What steers today’s success mindset? Increasingly, non-conventional drivers not just Success Mindset.

It all started a few years ago by taking an interest and asking a question:  “So, how is your day going?”  In most cases it would then lead to asking a follow-up question:  “How long have you been driving for Uber?”

For those of you who may not know, Uber is an on-demand, ride-sharing service that is an alternative to a taxi or limo service.  Anyone with a valid driver’s license who passes a safety inspection of his or her vehicle, along with a few other requirements, may offer their own personal “taxi” services.  It is a simple, digital-based application that connects drivers and passengers.

Uber drivers are self-employed.  They set their own hours and operate throughout most urban and many suburban areas in the United States and more than 60 other countries.  They operate autonomously through a digital relationship with the company.  There are other competing ride-sharing services, such as Lyft and Curb, to take you from point A to point B.  Due to the lower price point, people opt for these services as an alternative to driving to work, to avoid the hassles of heavy trafficked areas or for a night on the town.

The initial dialogue I shared above has augmented me with many fascinating stories of drivers with whom I have come in contact over the last several years.  I’ve used Uber services more than 250 times and have grown to appreciate the diversity and varied mindsets that motivate people to engage in this part of the “gig economy” – a labor market noted for freelance work and short-term contracts instead of permanent jobs.

During my Uber rides, at least half of the time, I have a 15-to-30-minute chat with each driver.  Sometimes the conversations are just about practical matters and different kinds of everyday issues, and sometimes delve into deep meanings and values.

Many drivers are taking advantage of the flexibility of the “job” as part-time or full-time drivers.  Some depend on the earnings completely while others are holding down two full-time jobs.

The digital world has greatly facilitated the prospect of starting your own business with no money or experience, just the desire to pursue your goals and dreams.  The motivations are as uniquely different as each individual.

So – why my focus on Uber drivers, and why the conversations?

Well, in the business world, I’m curious about what makes others tick.  I’m fascinated with an “unconventional” business model that attracts all kinds of people, from different walks of life.  I’m learning about the reasons behind what they do and how they’re pursuing their deepest aspirations.  I’m particularly interested in how Uber drivers approach success through continual learning and individualized pathways to growth.  I’ve come to love their seemingly boundless curiosity and optimism about how to achieve their goals through the freedom and flexibility that driving affords them.

For drivers who are in it for the long term, it starts with their freedom to chart their own course.  The freedom to do what they want, when they want, and for their own reasons.  This allows them to define success by whatever personal criteria motivate them and satisfy them.

Not all drivers are wired this way.  Many are just trying out driving.  It’s not an easy job – many long hours in the car with good, bad and indifferent passengers.   Their income is in the low-to-medium-wage level.  From my car-ride chats with them, it appears that top full-time drivers make around $50,000 annually.

So why would anyone want to put themselves through this?  Lots of reasons.

There is this young high school English teacher who picked me up early one morning.  He had been driving for the past nine months to earn extra money to pay off his student debt.  He wanted to pay off this debt in five years instead of the typical 10-year time frame.  He was getting married in six months and wanted to buy a home and have a family.  He drove between 5 a.m. and 8 a.m. each school morning.  Then he headed to school, taught English, and a few times each week drove after school to earn extra income.

He had become deeply frustrated with the weight of his student debt and wanted that angst to be shortened – to remove this obstacle to buying his first home.  His teaching schedule enabled him to earn extra pay with a few rides each day nearby his home and school.

Some drivers I’ve met are only a month or two into driving.  Sometimes it quickly becomes apparent they don’t enjoy driving and they don’t necessarily have a defined goal or purpose other than to earn a little extra income.  It’s almost as if they are still searching for some way to sustainably pay the bills, for something worth their time and effort, which ultimately fizzles away into another unsuccessful job search.

Conversely, on the other end of the spectrum, I’ve had a few drivers who were not driving for the money.  They had other non-financial reasons.

One driver sticks in my mind because of his noticeably positive demeanor combined with a difficult grasp of the English language.  He was very happy throughout the drive and proud he was a new immigrant learning to speak English.  For the past four months he had been driving three hours on Saturday and the same on Sunday to learn English.  Just to learn English – that’s it!

His full-time software programmer job did not put him in contact with English speakers, only those who spoke his native tongue.  After an awkward start to our conversation, it became clear that in order to advance in his career he first had to become proficient in English.  Driving and meeting people was his informal school of language immersion training.

This young man was completely focused on the results he wanted to achieve.  A better job with greater income and benefits that would await him as soon as he had mastered a new language.

Then there are those drivers who persevere out of very practical reasons:  The lawyer by day in a government job with six children and one on the way, who was just trying to pay the bills and put food on the table.  An Ethiopian immigrant from a family of 11 who is helping his brother establish a local Ethiopian mart offering specialty foods and coffee, both of whom need extra income to support their growing families (I understand from him that the Ethiopian Harrar coffee brand, with its strong fruity aroma of blueberries or blackberries, is excellent!).

Two very different Mongolian-born Chinese immigrants with very little education are augmenting their minimum-wage jobs to pay their bills and save a little money to pursue the American Dream.

I had a longer drive one day that ended with my driver asking to pay me for my time with him.  It was in late March.  When I asked him how his day was going, he replied, “Not so well.”  It turned out he was on his way to pick up his tax return from his accountant.  He worked full-time as a union electrician, and in the previous year had made about another $40,000 driving for Uber.  He had learned that morning he owed $12,000 in additional taxes and was not a happy camper.

I asked him if he wouldn’t mind sharing why he was working 80 hours a week.  He said he was driving so he could retire in seven years at age 55.  Otherwise, he’d have to work until age 62.  I asked him what kind of retirement plan he had as a self-employed driver.  Immediately it was revealed he was not taking full advantage of his available planning options.

That’s when it got interesting … for him.

He just needed to add two small features to his current retirement plan that would reduce his  $12,000 tax bill to $3,000.  He was absolutely ecstatic!

When we reached my destination, I had him write down what to do and run it by his accountant before implementing.  When he calculated the savings from this retirement option over the next seven years, he determined he could shave off two additional years and retire at age 53!

This gentleman was so elated, so grateful, and so eager to learn much more.  He was a great student – curious, attentive, positive, and determined to retire and gain the freedom he wanted as soon as it was practical.

You know, people do things for their own reasons.  I’ve met two wealthy gentlemen who each pick up a passenger on their way to work, and one on their way home.  They make about enough money each day to pay for gas, maintenance and auto insurance.  They are just plain practical.

There were other gentlemen in their late sixties to early eighties, at least a dozen of them, who just needed something to do.  They retired with nothing to do.  They still have a lot of gas in the tank and are intent on doing something.  They don’t want to be Walmart greeters or work for a traditional employer.  They like their freedom and still want the joy and satisfaction of being out and about doing something.  Meeting new people.  Maybe putting a smile on someone’s face, including their own!

Great conversations.  Lots of wisdom imparted from what they’ve gained over their many years.  I continue to learn from many of them about life.  It even astonishes and astounds at times – I never expected this would happen on my drives.

And, to be sure, there are the humorous ones.

I got picked up late one evening from a Florida airport by a gentleman driving a very luxurious six-figure sedan.  I had to ask why.  The curiosity was killing me.  This man had sold his business a few years ago for a very nice sum and moved with his wife to “heaven’s waiting room” (his words!) to enjoy warm winter days, the sun’s golden rays, and everything else Florida has to offer.

It seems his mother-in-law invited herself permanently to live with them a year earlier.  After a few months, he decided to begin driving and would head out almost every evening to take a break from his wife’s and mother-in-law’s incessant banter – again, his words (well not exactly – his were a tad more colorful).  He just needed a break.  His driving certainly costs him more money, just on the mileage and maintenance.  But it empowers him to escape and regain what he had envisioned when he moved to the Sunshine State.

What have I learned these past few years from my Uber drivers?  That many people are pursuing new, alternative, flexible approaches to the American Dream.  That they are deeply passionate about achieving better lives, and display a surprising amount of entrepreneurship – some of it quirky, to be sure – in their reach for freedom, more learning, more earning power, and more joy in the face of vastly different circumstances.

Some have just begun.  I was the first ride for one driver.  But another had been driving for five years and just completed his 15,000th fare.

Many are hard workers, frustrated by personal circumstances yet fiercely committed to persevere, to change the status quo, and transform their lives.

Yes, I’ve had those “dangerous” conversations about religion and politics, each of us tip-toeing around to find common ground and then generally having fruitful conversations.

People are endlessly fascinating.  My drivers have included individuals from remote African villages with no roads or electronic communication – and then that university professor driving to earn the income to pay for his second PhD.

They’re from all walks of life, every color and creed, young and old, from the age of 21 to 82, male and female.

Despite their wide diversity, they share common threads.  They are maximizing their freedom and flexibility to pursue their goals and aspirations as they can when they can.  Sometimes it’s the enjoyment of being outside (versus being in an office all day).  Sometimes it’s the beneficial surprises when meeting random passengers.  Sometimes it’s the deep satisfaction gained by providing a new kind of useful service to the community.

For some, they are leaving their pent-up frustrations behind and opening up new avenues.  Some simply like the driving, but for most it’s a means to an end.

Before trying Uber, it didn’t occur to me how different and how wonderful many of my transportation experiences could be.  It has also taught me how deeply entrepreneurial this country continues to be, and that through hard work and persevering resilience one can keep witnessing the new realities of the American Dream.

I love to watch “the little guy (and gal)” succeed and prosper by exercising the freedom our country affords.  By challenging themselves to use a new business model, by availing themselves of a new microchip application, and by embracing a non-traditional mindset to achieve their success, convention is being parked at the curbside.

That’s a good thing.

Oh!  By the way – if you ever decide, for whatever your reason, to drive for one of those ride-sharing services, don’t be surprised to hear from the backseat, “So, how is your day going?”



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