantee a loan is available. I’d wager that the earlier you talk to your financial aid office, the better you’ll be.

Not every Wisconsin school participates. As of the current list, that includes UW-Green Bay, La Crosse, Milwaukee, Parkside, Platteville, River Falls, Stevens Point, Stout, and Superior, along with Alverno College, Carroll University, Concordia University, Edgewood College, Lakeland College, Maranatha Baptist University, Marian University, Marquette University, Ripon College, St. Norbert College, and Viterbo University. If your school isn’t on that list, check directly with HEAB, since this list can change.

I’m hoping this post is helpful for current students seeking assistance as well as all my colleagues who work with students. TLP is a wonderful opportunity that all should be more broadly shared across our programs.

This post is for educational purposes only. Information is current as of September 2026. Program terms and eligibility can change, so confirm current details directly with HEAB before making decisions based on this post. If you have questions or topic ideas, reach out at josh@personalfinanceforeducators.com.

I officially launched this project in summer of 2024. The last few years (Phase 1) have really been about figuring out what I want this project to be about, finding my angle and perspective, and determining how I want to create and share content. The process of Phase 1 has helped me clarify my direction and identify ways I think I can be helpful to educators. At this point, I’m comfortable with where I’ve landed in terms of voice and format (though I do plan to keep experimenting with the podcast), and I intend to keep creating content as I consider new questions, find resources, and build tools. The next part (Phase 2) isn’t about changing any of that. Instead, it’s about integrating this project into my professional scholarship, and about digging in further to understand what teachers actually need.

Bringing this into my research

Up to this point, I’ve run Personal Finance for Educators alongside and largely apart from academic work rather than through it. That’s the part I’m planning to change in Phase 2. I’m leaning into how I can utilize my position as a teacher educator to bring greater relevance to the content I create. To this end, I’m developing a formal research study on teacher financial literacy in Wisconsin.

The core of that study will be a survey I plan to send to K-12 teachers across Wisconsin. My goal is to have better evidence of what educators know, or don’t know, about personal finance: where the gaps are between the Wisconsin Retirement System, salary structures, and what teachers understand about their own paycheck and benefits. As I discussed in a previous post, I think personal finance education is a missing piece in our teacher retention efforts. We need to support folks in understanding their own personal finance context, the opportunities, potential pitfalls, and broader financial picture.

Along with the research study, I’ve also started to branch out into giving conference presentations on personal finance. Last May, I presented at the Wisconsin Mathematics Council Annual Conference, and this fall I’ll be giving a talk at WI-AMTE’s fall conference. Conceptualizing this project as scholarship that sits at the intersection of mathematics teacher education and financial literacy is a new way for me to think about this work, one I anticipate will be generative.

Two Goals for this Year

This year, I have two goals for the project.

Goal 1: Handbook Chats. Starting this fall, I’d like to start hosting handbook chats. The idea is simple. I meet with one or a few educators and we take a walk through their district handbook. As I have discussed previously, handbooks are dense, full of policy language, and can be intimidating at first glance. Moreover, if you only look at one handbook, you might not recognize what’s unique about a district, or what’s missing. I want to chat with folks and help them understand what’s there, from sick leave, to benefits, to pay schedules, whatever’s relevant to them. This is partly about helping individual teachers, and partly about learning. Every conversation like this tells me more about what’s actually confusing people, which feeds back into the tools and the writing.

Goal 2: More presentations. I’m also hoping to give more presentations this year, for teachers in districts across Wisconsin. I’ve done a few of these already, at the Wisconsin Mathematics Council conference and at UWL for preservice teachers, and they’ve been very useful in helping me identify questions and potential topics for discussion. If you’re part of a district or organization that might want a session on anything I’ve blogged about, whether it’s the WRS, understanding a paycheck, or something else entirely, I’d like to hear from you.

Circling Back to Purpose

At the outset of the project, I set forth the following goals:

• Build relationships and foster a supportive community for educators.

• Identify and discuss resources, tools, etc. useful for personal finance.

• Think through strategies and approaches for different financial education topics.

• Share my perspective on education, teaching, and learning.

I think these goals still capture what I’m trying to do two years on. Phase 1 was about building a foundation. Phase 2 is about gathering more data and using it to direct the project toward those things that teachers have said they want and need.

I’ll likely share more on the survey, handbook chats, and presentations as they come together. If you’re a Wisconsin teacher and any of these things sounds like something you’d want to be part of, please reach out: josh@personalfinanceforeducators.com.

~Josh

August brings a different kind of weight than June. The path up the mountain stretches far ahead. The question is whether you go into the climb with a plan.

My goal with this post is to offer one specific objective that I think most teachers can accomplish: making regular contributions to a Roth IRA. At the end of my last post in this series, I discussed how a modest contribution could allow someone to retire at 55 with full income replacement. But I left an important question open: where does the money actually come from?

I’m going to refuse to the obvious answer, which is extra work during summer. I’m not arguing that summer work isn’t feasible, but I view summer break as one of the genuine structural benefits of the profession. As I’ve discussed previously, that time has real value. A young educator in their 20s might see extra income as a worthwhile trade. But I think many folks eventually reach a point where total control of time becomes more valuable than the income that could be earned with it. Thus, I don’t want to make contributions to a Roth dependent on summer’s expense.

With summer off the table, that leaves the school year. I’m going to set a specific goal: an extra $2,400 a year, funded entirely by duties already built into the job. On a 10-month teaching calendar, $2,400 works out to $240 a month. As I discussed in the last post, this is likely enough to bring Pip close to full income replacement at age 55.

Set a contribution target. Find a way to reach it during the school year. That’s the game plan.

What Extra Duties Actually Pay

In most districts, there are a variety of opportunities to earn additional income by taking on responsibilities. They range in time commitment and duration. In addition to the income, some of these roles are genuinely rewarding ways to engage with students and the broader school community. For some folks, the relational benefits are at least as valuable as the monetary ones. Based on my own analysis of handbooks from districts across Wisconsin, here’s a rough picture:

These numbers vary by district and should be spelled out in your employee handbook or a supplemental compensation document.

Three Ways to Reach $2,400

The same target can be assembled from very different building blocks, depending on your interests, schedule, and stage of career.

Option 1: A single big commitment. One role does most of the work. In the Verona Area School District, for example, a JV coach or 7th/8th grade coach earns $2,335 — close enough to our target that one small additional duty bridges the gap. A head coaching stipend for sports like cross country, volleyball, or soccer pays $3,498, clearing the target on its own. The Fall Musical Director or Spring Play Director earns $2,916, which also clears it. The right choice depends on your interests, schedule, and energy. Some roles carry significantly more time commitment than others. That’s not a reason to rule them out, but it’s a reason to think carefully about whether the role fits your season of life.

One additional option worth mentioning: teaching an overload section. A single semester overload would exceed the target on its own, and two semesters would clear it comfortably. That said, an overload is a significant commitment and not something I’d recommend to anyone in their first few years.

Option 2: Combining several medium commitments. A club advisor role in the $800–$1,000 range, plus a mentoring stipend for one new teacher ($500–$750), plus a semester of lunch supervision ($400–$600). Three modest commitments, none of them dominating your week, adding up to the target. You can make these choices seasonal so they don’t overlap, spread them out for consistent income across the year, or stack them if your schedule allows.

Option 3: Steady accumulation. Several small duties done consistently — occasional class coverage, a smaller club, a committee or two. This suits someone who would rather spread the load across low-intensity tasks than commit to one larger role. The key with this approach is consistency: you’ll need to track your income across duties to make sure you’re hitting the goal.

Reframing Your Work: What Are You Actually Deciding?

A central point I’m trying to make here — beyond showing that the math is feasible — is that thinking in terms of goals is a useful way to shift your perspective.

Instead of asking: Is this duty worth the extra time? you can ask: How does this duty help me reach my Roth IRA goal?

If you pre-commit that money to your Roth IRA and set up automatic contributions from your bank account, you’re building a system rather than relying on monthly discipline. The money never lands in your checking account. It never gets absorbed into everyday spending. It never requires you to remember.

One decision. One routing. Many years of compounding.

A Note of Caution

Teaching is demanding, and time and energy are finite. I’m not arguing that every teacher should pile on extra duties. Early-career teachers in particular often need to protect their bandwidth while building the craft — and protecting summer is part of that same instinct.

My point is narrower: if you were already considering a duty, or one is available that fits your interests and schedule, the financial case for routing that income to a Roth IRA is strong. The club advisor role, the mentoring, the covered class: these come and go with the school year. What has the potential to stay is the money you earn and its interest.

The Bigger Picture

In earlier posts I’ve described the pension as a kind of floor: a guaranteed income that arrives every month regardless of the market. I showed that at 7.5% returns over 32 years, $100 a month grows to about $156,820 and produces roughly $615 a month in retirement income at a 4.7% withdrawal rate. The full $2,400/year target scales to roughly $376,000 in the Roth and about $1,476 a month in retirement income, on top of the pension and Social Security floor. These are projections based on standard compound growth assumptions. The market determines how accurate they turn out to be.

Extra duties aren’t the only way to fund a Roth. But they’re one of the cleanest paths available to teachers, precisely because they’re already embedded in the structure of the job and don’t cost you your summer. The opportunities are already there. The only question is whether you connect them to a goal or let the income disperse into the ether of everyday life.

Feel free to ignore this choice — it’s your time. A modified version where you work summers early in your career and ease off later could put you in a stronger financial position, since contributions made in your 20s have more time to compound. But I would think carefully before converting your mini-sabbaticals into a steady income stream.

As always, I’m a mathematics educator, not a financial advisor. This post is for educational purposes only. If you have questions or topic ideas, reach out at josh@personalfinanceforeducators.com.

We’re a month into summer, and it’s a natural time for educators to reflect on the past year. The end of a school year carries real weight. As June approaches, the pressure builds, the emotions run high, and getting to the end feels like reaching the top of a mountain. You made it. You also know you’re going to have to climb it again in a few months.

One question that can come up during this time is whether pursuing a career outside of education might be worthwhile. There are plenty of reasons this question might come up from the workload, to the stress, to the low salary. To be clear: I think asking this question and exploring one’s options is fine. I believe folks should make informed decisions and enter (or leave) the profession with eyes wide to the trade-offs. Moreover, I think there are simply too many variables and contextual factors to make general claims about there being a “right” or “best” decision. Life is complicated. Choices are too. I’m not here to shame anyone. Instead, I’m interested in how I can support educators in thinking through a question like: what might be the benefits and drawbacks of taking a particular job?

All of this got me thinking: could I build a tool to help someone think through the financial side of this decision? Not the whole decision, just the big-picture money part. So, that’s what this post is about: showcasing a tool that attempts to roughly compare the financial value of a teaching position against a position outside of education. With the caveat that this is genuinely an apples-to-oranges comparison, this post walks through a sample of what the tool can do by looking at a made-up comparison case.

In every post so far, I’ve been following a teacher I’ve named Pip who lives in Wisconsin and is working toward retirement at 55. As I’ve discussed previously, retirement at 55 is financially achievable, and with modest additional savings through a Roth IRA Pip could retire with close to 100% of their pre-retirement income. But how does this compare to someone who graduated with a teaching degree and chose to work outside of teaching?

This post tries to answer that. I want to introduce a new character, Oliver, and run the two paths side by side. Oliver is Pip’s friend. Same age, same goal (retire at 55), same degree (education), but a different career. He works in the private sector as a corporate trainer, starting at $55,000 a year.

I want to be upfront about what this comparison is and isn’t. It’s not an argument that teaching is better or worse than private sector work. The two paths are genuinely different, and which one looks better depends heavily on assumptions and context that vary by person. What I want to do is show how the tool I built can help with getting a high-level overview of the numbers.

The Starting Point

Pip and Oliver both start working at 23. The assumptions I used are:

Oliver starts with a 22% salary advantage, a slightly higher raise rate, and more take-home pay. His company offers a 4% match to a 401(k) and he contributes fully to get the match but not any more. This makes his total retirement contribution a smaller percentage of his income. Pip starts lower, contributes more to retirement as a percentage, and works within a defined benefit system rather than a market-dependent one.

One assumption worth naming: both stay on their path for 32 years. That’s realistic for Pip in a way it probably isn’t for Oliver. WRS covers all Wisconsin public school districts, technical colleges, and the UW System, so Pip can move freely across any of those employers without any pension friction. For Oliver, 32 years at a single employer (or even a single 401(k) provider) is an optimistic assumption. Job changes are common in the private sector, and while rollovers preserve the balance, they add friction and decision points that the WRS system eliminates entirely. The comparison is cleanest as stated, but it’s worth keeping that asymmetry in mind.

Thirty-Two Years Later

By the time both reach 55, the salary gap has grown considerably. Oliver’s 3.5% annual raises on a higher starting salary produce a final salary of roughly $159,800. Pip’s final salary is around $96,800. That gap matters, not just for what each person earns during the working years, but for how much retirement income each needs to replace their lifestyle.

On the retirement savings side:

A few things worth noting. Pip contributes more total dollars than Oliver, $312,014 vs. $252,272, despite earning considerably less throughout the career. That’s entirely a function of the WRS contribution rate (14.4% combined) vs. Oliver’s 8%. The higher contribution rate builds savings discipline into the structure of the job rather than leaving it to individual choice.

The raise rate matters more than it might seem. Pip’s 2.5% annual raises compound into a final average salary of $94,410, which drives the WRS pension formula directly. A half-point difference in annual raises produces a meaningfully different pension at the end, which is why the tool lets you adjust this assumption.

Oliver’s monthly figure assumes he draws down his balance at 4.7% annually, the same rate used elsewhere in this series. His balance at 55 also requires a 72(t) SEPP distribution to access penalty-free before age 59½, a workable but inflexible arrangement worth understanding before relying on it.

Neither Pip nor Oliver can access Social Security until 62 at the earliest. Oliver’s benefit will be higher, reflecting his higher lifetime earnings, but that advantage doesn’t arrive until at least seven years into retirement for both.

Where Pip Has the Advantage (in this scenario)

The income is guaranteed. Pip’s $4,028/month arrives regardless of what markets do in the years immediately following retirement. Unlike Oliver’s drawdown, it isn’t subject to sequence of returns risk — a bad decade at the start of retirement can permanently impair a drawdown portfolio in ways a pension is immune to. The WRS also periodically adjusts benefits based on investment performance. These adjustments can go up or down, but the base benefit is protected.

Accelerated payments. The WRS system gives Pip the option to take accelerated payments from 55 to 62, which add projected Social Security amount onto the monthly pension during that window. When Pip becomes eligible for Social Security at 62, the pension adjusts back down. It is not strictly more money, but it provides a different kind of income flexibility in the early retirement years.

No early access friction. The WRS pension starts at 55 cleanly by design. Oliver needs a 72(t) SEPP arrangement to access his 401(k) before 59½.

Survivor benefits. Pip can elect a survivor benefit option that continues payments to a spouse for their lifetime, at the cost of a reduced monthly amount. Oliver’s 401(k) balance is inheritable, but the mechanics are different.

WRS portability is broad. WRS covers all Wisconsin public school districts, technical colleges, and the UW System. Pip can move freely across any of those employers without any pension friction. This is a larger system than most people realize.

There is space to pause without significant penalty. If Pip takes a 3 to 5 year break mid-career (e.g., for family, health, or other reasons) and returns to teaching before 55, the pension penalty is smaller than the raw service year difference suggests. The WRS formula depends on both years of service and final average salary. A teacher who teaches 27 years but finishes at 55, after a break, still earns a pension based on their age-55 salary. The break costs service years but doesn’t reset the salary clock. A mid-career pause costs less in Pip’s system than in most.

Where Oliver Has the Advantage (in this scenario)

Higher salary during the working years. Oliver earns roughly $63,000 more per year by the end of his career. That’s a significant difference across three decades, and it means Oliver has more runway to save beyond the employer match if he chooses to.

The balance is inheritable. Oliver’s 401(k) passes to heirs. Pip’s pension may provide survivor benefits for a spouse but generally does not pass to children or other heirs. Oliver will need careful tax planning if he wants to pass that balance on without a significant tax burden.

Career flexibility beyond Wisconsin. Oliver can change industries, move states, or shift employers without any system-level friction. His contributions follow him anywhere.

Upside is uncapped. The 7.5% return assumption is conservative. Oliver can choose more aggressive portfolio allocations, which could meaningfully increase his balance and monthly income at retirement. Pip's pension is fixed by formula regardless of how well WRS investments perform. That said, Oliver's freedom to adjust allocations also comes with the risk of poor choices and the constraints imposed by his 401(k) custodian.

Higher Social Security eventually. Oliver’s higher lifetime earnings produce a larger Social Security benefit. That advantage arrives at 62 at the earliest, seven years into retirement for both.

The Apples-to-Oranges Problem

The reason this comparison resists a clean conclusion is that the two instruments are fundamentally different.

Pip’s pension is an annuity, a guaranteed monthly income stream for life, backed by the State of Wisconsin, and more protected against market conditions and longevity risk. All the money contributed by Pip and employers over the years is gone at 55. It cannot be cashed it out. Oliver’s 401(k) is a balance, a sum of money that needs to be managed, protected from sequence risk, drawn down carefully, and potentially outlasted.

An annuity and a balance are not the same thing, and converting one to the other for comparison purposes requires assumptions that can swing the result significantly. The $4,028 vs. $3,293 monthly figures are a reasonable starting point, but they rest on a specific return assumption, a specific withdrawal rate, and a specific career length. Change any of those and the comparison shifts.

What the numbers do show clearly: Pip reaches 55 with a higher monthly income than Oliver despite earning substantially less, and does so with guaranteed rather than projected income. Oliver reaches 55 with a much higher salary, more flexibility, and a balance he controls, but faces more complexity in actually executing a retirement at 55.

Neither outcome is obviously better. They reflect different tradeoffs that different people will weigh differently.

The Tool

The assumptions above are a starting point, not the answer. A teacher with a higher starting salary, a private sector worker with a more generous match, or someone expecting to work 28 years instead of 32 will see a different picture. The tool lets you adjust the variables and see how the comparison shifts.

Paths to 55 Tool

Give it a try and let me know what you think.

~Josh

If you enjoyed this post, please share it with a friend! As always, I’m a mathematics educator, not a financial advisor. This post is for educational purposes only. If you have questions or topic ideas, reach out at personalfinanceforeducators@gmail.com.

The Wisconsin Teacher Salary Analyzer, which I wrote a post about earlier. This tool allows you to download public salary data from DPI, upload it to the tool, and in under a minute you get a clean summary: salary range, averages by experience, and a slider so you can see what a teacher with X years of experience is typically earning in that district. There’s also a comparison version if you’re weighing two districts against each other. The whole thing runs in your browser, no account needed.

The Handbook Analyzer, which is still in development. This tool allows you to upload a district handbook PDF, and the tool uses Google’s Gemini AI (free with a Google account) to pull out what matters: compensation structure, health benefits, retirement options, notable clauses, and what’s missing. There’s also a search box so you can ask specific questions about the handbook directly. It won’t replace actually reading your handbook, but it’s a fast way to get oriented.

The episode also covers why I’m building these tools in the first place and how I’m using AI to do it. If you’re curious about the process, not just the output, give it a listen.

A note that the podcast includes a screen recording, so if you watch it on Spotify you can see me using the tools.

As always, if you find this project useful, please subscribe and share with a colleague or two. Feedback helps me make these tools better for everyone. You can reach me through josh@personalfinanceforeducators.com or leave a comment below.

~Josh

Why I’m Building These With AI

These tools are built using generative AI — specifically Claude.ai. I’m not a professional developer, and I wouldn’t be able to build these without it. You might have some mixed feelings about the use of AI in education (I certainly do) but this is a very different use that I find compelling because it doesn't just enable someone like me — a well-intended nerd with no formal development background — to build things. It fundamentally changes what's worth building.

There are three things in particular that I want to highlight:

Specific in focus. AI makes it practical to build a tool that does exactly one thing for exactly one person in exactly one situation. The salary analyzer isn’t trying to serve every use case — it’s trying to answer a specific question that Wisconsin educators actually face. A general-purpose tool built for a mass market wouldn’t go this narrow.

Local and private. These tools run entirely in your browser. Nothing is stored or shared. Your data, your district comparisons, your financial situation are sensitive. That’s a deliberate choice, and it’s only practical because the processing happens on your device.

Non-monetizable by design. There’s no business model for a free WRS retirement estimator with no ads and no upsell to a financial product. No developer is going to build that. Generative AI makes the cost of creation low enough that the absence of a business model doesn’t matter.

That’s the philosophy behind this series and it aligns well with the philosophy of the project. Each tool starts with a real question, and exists only because it’s useful — not because it’s profitable.

The Transparent Salary Problem

This tool came out of a simple question:

What is a reasonable salary for a teaching position at a given district in Wisconsin?

My first instinct was to find the salary schedule for that district. Salary schedules used to be straightforward public documents — a grid showing exactly what a teacher earns at each combination of experience and education level. Increasingly, that’s not what I find.

Based on my own experience, confirmed by others in the field:

• Salary schedules are harder to find on public websites than they used to be.

• Districts have introduced structures like “Total Compensation” or Tiers that make it unclear what a raise from year to year actually looks like.

• Some districts describe only a process for determining pay, with vague language about how initial salary is calculated.

• Handbooks — which sometimes contain salary information — are also harder to locate online. (If you’re willing to share examples, I’d love to see them.)

None of this is necessarily intentional opacity. I’m not saying there is a coordinated effort by administrators to hide this information. But the practical effect is that a teacher evaluating a job offer, or trying to understand where their salary stands, has fewer clear answers than they should.

What the Public Data Offers — and Where It Falls Short

A different approach to answer the question is to start from the available public data. Wisconsin does make salary data publicly available through the DPI. Two sources in particular:

• The DPI Public Teacher Salary Report provides annual, school-level data including salary ranges, fringe benefits, and years of experience.

• The DPI Public All Staff Report goes deeper — individual staff members, specific assignments, actual salaries. It’s the most granular public data available.

The Teacher Salary Report is useful context but too general to answer the question of what a specific position should pay.

The All Staff Report is more useful, but working with it directly presents two problems. First, it’s genuinely overwhelming to someone who isn’t a frequent user of spreadsheets. The raw data isn’t designed for someone trying to answer a focused question. Second, that data lists individual names, which gives me pause. This is public data, and I’m not suggesting it shouldn’t be. But I’d rather focus on the numbers than on the people behind them. It’s too easy to start devaluing people for decisions about salary that they didn’t make. Teachers didn’t design the compensation system they work within. The goal here is to use data to understand and improve that system — not to scrutinize individuals.

A Note Before You Dig In

These tools are in active development. They’re designed to help you explore questions and estimate possibilities — not to replace professional financial advice or serve as the final word on any decision. If you find something that isn’t working as expected, please let me know.

The Tool

That’s what led me to build the Wisconsin Teacher Salary Analyzer.

It lets you download the public DPI data, analyze salary ranges for any Wisconsin district, filter out outliers, estimate earnings based on years of experience, and compare across multiple districts — without names, without raw data overwhelm, and without needing to know anything about spreadsheets.

If you’re a teacher evaluating a job offer, curious how your district compares to neighboring ones, or just trying to understand what the data actually says about educator pay in Wisconsin — this is built for you.

Try It — and Tell Me What You Think

Try the Wisconsin Teacher Salary Analyzer →

This tool is free, runs in your browser, and requires no account or login.

If you use it, I’d genuinely love to hear what you think. Does it answer the question you brought to it? Is something confusing or not working as expected? Are there features that would make it more useful?

Feedback — positive, critical, or just a report that something broke — helps make these tools better for everyone. You can reach me through josh@personalfinanceforeducators.com or leave a comment below.

In the last post about Pip, I explored one possible path to retiring at 55 using the Wisconsin Retirement System (WRS). This is not the only path, and it won’t be the right fit for everyone — but I think it’s worth understanding what this path can actually look like. Using the WRS Benefits Calculator, I found that with accelerated payments, Pip can retire at 55 with a consistent monthly income of roughly $3,550. That’s Pip’s floor on day one of retirement — and it stays consistent because the accelerated payment structure is designed to work together with Social Security at 62, smoothing income across that transition.

That $3,550 floor works out to about 71% of Pip’s pre-retirement gross salary of $5,000 per month. It’s a solid foundation. But what if Pip wanted to build above it? That’s where the Roth IRA comes in.

In this post I want to explore a simple question: what do modest, consistent Roth IRA contributions over a 32-year teaching career actually produce? Specifically, I want to look at five contribution levels — $100, $200, $300, $400, and $500 per month — and see how they change Pip’s retirement picture at 55.

A Note on Assumptions

Before diving in, a few things worth stating clearly:

I’m using the accelerated payments option from the previous post, with retirement at 55 as the goal. The accelerated payment structure is specifically designed so that when Social Security is added at 62, Pip’s total monthly income stays roughly consistent. In other words, $3,550 is Pip’s floor at 55, and it remains the floor after 62. This is one path. I’m hoping to explore other paths with future posts (e.g., regular payments, retiring at 57).

For Roth IRA growth, I’m using a 7.5% annual return. I generated these estimates using NerdWallet’s Roth IRA calculator, which you can access at https://www.nerdwallet.com/investing/calculators/roth-ira-calculator. I encourage you to plug in your own numbers and try out rates, annual contribution amounts, time horizon, etc. A 7.5% return is a reasonable long-term assumption for a broadly diversified index fund, but returns are never guaranteed.

For withdrawals, I’m using a 4.7% annual withdrawal rate. You may have heard of the 4% rule, a figure comes from researcher Bill Bengen’s original work in the 1990s. Bengen has since updated his research and suggests 4.7% is a more accurate figure (read about it in his new book!) I’ll use 4.7% here, but either way the point is the same: a reasonable, sustainable withdrawal rate applied to whatever Pip has saved.

A note on the contribution tiers: $100–$300 per month represents what I think of as the realistic planning range for most early educators. It is meaningful and achievable. The $400 and $500 per month tiers are aspirational targets representing a longer-term goal as career and income grow, rather than a first-year expectation. I’ll discuss where this money might come from in the next post.

As always, I’m a mathematics educator, not a financial advisor. These are illustrations, not recommendations.

What Does Pip’s Roth IRA Look Like at 55?

Pip starts teaching at 23 and retires at 55 — 32 years of contributions. Here’s what those contributions grow to, and what they can generate monthly starting at retirement.

Note: monthly pension reflects the consistent monthly income Pip can expect from retirement at 55 onward, accounting for the accelerated payment structure and Social Security at 62. Roth IRA values generated using NerdWallet’s Roth IRA calculator at 7.5% annual return.

What Do These Numbers Tell Us?

A few things stand out when I look at this table.

First, even the most conservative scenario is meaningful. At $100 per month, Pip adds $615 per month to their retirement income starting at age 55. That brings total monthly income to $4,165 — 83% of pre-retirement gross salary. For context, Pip’s take-home pay while working was likely closer to $3,800–$4,000 after taxes and pension contributions. In other words, even the smallest contribution scenario gets Pip close to — or at — full income replacement in retirement, starting at 55.

Second, you might notice there is a clear relationship between contribution and Roth IRA value. Each additional $100 per month in contributions adds approximately $156,820 to the Roth IRA at retirement, and roughly $613 per month in retirement income. This linearity makes the math intuitive: every $100/month commitment today translates to roughly $600/month in retirement income.

Third, I think the $200/month scenario is particularly compelling. At 96% of pre-retirement salary, Pip is essentially at full income replacement. For many teachers, I think $200 per month is a sweet spot — meaningful and achievable without requiring extraordinary effort.

Fourth, the $400 and $500 per month scenarios are worth knowing about for planning but not something to focus on if you have a long career path ahead. They represent what becomes possible as a career matures, income grows, and you find your groove in the teaching lifestyle.

A Note on Where the Money Comes From

When I look at these tables, a natural question arises: where does $100–$300 per month actually come from on a teacher’s salary?

One answer people often reach for is discretionary spending. Just eat at fewer restaurants, reduce a subscription, skip the latte. I understand the impulse, but I think this framing is misguided for two reasons.

First, it can come off as dismissive of the small things that make daily life sustainable. If that $5 coffee helps you feel grounded and ready for everything the classroom demands, it’s not a frivolous expense — it’s self-care. Telling teachers to cut it out misses the point.

Second, and more importantly, I think there’s a better way to think about this — one that fits more naturally with the teaching lifestyle. Teaching is a profession with built-in opportunities to generate additional income that don’t require a second job, a new employer, or monthly discipline to execute. The path to $100–$300 per month doesn’t have to mean sacrifice. It may simply mean connecting an opportunity that’s already there to a goal that matters. I’ll explore this in the next post.

The Bigger Picture

What I want readers to take away is how the pieces of this path fit together. The pension provides a guaranteed floor — income that arrives every month at 55, regardless of market conditions, and stays consistent as Social Security fills in later. Both have provisions that can adjust with inflation over time. The Roth IRA builds above that floor from day one of retirement, providing flexible, tax-free income that Pip controls completely.

Together, they create a retirement picture that is both stable and adaptable. The pension tells you what your floor is. The Roth IRA determines how high above that floor you can go.

There is also a psychological dimension worth noting. Knowing that you have a Roth IRA growing alongside your pension changes how you feel about your financial stability. It gives you peace of mind when sudden shifts happen (e.g., illness, losing a job). It also gives you options for how you spend in retirement. Maybe you draw from it heavily in your late 50s and early 60s (your go-go years). Maybe you use it for a large purchase or a once-in-a-lifetime trip. Maybe you leave some of it to your family. The floor is there either way. The Roth is what gives you room.

As I noted, this is one path among many. In future posts I’ll explore what happens if Pip uses regular payments instead of accelerated, waits until 57 to retire, or adjusts their contribution rate over time. Each path tells a different story and serves a different set of goals.

For now, the takeaway is simple: $100 a month, started early, makes a meaningful difference at 55. And in the next post, I’ll make the case that teaching already gives you a natural way to find it. Extra duties, club advising, mentoring stipends, covering classes — these are already part of the landscape of the profession, and they pay real money.

If you enjoyed this post, please share it with a friend! As always, I’m a mathematics educator, not a financial advisor. This post is for educational purposes only. If you have questions or topic ideas, reach out at personalfinanceforeducators@gmail.com.

The report points clearly to retention—not recruitment—as the core problem. But there’s a factor the data can’t fully capture: the cost of financial confusion on early-career decisions.

My latest post argues that personal finance literacy belongs in teacher induction programs—alongside mentoring, workload support, and the other tools we know help educators stay.

Read the full post here.

If you have questions or topic ideas, reach out at personalfinanceforeducators@gmail.com or drop a comment below.

~Josh

The concern around AI disruption is real and growing. However, if you listen to some of the loudest voices in tech, they might convince you that teaching is a legacy profession that is ripe for disruption by a more efficient, adaptive algorithm.

As someone who has spent my career in and around schools, and as someone who looks at the integration of mathematics and technology, I see a different story. History is littered with “teacher-replacement” technologies that promised to democratize expertise and render the classroom obsolete. In the 1960s, we had the Midwest Program on Airborne Television Instruction (literally broadcasting lessons from a plane). In the 2010s, we had the MOOC revolution.

In every case, the technology became a useful tool, but the “replacement” never happened.

In my latest blog post, AI and Teaching: Why I’m Not Losing Sleep, I discuss my perspective that: teaching is a relationship profession that uses content as its medium.

While AI is categorically more sophisticated than previous tools, I don’t see it as replacing the “relational core” of teaching—the moral authority, the accountability, and the diagnostic judgment that comes from knowing a student’s concerns and potential.

If you are a new teacher or someone planning a long-term career, I believe you should be reasonably confident. The digital flood is coming, but for those of us centering our work on human relationships, I think the levee will hold.

If you have questions or topic ideas, reach out at personalfinanceforeducators@gmail.com or drop a comment below.

~Josh

The latest episode of the Personal Finance for Educators podcast is out!

In this episode I make the case for why the Roth IRA is one of the best financial tools available to teachers. I discuss the basics of how a Roth IRA works, why the tax benefits are generally a good fit for educators, and how it can complement a pension in retirement. If you’re a teacher wondering where to put your money beyond your pension, this is a good place to start.

🎙️ Listen to it on Spotify | Apple Podcasts

This episode is based on my most recent blog post, The Teaching Lifestyle and the Roth IRA: A Perfect Pair, which goes deeper on the details and is a good reference to return to as you think through your own situation.

📖 Read the blog post

If you have questions or topic ideas, reach out at personalfinanceforeducators@gmail.com or drop a comment below.

~Josh

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If you've found your way here, chances are you're an educator looking for ways to think more intentionally about your financial life. Welcome!

My name is Josh. I’m a mathematics educator based in Wisconsin. My professional focus is on supporting preservice and in-service educators as they engage in the meaningful work of teaching. A few years ago, I started noticing something: most of my preservice teachers consistently lack access to clear, practical, educator-specific financial guidance. It certainly isn’t something we teach them in a typical teacher training program. Moreover, having worked in education for over 20 years, I’ve seen time and time again the generic advice that doesn’t account for the realities of a teaching lifestyle. So I started the Personal Finance for Educators project to fill that gap.

I like to think of this project as a teacher’s lounge for teacher personal finance. It’s an informal space with some scattered tables, mismatched chairs, and a refrigerator that needs some attention. There are no sponsors, no conflicts of interest, and no monetization plans. You won’t find anyone trying to sell you anything here. It’s just me (and maybe a friend or two) sharing what I’ve learned, with the goal of helping other educators achieve financial stability and freedom. So, pull up a chair, pour yourself a cup of coffee, and enjoy some of the treats that a colleague brought in.

What the project looks like

Currently, Personal Finance for Educators has three main components:

The blog (personalfinanceeducators.com) is where most of the long-form content lives. Posts cover topics like estimating your pension benefit, understanding your employee handbook, and thinking through the financial dimensions of the teaching lifestyle. I’ve been working on it since mid-2024 and have built up a small library of posts.

The podcast launched in summer 2025 and is available on Spotify and Apple Podcasts. It covers some things the blog does and some things it doesn’t. If you haven’t listened yet, that’s a great next step.

I’ve also been doing presentations for educators as opportunities arise. If you’re interested in bringing something like that to your school or program, reach out.

Why Am I Starting A Substack?

In a word: reach. The blog, podcast, and presentations each serve a purpose, but they operate as separate spaces. Substack gives me a way to connect the pieces and get new content in front of more educators more efficiently. If it also helps build a bit of community along the way, even better.

What to do next?

If you’re new, subscribe to the substack and then start with the blog or pull up the podcast. If you have questions or topics you’d like me to cover, I’d like to hear them. Send me an email at personalfinanceforeducators@gmail.com

If you are already aware of this project and have found content useful, subscribe to the substack to be notified of new posts and share it with a colleague or two (or four!).

Thanks for being here.

~Josh