Best of Jonathan’s HumbleDollar Posts
I wanted to take some time and dig into Jonathan's earliest posts on HumbleDollar. Posts that even the most loyal readers may not have read. With that, I also summarized some main takeaways and learnings that can help us all better navigate our own complex lives.
As I was digging into the early articles, I kept coming back to the piece he wrote, "The C Word."
In that reflection, Jonathan shared the discovery of the cancer that would take his life. Yet even then, he wrote about gratitude, small daily joys, and the power of focusing on what we can control. Despite a limited prognosis, he remained positive.
Specifically, he reflected on uncertainty, risk, and generosity: how life is unpredictable, yet we can act to protect those we love and help others along the way. Even confronting mortality, he remained committed to his purpose, emphasizing that he wanted to continue sharing his learnings with, "I intend to keep HumbleDollar going."
It's inspiring to me that he wanted this site to continue, and I want to honor that and continue sharing that message. It's up to all of us to do so. With that, let's dive into some of those older posts.
Careers and Early Adulthood
Passion may pay less, but it pays in fulfillment
In "Career Day," the earliest post on the HumbleDollar site, Jonathan emphasized that there's a tradeoff between money income and psychic income. Passion may pay less, but it pays in a different currency. Your goal is to find the appropriate balance.
Start financial planning early
In "Tips for Grads," Jonathan shared advice for those early in their careers by committing to simple, yet not easy, decisions:
> Save for retirement from day one.
> Keep housing costs low.
> Choose broadly diversified, low-cost investments to avoid large tax mistakes with individual stocks later on.
Think long-term about your life and career
"Take the Long View" reminds us that longer lifespans mean extended careers and uncertain retirements. Planning ahead isn’t optional. It’s necessary for both happiness and security.
Even with recent events, Jonathan still hammered home this point.
Happiness and Spending
Small, frequent pleasures bring more joy than rare, expensive purchases
In reflecting on "Buying Happiness," Jonathan emphasized that we gain greater happiness from frequent small purchases or spending on others, rather than buying big-ticket items.
That $100,000 car you've always wanted to buy? The feeling will fade away. Undoubtedly.
Do things with others and capture memories
In "Simply Happy," he added that fun is amplified when shared: go to dinner, a concert, or a hike with someone else, take photos, and savor those moments long after they happen. This will be especially helpful to reflect on in later life.
A great lesson I liked from that piece is that you should pause to admire your surroundings and possessions, and reflect on how lucky you are.
Happiness is amplified by attention.
Keep fixed costs manageable and avoid long-term debt
In "Financial Wellness," Jonathan emphasizes controlling housing, transportation, and other fixed costs to reduce stress and maximize savings.
This is how you can truly achieve financial freedom - by keeping your expenses low.
Humility and Money Mindset
Embrace humility in financial life
In "Why HumbleDollar?" Jonathan explained that overconfidence, unrealistic expectations, and impatience often lead to disappointment.
Recognizing the limits of money’s power is the first step toward a wiser approach. You can't get far with money if there are bigger issues at play.
We aren’t smarter than the market
This is perhaps the lesson that has carried forward for decades and one that has resonated widely. Focus on low-cost, broadly diversified index funds rather than trying to beat the market by picking individual stocks.
There are too many articles to include that repeat this advice. In "Mistakes Compounded," Jonathan shared a great reminder: "To recoup a 50% loss, you need a 100% gain." This is why investing in individual stocks can be dangerous.
This is also how I manage my own portfolio - broad-based index funds. Simple and effective.
Risk
Appreciate the bad things that didn’t happen, and plan for them
The "Happy Thoughts" post teaches us to recognize the dangers we’ve avoided and to prepare for unlikely but possible events through insurance, emergency funds, and portfolio diversification.
"But a string of good years in the stock market can cause folks not only to question the value of bonds," which is very timely advice, even though it was written back in 2016.
"We can control risk, but we can’t eliminate it. I’ve spent decades managing both financial risk and potential threats to my health. But despite such precautions, sometimes we get blindsided."
This quote, from "The C Word" reflection, is very powerful. There is always risk, regardless of which activity you engage in. The goal is to be mindfully aware of it.
Investing and Money Management
Tax-loss harvesting is overrated. Focus on long-term, tax-efficient asset placement.
"What Tax Losses?" explains that holding tax-efficient funds in taxable accounts and tax-inefficient ones in retirement accounts is often a smarter strategy than chasing paper losses.
Compounding works both ways
Debt can grow as fast as wealth.
"Mistakes Compounded" illustrates that investment gains and losses don’t add linearly, and that credit card debt can snowball if ignored.
Small decisions can have a big impact over a long period of time.
Family and Legacy
Family is a great asset
In "Keeping It Private," Jonathan explained how he provided a private mortgage to his daughter and explored how financial products could work better when structured within the family. Sometimes, setting the next generation for success is our responsibility.
Generosity isn’t optional. It’s a way to recognize the inherent goodness of others.
Across multiple posts, Jonathan reflected on how sharing time, money, and attention can enrich both giver and receiver.
Even in the face of illness, Jonathan's writing was about empowerment, perspective, and gratitude. He didn’t just share personal finance tips. He taught us how to live well and prioritize what truly matters. The legacy he leaves is not only the wisdom in his words but also the way he lived, especially during the last 15 months.
Bogdan Sheremeta is a licensed CPA based in Illinois with experience at Deloitte and a Fortune 200 multinational. He shares insights on taxes and personal finance through his newsletter. He has over 140,000 followers on X and 130,000 on Instagram.
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