Tag Archives: investing

Why We’re Still Choosing to Rent

Too often, when people think about housing costs, they only look at the mortgage payment. In reality, the cost of owning a home is much broader. It includes principal and interest, property taxes, insurance, utilities, maintenance and repairs, HOA fees, and the opportunity cost of having so much money tied up in a single asset.

On a typical $300,000 home, those annual carrying costs can easily be more than $50,000 and look something like this:

CategoryAnnual Cost
Mortgage (Principal & Interest)$18,000
Property Taxes$5,000
Homeowners Insurance$2,500
Utilities$8,400
Maintenance & Repairs$6,000
HOA Fees$1,200
Opportunity Cost of Equity~$12,000

(For the purpose of looking at our own situation, I’m going to ignore the opportunity cost. Yes, our house has almost doubled in value since we bought it, but we purchased it back in 2001. Once inflation is taken into account, the appreciation is barely keeping up with inflation.) Anyway, here are our actual monthly housing costs from when we chose to pay off the house to last year..

Category20192025
Mortgage & Interest$950$0
Property Taxes$400$600
Insurance$150$300
Utilities$400$700
Maintenance & Repairs$300$600
Total$2,200$2,200

After paying off our mortgage, our housing costs were…

…exactly the same.

Within five years, increases in taxes, insurance, utilities, and maintenance have completely absorbed the savings from the eliminating principal and interest payment. The “cost to carry” a house just keeps climbing and there is no relief in sight. 

Now, if we wanted to stay in the same four-bedroom suburban Dallas house forever, ownership would almost certainly still beat renting. Landlords want to make a profit, after all. But that’s not the comparison we’re making.  It is not apples to apples, but apples to grapes. We’re comparing a house we no longer need with a lifestyle we actually want.

Katie and I don’t need four bedrooms. We don’t need a yard to maintain, proximity to schools, or a garage full of stuff. We don’t even need (or want) to stay in the same place year-round. By downsizing, taking advantage of geographic arbitrage, and remaining flexible enough to move when rents rise or our interests change, we’ve been able to build a lifestyle that costs less while giving us experiences we value more.

Some people push back on our decision to rent, and I get it.  For many, homeownership represents stability, permanence, and security. Some of our best friends are perfectly happy to nest in the same house they’ve lived in for decades, surrounded by memories and possessions, until they are wheeled out (hopefully many years from now).

There’s nothing wrong with that.  For them.

For us, though, the opportunity to wake up overlooking downtown Omaha one season and the Atlantic Ocean the next isn’t a compromise or a way to save money. It’s exactly what we were hoping for. Having the freedom to explore different communities and different ways of living isn’t a bug in our plan. It’s one of its biggest features. 🙂

The Takeaway

I think homeownership is often oversold as a path to wealth.. It can be a good tool for forced savings, but it isn’t the only path to financial success, and it isn’t automatically the right answer for every stage of life.

Our priorities have changed. We value flexibility over permanence, experiences over square footage, and optionality over accumulation. Renting while we slow travel lets us experiment with different communities, avoid unexpected maintenance headaches, and adjust our plans whenever life changes.

Will we own another home someday? Maybe. But after this first year on the road, we’re more convinced than ever that renting isn’t a temporary compromise while we figure things out.  For us, it’s exactly the lifestyle we’ve been trying to buy all along.

The Pillars of Financial Independence

I just finished listening to a ChooseFI podcast where Brad Barrett and Jackie Cummings Koski went back to the basics of Financial Independence and it made me reflect on my own FI journey. I’ve been listening to ChooseFI since it first started almost ten years ago, and the idea of the “pillars of FI,” or the basic principles that, if embraced, will inevitably lead to financial independence really resonated with me on my path to early retirement.

The FI community doesn’t use the language of these pillars as much anymore, but it stuck with me. Over the years, Katie and I have tried each of these pillars out with varying degrees of success. Today’s podcast conversation prompted me to take stock and reflect: which ones actually made the biggest difference for us?

1. Low-Cost Index Fund Investing

Instead of trying to beat the market, we stuck with broad, low-fee index funds. This alone saved us a fortune. Early on, I got suckered into a high-fee annuity that bled me dry with commissions and surrender charges. Switching to index funds like VTSAX completely changed our trajectory.  Our nest egg would be only a fraction of what it is today if we hadn’t gotten smarter about this one.

2. Affordable Housing

Housing is usually the biggest expense, so keeping it under control matters. Many in the FI world “house hack,” but being a landlord never appealed to me (One of the reasons we are traveling now is so I don’t have to take care of my own home, much less one that renters are living in 🙂).  Our version of this pillar was simple: we bought an older starter home when we got married and resisted the urge to upgrade along the way.. It wasn’t glamorous, but it was cheap, easy to maintain, and close to work. That decision freed up thousands each year for investing.

3. Buy Gently Used Cars

Cars lose value fast. We’ve driven used cars for 8–14 years each (and counting.  Bertha is still chugging along as our back in Dallas car), avoiding car payments while watching our savings grow. No regrets here—this one was an easy win for us.  What is the point of having a pretty car and then parking it in a high school lot every day? 

4. Crush Your Grocery Bill

Early on, meal planning and cooking at home saved us hundreds every month. Now that we’re in a more comfortable spot (and aren’t feeding two kids), we’ve loosened up on this one. It was a powerful lever in the beginning, though.

5. Tax Optimization

When we could, we took full advantage of accounts like 403(b), 457(b), but we prioritized funding our Roth IRAs. As teachers in relatively low tax brackets, paying taxes up front made more sense to me than deferring them. I can’t imagine our tax rate being much lower in the future.

6. College Hacking

We cash-flowed our own advanced degrees with side hustle money. For our boys, we wanted them to have skin in the game so we set a boundary: we’d cover the equivalent of two years at community college plus two years at a state school. If they graduate for less, they keep the difference. Kid #1 used every penny; kid #2 has a path to graduate early and spend the difference on grad school or pocket the savings. Either way, the cost was predictable for us.

7. Travel Rewards

This hasn’t necessarily sped up our FI path, but it certainly has made the journey more fun. In our version, we’ve leaned heavily on travel hacking to fund dozens of budget-friendly trips rather than blowing money on a few luxury ones.

8. Cut the Cord and Premium Cell

We ditched cable years ago, but have added so many streaming services back that I don’t think we actually saved much. Same with cell phones.  We could optimize here, but at this point, we’re fine with the splurge.

9. Multiple Income Streams

This was huge for us.  Some years we had the equivalent of three full time salaries!  Side hustles paid for extras (like advanced degrees and travel) and also boosted our investments. Our family rule: half of any side hustle income went to the family budget for extra fun or unexpected expenses, half was personal money for the earner. That balance kept us motivated and moved us much faster toward FI.

10. Savings Rate & The 4% Rule

At the end of the day, Financial Independence comes down to saving enough so your investments can cover your expenses. Some years we hit a 50% savings rate; other years, one or both stepped away from W2 work to invest time into a side business and our rate dropped. The point is, we always had the basic framework in mind: spend less, invest more, and track progress against the 4% rule.

Looking back, every pillar helped in some way, but for us the biggest levers were multiple income streams, keeping housing and car costs low, and investing in low-cost index funds. Those three principles alone got us most of the way to where we are.

So what about you? Have you seen this list before? Which of these pillars could have the biggest impact on your financial path?

yellow bicycles

Urban Biking & Slow Travel: My New Favorite FI-Friendly Habit

A lot of people in the FIRE community are passionate about biking.  Some even go as far as replacing one (or both!) of their cars with a bicycle. While I admire that level of commitment, I’ll be honest: I’m not quite that gung-ho. Our slow-travel lifestyle isn’t exactly conducive to hauling a personal bike across the country, and I’m definitely not strapping one to a plane 🙂 

But here’s what has surprised me: using urban bike-share programs has become one of my favorite ways to explore a city. It’s the perfect “middle ground” for someone like me that is interested in the FI mindset, but also trying to live practically while bouncing from Honolulu to Kansas City to Omaha to Boston. This Fall alone, I’ve used bike shares in every one of those cities, and each experience has reinforced how useful (and fun!) they can be.

It expands your reach.
Walking a city is great, but it can limit your radius to a few miles. With bike share, suddenly the entire waterfront, the next neighborhood over, or that park you’ve been meaning to visit becomes accessible without giving up the pedestrian feel of truly experiencing a place. It’s slower and more immersive than driving, but infinitely faster than walking. A perfect sweet spot.  One thing I like to do is to grab a rental bike and go 4-5 miles in one direction to get a feel for an area, park the bike, then work my way back on foot.

It saves money.
Bike share programs are shockingly affordable. A few dollars unlocks a full day of mobility with no gas, no parking fees, no rideshares, etc.  In Omaha, for example, the Heartland month pass got me unlimited access to bikes throughout the metro area for around $20.  And while I’m not trying to replace a car with biking anytime soon, even occasional use can offset Uber rides or rental car time. For travel, especially slow travel, those savings add up.

It’s good for the environment.
One less car trip means fewer emissions. It’s a small thing, but choosing bikes over short car rides is exactly the kind of low-friction habit that makes the FI lifestyle more sustainable both financially and environmentally.

And honestly… riding a bike is just fun.
There’s something childlike and joyful about pedaling through a new part of the city. No agenda. No stress. Just moving your body, noticing small details, and feeling connected to the place you’re exploring.

As I continue this slow-travel journey, bike-share programs have quietly become one of my favorite tools. They let me explore more, spend less, and stay present in the spaces I’m temporarily calling home.

If you haven’t tried urban biking yet, especially while traveling I encourage you to give it a shot. Start with a short ride along a river, a downtown loop, or a neighborhood you’ve never visited. You might find, like I did, that it’s one of the simplest ways to make a city feel more accessible, more affordable, and a whole lot more fun.

CampFI: Four Ideas That Changed the Way We Think About Financial Independence

Earlier this month, Katie and I had the opportunity to present at CampFI Rocky Mountain (week 2.5) about our journey after reaching financial independence. We talked about our experiment with “slomadic” living, spending several months at a time in different parts of the country while trying to figure out what we want this next phase of life to look like.

Typically, people ask us about the logistics. How do we find housing? What do we do about mail? How do we handle healthcare, taxes, or travel rewards?  Those are interesting questions, but they aren’t really the biggest lessons we’ve learned. For this presentation we decided to focus on four themes that kept showing up over and over again throughout our journey. They have influenced almost every major decision we’ve made this year.

More Than One Right Answer

I love the Financial Independence movement, but the focus on optimization can lead to analysis paralysis.  Plus, as teachers, Katie and I are well aware of the multiple choice mentality that has conditioned many of us to believe that every question just has one correct answer.

Luckily, life doesn’t work that way. Should you pay off your house or invest? Retire early or keep working? Move across the country or stay close to family? The answer is often, “Yes :)”  

One of the most freeing ideas we’ve embraced is that decisions are rarely binary.  There are usually several good choices. We can be happy choosing A, B, OR C.  Once we accept that, decision-making becomes much easier.  We spend a lot less time trying to optimize every single variable and more time asking whether a choice fits the life that we are trying to build.

Freedom Is Better Than Wealth

This may be the biggest surprise of our FI journey. Looking back, many of our best financial decisions weren’t really about maximizing money. They were about maximizing options.

Katie left a higher-paying corporate career because education gave us work we enjoyed and schedules that fit our family. Later, side hustles, teaching online, and consulting gave us even more flexibility. Instead of making one giant leap into retirement, we gradually reduced the work we no longer enjoyed while keeping the parts that were still meaningful.  

The crazy thing?  In chasing freedom, the money followed naturally.  Financial independence didn’t simply increase our net worth. It increased our ability to say yes to opportunities (and our ability to say no). That has turned out to be far more valuable than just chasing dollars.

Simple Is Better Than Complex

If you’ve followed this blog for very long, you’ve probably noticed this theme already.

Simple investments. Simple travel. Simple spending. Simple housing.

I enjoy reading about complicated financial strategies just as much as the next FI nerd, but I’ve learned that complexity often creates more opportunities for mistakes. The same has been true in our personal lives. I can understand the appeal of real estate investment or the concept of RV travel, but the devil is in the details.  In both cases there are just too many variables and opportunities for friction for us right now.  We’ve realized we don’t need a large house, multiple properties, elaborate travel plans, or a complicated investment portfolio to be happy.

Simple systems free up mental energy for the things that actually matter.

Zero-Based Thinking

This has probably become our favorite mental model. Every once in a while, we like to ask ourselves a simple question:

“Knowing what we know today, would we make the same decision again?”

Sometimes the answer is yes, but sometimes it isn’t.

I really enjoyed teaching at the university, but after COVID permanently shifted the bulk of the teaching online, it no longer fit what I wanted to do. The four bedroom house by the elementary school and across the street from the community pool was perfect while raising kids, but isn’t the house two empty nesters need today.  The dependable sedan was great for commuting in city traffic, but not ideal for cross country moves.

Even our current experiment with slow travel is really just one long exercise in zero-based thinking. Instead of assuming we know where we want to spend retirement, we’re intentionally testing different possibilities before making another long-term commitment.

Looking Ahead

When we accepted CampFI’s invitation to speak, my first draft had us spending most of our time talking about geo-arbitrage, budgeting, and logistics.  Instead, we found ourselves talking about philosophy. How do you make decisions? How do you define success? What kind of life are you actually trying to build?

I hope the presentation was helpful for the people who attended, but I also hope these four ideas are useful for anyone pursuing financial independence, whether retirement is five years away or fifty.  After all, FI isn’t just about accumulating enough money to stop working. It’s about building a life that gives you the freedom to make the choices that matter most.

Are We Doing “Slow Travel” Wrong?

My amazing wife, Katie, and I have been having a bit of a debate lately.

It centers around the concept of “slow travel” and whether we’re actually doing it.

We used to spend a lot of our travel time rushing from place to place. Airports, rental cars, hotel check-ins, repeat. That phase of life had a goal. We wanted to get our boys to all 50 states before they graduated, and we (almost) did it. It was fast, chaotic, and a lot of fun.  Now we are in a different phase of life and things are different. At least, they’re supposed to be.

What Is Slow Travel?

Generally speaking, slow travel is an approach to travel that emphasizes extended stays, local experiences, and a more relaxed pace instead of rushing through a checklist of destinations. (In other words, the opposite of what we did when we were knocking out all 50 states during our Summer breaks 🙂) In our version, we stay in an area for 3-6 months and explore potential locations for our forever home.

From a financial independence perspective, slow travel also makes a lot of sense for us. It replaces short, expensive trips with longer, more sustainable stays and substitutes everyday living in a new location for traditional vacations. It also lets us take advantage of geographic arbitrage, using the local cost of living to control our expenses.  In this model, at some point, the line between travel and normal life starts to blur.

That part has been working great for us so far.

Where It Gets Complicated

But what happens when you’re living somewhere for three to six months… and you want to take a trip?  Maybe I want to go to a conference.  Or we want to take a quick road trip. Maybe there’s a place we want to see, but have no interest in living in.  Are we betraying our “slow travel” ideals?

Probably Not

The more we’ve talked about it, the more it feels like a debate about semantics.  After all, it would be a little silly to let a definition stop us from doing something we want to do, especially after working so hard to create optionality in our lives.

Slow travel works well for us as a general approach. It helps us slow down, spend less, and actually experience the places we visit.

But it’s not going to stop us from:
• Taking a quick sightseeing trip when we just want an overview
• Visiting a more expensive place for a few days instead of a few months
• Or making a one-time trip somewhere we simply want to see

The Bottom Line

“Slow travel” is a useful framework for us, not a law.  “More what you’d call ‘guidelines’ than actual rules” 😉  In the end, financial independence isn’t supposed to limit your choices, but to give you more of them.

Lessons From the First Year: Geography Does Not Automatically Change You

We just finished our first year of “slomadic” living, trying out different parts of the country and different styles of life with urban living in Omaha, Nebraska and beachside living in Myrtle Beach, South Carolina. Along the way we learned a lot, but one of the biggest lessons has been surprisingly simple:

No matter where you go… there you are.

It is a cliche, but changing locations does not automatically create a different life or identity.

I think many people, especially those dreaming about retirement or relocation, just assume that a new environment will naturally transform them. Move near the beach and suddenly you become healthier, calmer, and outdoorsy. Move downtown and you become more social and cultured. Relocate to the mountains and somehow life becomes simpler and more peaceful.

Sometimes circumstances absolutely help. But our experience so far is that most of our internal habits traveled with us.I exercised about the same amount in Omaha as I did in Dallas. I was not magically better at meeting new people in South Carolina than I was in Nebraska. My personality, routines, and habits all packed themselves into the car and came with us 🙂

That realization has actually been helpful. Financially, this matters because ,in retirement, people often spend aggressively trying to solve problems that are not primarily financial:

  • burnout
  • dissatisfaction
  • loneliness
  • boredom
  • stress
  • unhealthy routines

A new house, a different city, or a dream retirement destination may improve your circumstances, but it does not automatically create personal transformation. That feels like an important counterbalance to some FIRE narratives. Financial independence creates capacity for change, but not automatic change itself.

FU money can remove constraints. It can buy flexibility, autonomy, and time. It can allow you to leave situations that are making you miserable. Those are incredibly valuable things. But money alone cannot independently create:

  • meaning
  • structure
  • relationships
  • discipline
  • purpose
  • community

Those things still require intentional effort, regardless of location.

In some ways, slow travel has actually highlighted this lesson more clearly for us because each move acts like a little reset button. You quickly discover which parts of your life were truly tied to location and circumstance and which parts were really tied to you. For me, one of the biggest lessons from year one has been realizing that while geography can support growth, it cannot substitute for it.

The encouraging side of that realization is that happiness may be more portable than we sometimes think. If you already enjoy simple routines, movement, exploration, reading, or spending time with people you care about, those things can travel with you almost anywhere.

The challenging side is that unresolved issues tend to travel too 🙂  

Lessons From the First Year: Lifestyle Inflation Has a Hedonic Ceiling

We just finished our first year of “slomadic” living, trying out different parts of the country and different styles of life with urban living in Omaha, Nebraska and beachside living in Myrtle Beach, South Carolina. One of the lessons we have learned has been to be careful about making long-term decisions based on things that feel amazing in the short term but quickly become routine.

The ChooseFI community talks a lot about “hedonic adaptation” as one of the biggest hidden obstacles to financial independence. The basic idea is that people quickly adjust to improvements in lifestyle, income, possessions, or comfort. What initially feels luxurious slowly becomes normal, and the emotional boost fades much faster than the bill.

That idea connects directly to lifestyle inflation. As income rises, spending tends to quietly rise along with it. Bigger houses, newer cars, nicer hotels, upgraded neighborhoods, subscriptions, dining out, and premium experiences all start to feel justified because they are now “affordable.” The danger is that expenses expand just as fast as earnings, delaying financial independence indefinitely.

For most of our journey toward FI, Katie and I worked hard to avoid that trap. We tried to frame spending decisions around buying freedom instead of accumulating “stuff.” We were never particularly interested in keeping up with the Joneses, and we scratched our itch for luxury experiences without permanently inflating our lifestyle was through travel hacking using points and miles rather than higher spending.

It gets tougher in a nomadic life, though.  Instead of making one decision to buy a cheer house and then benefiting for years, every relocation gives us another opportunity to overspend.  So our challenge keeps resetting itself every time we move.

When you arrive somewhere new, it is very easy to convince yourself that certain upgrades are absolutely worth it. A slightly nicer neighborhood. A better beach view. A more walkable location. A premium gym. Better weather. More restaurants nearby. And honestly, some of those things really do improve quality of life.

The problem is that emotional adaptation happens quickly.

The ocean view that feels magical the first week may become the thing you barely notice while washing dishes. The rooftop lounge becomes background scenery. The upgraded apartment starts to feel normal instead of special. Financially, that matters because recurring lifestyle costs persist while emotional returns decay.

That does not mean upgrades are bad. Some improvements absolutely create durable satisfaction. Better health, lower stress, walkability, proximity to friends, and environments that align with your values can all be worth paying for. The key lesson for us has simply been to become more intentional about distinguishing between upgrades that create lasting value and upgrades that mainly create temporary excitement.

I think this becomes especially important in retirement and FI planning because permanent fixed expenses compound risk over time. Things like second homes, timeshares, boats, RVs, luxury neighborhoods, and high-maintenance lifestyles may sound exciting initially, but they also create ongoing financial obligations long after the novelty wears off.

Ironically, one of the things we are learning is that flexibility often produces more happiness than permanent escalation.

Temporary access to desirable experiences can outperform ownership both financially and psychologically. Spending a few months living near the beach may deliver much of the same joy as owning beachfront property, but without the taxes, insurance, maintenance, and long-term commitment. Visiting interesting places, rather than permanently upgrading every aspect of life, may actually preserve more appreciation and excitement over time.

At least for me, that has been one of the biggest lessons from year one. Sometimes the sweet spot is not maximizing luxury. It is creating enough flexibility that life continues to feel interesting before adaptation quietly turns everything back into normal

Lessons From the First Year: The Value of Temporary Living

We just finished our first year of “slomadic” living, trying out different parts of the country and different styles of life. So far that has included urban living in Omaha, Nebraska and beachside living in Myrtle Beach, South Carolina. Along the way, we have learned a lot, but one of the biggest lessons is that there are real advantages to medium-term stays and temporary living arrangements.

One of the big benefits of snowbirding, slow travel, sabbaticals, or extended rentals is that they allow you to test a future life before committing your capital to it. That may sound obvious, but I think many people underestimate how different a place can feel when you are actually living there instead of simply visiting.

That is the real financial insight for me: experience can be more valuable than ownership.

At first glance, renting for a few months may seem financially inefficient compared to buying. After all, you are paying rent without building equity. Because we still own our home in Texas, you could certainly argue that paying for temporary housing in another location at the same time is not the most optimized use of our money.

And mathematically, that is fair.

But when I compare a few months of rent to the potential cost of making a major relocation mistake, the equation changes pretty quickly. 

  • Buying in the wrong area
  • overestimating how often you will use a second property
  • Purchasing a “money pit” timeshare, RV, or boat that you won;t use enough
  • Misjudging the climate or pace of life
  • Locking yourself into a lifestyle you only liked in theory or in the short term

All of these can become enormously expensive lessons. In comparison, a few months of rent feels like cheap insurance 🙂

One thing we have learned repeatedly is that visiting a place and living in a place are completely different experiences. Vacations tend to highlight scenery, attractions, restaurants, and novelty. Daily life highlights grocery stores, traffic patterns, workout options, healthcare access, weather, and whether the rhythms of the place actually fit your personality. Those ordinary Tuesday factors matter a lot more than most people realize.

I think this idea is especially powerful for people pursuing financial independence or retirement. Many people spend years optimizing for a future life they have never actually tested. They dream about living in an RV, sailing around the world, relocating to the mountains, moving to a beach town, or settling into downtown urban life, but then commit large amounts of money before figuring out whether they truly enjoy the reality of those lifestyles.

Short-term trials create clarity. They reduce the odds of making expensive permanent decisions based on fantasy instead of experience. That may be one of the biggest lessons from our first year. Sometimes flexibility is more valuable than optimization, especially while we are still figuring out what kind of life we actually want to build.

How Can Public School Teachers Retire?

Many of my peers in public education are financially, intellectually, and emotionally unprepared for retirement.  They are in their 40s, 50s, and even 60s, yet many have not built substantial independent retirement savings. Instead, they are relying almost entirely on their state pension systems to support them for the rest of their lives.

Personally, I will be grateful for my pension when I qualify, but I don’t fully trust state governments to protect my long-term financial future. In Texas, for example, teacher pensions have no automatic cost-of-living adjustment (COLA). That means inflation rapidly attacks the value of your pension every single year.  A pension that feels comfortable today may feel very different 15 or 20 years into retirement.  Just think about living, today, on a percentage of what you earned 20 years ago.  Yikes!

That’s why I believe teachers need to think beyond simply “earning a pension.” If you want options, flexibility, and the ability to live a rich and meaningful life later on, you need a strategy to take care of yourself independently.

One possible “catch-up” strategy is surprisingly simple:

Stop teaching in public schools.

No, seriously.

I understand the inertia. Staying in a system you know is emotionally comfortable. Many teachers also feel a deep sense of responsibility to public education and the students they serve. And honestly, our public schools desperately need experienced, high-quality educators.

But financially?

The math can become very compelling once you become pension eligible.

The Power of “Double Dipping”

Many public school teachers reach a point where they qualify for full retirement benefits under systems like Teacher Retirement System of Texas through the “Rule of 80”: where they are eligible to retire when their years of service and age add up to at least 80.

For example:

  • Age: 55
  • Years of service: 25
  • Salary: approximately $80,000

Under the Texas pension formula, the annual pension would be roughly:

P=0.023×(Years of Service)×(Average of Highest 5 Years)

In this example, that works out to approximately:

0.023×25×78,000≈44,850

or about $45,000 per year for life.

Now here’s where things get interesting.  Suppose that teacher retires immediately and takes a second full-time job at a private school, small college, educational company, or nonprofit making $60,000 per year.

Suddenly, their income becomes:

Income SourceApproximate Amount
Pension$45,000
Second Career$60,000
Total$105,000

Even assuming that the teacher takes a paycut to move into a different position, that teacher just increased their effective income from $80,000 to over $100,000 per year. 

Immediately.

“But Won’t My Pension Be Bigger If I Stay?”

Sure.  Every additional year worked increases the pension. In our example, staying one more year might increase the annual pension by roughly $2,000 per year for life.

At first glance, that sounds compelling.

But here’s the catch:

To earn that extra future pension income, the teacher gave up:

  • one full year of pension payments now (~$45,000)
  • plus the higher combined income available through a second career

In this example, staying another year in public education means choosing:

OptionAnnual Income
Continue teaching$80,000
Retire + second career$105,000

So the teacher effectively gives up about $25,000 today in exchange for increasing future pension income by about $2,000 per year later.

That creates roughly a 12-year payback period after retirement before the decision to stay actually “wins” financially.  That doesn’t make staying wrong. but it does mean the decision deserves deeper analysis than many teachers give it.

Another major factor that has changed recently is the repeal of the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO). For decades, many public school educators were discouraged from pursuing Social Security-covered work because those rules could dramatically reduce or even eliminate the Social Security benefits they had earned through other employment. With those provisions now repealed, a teacher who retires from a public pension system and then works in a private school, college, nonprofit, or corporate setting may also significantly increase their future Social Security Administration Social Security benefits.

That doesn’t just offset potential pension increases.  It also creates an additional retirement income stream beyond the pension and personal investments. More importantly, unlike many teacher pensions, Social Security includes annual cost-of-living adjustments (COLAs), helping protect purchasing power against inflation over time. For many educators, this creates a much more diversified and resilient retirement strategy: pension income, Social Security income, and personal investments all working together instead of relying almost entirely on a single state pension system.

The Emotional Side of Retirement

For many educators, the biggest challenge is not math.

It’s identity.

Teaching becomes who we are. The routines, the calendar, the mission, the relationships, the feeling of being needed.  Those things can be hard to walk away from and many teachers subconsciously assume retirement means “stopping work entirely.” 

But for many educators, a better model may be to retire from the pension system, but continue meaningful work elsewhere to reduce stress, regain flexibility, and dramatically increase savings potential.  Some people even use geographic arbitrage by moving to another state, working long enough to vest in a second pension system, on top of double dipping.

The Real Opportunity

Of course, this strategy only really helps if the increased income is used intentionally.

If you simply inflate your lifestyle, buy more stuff, and spend every extra dollar, you may still end up financially stressed later on. The better option?

Use the increased income to rapidly build investments and make up for years of low retirement contributions. A teacher who suddenly increases their household income by at least $20,000–$30,000 per year and consistently invests the difference can radically transform their long-term financial picture.

The pension becomes a foundation rather than the entire plan. And that creates something many educators desperately need:

Options.

Tax Time!

I appreciate the classic joke that always circulates this time of year…

Government: “You owe us money. It’s called taxes.”
Me: “Do you know how much I owe?”
Government: “Of course, but you have to figure it out for yourself”
Me: “I’ll just pay what I think is right?”
Government: “Yes, but guess wrong and go to jail.”

Despite the sentiment, I actually think tax season is a useful annual check-in on our finances and our planning.

I just finished filing our taxes for the year. I’m no expert, but I hired professionals for a few years and did our return alongside them. When we consistently came up with the same results, I figured I’d keep doing it myself.

A few takeaways from this year:

Our General Drawdown Strategy

Now that we are “retired,” our income doesn’t just show up on a W-2. We build it intentionally. Our general order:

  1. 1099 consulting income first

 Uncle Sam really does encourage small business. If we bring in, say, $30,000 in 1099 revenue, after legitimate business expenses (unreimbursed travel expenses, software subscriptions, home office, mileage, etc.), that might drop to $22,000–$24,000 of net income.

  1. Fill the rest of the 12% bracket with 457 distributions 

(from my University job.  One of the occasional perks of working in education is having access to the money I invested in this type of account penalty free before 59 1/2)

For 2025, married filing jointly:

  • Standard deduction ≈ $30,000
  • 12% bracket tops out around $94,000 taxable income
  • Which means gross income can be roughly ~$124,000 before hitting the 22% bracket

But we rarely go anywhere near that. This year we targeted closer to $70,000–$75,000 of total MAGI.

Example:

  • $30,000 net 1099 income
  • $40,000 from 457
    = $70,000 total income

After the ~$30,000 standard deduction, only ~$40,000 is taxable and it is almost entirely in the 10% and 12% brackets.  That’s intentional. We are using low brackets now before our pensions start in a few years..

457 vs. Long-Term Capital Gains

We could sell appreciated investments and realize long-term capital gains. This is a common recommendation for early retirees since, for married filing jointly, the 0% capital gains bracket runs up to roughly $94,000 taxable income. With the standard deduction, you can often realize almost $100 thousand in long-term capital gains and pay $0 federal tax.

That’s powerful.  It is also a great example of how the system is skewed towards wealthy stock owners rather than wage earners.  Even the next bracket for LTCG is only taxed at 15% 🙁   But here’s the wrinkle for us, and many others:

ACA subsidies create a “hidden tax bracket.”

ACA subsidies phase out based on Modified Adjusted Gross Income (MAGI) as a percentage of Federal Poverty Level (FPL).

For a household of 3, 2025 FPL is roughly $25,820.

  • 200% FPL ≈ $51,640
  • 250% FPL ≈ $64,550
  • 300% FPL ≈ $77,460

If we let MAGI creep from $64,000 to $78,000, we might:

  • Lose thousands of dollars in premium subsidies
  • Effectively face a marginal rate north of 20–30% when you combine taxes + lost subsidies

That’s the “hidden bracket.” So even though capital gains are taxed at 0%, they still raise MAGI — which can cost us real money.

ACA Subsidies: A Real Planning Tool

One of the most frequent questions we get about retirement is healthcare. We’re currently using the ACA. Even without subsidies, we’re getting a better plan for about the same price we paid as public school teachers in Texas (which tells you how bad public educator plans in Texas are).

This year we deliberately stayed just below a key subsidy threshold. Example:

If our MAGI had been:

  • $64,000 → strong subsidy
  • $72,000 → meaningfully reduced subsidy

That $8,000 difference in income might have cost us $2,000–$3,000 in lost premium assistance.

The biggest wildcard in our planning right now is the return of the ACA “subsidy cliff.” Democratic policies provided “enhancements” so that subsidies gradually phased out as income increased, and even households above 400% of the Federal Poverty Level (FPL) still received some help if premiums exceeded a set percentage of income. Despite the recent shutdown, the Republican party held firm on removing those enhancements so the old rule is back: cross 400% of FPL by even one dollar and subsidies drop to zero. For a household of three in 2025, that line is roughly $103,000 of MAGI. If your income is $102,900, you might receive thousands of dollars in premium assistance. If it’s $103,100, you get nothing and will owe the entire subsidy back at tax time. That creates an extreme marginal “tax” on just a few extra dollars of income, which is why we have to be careful about managing MAGI. It’s not just about income tax brackets anymore; it’s about avoiding a cliff that can turn a small planning mistake into a five-figure swing.

This year was good practice.  Not only was it the last year of enhancements before the cliff returns, but In a few years, when our household drops from 3 to 2 and my pension income starts, those margins will matter even more.

State Taxes: There’s No Free Lunch

At tax filing time, I do have a brief moment of gratitude that we are official residents of Texas and don’t pay a state income tax. When your federal return is finished and there’s no separate state return to file, it does  feel pretty good.  For a moment. Then I remind myself: Texas absolutely gets its revenue.

Even now, in a lower-income early retirement phase, we still pay:

  • Property taxes are often in the 1.8–2.5% range.  On a $300,000 home, that’s $5,400–$7,500 per year.
  • State + local sales tax of 8.25% in the Dallas area, which is among the highest combined sales tax rates in the country.

And unlike an income tax, these are regressive and don’t scale neatly with our earnings.

If our income drops from $120,000 to $60,000, the property tax bill doesn’t get cut in half. The county doesn’t care that I’m strategically harvesting long-term capital gains or staying under an ACA threshold. The appraisal district still wants its check.  And sales taxes? Those are inherently regressive. The family earning $60,000 and the family earning $600,000 both pay 8.25% at the register.

Texas makes a policy choice: tax consumption and property instead of income. That structure can be very attractive during high-earning years. If you’re making $250,000+, avoiding a 5–8% state income tax is meaningful. But in retirement, especially early retirement, the tradeoffs feel different.  There’s no such thing as a tax-free state, only different ways of collecting the bill.

Kids, Tax Credits, and Reality

I’ve been telling our youngest that he’s useless to me now that he has aged out of the Child Tax Credit (which ends at age 17).  Turns out that wasn’t entirely true.

The American Opportunity Tax Credit (AOTC) can be worth up to:

  • $2,500 per year
  • 100% of the first $2,000 in qualified expenses
  • 25% of the next $2,000

If you’re paying tuition, that’s meaningful. So as long as he stays in school and we’re within the income limits, I guess I’ll let him slide 🙂

The Bigger Picture

Unlike some people I talk to, I don’t actually mind taxes.  It’s like a subscription fee for living in a functioning society. Call me crazy, but I like things like roads,public schools, National Parks, libraries, basic social stability, and caring for my fellow man.

Do I think the system is perfect? No.
Do I think rates should probably be higher, especially at the top end of the wealth spectrum? Yes, absolutely.

But while the tax code exists in its current format, staying informed matters.

This year we:

  • Stayed in the 12% bracket
  • Managed ACA subsidies
  • Used business deductions appropriately
  • Leveraged education credits
  • Reduced future tax exposure by drawing down tax-deferred accounts before pension income begins

That’s not “beating the system.” It’s understanding the rules of the system you’re playing in. And when you treat tax season as a strategy session instead of a punishment, it becomes one of the most powerful financial planning tools your family can have.