January Newsletter – Regrets on Overcomplicating My Investing Life

Monthly Newsletter 2025-11-20

Jim is guilty of being more of an optimizer than a satisficer with his investments, and that isn't always such a great thing. Let's talk about it more below in January's financial tip of the month.

SPONSORED BY

Medical Student Loan Refinancing Alert – Lowest Rates in 3 Years for Physicians: Act Soon! – Starting at 3.27% Limited time offer – act now before rates change. Juno uses group purchasing power to negotiate better student loan refinancing rates and benefits for physicians. For a limited time, rates have dropped to the lowest in 3 years, starting at 3.27% for physicians. On top of that, WCI members get $500+ cash back when refinancing through Juno. Check your rate without affecting your credit here. Want to speak to a doctor? Book time with Dr. Okafor for free. Don't miss the chance to lock in historical low rates.

ANNOUNCEMENTS

	BOGO Free Online Course Sale – Start your year off right with a jumpstart on your financial education. With any online course purchase, including our best-selling Fire Your Financial Advisor Series, get FREE access to the CFE24 Course (a $789 value). CFE24 includes 37+ hours of expert-led finance and wellness presentations from our annual conference and 16 hours of CME/CE credit. The option to gift a course is available, and many courses are CME-eligible. Go to Course Sale
	WCICON26 Swag Bag Deadline January 9th – Join your White Coat Investor community March 25-28, 2026, in the Red Rocks of Las Vegas. The Physician Wellness and Financial Literacy Conference is CME-eligible and likely the best investment you could make in yourself. Plus, it's known for swag bags filled with items you actually want, including books from a selection of speakers. Both in-person and virtual conference attendees must register by January 9th to secure their swag bag. Learn More and Register
	The Ultimate Roth Workshop – Hosted by The Financially Empowered Women community, featuring guest presenter Dr. Jim Dahle. Join us January 14 at 6 PM MT for this practical workshop. You'll learn when to use the Backdoor Roth, Mega Backdoor Roth, and Roth conversions and how to avoid the most common Roth-related mistakes. Dr. Dahle will also walk through a step-by-step tutorial showing exactly how to execute a Backdoor Roth correctly, from start to finish. Register for Free Event
	Expert Witness Startup School Enrolling Soon – Diversify your income using the skills you already have as a doctor. Prior students report earning $50,000–$100,000 in their first year as an expert witness. Enrollment opens January 14. Bonus: Get a free WCI course with enrollment ($789 Value). 35+ hours of material from our annual conference, including up to 17 hours of CME/CE credit available. Learn More and Join the Waitlist

MARKET UPDATE

Data sources: Morningstar and SPGlobal Now that 2025 is over, we can officially say that it was yet another fantastic year to be in US equities. Not quite as good as 2023 or 2024 (when you earned 20%+ on your money), but making 17% in the stock market in 2025 has to feel great. Hopefully, you kept your money in stocks even when the market temporarily went terrible in April. It was an even better year for international stocks (only once in the past seven years prior to 2025 had international stocks beaten US stocks). Combine that with the success of emerging market stocks, and it seems clear that investing outside the US was a good bet last year. With the chaotic landscape the federal government has been navigating, will that international dominance continue in 2026? This is the eighth-straight month microcap stocks have been winners. Gold reached a record high in December and had its best year in more than four decades. Silver was even better. But remember: as Robert Frost once wrote (and as Ponyboy in the Outsiders once recited), "Nothing gold can stay" (though to be fair, Frost was talking about nature and Ponyboy was probably talking about the youth and spirit of the Greasers). Not a great year for Bitcoin. It probably won't deter anybody who truly believes in crypto, though.

REAL ESTATE OPPORTUNITIES

Goodman Capital – A New York City-based alternative real estate investment firm with 50+ years of collective experience creating and preserving wealth through conservative, senior-secured private real estate lending investments. Serving 1,000+ investors, both domestically and abroad. Mortar Group – A vertically integrated investment manager specializing in secure multifamily real estate in prime New York niche neighborhoods. Preferred by investors seeking high yields but steady returns, Mortar offers a unique solution in the alternative investments market. Please consider these introductions and be sure to do your due diligence prior to investing in any real estate investment opportunity.

STAFF ADVENTURE

Summer in New Zealand with COO Brett Stevens

Years ago, my wife Jessica gave me a digital photo frame that sits on my desk. It's filled with photos of our family having adventures and making memories together—some from around the world, many from right at home. Those photos and the experiences they represent are among my most prized possessions. In the WCI world, where we spend so much time thinking about "return on investment," this is my personal "return on life." About six years ago, I made a career change and began running the WCI business. I was excited about WCI because of its impact and potential but also because it allows me to work from anywhere in the world. Right now, I'm in the middle of 10 weeks enjoying summer in New Zealand. The kids switched to online school, and both Jessica and I can work remotely. The time difference works perfectly: I start my workday at 5am here, which is 9am the previous day in Utah. I finish mid-afternoon, and almost every day, we head outside to do something active together. We move to a new Airbnb each week. We've hiked, sandboarded, run, swam in oceans and lakes, canyoneered, mountain biked, rafted, zorbed, boogie boarded, kayaked, explored glaciers, and spent time with locals. One of the biggest surprises has been how much extra time we have without many of the (good) distractions of home. Extended family dinners, events, home projects, church responsibilities, holiday parties, and countless other activities have been replaced with simpler days and more focused family time. Many of those things are great, but there's something refreshing about a simpler life for a few weeks. This photo captures the adventure I was most excited about: running a raft off Tutea Falls on the Kaituna River. At 23 feet, it's the highest commercially runnable waterfall in the world! We even kept the rubber side down!

BEST OF THE MONTH

Best of WCI Why Physicians Should Retire as Multi-Millionaires – Here's Jim's hot take of the month: A doctor who doesn't retire as a multi-millionaire has failed. I'm Leveraged to the Gills at Nearly $2 Million! Watch Me Swim – This anonymous guest poster has tons and tons of debt. Somehow, he's totally comfortable with it all. What We Learned When Our Tenant Was Arrested on Drug Charges – WCI columnist Margaret Curtis' real estate investing career took an unexpected turn recently. How to Avoid Getting Scammed – There are plenty of fraudsters and scammers in this world. You need to learn how to protect yourself against becoming their victim. The Best Financial Books for Teens, as Noted by a Teen Who Loves Finance and Reading – New 15-year-old columnist Roman Remke makes his WCI debut and shares his favorite financial books. This is a great list if you have teens at home. Truth, Lies, and Hype: Sorting Through the Messaging Around Real Estate Investing – There's so much hype around real estate investing that it's sometimes difficult to find the right balance. The Overlooked Tax Strategy That Could Save Doctors 6 Figures on Their Taxes – Here's what you need to know about cost segregation and whether it could be worth it for you. Flat-Fee Planning for Physicians, and Why the AUM Model Deserves a Second Opinion – Financial planning can get complex. But does that mean fees should rise as your wealth grows—even if your level of complexity stays the same? Living Against WCI Advice (AWA) – Columnist Francis Bayes doesn't subscribe to every philosophy at The White Coat Investor. He explains why (and how he thinks his decisions will turn out). How to Never Run Out of Money in Retirement – Are you afraid of running out of money in retirement? Use these strategies to ensure this does not happen to you.

New Podcast Episodes Be sure to check out The White Coat Investor Podcast if you haven't yet. 30,000 to 40,000 are listening to every episode. If you'd like to leave a question to be answered on the podcast, record it here. #451 – Roth IRAs and 529s (Sponsored by SoFi) #450 – When You Win the Game, Stop Playing with Bill Bernstein (Sponsored by SoFi) #449 – Unions, ACATS Fraud, Vesting, HSAs, and ETFs: What Doctors Need to Know (Sponsored by SoFi) #448 – Smart Retirement Moves for High-Income Professionals (Sponsored by Laurel Road) The Milestones to Millionaire Podcast has short episodes celebrating your accomplishments. #255 – PA Becomes a Millionaire and Finance 101: Backdoor Roth IRA Process (Sponsored by Goodman Capital) #254 – Hospitalist Becomes a Full-Time Entrepreneur and Finance 101: Tax Loss Harvesting (Sponsored by Student Loan Advice) #253 – A Dentist Acquires Enough to Run for Mayor and Finance 101: End of Year Giving (Sponsored by Resolve) #252 – Psych Resident Maxes Out Spousal and Personal IRAs and Finance 101: Boosting Your Income (Sponsored by Surveys for Money) #251 – Dermatologist Hits $750,000 Net Worth Before Finishing Residency and Finance 101: The Basics of Real Estate Investing (Sponsored by Resolve)

Best of the Web Every month we recommend (about) 10 articles from across the web. Thank you to those who send us suggested articles. Retirement Survey and Insights 2025 – Goldman Sachs did a survey with some surprising results, including that more people making $300,000+ live hand to mouth than people making $200,000-$300,000. Doctors Retire Differently. Here's What They Know and You Don't – This article was OK (it quotes some goofy physician financial blogger), but we thought the title was spectacular. Wish we could write them that well. A Fall from Grace – From the American Journal of Sports Medicine, this article explains why people don't trust doctors nearly as much as they used to. There are serious consequences to that loss of trust. $27,000 a Year for Health Insurance. Can We Afford That? – If you think physician financial illiteracy is a big problem to tackle, take a look at our healthcare system. A pretty thoughtful piece about one of our most challenging problems. The Backdoor Roth IRA After an Excess Contribution to a Roth IRA – WCI podcast guest Sean Mullaney wrote this and sent it to me. For years, we've told people who screwed up their Backdoor Roth IRA process to do an IRA recharacterization to fix it. Sean argues that a corrective distribution is better. He's probably right, although either is still a reasonable solution to this hopefully one-time problem. The Four-Year Rule for Retirement Spending – Ben Carlson writes about an interesting solution to a common problem faced by retirees managing Sequence of Returns Risk. Theory is one thing, but what do informed people actually do? IRS Issues Trump Account Guidance – Lots of people asking about this, but we're waiting a few more months to run another post on it so we have more concrete details. If you don't feel like waiting, you might find the answers you're looking for here. Here's a look at a draft IRS tax return form to report it that you might use on your 2026 taxes. The Ongoing Fight Against Frivolous Tax Arguments – Don't use them. Filing returns and paying taxes are not voluntary. Avoid those who make frivolous arguments. Do We Need a Good Long Bear Market? – We may not "need" one, but it certainly wouldn't surprise us if we got one. Consider that most Wall Street professionals had not graduated college prior to 2008. Investing and Tax Planning Come Last – Mike Piper, like Jonathan Clements, gets it. Everyone wants to talk about the sexy stuff. Everyone is willing to pay for the sexy stuff. But the sexy stuff isn't the important stuff. Want more money in your investing accounts? Put more money in there by figuring out where else your money is going. Building a Bond or ETF Ladder – Despite that Jim was suckered into this post due to the accompanying picture of a via ferrata that he's positive Harry Sit did not take himself, it turned out to be a pretty good post. Lots of cool new products to make laddering bonds easier out there. Real Life Experience with a Deferred Fixed Annuity (MYGA) – Harry bought his first and last MYGA, too. Trump Account Tax Headache – While this may be changed before you can actually contribute to a Trump account, right now doing so requires you to file a gift tax return.

TIP OF THE MONTH

By Dr. Jim Dahle, WCI Founder One of the biggest regrets I've had about my financial life was overcomplicating it.

There is a spectrum between optimizers (aka maximizers) and satisficers (comes from a combination of "suffice" and "satisfy"), and we're all on that spectrum somewhere. Optimizers try to wring every dollar they can out of portfolio and tax and career management. Satisficers are always looking for "good enough." They want to get the important things right but otherwise keep everything as simple as possible. Simplicity has great value in and of itself. For example, somebody could self-manage a simple portfolio but might require professional help for a complicated one. If that complicated one isn't at least paying for the help required, it's not worth it. But this concept of optimizing vs. satisficing applies to all kinds of aspects of your financial life besides portfolio management. I'm certainly guilty of being more of an optimizer than a satisficer. I mean, I write a financial blog. I'm clearly a bit of a hobbyist. But I can look back at tons of things we've done over the years, most of which made us at least a little bit of money, and say, "That wasn't worth it." Now I see WCIers doing similar or even more complex things to save a little money, eke out a little extra return, get a little more asset protection, or whatever, and I just shake my head. Here are some that I've seen on the morning I wrote this. Paying Kids One WCIer family was trying to figure out how to pay their children more so their kids could make larger Roth IRA contributions. The children do some baking for a little family business, but they could also model for the website of this baking company. The parents wanted to know if they could pay them the going rate for models for their baking work. I've paid my kids to be models (to actually be models) in the past, so I'm probably just as guilty of this sort of thing. But in retrospect, it really didn't move the needle much. Starting Corporations I'm amazed at what hoops people are willing to jump through for serious tax preparation and ongoing hassles. Forming and maintaining corporations is hardly hassle-free. One WCI forum member responding to the person asking about how to pay their baker kid more pointed out that they actually formed a corporation for a little bit of work their kids were doing. This was a multi-decamillionaire, mind you, who was certainly way past having "enough." Sometimes it's just better to have your children be household employees for small amounts of side job kind of work (saves FICA taxes). This doc's brilliant ideas were probably costing him money, plus massive additional financial complexity. I might be a little guilty of doing this, too, having made the mistake of having a kid be self-employed. We had to refile that tax return to get back the FICA taxes. HSA Games Another doc wrote in trying to figure out how to take maximum advantage of an HSA without dramatically overfunding it. Heaven forbid you just use your HSA to pay your healthcare expenses as you go. I wish we'd done that all along. Now, we have an overfunded HSA and plenty of lost receipts, and guess what we're doing with that HSA now? Spending it as we go along. Wyoming LLC Games Yet another doc was advocating for a Wyoming LLC, primarily to try to hide his short-term rental properties from creditors. While rental properties absolutely do belong in LLCs for both internal and external asset protection reasons, "anonymity" is highly overrated in a real asset protection situation. If you own rental properties or you're a doc, your potential creditors already assume you're rich. They're not going to avoid suing you because they don't know EXACTLY how much you're worth or they aren't 100% sure who the person behind the rental property is. When you're put under oath and asked about your assets, you're going to have to reveal them anyway (or risk going to jail). Tax-Gain Harvesting Maybe I'm still just as bad at this as ever. My oldest is now independent of us, and her 20s fund UTMA (now just her taxable brokerage account) has appreciated shares in it. Her taxable income is way below the top of the 0% long-term capital gains bracket, so we did a little tax-gain harvesting transaction last month to update her basis and realize some capital gains in the hopes of reducing her future tax bill. I asked her if she wanted to pay an extra $5,000 in taxes 2-10 years from now, and her answer was "no." It didn't take much time, but it did remind me of the fact that I filed an otherwise unnecessary tax return for her for most of a decade to carry forward capital losses that never actually saved any taxes because I got all excited about tax-loss harvesting in her account many years ago. What a dolt. Don't be a dolt. When facing a choice that will involve a more complex financial life, weigh the benefits carefully against the additional required work, hassle, and complexity. Bounce it off your probably-not-a-financial-hobbyist spouse, too. The hassle that you might think is no big deal might later cause them months of worry. Let simplicity be the default and have a good reason to deviate from it. The White Coat Investor

Past Newsletters December Newsletter – More SALT in 2026 Could Be Great for Your Financial Health November Newsletter – How to Prepare for Financial Incapacity as You Age October Newsletter – What Is a Cost Segregation Study, and Should You Bother with One? September Newsletter – Going 1099 Is Not a Magic Elixir August Newsletter – Getting Your Financial Education Early Can Be Worth Millions Click here for all past newsletters.

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