My Final Lessons Learned After 10 Years and 32,000 Rides

— By Jay Cradeur —

I am hanging up my driving shoes. I will not be setting a 4:30 a.m. alarm, even though I still wake up around 5:00 most days. I will not be filling my 2017 Honda Accord Hybrid with gas. I sold it on December 23rd. And I will not be driving anyone to the airport for a very long time.

After ten years and 32,000 rides, I am officially retiring from rideshare and stepping away as a Rideshare Guy contributor.

5 Lessons From a Veteran Rideshare Driver

When you stay in this business long enough, most advice falls away. The surge tricks fade. The app hacks stop mattering. What remains are the lessons that hold up year after year. These are not flashy ideas. They are the things that allowed me to do this work for a decade without burning out early or flaming out financially.

These five lessons are what made the difference between short-term success and a career that actually held together and propelled me into a bigger, brighter future.

1. Longevity Comes From Structure, Not Hustle

If you want to last in rideshare, long hours are not enough. Hustle alone will not save you. You need structure. You need goals, rules, and well-earned habits. You also need to take care of your body and keep your mind sharp. Rideshare does not punish laziness right away, but it absolutely punishes a lack of structure over time.

When I think back to my full-time driving years, my back was constantly killing me. I was spending so many hours in the car that I had no room left in the day to work out or stretch. Driving became the entire day. That was the warning sign.

The fix was not driving less. The fix was adding structure. I joined 24 Hour Fitness and blocked out a daily workout in the middle of the day. When the rides slowed, I went to the gym instead of pushing through. That adjustment, along with a revised diet, extended my driving career more than any earnings strategy ever did.

2. Flexibility Only Works With Boundaries

Discipline was the greatest gift rideshare gave me. Setting my own rules, sticking to them, and seeing how that discipline carried into the most critical areas of my life changed everything. Freedom without rules leads to drift. Freedom with boundaries creates growth.

My number one rule was simple. Set a goal and stick to it. In Sacramento, that goal was $200 for early mornings on Friday, Saturday, and Sunday. $600 for the weekend. Nothing complicated. 

That single number forced discipline into my life. It meant waking up early. It meant showering and starting at 3 a.m. while others were sleeping. It meant filling my car with gas and cleaning the car the night before.

By around 8 a.m., I usually hit the goal. If I didn’t, I drove until I did. The rest of the day was mine. As a rideshare driver, you are your own business and your own boss. If you ignore the boss, you will not get fired. You do not fire yourself. But if you ignore your own standards, you will not grow either.

3. Most Income Problems Are Priority Problems

In almost every city, drivers can come close to their earning ceiling if they are willing to work when others will not. Early mornings. Late nights. Airport runs. The money exists. It just lives in inconvenient hours. 

What is your priority? 

Sleeping in, or making money and achieving your financial goals?

I figured this out early. In December 2015, I started driving in Sacramento and quickly realized that if I wanted to do this seriously, I would need to drive in San Francisco, and I would need to drive early. That decision changed my income trajectory completely.

As a result, I made over six figures for four consecutive years. That would not have happened if I slept in and stayed comfortably in Sacramento. There was nothing magical about it. I simply showed up when and where passenger demand was high, and driver supply was low. 

Complaining about pay never moved my income. Changing my schedule did. Clearly defining my priorities did.

4. Burnout Is Predictable If You Know the Signs

Burnout does not come out of nowhere. It sends warnings first. Body aches. Constant headaches. Weight gain. Feeling sluggish. Fewer tips. A general loss of enthusiasm. Those signals matter.

For me, burnout showed up in two forms. Physical pain was the first. The second was harder to admit. No matter how much I enjoyed driving, it was never going to take me where I wanted to go financially. I have significant wealth goals. When you hit the ceiling of a job and realize there is no next level, the enthusiasm drains out fast.

Being stuck at work, which you have maxed out, slowly creates quiet burnout. The solution is not denial. The solution is to plan and act on those plans.

5. Rideshare Works Best When It Serves a Larger Plan

I always knew rideshare was not a forever career. Either the body gives out, or technology changes the rules. Robotaxis are coming for our jobs. 

So what are you going to do about it? 

For me, the next chapter is day trading. For others, it might be a business, education, investing, or something else entirely.

This isn’t bad news. What an opportunity we all have! We can earn money from rideshare driving while planning our future. There are a few places in the world where this is possible at scale. The real question is not what your passion is. 

The better question is: what do you do better than most people, without trying too hard?

That is where you should plant your flag. I have always been strong with computers. I have good hand-eye coordination. I spent most of my life in sales, assessing situations under pressure. All of that led me toward day trading. 

What is it for you? Figure that out, and rideshare becomes a launchpad instead of a trap.

Key Takeaways

Rideshare can absolutely work long-term, but only if drivers treat it intentionally. Structure matters. Discipline matters. Self-awareness matters. And having a plan for what comes next matters most of all. 

While the world spins itself into chaos over politics and noise, this is the time to stay focused and optimistic. You can still build a fantastic future.

I recently watched a movie called Song Sung Blue. I absolutely loved it, as will any Neil Diamond fan. Hugh Jackman plays a character named Lightning. When someone asks him how he is doing, he smiles widely and says, “I’m huge.” 

You are huge, too. 

Figure out what makes you even more huge and do it. Then that morning coffee on your airport run will taste that much richer. 

Be safe out there.

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