Where does motivation come from?

I fought back tears as I drove down Meeting street on my way to an evening class. I drove right past the school and eventually found myself parked alongside the Charleston Battery. As the sun went down over the harbor, I felt all this stuff I'd just shoved into the basement of mind suddenly bursting out. I was miserable. But until now I couldn't admit it to myself.

For nearly a year, I'd been working a 9pm - 5pm law firm job and would rush downtown to the law school for class from 6pm - 9pm. I'd run through a drive thru on my way home and study from 10pm until I fell asleep. Then I'd wake up and do it all over again. I'd been putting all this pressure on myself, and I was doing everything I thought I was supposed to do. Attending every class, building my resume with law firm experience, doing law journal and recently qualified for the moot team.

There was only one problem. I hated every minute of it. I thought if I could just push through for a little longer it would get better. It didn't, and as I slumped in my car it dawned on me that I was trapped with no way out. I'd worked harder than I'd ever worked for anything in my life and I'd forked over nearly six figures in tuition at this point. Plus I had a pretty big ego. Quitting seemed like failure and I didn't want to look like a failure to all my family, friends, and colleagues.

Poverty kills pride

Fast forward one year. I finished law school, but after declining my old firm's job offer, I was batting 0/50 on the job hunt. Eventually we ran out of money and had to move a ways off where housing was much cheaper. I remember going to the grocery store, buying the essentials, Ramen noodles, a gallon jug of water (our water wasn't drinkable), and then being in line at the register hoping we could squeeze $12 dollars onto the credit card before hitting the max.

I was more motivated that ever to find work. I didn't care what it was. If it meant not having to worry about buying $12 worth of groceries, I would do it.

Poverty is great for killing pride. Determined and no longer hindered by a sense of entitlement, I went out and took the first job I was offered. Starting the next day, I would be driving a shuttle bus out on Kiawah island.

It was a huge relief to finally have a source of income, but my first few shifts were brutal. I took home barely enough money to cover my gas. This was supposed to be a tipped position so the base pay was like $2/hr or something.

In theory this sounded fine, but there was one big problem, most guests didn't realize you needed to tip the shuttle driver. It was a complimentary service and we weren't supposed to solicit tips directly. It probably didn't help that I kept getting lost that first week. The little map they gave me was useless as I tried to find my way in the dark (on an island without street lamps).

The first shift I took home $12.

The next shift $5.

I got angry. And it wasn't just about the resort's tipping policy, it was the whole thing. Four year degrees, law school, government promises, all of it. I was ready to burn the whole thing down. I was tired of giving other people authority over me and letting their rules govern my life. What good had obedience done me?

It was time to break the rules and start doing things MY WAY.

From then on, I started stuffing the shuttle's cupholder full of bills before each shift. I placed it right up front where it was clearly visible from the moment guests got in. The change was instant. $50 in tips during my next shift. Now nearly every single guest tipped me something.

The more I engaged with guests, the better I got at figuring out how to read them and what they were interested in. Over time my tips increased as I made personal connections with every single guests. They'd even request me specifically to pick them up during their stay.  

I turned it into a game to see how much I could make in tips every shift. Every trip, I did all I could to increase my odds: taking them along a scenic route, sharing the history of the island, or offering dinner suggestions for a night out in Charleston. After a few months, I was regularly earning $5, $10, and $20 tips from guests. On a few occasions, someone would drop me a $100.

During the early morning shift, I was often tasked with delivering newspapers and amenities to the ultra high net worth VIPs on Flyway Drive. I used even these mundane errands to fuel my internal drive. As I stepped inside these magnificent $5M - $10M homes, I was always inspired and felt this surge of motivation to make owning a home like this a possibility in my own life. I tried to picture myself in the place of the many residents I encountered... as an old man in my own beautiful home out there... with my children and grandchildren all around me.

I never missed a photo op when a pick up perfectly coincided with sunset over the Ocean Course.

This job was just what I needed to survive financially and regroup during this transitional period in my life. Each day as I chauffeured guests up and down the island, I breathed in their positivity and asked about their success stories. Many were entrepreneurs who'd built their companies from scratch and would offer me encouragement.

The Power of Intrinsic Motivation

The shuttle gig gave me time to reflect and re-examine my life and what I wanted. Until that point, I'd spent most of my life doing whatever I thought would be impressive to other people. I didn't really even know what I wanted. So I listened to podcasts, I journaled, I read all the cliche self help books like, What Color Is Your Parachute. The debt situation was obviously horrible and growing by the day, but I knew I'd need to chart a totally different career path before I could put a dent in it.

As I invested more time in myself, I figured out what I actually wanted and just went for it. For years I relied on external motivators, but now I was really driven by my own internal source. This is just the beginning of a 10 year journey where I started in abject poverty with $250k in debt with no career prospects, and I'm going to end it with no debt, unlimited career potential, and having sold the business I started in a multimillion dollar acquisition. If you'd like to keep reading check out what happened next, why/ how I taught myself to code, building my first business, and selling it.