Financial Planning Through Changing Presidencies: My Journey – Technologist

With Donald Trump set to become the 47th President of the United States, it’s natural to wonder what this new administration could mean for your finances.

For most people under 30, a change in leadership might not significantly impact financial planning. In your 20s, you’re often not earning enough or rich enough for a president’s tax policies to have a dramatic effect. After all, no president is likely to increase taxes on middle- or lower-income earners.

That said, beyond tax policy, programs like student loan forgiveness, down payment assistance, tax breaks on tips, stimulus packages, and expanded child tax credits can make a real difference for many young Americans, often shaping financial behaviors and decisions in a direct way.

As you get older—and hopefully wealthier—you might face the question of whether to keep grinding or finally take things down a notch. Everyone has a unique level of drive when it comes to building wealth.

Ultimately, we’re each responsible for our own financial well-being. But looking back, I can see how various presidents have nudged my path in subtle, sometimes unexpected ways.

I thought it’d be interesting to revisit how past presidents from both parties have influenced my financial planning and life in my 30s and beyond. I hope you share your own stories of how different presidents’ policies have shaped your financial journey, too.

Financial Planning Under President Obama (January 20, 2009, to January 20, 2017)

Barack Obama was president from January 20, 2009 – January 20, 2017, stepping in just six months before I launched Financial Samurai. I was between 31 and 39 years old during his time in office.

In mid-2009, he felt almost like a savior—the economy was reeling, and I’d lost 35% – 40% of my net worth in six months during the global financial crisis. Many friends and colleagues were losing their jobs. I was worried I might lose everything after 10 years of working 60+ hours a week.

Thankfully, the economy bottomed in July 2009, and began to recover. With each month that passed by, I gained more peace of mind and confidence, working hard to rebuild my net worth. I continued to save every paycheck (50% of my after tax salary), and 90% of every year-end bonus to one day break free.

My goal was to achieve a $3 million net worth and generate $80,000+ a year in passive income so I could eventually get out of finance for good.

Higher Taxes Reduced My Motivation to Continue Working

All was going well until the Obama administration decided to raise the top marginal income tax rate from 35% to 39.6% and introduce an additional 2.3% Net Investment Income tax for individuals with modified adjusted gross incomes (MAGIs) above $200,000 and couples above $250,000. The goal was to raise taxes to help pay for the Affordable Care Act.

I’m all for everyone getting more affordable healthcare and coverage; disease and accidents don’t discriminate. However, I had my doubts about the government’s ability to truly lower healthcare costs for Americans.

After enduring 60-hour workweeks and navigating corporate politics, these higher taxes became the tipping point. Instead of whining about them, I negotiated a severance in early 2012 to win back my freedom. I decided I would rather live freely than spend 24 out of every 60 hours a week working for the government before I could keep any of my money.

My physical health was deteriorating, plagued by chronic back pain, sciatica, teeth grinding, and tremendous stress. I just needed a catalyst or two to help me quit the money chase. I found both with higher taxes and coming up with the severance negotation idea.

President Obama’s tax policies made me healthier. Choosing to retire early instead of striving to retire rich may have also extended my life expectancy. For this I’m thankful.

Financial Planning Under President Trump (January 20, 2017, to January 20, 2021)

From June 2012 until January 20, 2017, life was pretty relaxing. It was nice to no longer have to work 60+ hours a week for the privilege of paying lots of taxes. Although I earned a lot less, I was happier.

This was the time when I strongly started to believe that money doesn’t buy happiness. Instead, autonomy, purpose, freedom, and friends are what made me happy. So long as I had enough to pay for basic necessities, it was enough.

Every year that passed made me question why unhappy workers were willing to kill themselves in the office to make more money they didn’t need. The more removed away from work I was, the more bizarre I found working for another adult to be, while forsaking what you truly wanted to do.

All was going well until Donald Trump took office on January 20, 2017. Then my financial outlook shifted again.

The Desire To Work Again Goes Up Under Trump

After Trump passed the Tax Cuts and Jobs Act on December 22, 2017, I felt motivated to earn more money again. It had been five years of relatively leisure living up until then. These tax cuts also coincided with the birth of my son in April 2017, which added a powerful urge to build wealth.

Under the TCJA, the top individual tax rate decreased from 39.6% to 37%, the 25% bracket was lowered to 24%, the 15% bracket was lowered to 12%, and the 10% bracket remained the same, though its income thresholds were adjusted upward.

According to the Tax Policy Center, in 2018, about 80% of taxpayers received a tax cut as a result of the TCJA, with the average reduction in tax liability estimated at around $1,600 for those who benefited. The tax cuts are set to expire after 2025 for individual taxpayers unless extended by future legislation.

The idea of going back to work grew in 2018—not only for more income but also to secure subsidized healthcare. At the time, our monthly premium had climbed to $1,890, alongside an additional $2,000 a month for preschool.

Today, our monthly unsubsidized healthcare premium for a family of four is $2,500 for a silver plan. I’m not sure how the government thinks this is affordable for anybody earning more than 400% of the Federal Poverty Level limit.

Gift Tax Exemption Increase Was Motivating To Build More Wealth

Trump’s administration also doubled the estate tax threshold to $11.18 million per person in 2018 (currently $13.6 million per person in 2024). This change felt like hitting a mental “Go” button, especially since my net worth of $3 million in 2012 had steadily grown with the stock market over the following six years.

Paying a 40% death tax on every dollar above the estate gift tax threshold didn’t sound appealing. But with the estate tax threshold increased, I thought, why not work hard again for my children? The world is already an ultra-competitive place, thanks to technology, artificial intelligence, and globalization. A safety net is always nice.

Instead of rejoining the workforce, I ramped up my online business efforts. With my daughter born in December 2019, that rocket fuel to provide kept getting pumped into my drive. In my mind, with every additional family member, I would divide our net worth by one more person to evenly split. That meant my net worth was declining and needed a boost.

Being a stay-at-home parent with my wife while building wealth was a challenging win. However, chasing more income didn’t lead to happiness—just contentment, especially as a father. The larger my net worth grew, the less anxious I felt about their future.

Financial Planning Under President Biden (January 21, 2021 – January 20, 2025)

When Joe Biden entered office on January 21, 2021, my financial planning felt like it had come full circle. I retired under Obama, and now I wanted to re-retire under Biden. By the end of 2022, I was burned out again, juggling writing on Financial Samurai three times a week, publishing a weekly newsletter, and writing and promoting my bestseller, Buy This Not That.

I’m not sure anyone but authors truly understands how exhausting the book creation process is; it’s harder than stepping on a Lego in the middle of the night to go pee. But the hardest part was being a stay-at-home father to an infant and toddler, whom we homeschooled for 18 months during the pandemic.

With Democrats controlling both the presidency and Congress, I anticipated higher tax rates. However, Biden’s plan to raise taxes never materialized. Instead, we saw tremendous stimulus spending aimed at saving our economy from ruin.

At the time, the stimulus was vital for supporting small businesses forced to shut down and their employees. But, of course, we paid the price with elevated inflation for the next three years.

Three months after Buy This Not That was published, I gave myself a much-needed break. I had crossed off a bucket list item, and it was time to relax. That break was temporary, though, as Portfolio Penguin offered me another book deal that I couldn’t refuse—especially with my kids now in school. I wanted to set a good academic example.

Hard To Control Spending As A Parent

The hardest challenge a parent might face is resisting the urge to spend everything they have on their children. Parents naturally love their children more than anything, leading to an inclination to spend whatever it takes to keep them safe, happy, and inspired.

Abigail Van Vuren once said, “If you want your children to turn out well, spend twice as much time with them and half as much money.” I love this quote, but following it can be incredibly difficult—especially when you have the means to spend more.

For example, we value learning a second language, so we decided to send our kids to an expensive Mandarin immersion school for our kids. We also place a high value on owning a cozy home in a safe neighborhood, which is why we purchased a nicer home in October 2023.

As a result of these decisions, we now face the reality of needing to earn more. Without as much liquid net worth in stocks and bonds, we can no longer claim financial independence.

Financial Planning Under President Trump (January 20, 2025 – )

Trump’s return to office in 2025 helps my goal of achieving financial independence by December 31, 2027. I’m assuming there will be no new taxes and perhaps a continuation of the Tax Cuts and Jobs Act, which is set to expire at the end of 2025. Further, our investments now have a tailwind.

To manage our household income strategically, we’re aiming to keep our earnings within the 24% marginal tax bracket or lower in 2025 and beyond. This means staying at or below $400,000 in taxable income—enough to support our goals without excessive taxation. Without jobs, this isn’t hard to do, especially since our passive income took a hit in 2023.

On growing our net worth, we plan to stay focused, as I expect the estate tax exemption to continue increasing. For 2025, the gift tax exemption is $13.99 million per individual and $27.98 million per married couple, which provides ample room for estate planning.

Naturally, Trump’s return has split the country, with half elated and the other half disappointed. If you were hoping for Harris, it can help to focus on the positives. Perhaps there will be more focus on border security or a reduction in foreign wars. Each party has its vision for the country’s success.

The reality is, my financial plan would have fit just as well under Kamala Harris.

Family, Safety, Financial Independence In That Order

With two young kids, almost 5 and 7.5, my top priority is their safety and well-being. They’re too young to protect themselves, so it’s up to my wife and me to do everything we can. I hope that President Trump, along with our new San Francisco mayor, prioritizes safety.

As for financial independence, I find it becoming a lower priority—probably because I’m confident I’ll get there eventually. Now that both kids are in school full-time, there’s less urgency to achieve FI just to have more time with them, as they’ve already had most of our time during their early years.

Safety, on the other hand, feels less predictable. I’m trained in self-defense and keep our home secure. I also learned valuable lessons from a recent car collision scam on what not to do. But until my kids are adults, it’s hard to rest entirely.

Focus On What You Can Control

Ultimately, controlling what we can control is key to achieve financial independence. We decide how hard we work, how much we save, how we invest, and how we treat others—never underestimate the value of kindness!

Now that the election is over, my hope is for Americans to come together and find common ground. In the end, we all want a brighter future for our families.

Readers, what are your thoughts on Trump becoming the next president? How has your financial planning and outlook evolved under each administration? What changes, if any, do you plan to make under another Trump presidency?

If you have over $250,000 in investable assets, take advantage and schedule a free consultation with an Empower financial professional here. Complete your two free video calls with the professional by November 30, 2024, and you’ll receive a free $100 Visa gift card. There’s no obligation to use their services after.

With Trump assuming office in 2025, a range of economic policy changes are expected. Understanding which sectors will likely benefit or be hurt by his policies can help you adjust your investment strategy. It’s always wise to get a second opinion on how your investments are positioned, especially from professionals who frequently review portfolios for people in your demographic.

Speaking with a financial professional in 2013 helped me realize a major blind spot—I was being too conservative despite being young with so much potential. That conversation pushed me to invest my idle cash (52% of a portfolio) in stocks and real estate, which has since boosted my net worth by over $1 million.

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