A couple of years ago, due to major improvements in tax planning software and recognizing how much my clients may value it, I added the service of preparing tax projections for them each year. I am not a tax preparer, but I would argue that the service I provide is just as valuable. First off, I do it before the end of the year, when actions can be taken to increase tax withholding or estimates, if necessary, or to implement tax-reducing strategies. After December 31st of the tax year, nothing can be done to change the tax outcome.

In the spirit of helping to reduce your tax anxiety, I will share some of the key items I look at when doing mid-year tax projections and some strategies to help you reduce your tax bill.

1. I look at pay stubs to see if too little or too much tax is being withheld.
It’s better to be just right because you could pay a penalty if too little tax is taken out during the year, and if it’s too much, yes, you will get a refund, but you lose the ability to use that cash during the year.

This applies not just to wages, but also to pension income. In fact, pension withholding is often more likely to be off because people don’t revisit their elections after retirement.

If you want to do a quick check yourself, pull out your most recent pay stub (or pension statement) and look at your year-to-date federal withholding and your year-to-date income. A rough rule of thumb is that your withholding should be in the ballpark of your expected effective tax rate. If you’re in a higher income bracket and only 10–12% is being withheld, that’s often a sign you may come up short.

One more important wrinkle: Social Security does not have taxes withheld automatically. You have to elect withholding (using Form W-4V), and many people don’t—especially in the early years of retirement. That can quietly create a tax bill if you’re also receiving pension income, IRA withdrawals, or investment income.

For a more precise answer, the IRS Tax Withholding Estimator is actually quite good. It walks you through your income, deductions, and credits, and tells you exactly how to adjust your W-4 (or W-4P for pensions). It’s not something most people are excited to do—but it can save you from an unpleasant surprise in April.

That works well for people with withholding—but not everyone has that built in. Read on.

2. Self-employment income is a bit trickier.
Unlike a paycheck or pension, there’s no automatic withholding—so you have to be more intentional. Not only are you responsible for income taxes, but you are also responsible for self-employment tax (Social Security and Medicare), which can take people by surprise. I often see this with high earners who are used to being W-2 employees—when they shift to self-employment, they don’t realize how much more needs to be set aside.

The general rule is that you’ll need to make quarterly estimated tax payments throughout the year. A simple way to stay on track is to set aside a percentage of each payment you receive—often 25% to 35%, depending on your income level and state. It doesn’t have to be perfect, but it should be consistent. If your income is uneven (as it often is), you can adjust as the year goes on rather than trying to get it exactly right upfront.

If you prefer something more precise, you can base your payments on last year’s tax (the “safe harbor” method) or project your current year income and calculate estimates accordingly. The key is not to wait until April—because that’s when self-employed taxpayers tend to get the biggest (and most stressful) surprises.

3. I check whether retirement savings are being maximized.
This is one of the most powerful ways to reduce taxes—yet it’s often underutilized or revisited too late in the year. For employees, that means making sure 401(k) (or 403(b)) contributions are on track to hit the annual limit, and for those over 50, taking advantage of catch-up contributions.

There’s also an important decision between pre-tax and Roth contributions. Pre-tax reduces your taxable income today, while Roth contributions don’t—but can provide tax-free income later. The right choice depends on your current tax bracket versus where you expect to be in the future, and it’s something worth being intentional about rather than defaulting.

For those who are self-employed, there’s even more flexibility. Options like a Solo 401(k) or SEP IRA, a Defined Benefit Plan, or a Cash Balance Plan allow for significantly higher contributions. And unlike employees, who generally need to make their contributions by year-end, self-employed individuals often have until their tax filing deadline—including extensions—to fund the employer portion. That creates a valuable window for tax planning after the year is over.

The key is being proactive. These contributions don’t happen automatically—you have to plan for them. Done right, this can both strengthen long-term financial security and meaningfully reduce your current tax bill.

4. I look at charitable giving.
I start by understanding how much a client wants to give to charity in a given year, and then we discuss the most tax-efficient way to do so. For example, instead of writing checks, donating appreciated securities can be far more advantageous—you avoid capital gains tax and still receive a deduction for the full market value. Utilizing a donor-advised fund makes this process simple and more strategic. For clients who have reached a certain age, Qualified Charitable Distributions (QCDs) from an IRA can be an excellent option, allowing them to give directly to charity while reducing taxable income.

Charitable giving can also play a role in whether you itemize deductions or take the standard deduction. In some cases, “bunching” donations into a single year can push you over the standard deduction threshold and increase your overall tax benefit. Like many of these strategies, a little planning ahead of time can make a meaningful difference.

5. I look at equity compensation, especially RSUs.
For clients who work in tech, this is a big one. When RSUs vest, they are taxed as ordinary income, and companies typically withhold taxes automatically. The problem is that the default federal withholding rate is often 22% (rising to 37% only for very high amounts), while many of my clients are in the 35%–37% tax bracket. That gap can result in a meaningful amount owed at tax time if it’s not addressed. The shortfall can be made up with estimated tax payments or adjusting withholding.

6. I project investment income and look for opportunities to manage it.
Investment income—dividends, interest, and capital gains—is another key piece of the puzzle, and one that can be unpredictable. I estimate, as best as I can, what this income will look like for the year and incorporate it into the overall tax picture. I also check for any capital loss carryforwards that can be used to offset gains, which is often an overlooked opportunity.

One area that can be especially frustrating is mutual fund capital gain distributions. These are largely out of your control and can vary significantly from year to year, sometimes creating unexpected taxable income even if you didn’t sell anything. It’s one of the reasons tax projections are so valuable—while we can’t predict them perfectly, we can at least plan for the possibility. It’s also a reminder that mutual funds are best held in retirement accounts.

In addition, I look for opportunities to do tax-loss harvesting—selling investments at a loss to offset gains elsewhere. This can be especially valuable in volatile markets. Even if there aren’t gains to offset today, harvested losses can be carried forward to future years.

7. I encourage clients to track key deductions throughout the year.
This may sound simple, but it can make a real difference. I encourage clients to keep track of charitable contributions and medical expenses throughout the year, rather than trying to reconstruct everything at tax time. These are two areas that can meaningfully impact whether you itemize deductions, especially in years when expenses are higher than usual.

Even if you don’t end up itemizing every year, having good records gives you flexibility. It also makes it easier to identify opportunities—like bunching charitable contributions or recognizing a year when medical expenses may be deductible.

For self-employed clients, this is even more important. Having a good system in place to track business expenses throughout the year—not just at tax time—can reduce stress and ensure you’re capturing all legitimate deductions.

Those are the big ones.

Once I’ve made the tax projection as complete as possible—and it’s never perfect, because some things simply can’t be predicted, like mutual fund capital gain distributions or changes in income—I use it as a guide for action.

If it looks like a client will owe more tax than expected, I’ll flag it and suggest they loop in their accountant, who may recommend making an estimated tax payment. It’s much better to deal with it during the year than be surprised in April.

On the flip side, if it looks like too much is being withheld, I encourage clients to adjust their withholding so they can use that cash throughout the year. I’m always a little surprised how many people are comfortable getting a large refund—it’s often seen as a form of forced savings—but in reality, it just means you’ve given the IRS an interest-free loan.

The goal isn’t to get a big refund or owe a lot—it’s to get it right. And more importantly, to remove the uncertainty that makes taxes so stressful in the first place.

If you got through to the end, I am happy, as it means I might have made a post about taxes interesting! Thanks for reading.

By the way, a major change or life shift is usually the reason people hire financial advisors. It’s the catalyst, the final push that gets someone to take the steps to find an advisor. So, I am not unusual, and financial advisors are really just like everyone else when it comes to their money. We procrastinate, we worry, we hope we are doing all the right things. The difference is we know what the right things are!

This is what happened when I finally sat down and did the work. And why I am suggesting that you do it too: I felt proud, free, focused, and validated. After I verified the inputs, tweaked the data, and reviewed all the cash flow reports, I realized that I was on track and I could proceed with my plans. I know that getting fully reacquainted with my finances will help me to make better decisions going forward.

You can do this too. Even if the outcome isn’t as rosy as mine, doing the work of planning is invaluable. Even more so if you are falling behind on your financial goals.
Maybe you take a look and realize that you haven’t been maximizing your retirement savings - you can fix that. Or, your spending on clothing was a little too enthusiastic last year, you can set a new budget, or you realize you need to update the liability limit on your umbrella policy because of a change in your wealth. I guarantee that the hours spent focusing on your full financial picture will be worth it for the peace-of-mind planning brings.

There are many ways to start or update a financial plan. You can have an advisor do it, build spreadsheets, or find free tools online.

The most important things are:
-Know what is coming in and what is going out - hopefully that balances, and the going out part includes savings, especially maxing out retirement savings opportunities.
-You don’t run a deficit that ends up on credit cards. If it does, you work hard to pay those off.
-Do projections to see if your nest egg will grow big enough to cover expenses in retirement (along with any other income, such as social security).
-Review all your insurance policies with your agents to ensure proper coverage (at least every 2 years).
-Review your estate plan to see if it is up-to-date. And if you don’t have one, do one.

Some of the surprises I found when updating my plan:

-I know most expenses go up every year because of inflation, but it’s always surprising to see how much. Especially lately, insurance premiums! I plan to shop around again to see if I can do any better.
-I focus so much on my clients' investment outcomes that I forget to look at my own. The rising stock market has certainly been a positive. Reminds me of the importance of rebalancing my own accounts.
- I was an enthusiastic shopper last year. I blame it partly on my newfound love of fashion substack. So many great writers with fashion expertise who share their style wisdom and find the gems out there! Time for me to reset the budget.

I hope this post gets you motivated to look at your own finances. January is as good a month as any to do it!

Photo by Tamara Harhai on Unsplash-


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There are lots of reasons people make estimated tax payments (significant capital gains, no withholdings on Social Security, etc.), but this post is focused just on freelancers / self-employed creators — people who do not have taxes withheld from their pay and whose income can fluctuate from quarter to quarter.

👉 Quick reminder: Estimated tax payments are due on April 15, June 15, September 15, and January 15 (not every quarter).

Choose Your Own Adventure: How to Handle Estimated Taxes

Here’s the setup:

• 2024 net income: $70,000 → taxes ≈ $17,500

• 2025 net income estimate: $80,000 → taxes ≈ $20,500

Now, what could you do?

Option A: Skip everything until April

• Pay $0 in estimates until filing

• April 2026 bill: ~$20,500 + penalties & interest

• Penalties? Yes. (Estimate $1,100 for Federal taxes)

• Stress level: Stressful; big lump sum; likely penalties

Option B: Use 100% of 2024’s tax (Safe Harbor)

• Divide $17,500 by 4 → ~$4,375 per quarter

• April 2026 bill: ~$3,000 owed

• Penalties? No

• Stress level: Much more manageable; cash flow smoother

Option C: Use 90% of 2025’s estimated tax (Safe Harbor)

• Pay ~$18,450 over four estimates

• April 2026 bill: ~$2,050 owed

• Penalties? No

• Stress level: Best alignment with higher income; but requires accurate projections

💡 Note: If your 2024 AGI was over $150,000, you'll need to pay 110% of last year's tax (instead of 100%) to qualify for safe harbor protection.

Timing Matters: What If You're Behind?

Let’s say you skipped the June 15 payment and are just reading this now.

• The good news: You can still avoid penalties on future quarters by making payments going forward.

• The reality: You’ll likely face penalties on the missed quarter, but they’re calculated separately for each quarter. If you missed June but pay September and January on time, you’ll only be penalized for June.

• Best move: Pay something today (even if not the full quarterly amount) and continue with regular payments. The IRS penalty is based on how much you underpaid and for how long, so paying late is always better than not paying at all.

My Opinion & Recommendation

If you're the type who says, "I'll skip estimates and just pay it all in April", here's what I strongly suggest instead:

• Adopt Option B: use 100% of last year's tax liability, divide by 4, and make quarterly payments. No guesswork, no major surprises, no penalties.

• ⚠️ Yes — this option may result in a larger payment in April if your income rises, but that’s still far better than nothing + penalties + stress.

And if you truly have cash and want it over with:

• You can pre-pay your estimated tax in full (or front-load some payments). The IRS will apply it across the year.

• Just remember: you’re giving the government an interest-free loan. If the peace of mind is worth it, go for it — but make sure it doesn’t hurt your business cash flow.

Don’t Forget SE Tax

As a freelancer, one of the biggest surprises is the Self-Employment (SE) Tax — you’re paying both the employer and employee halves of Social Security and Medicare (about 15.3% on ~92.35% of your net income).

In our example, out of the total $20,500 in taxes, $11,304 is SE tax ($80,000 × 0.9235 × 0.153).

That SE tax gets added on top of your income tax — it’s a huge piece of the bill and a major reason why freelancers need to plan ahead.

How to Pay Estimated Taxes

You’ve got options:

• • IRS Direct Pay (https://www.irs.gov/payments/direct-pay) — the easiest way to send a payment straight from your bank account, no login required.

  • EFTPS (Electronic Federal Tax Payment System) — best if you want to schedule payments in advance; requires a setup process.

  • Check or Money Order — old school, but you’ll need to mail it with a voucher (Form 1040-ES) and have it postmarked by the deadline.

  • State Payments — if your state has income tax, you’ll need to pay through your state’s tax authority website separately.

  💡 Tip: Always keep a record (screenshot or confirmation number) of your payment. If the IRS ever says you didn’t pay, you’ll want proof.— the easiest way to send a payment straight from your bank account, no login required.

Final Thoughts

• Since today is September 15, the third-quarter deadline is here. If you haven’t made payments yet, use the safe harbor based on last year — it’s the least risky move.

• Even if you’re late, making something now reduces penalties.

• For next year: track your income monthly, estimate early, and don’t underestimate how fast things can shift.

Note: Tax amounts shown are estimates and will vary based on filing status, deductions, and other factors. To keep these examples simple, I’ve left out other income sources such as dividends, interest, or capital gains, which would affect the final calculation. Consult a tax professional for your specific situation.

For others, wealth has nothing to do with physical things. It’s about what money makes possible behind the scenes—the life changes that are invisible to those looking from the outside.

I recently experienced one of these “invisible upgrades” myself. While running errands, I made the mistake of starting a software update on my Tesla—without Wi-Fi. (Don’t do this!) When I came back, the doors wouldn’t open, and forcing the passenger side cracked the entire window. The car wouldn’t start either, so I called a tow truck, had the window replaced, left the car overnight, and took two Uber rides to get it all sorted.

This unexpected series of events took up most of my day. But here’s the thing: I didn’t freak out about the $400 repair or the extra transportation costs. In years past, an unexpected bill like that would have stressed me out. This time, it was just an inconvenience. And I was relieved to feel that way.

Key examples of these invisible upgrades:

· The ability to say no – No to a job that leaves you feeling unappreciated. No to a romantic partner who is verbally or physically abusive. No to a client or project you know will drain you.

· Peace of mind – When an unexpected expense pops up—a dental bill, a new roof, a car repair—you can take care of it without spiraling into stress.

· Better health outcomes – Not just affording a great doctor, but catching problems earlier, taking the time to recover fully, and keeping up with routine care without feeling like it’s an impossible scheduling challenge.

This experience reminded me of a passage in The Glass Hotel by Emily St. John Mandel that captured this perfectly. Reflecting on living with money, her character Vincent thinks:

“What kept her in the kingdom (of money) was the previously unimaginable condition of not having to think about money, because that’s what money gives you; the freedom to stop thinking about money. If you’ve never been without, then you won’t understand the profundity of this, how absolutely this changes your life.”

That’s it—the invisible, behind-the-scenes benefits of being financially secure. Not Instagrammable, not TikTok-worthy, but life-changing.

Do you have to be “rich” to access these invisible benefits? Not necessarily. And it’s not impossible to work toward them. You can design for them now, with the resources you have, by being intentional about where your money goes. And by knowing yourself well enough—your values, your preferences, your desires—to spend only on what supports those priorities, while covering life’s necessities, and saving and investing the rest.

That’s the real power of financial planning— growing wealth, of course, but as important: being intentional about creating a life that feels spacious, calm, and truly yours.

So, I’ll ask you—what invisible upgrade would make the biggest difference in your life right now? And what would you be willing to give up to get it?

And now, all you want is a break.
Not forever — maybe just for a year. Maybe until your nervous system resets or you find a boss who treats you like a human and a working environment that you feel good in.

But here’s the problem: you’re scared. And for seemingly good reasons — but are they really good reasons or just stories you’ve told yourself so many times they feel like truth?

I’ve worked with dozens of high-achieving women who hit this wall - usually around their early to mid-50s. Financially stable. Emotionally frayed. What are some of their stories?

💬 Story #1: “I’ll ruin my long-term financial plan if I quit for a year.”

• Not true for everyone. If you’ve saved aggressively, your portfolio may be able to support a pause, especially if your spending is reasonable.

• A year off at 57 is not the same as a year off at 37 — you’ve likely built enough financial slack to weather a break.

• Consider a Gap Year Budget and run a stress test. You might be shocked by how little it affects your long-term plan. The key is to use conservative assumptions, (for example, 5% investment returns instead of 8%), so you feel confident in the outcome.

💬 Story #2: “If I leave, I’ll never make the same money again.”

• This fear is real — and often gendered. But some of the most financially and emotionally rewarding pivots happen because of that break.

• What matters more is clarity: What do you want next? What are you willing to give up in exchange for peace of mind and health right now?

• A break is a good chance to explore the question – how much is enough?

• Sometimes a lower-paying but values-aligned role and a healthier work environment is the right next step — if the numbers work.

💬 Story #3: “Financial independence means freedom — and if I stop making money, I’ll lose it.”

• Financial independence doesn’t automatically mean emotional freedom. We’re socialized to value productivity, and it takes intentional work to disconnect worth from work.

• Stepping away from a toxic environment can give you the space to think again. To ask: What do I want from this next chapter? That is freedom.

• You may not need permission — just a plan.

🔧 Tactical Tips: How to Take a Break Without Breaking Your Financial Future

1. Can You Afford a Year Off?

• Start by estimating your total annual spending — including health insurance if you’ll lose employer coverage.

• Subtract any ongoing income (RSU vesting, rental income, any K-1 income).

• The gap can often be covered with cash savings or modest withdrawals from a taxable brokerage account.

• Run a stress test using conservative assumptions: no portfolio growth, or even a slight decline. See what it does to your long-term plan.

📝 You might find the impact is minimal — especially if you’re not withdrawing from retirement accounts or selling appreciated assets.

2. What About Health Insurance?

• COBRA lets you continue your employer plan, usually for up to 18 months, but depending on the state you live in can be 36 months — but it's expensive.

• ACA marketplace plans may be more affordable than you think, especially if your income drops during your break.

• HSAs can help if you’ve saved for future healthcare expenses — and distributions are tax-free if used for qualified expenses.

3. Staying Professionally “Fresh” While on Break

• You don’t need to disappear. Consider light consulting, project work, or volunteering in your field.

• Enroll in a course or certificate program — not necessarily to pad your résumé, but to stay engaged and curious.

• Keep your LinkedIn profile active. Even a simple post now and then helps signal that you’re still in the game.

• Meet colleagues and other people in your field for coffee just to stay in touch with what is going on.

🎯 This isn’t a shutdown — it’s a strategic pause.

4. Preparing Emotionally: Who Are You Without the Job?

• This can be the hardest part. We're conditioned to derive our value from our work.

• Practice your answer to “So, what do you do?” in a way that feels proud and intentional.

• Build in some structure: part-time projects, creative work, physical activity, travel, or simply time to rest.

💡 The more intentional your pause, the more powerful your return — or reinvention — will be.

🪞Permission, Redefined

Taking a break doesn’t mean you’ve failed.
It means you’ve succeeded enough to choose yourself.

If you’re a woman of independent means, burnout isn’t a luxury problem — it’s a signal. And your financial freedom isn’t just there to help you retire someday. It’s there so you don’t lose yourself before you get there.

What's holding you back from taking a break?

My story:
I was a mid-life career changer myself. I always dreamed of being an independent financial advisor, but I didn’t think I could do it. I told myself the stories and almost chickened out. I left a well-paying corporate career to start my own financial planning practice. It was scary, but exhilarating. It turned out to be not only the best financial decision but one of the best life decisions I ever made.

Bottom line: If you buy your own health insurance—whether you're self-employed, an early retiree, or between jobs—a bill moving through Congress could dramatically increase your premiums starting in 2026. Here's what's at stake and what you need to know.

What's Happening Right Now

The "One Big Beautiful Bill Act" (officially H.R. 1) passed the House on May 22, 2025, by a narrow 215-214 vote. Among its many provisions, the bill notably does NOT extend enhanced ACA subsidies, which expire at the end of 2025. The bill is now in the Senate, where Majority Leader John Thune has set a goal of passing it by July 4, 2025.

These enhanced subsidies help millions of Americans afford individual or family health insurance through the ACA marketplaces. Without congressional action, we're heading back to the pre-pandemic subsidy levels, which means much higher costs for many people.

A Quick History: How We Got Here

Original ACA Rules (2010–2020)

• Premium subsidies were available only to people earning 100%–400% of the federal poverty level (FPL)

• If your income was above roughly $51,000 (single) or $104,000 (family of four) in 2020, you got zero help

• Premiums were capped at varying percentages of income, up to 9.83% for those at 400% FPL

The Pandemic Changes (2021–2025) In 2021, the American Rescue Plan Act temporarily expanded subsidies, and in 2022, the Inflation Reduction Act extended these enhancements through 2025. The key changes:

• Eliminated the 400% FPL income cap—anyone could qualify if their premium would exceed 8.5% of their income

• Lowered premium contributions across all income levels, allowing people with incomes between 100-150% FPL to pay $0 in premiums for benchmark silver plans

What Happens in 2026? Without congressional action, the enhanced subsidies expire at the end of 2025, and we revert to the original, less generous rules.

What This Means in Real Dollars

The Congressional Budget Office projects that 4.2 million people will lose coverage due to subsidy changes alone. Here's what premium costs could look like if the enhanced subsidies expire:

45-year-old single woman, self-employed
Annual Income: $60,000
Monthly Premium (2025): $280
Monthly Premium (2026, projected): $600–$700
Annual Increase: $3,840–$5,040

55-year-old early retiree couple
Annual Income: $95,000
Monthly Premium (2025): $460
Monthly Premium (2026, projected): $1,200+
Annual Increase: $8,880+

60-year-old single woman, retired early
Annual Income: $80,000
Monthly Premium (2025): $400
Monthly Premium (2026, projected): $900–$1,100
Annual Increase: $6,000–$8,400

If Congress does not act, current ACA marketplace enrollees could see their premiums rise by an average of 75% or more in 2026. Some states will face even sharper increases—in 12 states using Healthcare.gov; average premium payments would at least double without the enhanced subsidies. Insurers are already submitting proposed 2026 rates that assume the enhanced subsidies will lapse.

Why This Matters to You

If you're self-employed, between jobs, retiring early, or don't have employer-sponsored health care—this could directly impact your wallet.

Since the enhanced subsidies took effect, ACA marketplace enrollment has grown by 88%, from 11.4 million in 2020 to over 24 million in 2025. States that President Trump won account for 88% of marketplace enrollment growth since 2020, so this isn't just a blue-state issue.

The recent growth has been driven primarily by low-income people, with signups by people with incomes up to 2.5 times poverty growing 115% since 2020. However, middle-income earners—the financial independence crowd—also benefit significantly from the current system.

What Happens Next

The Senate aims to pass its version of the One Big Beautiful Bill by July 4, 2025. Unlike culture-war provisions that might get stripped out, the subsidy expiration is budget-related and likely to survive the reconciliation process.

For the 2026 plan year, insurers must submit their proposed premiums by early 2025 and finalize them by August 2025, well before the November 2025 open enrollment period, which means we'll know the damage by summer.

What You Can Do

If you benefit from ACA subsidies—or care about keeping premiums affordable—this is the moment to pay attention:

1. Contact your senators. Senators Lisa Murkowski (R-AK) and Thom Tillis (R-NC) have expressed interest in extending the enhanced subsidies, showing this isn't purely partisan.

2. Plan ahead. Talk to your financial planner or insurance broker about 2026 scenarios. If you're considering early retirement or leaving a job, factor in potentially much higher healthcare costs.

3. Watch the calendar. The fall 2025 open enrollment period may be your last "normal" year for ACA pricing.

4. Spread the word. Forward this to your self-employed friends, yoga teacher, and neighbor who just left her corporate job. Nearly three out of four marketplace enrollees have incomes between 100-250% of the Federal Poverty Level, and many are small business owners or self-employed.

Final Thought

This change isn't just a health policy story—it's a personal finance story that could reshape the economics of independence. Enhanced subsidies have cut premium payments by an estimated 44% ($705 annually) for enrollees receiving premium tax credits.

Many Americans have built their budgets around affordable ACA coverage. If this bill passes as written, we could see a seismic shift that hits exactly the people this newsletter serves: the independent, the entrepreneurial, and the early retired.

The irony? This proposed change comes at a time when the enhanced subsidies have led to record enrollment growth, particularly in red states. Sometimes, the best programs are the ones that work so well you forget they exist—until they're about to disappear.

Sources: Congressional Budget Office, KFF, Commonwealth Fund, CNBC, NPR, and official congressional documents.

Bonds are making headlines right now thanks to fluctuating values and economic uncertainty, but here's what I've noticed: most people understand what it means to own Apple stock, but what about Apple bonds? You can own those too. It’s too bad there is a misunderstanding, because bonds might be exactly what your portfolio needs right now.

Think of this as your friendly bonds translator. I've formatted it as a Q&A to make it as painless as possible.

Q: What is a bond anyway?

A bond is a loan—and you are the bank.

When you buy a bond, you're essentially saying to the U.S. government, Apple, or your local school district: "Here's my money. Pay me back in 10 years, and send me interest checks twice a year until then."

Imagine you're running a small-town bank. Microsoft walks in and says, "Can I borrow $1,000 for 5 years? I'll pay you $25 every six months, and give you back your full $1,000 when the time's up." You say yes, shake hands, and now you own a Microsoft bond.

That's it. You're the lender. They're the borrower. You get paid for the privilege of letting them use your money.

Q: Why would I want bonds when stocks seem more exciting?

Because bonds are the steady friend who brings balance to your life.

If stocks are like that friend who's always dragging you to new restaurants and spontaneous weekend trips, bonds are like the friend who shows up with soup when you're sick and never forgets your birthday.

What bonds do that stocks don't:

• Predictable income: Most bonds pay you every six months like clockwork. No wondering, no hoping—just reliable money showing up.

• Portfolio insurance: When stocks have a meltdown, bonds often hold steady or even rise. They're like financial shock absorbers.

• Return guarantee: Hold a quality bond to maturity, and you get your money back (assuming no default—which means the borrower fails to pay you back as promised, though this rarely happens with high-quality bonds). Try getting that promise from a stock.

Here's the psychological benefit most people miss: bonds help you sleep better when markets get crazy. And when you're not panicking, you make better decisions with the rest of your money.

Q: Where do I buy bonds, and how much money do I need?

Individual bonds: You can buy them through brokers like Fidelity or Schwab, or go directly to TreasuryDirect.gov for government bonds. But there's a catch. Just like with stocks, you want a diversified portfolio—and that takes serious money, typically $50,000 to $100,000 or more. Think of it like a fruit salad: you don't want just melon and grapes.

Bond funds and ETFs are the easier path. They're like a pre-made fruit salad—instant diversification, professional management, and reasonable minimum investments. (Personally, I want strawberries, boysenberries, and bananas in addition to those grapes and melon.)

For many investors, the fund route makes more sense.

Q: Individual bonds vs. bond funds—what's the difference?

Individual bonds are like owning a rental property directly. You know exactly what rent you'll collect each month and when your tenant's lease ends. If you hold until "lease expiration" (maturity), you get your full investment back.

Bond funds are like owning shares in a real estate investment trust (REIT). You own a slice of many properties, managed by professionals. Your "rent" payments fluctuate based on the whole portfolio, and there's no set end date.

For most people, the fund approach wins because:

• No need to research individual "tenants" (bond issuers)

• Instant diversification across hundreds of bonds

• Professional management handles the details

• Easy to buy and sell

Q: Everyone keeps saying bonds are "sensitive to interest rates"—what does that actually mean?

Picture bonds and interest rates as two people on a seesaw. When one goes up, the other goes down.

Here's why: Let's say you own a bond paying 3% interest. Then the Federal Reserve raises rates and new bonds start paying 5%. Suddenly, your 3% bond looks like last season's smartphone—it still works, but nobody wants to pay full price for it.

Quick vocab check: You'll often hear "yield" and "interest rate" used interchangeably, but they're slightly different. Think of yield as "what you actually earn" based on what you paid. If you buy a bond at a discount, your yield is higher than the stated interest rate. If you pay a premium, your yield is lower. It's like buying a $100 item on sale for $90—your "yield" on that purchase is better than someone who paid full price.

What this looks like in real life:

• Your bond fund value drops when rates rise (even though you're still getting interest payments)

• Your bond fund value rises when rates fall

• The longer the bond's duration, the bigger these swings

About duration: This term sounds technical, but it's simply the average time it takes to get your money back from all the interest payments and final principal payment. A bond with 5-year duration is more sensitive to rate changes than one with 2-year duration.

Current reality check: Since April, we've seen this seesaw in action. The 10-year Treasury yield (remember, that's what you actually earn) jumped from about 4.16% to 4.39%. That might sound tiny, but in bond-land, it's like an earthquake. Here's why: that seemingly small 0.23% move caused many intermediate-term bond funds to drop 2-3% in value—sometimes in just a few weeks. Fears about government deficits and potential tariff-driven inflation have investors demanding higher yields—essentially saying "if there's more risk, we want more reward."

But here's the silver lining: As old, lower-paying bonds mature, funds buy new, higher-paying ones. It's like gradually upgrading your rental properties to command higher rent.

Q: Is now really a terrible time to buy bonds?

Actually, it might be one of the better times in years. Here's why:

The yields are finally attractive again:

• Short-term Treasuries: ~5%

• Corporate bond funds: 5-6%

• Tax-free municipal bonds: 4%+ (though the effective yield is much higher because you keep more of what you earn when some or all of the interest is tax-free)

For years, bond yields were so pathetic it was like getting excited about a 0.5% savings account. Those days are over.

Yes, prices have dropped. But think of it like a sale at your favorite store. The "merchandise" (bonds) is the same quality, but now it's marked down and offering better returns.

The headlines make it sound scary:

• "Bond prices are crashing!"

• "Rates could go higher!"

But remember: short-term volatility is normal. If you have a timeline of several years, these dips often turn into opportunities. The same principle applies to stocks.

Q: How do I choose the right bond fund?

Think of duration as a fund's "sensitivity meter" to interest rate changes:

• Short-term funds (~2-3 years): Like a steady sedan—less exciting, more stable

• Intermediate-term funds (~5-7 years): Like a good SUV—balanced performance

• Long-term funds (10+ years): Like a sports car—more thrills, more spills

Keep in mind that in normal market conditions, shorter duration typically means less volatility but also lower yields.

Smart approach: Mix and match based on your timeline and stomach for volatility. Or you can buy "all-weather" bond funds that hold all different types of bonds with different durations.

Q: What about taxes?

This is where bonds get interesting:

• Treasury bonds: Uncle Sam gets his cut, but your state leaves you alone

• Corporate bonds: Everyone gets a piece (federal and state taxes)

• Municipal bonds: Often federally tax-free, sometimes state tax-free too—especially appealing if you're in a high-tax state like California or New York. This tax advantage means a 4% municipal bond yield might be equivalent to a 5.5% or 6% taxable yield, depending on your tax bracket.

Pro tip: Keep bonds in tax-deferred accounts (like IRAs) when possible, unless you're using tax-free municipal bonds.

The Bottom Line

Bonds aren't the boring cousin of stocks—they're the reliable partner that helps your portfolio weather storms. Yes, they've had a bumpy ride lately, but that's created opportunities for investors willing to think beyond the headlines.

Remember:

• Bond prices and interest rates are joined at the hip—when one zigs, the other zags

• Duration matters—shorter duration typically means less volatility but also lower yields in normal conditions

• Bond funds make the most sense for most investors

• Current yields are the best we've seen in years

• Taxes matter, so choose your account locations wisely

The next time someone tells you bonds are boring, remind them that boring can be beautiful—especially when it's paying you 5%+ while helping your portfolio stay steady.

Disclaimer: This content is for educational purposes only and should not be considered personalized investment advice. Past performance does not guarantee future results. Bond investments carry risks including interest rate risk, credit risk, and the potential for loss of principal. Before making any investment decisions, please consult with a qualified financial advisor who can assess your individual circumstances and risk tolerance."

But if you love fashion like I do, it may be the perfect moment to embrace secondhand shopping.

The stigma around buying pre-owned clothing is largely gone. From online marketplaces to local consignment stores, resale is not only acceptable—it’s chic. Boutique labels like Rachel Comey and Apiece Apart have dedicated resale platforms, while brands like Everlane, Madewell, Patagonia, and Levi’s support the circular economy with recycling and resale programs.

Shopping secondhand is more than just budget-friendly—it’s an environmentally conscious choice. You reduce landfill waste, fossil fuel use, and reliance on cheap labor. You also give beautiful clothes a second life.

As someone who loves fashion and values high-quality garments, I’ve made secondhand shopping a regular part of my routine. It’s like a treasure hunt—fun, rewarding, and often full of surprises. Many resale stores (especially brick-and-mortar ones) have a unique personality. Some avoid fast fashion, others specialize in natural fibers or vintage. There’s truly something for everyone if you know where to look.

And when you sell your own gently used pieces, store credit often covers new purchases. Sometimes, I walk out with a gem without spending a dime.

🛍️ My Online Resale Strategy

Step 1: Use GEM to Search Multiple Platforms at Once

GEM is a resale search engine that combs through Poshmark, The RealReal, eBay, Etsy, Mercari, and more. If I’m looking for a specific item—like a Dehanche Hollyhock suede belt ($290 retail)—I start there. GEM found one listed on Poshmark for $190, new without tags. I offered $150 (declined this time, but it often works!). GEM also sends updates when new matches appear.

Step 2: Check Poshmark, eBay & The RealReal

• Poshmark: Great peer-to-peer deals. You can make offers.

• eBay: Excellent for discontinued or hard-to-find items.

• The RealReal: Authenticated luxury with markdowns. Their “See Similar” feature helps you branch out to other brands.

Example win: A Paige Tiana suede moto jacket for $55 ($67 with tax/shipping), originally $895 found on Poshmark (via Gem). I thought the listed retail price was high—but Paige leather jackets still retail for $799+. Every time I wear mine, strangers stop me to ask about it.

💡 Tip: Always read item descriptions carefully and magnify photos.

• Poshmark: No returns

• The RealReal: Returns allowed with a $12.95 fee

• eBay: Return policies vary by seller

Step 3: Use Google Lens for Visual Search

If I see a piece I love, I snap a photo and upload it to Google Lens. That’s how I found another pair of my favorite Loeffler Randall boots (so comfy)—$99 on Poshmark, originally $395.

🏬 My Favorite Resale Haunts in Oakland & Berkeley

If you live in the SF Bay Area, or find yourself there—these are the places I return to again and again. (Be sure and explore your city for options!) Each has its own aesthetic, philosophy, and selection. Whether you're looking to buy or sell, these shops are worth a visit. All of these stores have websites, and you can buy online, but the better experience and full selection of items are in the stores.

🧵 Radbird – Berkeley & Oakland

Radbird specializes in high-end and luxury resale—carefully curated, current styles, and always in pristine condition. They prioritize clothing made from natural fibers like cotton, cashmere, silk, and wool. Their motto: “Fast Fashion Is Dead.” And they live it.

The jewelry section is exceptional, and the owner and staff curate everything with care. I’ve found some of my all-time favorite pieces here—and I consign regularly.
One of the best perks? If you use your trade credit, you receive a 10% discount. Their consignment split is a generous 50/50.

🎯 ReLove – Oakland & San Francisco

ReLove stands out for its distinctive point of view. The selection is a mix of vintage, independent labels, and covetable designer pieces. It’s fashion-forward, thoughtful, and always changing. Their website describes it best:

"We buy vintage, independent labels and covetable designer clothes, shoes, accessories, and jewelry for women and men. We love natural fabrics, modern classics, pieces from your far-away travels, stand-out pieces, Japanese designers, vintage denim, kimonos, vintage sweatshirts and t-shirts, well-loved favorites, modern-trend, the wacky, the muted, the minimalist, and everything in between."

ReLove often buys items outright, offering cash or store credit on the spot, but also consigns select pieces.

Memorable purchase: A long, slim Dolce & Gabbana black lace skirt for $150—a similar one at Saks retails for $2,345.
Payouts: 35% in cash or 50% in store credit. Consignment: 50/50 split.

👖 Mercy Vintage – Rockridge, Oakland

Mercy is a destination for serious vintage lovers. It’s known for its impressive selection of authentic designer vintage and what they call “future vintage”—modern brands with staying power.

You’ll find Italian classics like Prada, Gucci, and Dolce & Gabbana, along with American vintage from the 1950s through the ’80s. Their vintage denim selection is especially strong.

Seller terms:

• 35% of resale value in cash

• 45% in store credit

• 50/50 for items consigned over $200

Recent find: Agolde’s Cooper Cargo jeans for $75 (retail: $228)

🧥 Sola Lucy – Montclair, Oakland

A well-loved staple in the East Bay, Sola Lucy carries a mix of high and low labels—and rewards the patient shopper. It's one of those places where, if you stop in regularly, you’ll eventually find something special.

As a seller, the experience is efficient and transparent. The day after consigning, you receive an email with your item list and pricing. Items go on the floor right away, and turnover is quick.

Seller payout: 40% of the final selling price
Favorite score: A sky-blue H&M long wool coat for $30—and I get more compliments on it than anything I own

.

💎 Maribel – Lakeshore, Oakland

Maribel is vibrant and eclectic, with a curated collection of printed dresses, stylish handbags, and a standout selection of boots and booties. The jewelry case always catches my eye—it features both new designs and resale pieces.

It’s also where I discovered the work of local jewelry artist Morgania E. Moore, whose pieces are now some of my favorites.

💭 Final Thoughts

If you’re looking to stretch your clothing budget, reduce waste, and have fun doing it, resale is a smart (and stylish) choice. Shopping secondhand aligns with my values—and gives me joy.

And someday? After I retire from financial planning, I’d love to open a consignment boutique in Healdsburg. There’s only one store there now… and between you and me, I think I could run a better one 😉

It dates back to the California Gold Rush when a surprising number of Irish immigrants struck it rich. People started associating the Irish with financial windfalls as if they had some magical ability to stumble upon gold. Some historians say that due to the anti-Irish sentiment at the time, the phrase was originally meant as a backhanded compliment, implying that Irish success was purely accidental and not the result of hard work or skill.

Given Ireland’s long history of colonization, famine, and economic struggles, luck doesn’t seem like the right word. Resilience would be a better fit. But whether we like to admit it or not, luck plays a role in life—and in financial success.

***

I grew up in San Francisco’s Sunset District, a neighborhood full of Irish and Italian families. I’m neither, but I might as well have been honorary Irish by proximity. Half of my Catholic school classmates were Irish. When my friends and I hit 21, we frequently visited the Irish pubs along Geary and Clement Streets. My brother married into an Irish family with deep roots in Ireland and Irish traditions, and at my wedding (a couple of decades ago), my nephew—who traveled the country competing in Irish dance—performed a jig in front of all our guests.

The Irish had a reputation for luck, but what they really had was an unshakable sense of community, a deep appreciation for celebration, and an ability to roll with life’s punches.

***

Luck plays a bigger role in financial success than people like to admit. Morgan Housel, in The Psychology of Money, talks about how random factors—where and when you were born, who you meet, even the year you start investing—can shape your financial trajectory. In Success and Luck: Good Fortune and the Myth of Meritocracy, Robert Frank argues that luck is the missing ingredient in most wealth-building stories.

Take two people who make the same smart financial decisions—one started investing in 2009, and the other in 2007. Their experiences (and portfolios) will look completely different. Right place, right time matters.

But while no one controls luck, we can set ourselves up to take advantage of it. The Irish miners in the Gold Rush didn’t just sit around waiting for gold to land in their laps—they panned, dug, and staked claims. The same idea applies to money. Hoping for a windfall isn’t a financial plan. Saving, investing, and being prepared when opportunities come along is.

***
I have recommended Morgan Housel’s book in past posts, and another great behavioral finance book is The Soul of Wealth by Daniel Crosby. Read a chapter at a time and watch your financial behavior shift for the better - with a little luck!

Core Wardrobe vs. Core Portfolio

A capsule or core wardrobe is built on timeless, high-quality pieces that make getting dressed effortless and stylish. A well-constructed wardrobe saves you time and frustration, ensuring you never feel like you have “nothing to wear” even when your closet is full.

Similarly, a core investment portfolio creates a strong foundation that will adapt to different market conditions. A well-constructed portfolio provides peace of mind, eliminating that nagging doubt about whether you’re managing your money wisely.

Both provide a sense of control and peace of mind.

👗 Core Wardrobe: Classic, versatile essentials that form the backbone of your style. 📈 Core Portfolio: Reliable, diversified investments that form the foundation of your investment strategy.

Choosing a Foundation: Color Palette vs. Asset Allocation

Just as a strong wardrobe starts with a foundation of key colors, a solid portfolio starts with a foundation of core asset classes. Getting dressed becomes a headache if you have too many mismatched clothing pieces. A cohesive wardrobe, built around a few well-chosen colors, ensures that everything works together effortlessly.

In investing, this translates to your asset allocation—the balance between stocks and bonds that determines your portfolio’s risk and return potential; and then drilling down further into the sub-asset classes: Large U.S. Stocks, Small U.S. Stocks, International Stocks, and different types of bonds.

Stocks (Equities): Higher potential returns but more volatility.
Bonds (Fixed Income): Lower risk, steady income, and down-market protection.

The higher your stock allocation, the higher the potential returns and the higher the swings. Bonds provide stability, much like those go-to wardrobe staples that keep your outfits grounded.

The Essentials: Wardrobe Staples vs. Portfolio Components

Just as every wardrobe needs staples, a strong portfolio does too, with a mix of sub-asset classes.

A classic capsule wardrobe typically includes:
✔️ Jeans (barrel, skinny, straight, wide, flared, tailored, baggy—your call!)
✔️ Black pants—when you need to look polished.
✔️ White shirt and white t-shirt (or cream, if white washes you out—I see you!)
✔️ A trench coat—(make it leopard to uplevel the chicness).
✔️ A few sweaters in flattering colors.
✔️ Sneakers, flats, booties, and sandals—for versatility.
✔️ A black leather jacket—for some edge.

Similarly, a well-diversified portfolio might look like this:
📊 Core Portfolio Allocation
🔹 25% Large Cap U.S. Stocks (the “black pants” of investing—versatile and reliable)
🔹 7% Mid Cap U.S. Stocks (adds variety, like a great jacket)
🔹 3% Small Cap U.S. Stocks (a little risk, like a statement piece)
🔹 20% International Stocks (broadening horizons, like a fabulous travel wardrobe)
🔹 5% Emerging Markets Stocks (high risk, high reward—like fashion-forward accessories)
🔹 40% Bonds (stability—your timeless trench coat)

Avoiding the “Nothing to Wear” (or Invest In) Crisis

Even though I love fashion, I’ve stood in front of my closet thinking, Ugh! I have nothing to wear! It can be frustrating and shame-inducing when you mentally count up the amount of time and money spent accumulating all the items in your closet. Those same feelings crop up when people open up their investment statements and are confounded by what they see.

Getting down to basics can help. In fact, if your capsule wardrobe or core portfolio ever feels a little boring, that’s actually a good thing. Their purpose isn’t excitement—it’s reliability. That said, there’s room for a little variety. Just as you might add a trendy piece—like this season’s fringe (see what fashion insiders say here)—you may decide to put some money into high-risk, high-reward investments. But keep them as accents, not foundations.

If you’ve ever curated a thoughtful wardrobe, you already understand the principles of smart investing: balance, quality over quantity, and knowing when to take risks. And if you haven’t? Well—maybe it’s time to get both your closet and portfolio in order.

Want to read more about building investment portfolios? This Investopedia article explains it in four steps, and here is another article from Forbes.

Substack is full of fun reads on capsule wardrobes. Here are a few: from The Daisy Edit and Wear We’re Going. I love this one from Field Study on how to build your dream wardrobe and not go broke! Or search for “capsule wardrobe” and you’ll find many other articles.

Important Disclosure: The content provided does not consider your particular circumstances and does not constitute personal advice.

Mostly go up, with occasional drops along the way.

Historically, those drops are far less frequent than the uptrends. After all, the average annual compounded return of the S&P 500 over the past 30 years (1995-2024) is 10%. That kind of return would not be possible if the market declined more often than it rose.

To put this into perspective:

• If you had invested $50,000 in the S&P 500 in 1995, your investment would be worth approximately $793,155 today—even though along the way, the market dropped by as much as 38.49% in a single year (2008) and rose by as much as 34.11% in a single year (1995).

Yet, I get it. The headlines are discouraging.

Every day, Trump says or does something that seems determined to throw the economy into chaos. Tariffs on Mexico, Canada, and China. Tariffs on all steel imports. Disbanding entire federal agencies. Appointing people to powerful positions who have zero experience. It can feel like we’re watching a slow-motion train wreck.

But here’s the thing: We’ve been here before.

There have been many moments in recent history when it felt like the world was ending, when investors panicked, and when people swore, “This time, it’s different.”

Yet, time and time again, the market recovered.

So let’s take a walk down memory lane and revisit some of these moments of financial doom and gloom.

1. The COVID Crash (March 2020)

"This is the end of the world as we know it."

No event in modern history disrupted businesses and individuals’ lives quite like COVID-19. Entire economies shut down. Travel halted. The global supply chain crumbled. The stock market plunged 34% in just one month, one of the fastest and deepest bear markets ever.

Yet, despite the chaos, the S&P 500 rebounded within months and went on to hit new highs. If you had stayed invested, you would have been handsomely rewarded.

2. The December 2018 Market Rout

"The Fed is going to crash the economy!"

In late 2018, the market had a near-bear market drop of 20%, triggered by the Federal Reserve raising interest rates and fears of an economic slowdown.

By early 2019, the Fed softened its stance, and markets roared back to life—fully recovering in just a few months.

3. The U.S.-China Trade War (2018-2019)

"This trade war will sink global markets!"

Trump imposed harsh tariffs on China, and in response, China retaliated. Investors feared a prolonged economic cold war. At multiple points in 2019, markets tumbled as headlines screamed about impending disaster.

Yet, despite the tension, markets ended 2019 at record highs.

4. The 2008 Financial Crisis

"The economy is collapsing!"

The housing market imploded. Lehman Brothers collapsed. The S&P 500 crashed nearly 40% in 2008. People truly believed we were heading into another Great Depression.

Yet, those who stayed invested saw their portfolios fully recover within a few years as the longest bull market in history took off.

5. The Inflation and Interest Rate Panic (2022)

"The Fed is killing the stock market!"

After the COVID stimulus, inflation soared to a 40-year high, leading the Federal Reserve to hike interest rates aggressively. Stocks took a beating—the S&P 500 fell 19.4% in 2022.

But what made 2022 even worse? Bonds, which are usually a safe haven during stock downturns, also had their worst year in decades. The Bloomberg U.S. Aggregate Bond Index dropped 13%, an almost unheard-of decline for an asset class meant to provide stability.

For many investors, there was nowhere to hide.

But as inflation cooled and the Fed slowed its hikes, markets rebounded strongly in 2023 and 2024. Those who stayed invested were rewarded once again.

Volatility: Expect It, but Don’t Fear It

With so much uncertainty around Trump’s policies, it’s almost guaranteed that volatility will spike. Markets hate uncertainty, and drastic policy changes—whether it’s tariffs, tax cuts, or regulations—cause investors to react, often emotionally.

But here’s the thing: volatility is normal.

The S&P 500 experiences, on average, a 14% decline every single year, even in years when the market ultimately finishes positive. Spikes in volatility don’t mean doom—they’re just a feature of the market.

What matters is staying invested despite the noise.

What About a Recession?

Recessions do impact stock market returns. And while most economists don’t see a recession in the next couple of years, it’s worth considering whether Trump’s policies could trigger one.

Some factors that could increase recession risk under Trump:

• Trade wars and tariffs could disrupt supply chains and increase costs for businesses.

• Aggressive tax cuts without spending cuts could drive up the deficit and lead to financial instability.

• Deregulation in key industries could create bubbles (think: the 2008 mortgage crisis).

That said, recessions are normal. Since 1995, we’ve had three recessions—each one felt painful, but the market recovered and reached new highs. Timing recessions is nearly impossible, and trying to jump in and out of the market based on recession fears often does more harm than good.

So, Is It Different This Time?

In the moment, every crisis feels like the worst one yet.

• In 2020, we thought the world was ending.

• In 2018, we feared the Fed was crashing the market.

• In 2019, we panicked over tariffs and trade wars.

• In 2008, we saw the worst financial collapse in decades.

• In 2022, we thought inflation and rate hikes would wreck everything.

Yet, the market kept going.

That’s why I’m not losing sleep over Trump’s policies—not because they aren’t disruptive or reckless, but because markets don’t hinge on one person or administration.

The market is bigger than politics. Bigger than any one president. Bigger than fear.

So, the next time you hear someone say, "It’s different this time,"—
Just smile and remember:

It never is.

Disclaimer

The information provided in this article is for educational and informational purposes only and should not be considered investment, tax, or legal advice. Past performance is not a guarantee of future results, and all investments carry risk, including the potential loss of principal.

The views expressed are my own and do not necessarily reflect the opinions of any firm or organization with which I am affiliated. While efforts have been made to ensure accuracy, I do not guarantee the completeness or reliability of the information presented.

Before making any financial decisions, consult with a qualified financial advisor, tax professional, or legal expert to assess your specific situation

However, I recently realized something: I could easily pay for dozens of Substacks without thinking twice. And now, whenever I go to push the buy button, I stop and ask myself: How many Substacks am I paying for now? How much am I actually spending on this? I love Substack, but I don’t want to go overboard.

At the same time, I feel conflicted. I want to support these writers. It feels unfair to read their work without contributing, especially when they’re pouring their energy, creativity, and vulnerability into their writing. These are voices worth supporting.

Then, this morning, while reading yet another fantastic free Substack that I felt I should be paying for, I had an epiphany: Why not stop agonizing over this and just set a budget? As a financial advisor, I help my clients do this all the time—why it took me so long to apply it to myself is beyond me.

Here’s what I believe about budgeting: You can’t have everything, but you can absolutely decide what experiences and things you value most, and then allocate your money accordingly. You purposefully spend on what brings you joy and fulfillment—and cut back on the things that don’t matter as much to you.

For example, I could decide that I’d rather spend my reading dollars on Substacks instead of magazines or newspapers. Or, that I’m willing to skip a couple of coffee shop visits or a new sweater so I can subscribe to more writers I love. You get the idea.

The next step in any budgeting process is tracking your spending—knowing exactly what you’re currently paying and then deciding how much is reasonable.

So, I went to my settings in Substack, clicked on "Subscriptions," and discovered that I subscribe to 72 Substacks! (I had no idea.) Out of those, I’m a paid subscriber to 12. But I didn’t know how much I was actually spending, so I dug deeper and clicked through each one to find the details.

Turns out, I’m spending $909.00 per year. I tend to buy annual subscriptions, and my very first paid Substack was The Quiet Life by Susan Cain, followed by Wordy Bird by Susan Orlean (both of which I highly recommend!).

So, I’m already making a significant investment in Substack. Now, the real question: Do I want to spend more? Is that a prudent decision? And if so, how much more?

Since I’m literally working through this budgeting exercise as I write this, I haven’t settled on an answer yet. But I will decide on a spending cap—one that aligns with my values and trade-offs.

What About You?

If you’ve discovered the joys of Substack, you might be facing a similar dilemma. Have you thought about how much you’re spending? Does it align with what you truly value? I’d love to hear your approach.

I feel great knowing I’ve taken the time to evaluate my spending, ensure it matches my values, and set a conscious limit. Whether I choose to cut back or subscribe to even more, I’ll be doing it with intention. And that is the essence of smart financial decision-making—whether it’s Substack or anything else.

I’m not particularly good with mechanical tasks, but I mastered the Breville quickly. I highly recommend it—not just for the coffee, but for the joy of the ritual itself.

This new coffee maker—and my morning coffee habit in general—got me thinking about habits. Specifically, could I apply the same joy and ritual I find in making coffee to other habits I want to build?

If you've ever read James Clear's Atomic Habits, you know he talks about layering habits—pairing something you already enjoy with a behavior you're trying to cultivate. For instance, I could resolve that before I boot up the Breville for my morning espresso, I drink a full 8-ounce glass of water. Then, after I finish my coffee, I could head downstairs to prepare for the day. By linking these steps, I could turn the ritual I already love into a launching pad for healthier habits.

This got me thinking about money habits, too—and how we engage with our finances in general.

Why Money Habits Matter

Here's the thing about money: it's always in the background of our lives, whether we like it or not. Bills get paid, paychecks or Social Security checks arrive, and subscriptions renew. Before automation, we were forced to sit down and attend to these tasks, which often led to more awareness of our finances. But now, with most financial tasks on autopilot, there’s no forcing mechanism to take a moment, sit down, and think about whether we’re headed in the right direction.

People tend to get very motivated to dive into their finances when something big is happening—planning a wedding, buying a house, starting a business, or dreaming about quitting their job. During those moments, they're all in, analyzing every dollar. But in the day-to-day, money management tends to be more of an afterthought.

Make Money Management a Ritual

What if we treated our finances like a morning coffee ritual—something we actually enjoy?

It doesn't have to be complicated or time-consuming. It could be as simple as setting aside 15 minutes once a week to check in with your money. During this time, you could:

• Look over your spending for the week. Did anything surprise you? Some people like to use budget apps to manage their spending.

• Check your savings progress. Are you closer to that big goal?

• Think about your priorities. Are you spending in a way that aligns with them? Here is a fun ebook to inspire you.

Even small check-ins like these can help you feel more connected to your money. And when you're in the habit of engaging regularly, the big financial moments—like buying that house or taking that dream vacation—feel less overwhelming because you've been paying attention all along.

Don’t Wait for a Financial Milestone

Just like drinking a glass of water before coffee, getting into the habit of engaging with your money is a small action that builds big results over time. We all know that staying hydrated is one of the pillars of good health (and good skin!) just as we know that head-in-the-sand behavior around money can lead to trouble. But when you're checking in regularly, you're prepared for whatever life throws your way.

So here's my challenge: Find a way to make money management part of your routine. Whether it's Sunday mornings with coffee or Friday evenings with wine (or sparkling water!), make it something you do regularly. You might even find yourself looking forward to it—and who knows, you could become your own financial barista in the process.

Other notes: Substack is a treasure trove for women over 40 who love fashion. So far, I have discovered Jane On Jeans, What Looks Good, and Hi Everyone With Hillary Kerr, to name a few that I enjoy. Their styling tips and willingness to highlight sales might actually save you $$ too.

There’s something magical about the holidays and the first days of the New Year. Time seems to slow down just a bit, allowing me to indulge in reading a good book or simply staring into the fire, coffee in hand, with music playing softly in the background.

But this week, my heart feels heavy. The devastating fires in Southern California are a stark reminder of how unpredictable life can be. I can’t imagine how the people who lost their homes must feel. I can picture the scenes before the fires started: clear skies, shimmering ocean views, and the hillsides of Malibu, Altadena, and Pasadena sparkling in the sun. And then, in a heartbeat, everything changed.

Living in the Oakland Hills, I understand that fear all too well. Our home is surrounded by trees, perched on narrow, winding streets that could quickly become impassable in an emergency. Fire season here peaks in the fall, and we breathe a collective sigh of relief when the rains finally come, and the danger recedes.

Because of the increasing fire threat, our homeowner’s insurance has tripled in the past two years. Climate change is undeniable to insurance companies—they’ve seen the data and adjusted their prices accordingly. While it’s too soon to say how the recent Los Angeles fires will impact the insurance market, one can only hope policymakers step up to protect those who simply can’t afford skyrocketing premiums.

The news from Southern California has spurred my husband and me into action. It’s easy to procrastinate on emergency preparation—there’s always something more pressing, and no one enjoys imagining worst-case scenarios. But time moves fast, and I’d much rather be ready than regret being caught unprepared.

Here’s what we’re doing this weekend:

1. Refreshing Our Emergency Backpacks

We have go-bags in our hall closet but haven’t reviewed them in ages. It’s time to restock with essentials:

• Freshwater bottles

• Non-perishable snacks

• Small bills in cash

• An extra pair of glasses or contacts

• Sneakers

• A fleece or windbreaker

• A change of underwear

• Sunglasses and sunscreen

• Necessary medications

2. Discussing Our Evacuation Plan

What if one of us is home and the other isn’t? Where will we meet if it’s unsafe to return home? Do we try to drive down the hill, up the hill, or go on foot? We’re also considering alternatives—heading to a friend’s home or a safe public place out of danger’s way.

3. Getting Our Critical Documents Organized

We use Dropbox and have a fairly good filing system for our critical documents, such as tax returns, insurance information, and property information. We also know we can retrieve most financial information online. However, we made a list of documents that we felt were important, and if we didn’t have them filed, we took photos and uploaded them, such as passports, social security cards, health insurance cards, and marriage and birth certificates.

4. Doing an Inventory of Our Possessions

Our home was robbed a couple of years ago, and to be reimbursed for our losses, we had to provide a detailed account of each item, including a description, date of purchase, and estimated value. If we had invoices or receipts, we were asked to provide them. So, I know that when everything is destroyed in a disaster such as a fire, the insurance companies will want that type of information. We decided to take videos of all the rooms in our house and store them in the cloud. For specific, more valuable items such as artwork, electronics, or furniture, we are doing our best to locate the receipts and upload them to our Dropbox. This task will take more than one weekend to complete.

I feel grateful to live where I do, surrounded by nature, but it comes with risks. Fires, earthquakes, mudslides, and occasional falling trees are real dangers. And the L.A. fires are a reminder to be just a little more prepared.

During our getaway, my husband and I enjoyed an Italian varietal wine tasting at Idlewild at their tasting room in town and a tasting at Overshine Wine Co, sipping Chardonnay and Zinfandel while listening to the proprietor's collection of soul music. We also took a bike ride on Westside Road—a long and winding wine country road, breezing past vineyards, rustic wineries, and beautiful homes with the winter sun keeping us warm enough while the cold winter breeze refreshed us. An added treat: my nephew and his family came for a homemade roast chicken dinner on New Year's Eve. All of these experiences were delightful and memorable, and it was a magical time.

Healdsburg also has some darn good shopping, including several women's clothing boutiques. My guilty pleasure is style and fashion. My love of clothing started long ago when I was a teenager (and raided my sister's wardrobes because I always wanted something new to wear) and has never waned over all these years. Every New Year's Day, my favorite Healdsburg boutique has a one-day half-off everything sale. This particular boutique carries a carefully curated selection of clothing by designers in Italy, France, Germany, Iceland, Denmark, Japan, and NYC.

Needless to say, I'm like a kid in a candy store when I enter this boutique on sale day. Women line up early to get the best chance at scoring a beautiful piece of clothing, and for the last few years, I have been first in line! I bought several items at excellent prices, including a cream-colored ribbed cotton/wool sweater by Yohji Yamamoto and an open-weave black cashmere Isabel Benenato cropped sweater. I plan to wear both pieces often.

Will I enjoy wearing these new clothes as much as I enjoyed my experiences in the wine country?

Can I afford both the experiences and the things I want?

I’d love to say yes to everything. But life, and finances, don’t work that way. Unless a person has an infinite supply of funds (which I don’t), being a mindful spender becomes essential.

For me, mindful spending is about being intentional and thoughtful with my choices, making sure they align with both my values and my financial reality. The wine country getaway and the boutique shopping spree both brought immense joy, as I knew they would.

If you’re like me—a woman who loves things as much as experiences—you might wonder how to balance it all. This is what I have done:

Clearly define what you truly value and what brings lasting fulfillment. What’s worth spending on, and what isn’t? Equally important: recognize the trade-offs. What are you willing to forgo to say yes to the things you love most?

When I planned the Healdsburg getaway, I decided we’d skip the expensive restaurant meals and enjoy happy hours and simple dinners-in instead. That choice saved dollars for the things and experiences we enjoy more—like that beautiful cream sweater:) Every time I wear it, I’ll remember the laughter, the vineyards, and the wonderful time we had saying farewell to 2024.

These are books that got me thinking about women and money—how we earn it, how we spend it, and how we value it. They’re not personal finance guides, but stories that quietly (or not so quietly) shine a light on the things we get right, the things we get wrong, and the way money weaves through our lives. They’re perfect for gifting—to friends, family, or even just to yourself.

Classic Novels

I love classic novels about women, but I’ll admit, sometimes they make me want to scream. It’s hard not to feel frustrated at how dependent women were on men back then. It’s a reminder of how far we’ve come—and, let’s be honest, how far we still have to go. When I started my blog, I named it Of Independent Means as a nod to this progress and as a little tribute to one of my favorite books, A Woman of Independent Means by Elizabeth Forsythe Hailey. Bess, the protagonist, is still an inspiration to me.

1. The House of Mirth by Edith Wharton
Lily Bart is smart, beautiful, and completely trapped. In her world, a woman’s financial stability depends on marriage, and Lily knows it. Wharton’s book is sharp and devastating, a cautionary tale about what happens when appearances become everything.

2. Pride and Prejudice by Jane Austen
Okay, yes, it’s a love story. But it’s also about money. Austen was way ahead of her time in how she tackled the economics of marriage. Elizabeth Bennet’s independence and wit are as refreshing today as they were when Austen first wrote her.

3. Little Women by Louisa May Alcott
It’s impossible not to love the March sisters. Each one has a unique relationship with money: Meg dreams of luxury, Jo wants independence, and Beth… well, Beth just wants everyone to be happy. It’s a timeless reminder that money is about values, not just numbers.

4. A Woman of Independent Means by Elizabeth Forsythe Hailey
Told through letters, Bess Steed Garner’s story is a quiet triumph. She navigates love, loss, and financial independence with resilience and wit. Bess isn’t perfect, but she’s unforgettable—and proof that women can shape their own destinies.

Contemporary Fiction

5. Trust by Hernan Diaz
If you love books that make you think, Trust is for you. It unravels the story of a wealthy couple—but whose version of the story can you believe? At the heart of it is a sharp and subtle commentary on power, money, and the hidden roles women play in building legacies.

6. The Cost of Living and Real Estate by Deborah Levy
Deborah Levy writes about life’s transitions with such honesty it’s almost startling. In The Cost of Living, she examines what it really takes—financially and emotionally—to rebuild a life on your own terms. Real Estate continues this exploration, reflecting on what home, ambition, and ownership mean for women today.

7. The Joy Luck Club by Amy Tan
Mothers and daughters, cultural expectations, and money. Tan weaves these themes together beautifully in this multi-generational story. It’s about sacrifice, identity, and the complicated ways financial success shapes relationships.

8. The Henna Artist by Alka Joshi
Lakshmi escapes an unhappy marriage and builds a life for herself as a sought-after henna artist. Her story is about independence, survival, and the price women often pay to chart their own course. It’s empowering and deeply satisfying.

Nonfiction Narratives

9. Maid: Hard Work, Low Pay, and a Mother’s Will to Survive by Stephanie Land
Land’s memoir isn’t easy to read, but it’s important. It’s a raw, honest account of living paycheck to paycheck and the barriers that keep people (especially women) stuck in poverty. It’s also a testament to grit, resourcefulness, and the value of dignity.

10. Nomadland: Surviving America in the Twenty-First Century by Jessica Bruder
What happens when the American dream falls apart? This book follows a community of older Americans who live in vans, traveling across the country to find work. It’s a sobering reminder that economic instability can happen to anyone—and that experiences often mean more than possessions.

In Closing…

These books aren’t just about money—they’re about life. They remind us that financial decisions are often about so much more than dollars and cents. Whether you’re looking for a thoughtful gift or just something to curl up with, I hope you find a book on this list that speaks to you. And who knows? Maybe you’ll gift it to someone else next year.

Since Donald Trump was elected, I’ve read countless articles speculating about the potential impact of his proposed policies on the economy and stock market. His key economic priorities, as stated, include:

• Imposing tariffs on key trading partners such as Mexico, Canada, and China.

• Mass deporting undocumented immigrants.

• Limiting the Federal Reserve’s independence.

• Enhancing domestic energy production.

• Extending and introducing additional tax cuts.

• Deregulating industries.

Opinions are sharply divided. Some argue these measures could stimulate economic growth and curb inflation. Others worry they could lead to heightened inflation and ballooning national debt. Naturally, many clients have been asking whether it’s safe to remain invested as Trump and his administration determine how much of their agenda they can implement.

It’s worth noting that many of Trump’s economic proposals require Congressional approval. However, some can be enacted through executive orders or regulatory changes, and we can safely assume his legal team is hard at work identifying these opportunities. Ideally, his advisors include seasoned economists who will weigh the potential downsides alongside the upsides of these policies.

In the meantime, uncertainty is likely to drive increased volatility in the stock market. This is not unusual; markets dislike uncertainty, and Trump’s proposals are indeed bold and potentially disruptive. It’s uncharted territory, and the long-term effects of his policies remain speculative at best.

That said, volatility doesn’t necessarily mean the market will trend downward. It simply means that investors should prepare for a bumpier ride than they’ve experienced in the relative calm of recent years. History offers reassurance: the stock market has performed well under most Presidents, regardless of their political leanings or policy agendas.

For long-term investors, particularly those counting on their portfolios to sustain them through retirement, the most prudent approach is to remain invested and weather the inevitable ups and downs.

Here are some actionable steps to help you stay calm and focused during uncertain times:

1. Maintain a Cash Reserve
   Ensure you have enough cash on hand to cover your expenses and address any emergencies that might arise. This cushion can provide peace of mind and reduce the temptation to make emotional investment decisions.

2. Avoid Drastic Portfolio Changes
   Resist the urge to make significant changes to your asset allocation based on feelings about Trump’s policies. Reacting emotionally to short-term uncertainty can derail long-term goals.

3. Reassess Your Risk Tolerance
   If you feel overexposed to stocks and find the market volatility stressful, consider reducing your equity allocation. But don’t exit the market entirely in anticipation of a "better time" to reinvest — market timing is notoriously difficult and often counterproductive.

4. Limit Account Monitoring
   Checking your portfolio balance too frequently during volatile periods can amplify anxiety. Trust your long-term strategy and avoid the temptation to micromanage your investments.

5. Continue Saving and Investing
   Continue saving and investing as you have been. If you’re making regular contributions to your portfolio, maintain that discipline. Dollar-cost averaging ensures you buy more shares when prices dip, which can strengthen your portfolio over time.

Uncertainty is an inherent part of investing, and no administration, no matter how unconventional, changes the fundamental principles of sound financial planning. By focusing on what you can control and maintaining a long-term perspective, you’ll be better positioned to navigate any turbulence ahead.

I had been hopeful this time that a woman would make it to the White House—not a 'strong man,' but someone who could lead with both strength and empathy. My female colleagues and friends in financial advising were dismayed, too. I imagine some of my male colleagues were as well, though I suspect that many in the industry were satisfied with the outcome. After all, conventional wisdom says Republicans are "good for business": lighter regulatory burdens, higher corporate profits, and, theoretically, more wealth for advisors and clients alike.

They say Trump won because of the economy. As a financial advisor, I view the economy through a broader lens than just gas prices or the cost of a gallon of milk – we’ve had low unemployment, strong GDP growth, and a booming stock market. But for many Americans, the economy is defined by how much is left in their checking account at month’s end—a balance eroded by persistent inflation. Essential costs have climbed, and they haven't come down. For those feeling the squeeze, one of Vice President Harris's campaign issues—tackling food inflation—did not sway their vote. Americans wanted a change, and they voted for it. Although many factors likely contributed to the outcome, history tells us that financial strain often drives voting decisions.

Attending a conference in New York was a welcome distraction from the election results. Working in this male-dominated field is challenging, but among women, there's a strong camaraderie and shared drive to bring more of us into the industry and create a more inclusive environment. Of course, the election was on our minds, but we spent the day learning, refining our skills to better serve clients, and supporting each other through mentorship and sponsorship.

Outside the conference, New York City buzzed with its usual energy. Crowds of New Yorkers and tourists filled the streets, taking in the unseasonably warm weather and bright blue skies. Life goes on.

Whenever I’m in New York, I make it a point to see a play or musical. This time, I chose Suffs, which tells the story of the long fight for women’s voting rights in America. Did you know the suffrage movement spanned 72 years? After decades of effort by generations of women, the right to vote finally became a reality on August 18, 1920, with the ratification of the 19th Amendment. Many who voted for Harris may feel disheartened, but the suffragettes’ success reminds us of the power of persistence. Their achievement was hard-won because they refused to give up.

The Corporate Grind vs. The Freedom to Choose

The Fear That Lurks: "Will I End Up a Bag Lady?"

One of the biggest fears I hear from clients is the dreaded "bag lady" scenario. It's that deep-seated worry about whether there will be enough money to last through retirement. This fear often drives women to seek out financial advice. But eventually, another feeling creeps in, overshadowing even the fear of running out of money—the desire to be done.

After years of careful planning, these clients decide to take the leap and retire. I have had a few clients who retired earlier than planned, thinking they may take on some consulting work.

The Reality Check: Retirement Isn't All Rosé and Netflix

Here's the pattern I see play out more often than not:

Phase 1: The Honeymoon (Months 1-3)

Waking up with no alarm, no meetings, no expectations? Bliss. Every day feels like a Saturday.

Phase 2: The Couch Potato Phase (Months 4-6)

The novelty wears off. Netflix starts asking if you're still watching, and the answer is... you're not sure.

Phase 3: The Existential Drift (Months 6+)

You begin to wonder if retirement was a good idea. You might even land a part-time gig, but it feels too much like the grind you left behind.

The Positive Shift

And then, something magical happens. You find your rhythm—without work. You start exploring new (or old) passions. Your days start to fill with activities that bring joy and fulfillment

.

Ideas for Rediscovering Yourself:

• Join a book club or hobby group

• Volunteer for causes you care about

• Travel to places on your bucket list

• Take up a new sport or fitness routine

Preparing Financially for the "I'm Done" Moment

1. Build an emergency fund to cover 6-12 months of expenses

2. Max out your retirement contributions in the years leading up to your exit

3. Consider downsizing or relocating to reduce living costs

4. Explore healthcare options and factor in potential medical expenses

The Happy Ending

This isn't just retirement; it's reinvention. You've traded in the 9-to-5 for a rich life with experiences, connections, and joy. You've moved past the fear of not having enough and into the realization that you already do.So, if you're staring down the barrel of that "I'm done" moment, know this: The transition might feel rocky at first, but on the other side is a different life waiting to be lived. And it can be pretty amazing.

There's good news and bad news when it comes to Fed rate cuts. The good news is that, eventually, the rates that affect us consumers—mortgage, credit card, and car loan rates—will start to come down. It doesn’t happen overnight, but it happens. Lower rates mean borrowing money becomes cheaper, making loans more affordable and easier to pay back. If you're someone who buys big-ticket items (like cars, houses, or even that boat you’ve been eyeing), you’ll pay less in interest on loans. For those with credit card balances (though I’d advise not to make a habit of carrying those), lower rates offer some welcome relief.

In the last five years, mortgage rates have been on a wild ride. From 2019 to 2021, 30-year fixed mortgage rates hit historic lows, with rates dipping as low as 2.65% in 2021. This was largely due to the Fed slashing rates to stabilize the economy during the COVID-19 pandemic. But by 2022, inflation was surging, and the Fed responded by aggressively hiking rates. Mortgage rates climbed steadily, surpassing 7% by the end of 2022. At their peak in 2023, rates reached 7.52%, but have recently come down slightly to around 6.9%.

Now, here's why that matters: The difference between a mortgage rate of 2.65% and 7.52% is significant. On a $500,000, 30-year fixed-rate mortgage, your monthly payment at 2.65% would be about $2,104.82. At 7.52%, it jumps to $3,502.92! Over the life of the loan, you’d pay around $535,717 more in interest at the higher rate—enough to buy another house in some places!

As with most things in life, timing is everything. If you were lucky enough to buy or refinance between 2019 and 2021, you likely locked in an enviable mortgage rate under 3%. In fact, one in five American homeowners with mortgages have an interest rate that low. But for those looking to buy or refinance now, the story is different. With rates north of 6%, many potential buyers who would have qualified for loans just a few years ago are priced out of the market. Additionally, those with low-rate mortgages are reluctant to sell their homes, knowing they’d face much higher payments on their next mortgage. This has serious implications for the housing market, creating a shortage of homes for sale and driving prices even higher.

On the flip side, higher rates do offer one benefit: better returns on your savings. But here's the catch—traditional banks are notoriously stingy when it comes to passing on these higher rates to savings account holders. If you’re parking significant amounts of cash in a standard savings account, you’re missing out. Higher rates are a great opportunity to move your cash into a money market fund, a CD, or even a Treasury bill, where you can earn much more while still keeping your money safe.

As rates start to come down again, now might be the time to "lock in" higher savings rates before they drop further. Consider locking in returns through CDs, Treasury bills, or, if you’re willing to take a bit more risk, by buying bonds.

Conclusion: Timing is Everything

Interest rates move in cycles, reflecting broader economic trends. Whether you’re borrowing or saving, paying attention to these shifts can help you take advantage of favorable conditions. When rates are low, it’s a great time to lock in a good deal on a mortgage or loan. When rates are high, it’s wise to secure better returns on your savings. By being aware of where we are in the economic cycle, you can make smarter financial moves and get the best rates—whether you’re borrowing or saving.