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Beyond the Ballot Box: Safeguarding Your 'Work-Optional' Plan Post-Election

  • Writer: David Dedman
    David Dedman
  • Nov 13
  • 7 min read


Beyond the Ballot Box: Safeguarding Your ‘Work-Optional’ Plan Post-Election


Introduction: Election Aftershocks vs. Long-Term Vision

Few events stir the emotional pot of American life quite like a presidential election. For those of us in the high-pressure realm of medical sales, election results can feel especially meaningful—especially if you’re pushing hard to reach a “work-optional” lifestyle where your day job becomes a choice rather than a necessity. Every new administration brings a swirl of economic predictions, tax policy debates, and market prognoses, leaving you to wonder how those changes could ripple through your portfolio and your timeline for stepping off the quota-hitting hamster wheel.


Yet history shows that stock markets follow a more gradual and persistent rhythm. Short-term dips or spikes right after elections often look dramatic in the moment. Over the years, however, many have proven to be short-lived distractions. The bigger driver of long-term success remains your own strategy, not which party sits in office. Market fundamentals—such as company earnings and economic growth—generally outlast the sound and fury of any contested ballot count.


That’s why it matters to keep your eyes on the real prize: a future where your finances let you decide whether you continue to be on the road for sales calls or trade it for family time and more fulfilling pursuits. In other words, remain focused on going “work-optional,” far beyond any single election cycle.



Historical Market Performance: Trends Across Administrations

When a new administration takes office, headlines often point to drastic market overhauls. In practice, while short-term volatility can spike around election time, the broad direction of the markets historically keeps marching upward. Researchers have observed that since 1928, the S&P 500 has posted gains in 20 out of 24 election years, an 83% success rate. Yes, who holds the White House can nudge regulatory and tax policies in different directions, but the markets are influenced far more by broader economic cycles than by political labels.


The same pattern emerged after the 2012 and 2016 elections. Below is a snapshot of the S&P 500’s 12-month return following two recent presidential election cycles:


Election Year

President’s Party

12-Month S&P 500 Return (%)

2012

Democrat

+26.0

2016

Republican

+21.8



Both instances show that the market trended positively no matter the winning party. The deeper reason for this resilience often boils down to core economic drivers—the Federal Reserve’s policies, corporate earnings, and consumer spending habits—rather than a single president’s ideas. Medical sales professionals, eyeing a timeline for financial independence, may find reassurance in historical data: the market has historically trended upward through wars, recessions, and sweeping policy changes.



Potential Policy Shifts and Your Tax Bill

While the ups and downs of the market get headlines, tax legislation often underpins the biggest shifts for high earners. Elections open the door for new tax priorities that can reshape both your short- and long-term strategies. For folks sitting in the $200,000 to $350,000 income bracket, even slight changes to rates on ordinary income or capital gains can pack a punch.


With major tax provisions such as those enacted by the Tax Cuts and Jobs Act (TCJA) scheduled to sunset at the end of 2025, you may see the top federal income bracket inch from 37% back to 39.6%. Capital gains might also climb. Here’s a simple illustration of what’s been proposed in various policy discussions:


Tax Category

Current Rate

Potential Rate

Top Federal Income Tax Bracket

37%

Possibly 39.6%

Long-Term Capital Gains (High Income)

20%

Possibly 25%



Exactly how (and when) any changes take effect depends on the legislative process. Certain moves can be beneficial in anticipation of policy shifts, like Roth conversions if you believe you’ll be in a higher bracket down the road or tax-loss harvesting to lighten your taxable gains if higher rates loom. Staying informed on Capitol Hill’s twists and turns is important, but be cautious about making knee-jerk decisions. Pace yourself around what’s actually signed into law rather than reacting to campaign-trail chatter.



Sector-Specific Impacts: Diversification Over Concentration

One recurring theme after an election is the assumption that favored industries of the new administration will explode in value, while those out of favor with the powers-that-be will sink. Health-care policies, for instance, often spark big waves of speculation about how certain regulations, or the lack thereof, will affect medical sales. You might even notice your colleagues talking about doubling down on med-tech or biotech stocks because “this president is good for business.”


Yet labelling an entire sector as bulletproof can lead to overly concentrated portfolios. That’s risky even if you’re certain your slice of the healthcare landscape is about to boom. Medical sales professionals often already have exposure to their own firm’s stock through options, 401(k) holdings, or other incentives. If laws suddenly shift reimbursement models or drug approvals, that single-stock or single-sector risk can lead to an outsized hit. It’s generally safer to diversify across asset classes and industries.


If regulations tighten around prescription pricing or medical devices, for example, some healthcare stocks might stumble. Meanwhile, other corners of the market could flourish if they benefit from new trade policies or tax breaks. Spreading your bets by diversifying helps protect your “work-optional” plan from the unpredictable ups and downs of any one industry. Learn more about balanced portfolio construction on our Investment Management page.



Actionable Steps to Safeguard Your Plan

The reputation of elections for roiling the markets may be overstated at times, but it’s still wise to tilt your strategy in ways that buffer you from any near-term turbulence. The better prepared you are, the less likely you’ll be to panic-sell if a surprise outcome rattles a few market segments. Here are some steps that can keep you on track toward narrowing the gap between today’s job quota and tomorrow’s life on your own terms.


One key step is stress-testing your path to a work-optional life. Picture your portfolio and timeline if the market fell 20% tomorrow. Could you still retire, scale back hours, or switch to a lower-pressure role at the same target date? By projecting those scenarios, you see whether your contingency plans hold up, no matter who is steering economic policy.


It’s also important to align your risk tolerance with how your investments are allocated. If the idea of market jitteriness around election outcomes keeps you awake at night, you may want to shift a portion of your portfolio—perhaps from more speculative or volatile assets—into steadier, lower-volatility holdings. Of course, any reallocation should remain consistent with your broader, long-term goals.


Finally, don’t forget what truly drives your plan’s momentum: your saving rate, your discipline to keep investing consistently, and your ability to curb lifestyle inflation. Those levers are arguably more powerful than anything a political win can do for your nest egg. Instead of letting news headlines spark drastic moves, remain focused on the fundamentals that you can control.


If you’re wrestling with how to integrate these steps into a custom strategy, explore our flat-fee financial planning process or feel free to schedule a complimentary intro call. It’s often reassuring to have a trusted advisor help you chart the course.



Crafting a Post-Election Playbook

A well-designed plan shouldn’t require a radical overhaul every time a new president is sworn in. Instead, compose a “campaign-proof” game plan that can be refreshed periodically and adapted when real policy changes stick. You do this by drafting an Investment Policy Statement (IPS) or a comparable blueprint that outlines your objectives, acceptable levels of risk, and the guidelines for rebalancing.


Calculating a set time each year—such as right after the holiday season—works well for a portfolio review. You can re-examine contributions to retirement accounts, confirm if the market has thrown your allocation off-balance, and note any adjustments. Also keep tabs on new legislation around capital gains or deductions, especially if you’re considering Roth IRA conversions or accelerating income before rates shift.


Above all, keep the pilot’s seat. Emotions can be a huge liability for investors. A consistent, rule-based approach for taxes and investing helps counterbalance any sudden wave of anxiety or euphoria the political climate may bring. Even if your morning news feed is plastered with commentary about how the latest administration is “changing everything,” your year-round strategy always matters more for reaching your ultimate goal: getting the freedom to step away from the daily grind whenever you want.



Frequently Asked Questions

Is it wise to move all my investments to cash before or after elections?


Most evidence suggests that timing the market rarely yields reliable benefits, and going to all cash before or right after an election can mean missing out on potential rebounds. Over the past century, markets have shown a strong record of eventually moving upward, even after turbulent election headlines. Unless you need the funds immediately, a steady, long-term approach is widely considered prudent.


How soon after a new administration takes office should I make changes to my financial plan?


Consider waiting until actual policy changes are clarified and signed into law. Politicians often talk big during campaigns, and some proposals never become reality. Keep an eye on tax legislation as it moves through Congress and evaluate the specifics before making major shifts in your investment or tax strategy.


Are tax rates likely to skyrocket immediately after an election?


Most of the time, tax changes are not instant. Even if an incoming administration aims to raise rates, legislative processes and resistance from various stakeholders can slow or moderate the pace of change. Staying updated on specific measures that pass (rather than preliminary proposals) is the best approach.


What about reducing single-stock exposure in my own medical sales company?


Over-concentration in your employer’s stock is always risky, regardless of the political climate, because one adverse policy change can hurt both your paycheck and your investments. Lightening up on company shares over time and diversifying broadly can protect you from a perfect storm if regulations or market sentiment shift against your sector.



Conclusion: Staying Focused Beyond the Election Cycle

Presidential elections and the swirl of policies they bring can cause unsettling moments for even the most confident investors. But history tells us that the foundations of your financial life—income strategies, spending habits, risk tolerance, and steady contributions—are what ultimately determine how quickly you can attain a work-optional lifestyle. Elections come and go in four-year intervals, but you’ll be relying on your nest egg far longer.


Resist getting pulled into sensational headlines or knee-jerk trades. Instead, align your plan with long-term fundamentals and your personal mission: making work optional on your own schedule, for your family’s benefit, and for the chance to enjoy life beyond constant deadlines. If you find yourself wanting more personalized guidance—especially in fine-tuning your tax approach, investment allocations, or rebalancing strategy—consider taking our Free Financial Assessment. The journey toward financial independence should endure past the latest contest for the Oval Office, and that’s what truly counts.

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