Glenn's Driving Service
Getting vehicles and pets safely to their destinations since 2008

Now Seeking 3rd Driver

Driving broker is seeking a third driver to move personal vehicles within North America on a contract basis. No experience required, but personality and life circumstances matter. I will want to see your social media stream and learn about your past travel experiences. This gig probably won't replace a real job but it would give you a chance to see the country and get paid for it.

Customers: Please see the Main Page

Preferring a driver based in the Northeast USA (or several other key cities) who is ready to drive now, in spite of Covid restrictions.


I am an experienced cross-country driver with medical issues who is seeking responsible, independent drivers to move private vehicles around the country. I have already integrated one new driver into my team in May 2020, and now I am looking for another. The drives could go anywhere in the USA or Canada, but the most common route is the Northeast to and from Florida. You would be working on a contracted, per-drive basis on assignments I will prepare for you and closely monitor. I will be available to advise you on every aspect of the trip.

In addition to the page below, please read and understand the Main Page for customers. It will give you a good idea of what I am looking for.

First rule: Please don't phone me with your inquiry about this position. Calling me at this early stage automatically disqualifies you, because it means you can't read or follow instructions.

Second Rule: Please don't contact me if you only want a single car to drive to get you where you want to go. This is not our business model.

Instructions for contacting me and the information I need are found in the text below. All I ask is that you read this page fully before you respond and make sure it applies to you.

For nearly 12 years, I have been successfully driving other people's cars and pets around the country. It hasn't made me rich, but it has supported my chosen vagabond lifestyle. I have survived in this business because I have no fixed residence to maintain, going directly from drive to drive. I would have continued as a one-man shop except that I have now been slowed down by medical issues. I am recovering from chemotherapy for a curable form of cancer, lymphoma, and am currently restricted to the Boston area. I've been through this before in 2018, and it's not at all frightening. Treatment doesn't compromise my brain, but it could weaken my body and restrict my driving schedule.

I am gradually recruiting new drivers who can fill in for me while I manage their trips from afar. I will provide the jobs and determine the overall plan for the trip, then I will monitor it while it takes place. For this service, I will take a commission on the total fee (usually 20%). If this experiment works out, I will continue as a multi-driver shop even after my medical issues are resolved. I plan to take on new drivers only as long as there is sufficient business to support them.

The General Plan

Everything is in turmoil during the Covid crisis, but as the fog lifts, I expect there to be pent-up demand for getting cars and pets to their destinations. (For example, a lot of cars may have been stranded by the Covid lockdowns as people fly home.) As the world slowly returns to normal, this is how my business is shaping up...
  1. Customers continue contact me through my website (as they have for the past 12 years). I discuss their needs with them and define the parameters of the trip. I have no problem rejecting customers who my experience tells me are going to be more trouble than they are worth.
  2. I identify the driver who I believe is best suited for the job (who could be me). I negotiate a deal with the driver and connect them with the customer.
  3. Once the driver and customer have settled on the details of the trip, I make up a contract between them.
  4. The driver completes the drive as specified, under my active supervision.
  5. The driver collects the final fee.
  6. The driver pays me a commission on the final fee (usually 20%, but negotiable for each drive).
Driving sounds like an easy task that anyone with a driver's license can do, but there are a lot of complex judgment and communication skills involved, and I am highly selective about who I use. Keeping the car on the road is the easy part; the hard part is making responsible decisions and convincing me you are responsible. Your driving skills are less important than your personality and life circumstances and whether I feel I can communicate easily with you. Very few people have the traits necessary to sustain this kind of work, and the economics can be difficult for most people.

The Economics of Driving

The economics of driving do not make sense for most people, especially if you are already paying significant rent and utilities or have dependents to support. When you go out on the road, you'll be paying for your own lodging, which means essentially that you are paying double rent. By the time you get home, you may not make enough money to justify the trip.

My intention for now is to keep customer prices low, roughly $100 more than what I was charging before the Covid crisis. Airfare costs are included in my fee, so they are subtracted first. Then I am taking 20% of the remaining fee, which leaves you only 80% to provide the service. From this amount, you must pay your own lodging, food, taxes and health insurance, just like other contractors such as Uber drivers.

Here is a financial breakdown for a typical trip from Palm Beach, Florida to the New York Area, when you happen to live in the New York area. This is the typical trip taken by "snowbirds" who move to their condos in Florida every winter and return every spring. They fly while I drive their car, possibly with their pet.

Another issue is the regularity of work. Under ideal circumstances, you would be going from drive to drive, rarely returning home, but this holy grail is difficult to achieve. It took me years to get there, but I have been able to arrange it already with the 2nd driver I now have. My intention is to keep my stable of drivers small so each of us will have as much work as we want, but there are a lot of uncertainties in this.

If you sign on with my outfit, I'm pretty sure I can keep you busy in the short term, but I don't know how long business will keep up. Both the epidemic and the economy are huge wild cards. My first priority is keeping myself working, followed by my 2nd driver. You would be coming in with lower seniority, so if there isn't enough work for all of us, you might not be getting many drives. For now, you can't count on this gig as an adequate source of primary income. It is more like supplemental income if you enjoy driving, at times when you are idle and want to get out of the house.

Driving also an amazing way to see the country. For example, the right kind of person would be thrilled to drive the Alaska Highway and get paid for it. I've done that about seven times. (See my Facebook albums.) You control your own schedule (within boundaries we agree on) and are free to stop at will at museums and scenic attractions along the way, so long as they don't deviate much from the planned route and timetable. At whim, you are free to take local routes instead of the interstate. To maximize this amazing feature of FREE PAID TRAVEL, I will try to select drivers with the curiosity, initiative and past travel experience to fully exploit this feature. If you just want to rush through the drive to make money, this isn't the gig for you.

Like an Uber driver, you decide when you work, but you may have to make this decision weeks in advance when the drive is arranged. Once you commit to a drive, you are obligated to complete it, but you will choose the drives you accept and may have some ability to negotiate the dates.

For now, this can't be considered a real job. It's just a chance to make some extra money in your free time while seeing the country. It is probably best for someone with no dependents whose living costs are already low and whose natural curiosity is going to make the best of this travel opportunity.


Your personality and life circumstances are more important to me than your driving skills. In fact, if you tell me you were a limousine or truck driver before the crisis, I'm hardly interested at all. Anyone with a license can drive a car, but not everyone can independently pace themselves, make good judgment calls about unexpected events or work well with people on either end. I'm not particularly concerned about your work history—I only want to see that it shows initiative.—but I am interested in your life history, and I will be looking for ways to evaluate your personality. Frankly, most people can't be trusted to perform an independent task for several days without screwing it up along the way.

I hate having to judge people, so I have tried to make the qualifications as specific as possible, so you can judge for yourself whether you fit. These are the main requirements....

  1. You should be willing to fly and drive now (with a few days notice and assuming it fits your schedule) in spite of COVID restrictions. If you are not willing to travel now, wait until you are before contacting me.
  2. You should be between the ages of 25 and 69. Regardless of your chronological age, you should have the mental and physical flexibility of the young. For example, you should feel comfortable sleeping in an airport if the need arises.
      25 is the minimum age to rent a car without restrictions, based on insurance records of who has accidents, and I believe 70 around the time when driving skills begin to wane. Nonetheless, I may still consider you if you fall outside this age range but meet all other requirements.
  3. You should have a currently valid passport. This is necessary for the Canadian border, but it also tells me you are outward-looking.
  4. You should have a personal credit card with at least $500 of available credit.
      This is needed mainly to rent a car, which is an important transportation mode to and from drives (for example, moving between cities in Florida). You will always be pre-paid for airfare and rental car expenses, but rental car companies usually require a credit card for the deposit of up to $350 plus the rental cost. Although a debit card sometimes works, it forces you to take the rental company's full insurance of $34+/day, which is often more than the rental itself. With a credit card, you have cheaper insurance options. Having a credit card also tells me you are stable enough to have credit. It would be even better if you have a travel credit card which give you frequent flyer miles and a rental car collision damage waiver. If you have one, I'll be impressed.
  5. You should have already taken several cross country driving trips, on your own or with partners. These should be sightseeing trips, not just get-there-as-quickly-as-possible trips.
  6. You should be well-traveled overseas, commensurate with your age. Your travel should be independent, not a tour or cruise. It should also be self-motivated and exploratory, not just visiting family or traveling on business.
  7. You should have a public social media presence that I can examine. Instagram or Facebook are preferred, but I will consider other forms of social media.
      Social media is important enough that I have a whole section on it below.
  8. Most drives start or end in the Northeast, so ideally you should live somewhere between Boston and Washington. If you live elsewhere, I may still consider you, but the higher airfares may be a handicap. Outside the Northeast, the best cities are Chicago, Orlando, Los Angeles and Toronto. (Toronto drivers can serve drives beginning and/or ending in Canada but not drives wholly within USA.) I will consider drivers based in other locations, but the airfare costs of getting to most drives may make them financially impractical. (It may give you a chance for paid travel but with less take-home profit.) If you live outside the Northeast, driving is economical mainly when you can link several drives together in a long continuous trip.
  9. You should work well with animals. You don't have to own one, but you should be able to communicate with them on their level.
  10. You should not be smoker or a drug user of any kind, including marijuana. (Past occasional MJ use is okay, but if you're using it now, I don't want to hear from you. I have lost too many friends to it. It doesn't kill them, but it kills their initiative.) Alcohol only in moderation. You are expected to NEVER drink alcohol during a drive, even in your off hours.
  11. You should feel comfortable spending up to three weeks alone. You don't need constant in-person social interaction to be happy. Being stuck in a car for 8 hours a day should not seem like a burden for you. You have thoughts or listening projects to occupy you.
  12. No Trump supporters! This is the only form of discrimination I practice.
  13. You must have three people you can give me as references (but don't send them now!). Ideally, these should be people you have worked for who have seen you get a job done.
  14. Traits I value: intelligence, curiosity, conscientiousness, responsiveness, flexibility, initiative, stability, humor, literacy and a relatively introverted personality. Some of these traits will be evident in your social media stream. Others will emerge as we talk.
DO NOT APPLY IF YOU DON'T FULFILL AT LEAST 85% THE QUALIFICATIONS ABOVE, with an explanation for the other 15%.

Social Media

Since I probably won't be able to interview you in person (only by phone), I am relying on your social media presence to tell me more about who you are. To apply for this position, you must have a public social media account that I can examine and that you are comfortable giving to me. In my experience, social media doesn't lie, and it tells me a lot more about you than your words can. It should make me feel that I understand you.

You are welcome to check out my own Instagram and Facebook for my angle on life. Our interests do not have to match, but there should be enough synergy between us that we can easily communicate.

Here are some features I am looking for in your social media stream....

Beyond these points, I will give you wide leeway to be who you are. I just want to know who that is and whether it gives us a basis for communication.

How to Apply

Please DO NOT apply unless you are willing to drive and fly NOW, in spite of COVID restrictions, and meet nearly all the qualifications above. If you now feel obliged to remain at home, do not contact me until you are ready to move. Doing this job requires getting yourself to the airport, stepping on a plane, taking a bus or Uber to the car's location, getting in the car and driving it to its destination, stopping at gas stations and other services along the way. If you are not willing to do all of these things right now (with a few days notice), please don't apply yet.

Applying is straightforward. Just send me an email (at — Please spell it right.) telling me about yourself. Please keep it brief, no more than the equivalent of a single-spaced printed page.

You can structure this email however you want and tell me anything you think is relevant—given all the information I have provided above—but at minimum I will need to know the following...

  1. Your city of residence.
  2. Your age.
  3. Your phone number.
  4. Links to your public social media presence.
  5. Tell me a little about your current life circumstances and how you got there.
  6. Tell me a little about your travel history, especially overseas travel and your roadtrips across North America.
  7. Tell me a little about your professional career (but there is no need to go into much detail).
  8. You do not need to send me your resume, but if you have a LinkedIn page or online resume, I will look at it.
  9. Do you have a valid passport and a credit card? (If not, STOP. I can't talk to you.)
  10. What road accidents have you had in the past 10 years? Tell me about them.
  11. Anything else you tell me is up to you.
I will email you back as soon as I get your email, just to confirm receipt, but it may take me a day to analyze it. I will examine your social media profile and probably come back to you with questions or feedback.

Although I don't want phone calls about this position until I authorize them, you are free to email me with intelligent questions after you have absorbed all of the information herein.

A present, I am looking for only a single new driver to add to my team. Once I think I have found them, I may remove this page until I have integrated them. I will restore this page later only if I think there is enough work available to support a 4th driver.

Go back to the Main Customer Webpage

LAST UPDATED JUNE 3, 2020 - come back later for more refinements.