5 Strategies for Rideshare Drivers in Trump’s America

— By Jay Cradeur —

It’s November 2025. Donald Trump has been president again for over nine months. And while some people are cheering (or were cheering!), many of us on the ground feel the pressure rising. 

I am writing this just days after the Democrats won virtually every election across the country on November 4th. Apparently, many of us are feeling the negative impacts of the Trump administration. Let’s face it. Life feels different. And driving now feels different. The rules are changing. The tone of conversations has shifted. The economic landscape is more complex to interpret.

This is not just about politics. It’s about survival. You and I drive to make some money, and when we all go through significant shifts, we must adapt or fall behind. Whether you’ve logged a few hundred rides or you're closing in on 33,000 like me, it’s time to adjust. These five strategies can help you make the most of this new moment. They’re not about ideology. They’re about staying sharp, staying safe, and staying paid.

5 Strategies for Rideshare Drivers in Trump’s America

Every presidency changes things. But this one feels especially sharp for gig workers. The tax code is under revision. Labor laws are shifting. AI is advancing at a pace that exceeds expectations. 

Meanwhile, cultural tension is bubbling hot just beneath the surface of every conversation. We have armed troops wreaking havoc in many cities across the country. Nobody has been deployed in Sacramento, so I haven’t experienced it myself. 

I assume it can impact how people are feeling and managing traffic patterns. Drivers can’t afford to be asleep at the wheel. You have to read the road, and read the country too.

Here’s how I’m navigating it. Maybe it’ll help you, too.

1. Max Out the $25,000 Tip Exemption

One of the few bright spots for drivers right now is a new tax rule.

The first $25,000 in tips you earn may now be tax-free under Trump’s latest policy. That’s a big deal. You really need to be crushing it to earn $25K in tips. That means treating tips like part of your business strategy, not a lucky bonus. Track your earnings. Use a spreadsheet or a dedicated app to track your numbers.

Also, learn to ask for tips without asking. Offer great service. Have a clean car. Be present. Listen. Show appreciation. All of it matters. 

And keep in mind that while rideshare drivers are on the preliminary list of eligible workers to benefit from the revised tips law, the final ruling isn’t yet locked in. So stay informed. Don’t count your refund until the IRS blesses it. However, it is looking good for rideshare drivers.

2. Don’t Talk Politics in the Car

This one should be obvious, but I’ll repeat it. Trump is the most divisive political figure in recent memory. Bringing him up in the car is like tossing a lit match into a dry field. Even a casual comment can spiral into a debate. And once the mood sours, that tip is gone. You might even get a 1 rating for speaking your mind.

I’ve had passengers wear MAGA hats. I’ve had passengers wear rainbow shirts and pins with Biden's image. My policy is the same: keep it neutral. 

You’re not there to convert anyone. You’re there to give them a calm ride. The most challenging situation occurs when you have a passenger who wants to talk politics and whose views differ from yours. 

I recommend nodding and making acknowledgement sounds, such as “Sure” or “Can’t argue with that.” Don’t get tempted to argue. It can be tough to do, but bite the bullet and let your passengers have their moment.

That’s what gets you paid.

3. Ride the Red State Migration

If you’re serious about making money, follow the people. Millions of Americans are relocating, mostly from blue states to red ones. Texas. Florida. Tennessee. These states are seeing significant growth in population and infrastructure. But in some cases, they don’t yet have the driver supply to match.

I know a few hardcore drivers who plan seasonal trips to booming markets. They Airbnb a place for a few weeks, work hard, and bank cash. Then they move on. It’s not for everyone, but it’s worth exploring if you want to chase high-demand pricing and lower competition. Additionally, many of these states do not have a state income tax. That matters too.

4. Embrace the Independent Identity

Under Trump, it's clear the government will continue to define us as independent contractors. That means no benefits, no minimum wage, and no legal protections. 

But it also means freedom. For many of us, that is what drew us into rideshare driving. I work when I want. I get paid. Simple. You get to choose how much you work, where you drive, and how to structure your day. Use that. Don’t think like an employee. Think like a small business owner.

You can study your market, target busy zones, and optimize your schedule. You can write off expenses, upgrade your vehicle, and set income goals. You have to take this seriously. No one’s coming to save you.

5. Plan for the Endgame

Let’s be honest. The clock is ticking. Waymo is expanding. Tesla is pushing harder into self-driving. Trump’s support for deregulation, crypto, and AI is speeding up everything. And once autonomous vehicles go wide, the job changes. Maybe it disappears.

Additionally, AI is also impacting white-collar jobs. Those folks need money. And where are they going? Some of them are ending up behind the wheel. So, you have more competition, fewer rides, and shrinking margins. 

This is not a reason to panic. It’s a reason to plan. Start thinking about your exit ramp. Whether it’s investing, upskilling, or launching something new, don’t wait. I’ll write more about that next month.

Key Takeaways

This is not the same driving world we had two years ago. 

It’s faster, tighter, and more political. Some of these changes can work in your favor. Others are threats you can’t ignore. However, one thing is clear: you must be proactive. You have to work smarter. You have to treat this like a business, not a side hustle.

The drivers who last in Trump’s America are those who stay flexible and focused. My key takeaway is that the future looks bleak for rideshare drivers. Face the music. Begin preparing for a significant transition for drivers. Self-driving cars, AI, and government are changing the environment. Adapt or die.

You’ve got this. But don’t wait too long to rewrite your future. 

Stay safe out there.

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