Issue #23: May 2026

Congratulations to this month's sponsored giveaway winners:
Jenny H., Shi C., Alfred T., and Rachel A.

Life

We sold our house a few weeks ago and have been staying at my parents’ house while they are traveling.

We’ve started looking at homes again and recently applied for a mortgage, but honestly, the idea of taking on another large mortgage has been bothering me more than I expected. Part of me wonders whether a little more space is really worth another long term financial commitment.

I genuinely enjoy real estate, but lately I’ve also been feeling a little burned out. Sometimes on my commute to my other job, I listen to real estate podcasts, and recently I heard an agent talk about taking a year off. That conversation stuck with me.

Turning 40 last year also made me realize how quickly life moves. It feels like years can pass without much changing unless you intentionally make a change yourself.

Lately, we’ve been exploring the idea of worldschooling, or at least trying it for a month or so. I love the idea of exposing our kids to more of the world and helping them build connections and experiences outside of their normal environment. If anyone has tried worldschooling or something similar, I’d genuinely love to hear about your experience.

The truth is, I’m not really sure what the next step looks like for us.

Maybe we end up buying a bigger house and continuing life pretty much the same way. Maybe we try worldschooling for a month and realize it’s not for us. Or maybe we love it and decide to make bigger changes.

I do know this though: I want to be intentional about this stage of life instead of just drifting into the next version of it by default. I think I’m craving something new.

Personal Finance

Reminder (if you have kids): Open a 529 Early. The 15 Year Clock Matters.

One of the biggest reasons to open a 529 early is simple: time.

The earlier you start, the more time your investments have to compound tax free. And with the new Roth IRA rollover rules, starting early matters even more because the 529 needs to have been open for at least 15 years.

The key is consistency.

Set up automatic contributions and let time do the heavy lifting. Even if you do not have a lot of room in your budget right now, small amounts can add up over time.

Assuming historical-type long term returns similar to VTSAX over 20 years:
• $20/month = about $4,800 contributed + about $10,000 of growth = about $15,000 total
• $50/month = about $12,000 contributed + about $26,000 of growth = about $38,000 total
• $100/month = about $24,000 contributed + about $52,000 of growth = about $76,000 total
• $200/month = about $48,000 contributed + about $104,000 of growth = about $152,000 total
• $300/month = about $72,000 contributed + about $156,000 of growth = about $228,000 total
• A one time $4,000 contribution today with no additional contributions could grow to about $27,000 over 20 years
• A one time $10,000 contribution today with no additional contributions could grow to about $67,000 over 20 years

That means more of the ending balance came from growth than from your actual contributions.

And remember, 529 plans have become much more flexible than many people realize.

529 funds can generally be used for:
• College tuition and fees
• Room and board for students attending school at least half time
• Books, supplies, and computers
• Graduate school
• Trade and vocational schools
• Certain apprenticeship programs
• Up to $10,000 per year for K-12 tuition

Starting in 2024, unused 529 plan funds can also potentially be rolled into a Roth IRA for the beneficiary tax and penalty free.

A few key rules:
• The 529 must have been open for at least 15 years​
• Lifetime rollover limit is currently $35,000​
• Annual rollover limits still apply based on Roth IRA contribution limits
• The beneficiary must have earned income

This is a huge win for parents and grandparents who were worried about “overfunding” a 529.

And even if your child does not use all the money, you still have options:
• Change the beneficiary to another child or family member
• Save it for future education expenses
• Roll a portion into a Roth IRA under the new rules

Best case:
Your child gets tax free growth for education and a head start on retirement.

The new rollover rules make the 529 feel much more flexible and less risky than many people assume.

This content is for educational purposes only and is not financial advice. Please consult a licensed financial professional before making any investment decisions.

Real Estate

The New American Dream Might Be Flexibility

For a long time, the traditional path looked pretty straightforward:
Buy a bigger house. Fill it with more stuff. Keep upgrading.

And honestly, there is nothing wrong with that. Real estate has been one of the best wealth building tools for our family, and I still love it.

But lately I’ve been wondering if the definition of success is starting to shift a little.

Over the past few years, I’ve noticed more people prioritizing flexibility over square footage:
• More remote work
• More families traveling
• More people wanting lower fixed expenses
• More interest in experiences instead of just possessions
• More people questioning whether they want to spend decades optimizing around a house

Ironically, I’m writing this while actively applying for another mortgage and looking at bigger homes myself.

But after selling our house recently, I realized how much mental space comes with keeping life simpler too.

A larger house can absolutely improve quality of life. More room for kids, hosting family and friends, working from home, hobbies, and just breathing space. Those things matter.

At the same time, bigger homes usually come with:
• Bigger mortgages
• Higher property taxes
• More maintenance
• More pressure to maintain income at a certain level

I think more people are quietly asking themselves:
“How much house do I actually want my life to revolve around?”

For us, that question has led to conversations about traveling more and possibly trying worldschooling for a short period of time. Maybe we try it and realize we love having a permanent home base more. Maybe we love the flexibility.

I do not think there is one right answer.

Some people genuinely love building roots in a forever home. Others feel more alive keeping life lighter and more flexible.

But I do think it is healthy to pause occasionally and ask whether the lifestyle we are building is still aligned with what we actually value today, not just what we valued 10 years ago.

How do you feel about your current housing situation? Do you ever think about making a drastic change in your life? I love hearing from my subscribers!

If you have questions about real estate, reach out to me at realtordannylee@gmail.com. Follow me on IG @realtordannylee.