Why I left my well paying corporate career to drive for Uber and Lyft (and write for Steemit)

in #steemit4 years ago (edited)

BACKGROUND: I'm a writer, cryptocurrency enthusiast/investor, rideshare driver, and former banker. I recently switched from blogging on Wordpress to Steemit. Below is a blog post I wrote a few months ago about my decision to leave the comfort of my corporate job to travel and freelance (and how you potentially can as well).

If you were to look at my LinkedIn profile, my decision to quit my well paying corporate job to drive for Uber and Lyft may seem a bit confusing.

I had a fancy sounding job in finance, banking some of Silicon Valley's hottest startups.

I was getting a new job or promotion every year.

I was paid well and worked with smart people that I respected.

I sacrificed and worked long hours to build the practice from the ground up as an early employee.

Yup, I fit the mold of the typical ambitious Silicon Valley professional.

So after years of hard work and sacrifice, why did I, at the age of 28, decide to throw it all away by quitting; leaving a huge gap in my resume, a resume that took years to painstakingly perfect?

Even worse, why did I quit and then later take on a job as a Rideshare driver? An unskilled job with no benefits. A job you wouldn't brag about on a date or at a dinner party.

The answer lies within what my LinkedIn profile didn't show you. Which was that personally, I was quietly suffering from burn out and the deepest depression of my life.

How I looked starting the job (right), how I looked after (left)

Why was I burned out and depressed? There were multiple reasons, most were self inflicted and involved doing things for the wrong reasons:

Reason #1: I thought status and financial independence would make me happy.


Growing up, I wasn't popular. I was considered weird and found it hard to fit in. As a defense mechanism, I told myself I didn't fit in because there was something wrong with everyone else, not me.

I was also considered an underachieving screw up. I was rebellious and nihilistic. I didn't do things simply because I was "supposed to." So I never did well in school. I barely graduated high school and got kicked out of college once.

I developed a huge chip on my shoulder. I wanted to prove everyone that had ever doubted me wrong. I found making money and being "successful" was the perfect way to prove to the world that I didn't need anyone and that I could take care of myself. Without much of a social life, I based my self worth on my career (big mistake).

Reason #2: I had no semblance of work life balance.


To say that I got caught up with the tech startup founder hype would be a massive understatement. Growing up in Silicon Valley, I idolized legends like Steve Jobs, Elon Musk, Peter Thiel, and Mark Zuckerberg. I saw myself in them, I was an obsessive, eccentric, and anti-social workaholic, hell bent on changing the world.

In order to become like them, I had to optimize by minimizing all distractions that got in the way of my singular focus on business success, things like family, friends, and a significant other. In the cut throat world of business, my isolation was a competitive advantage. While everyone was too busy attending to personal social obligations, I could work more and get ahead.

The rewards I received reinforced this mentality. The more hours I put in, the more recognition I received, the more promotions I got, the more money I made, the more my self-esteem improved.

Reason #3: I didn't find a sense of purpose in my work. I was motivated by extrinsic rather than intrinsic rewards.


This would prove to be my major undoing. Unlike Steve Jobs and Elon Musk, I didn't have the burning passion to keep me going through the tough times. I never had an innate desire to get into banking, it just fell in my lap.

I worked in retail banking in college so I could put a professional sounding job on my resume. I graduated college in the middle of the great recession, so I took what I could get, which was a job in banking, this time at the corporate/commercial level.

I simply looked at banking as a means to an end, the end being money and status. I was in such a a rush to make my "fuck you money" that I didn't take the time to ask if this career path would make me happy. Silicon Valley's infatuation with becoming successful before turning 30 didn't help either, it always made me feel like I was falling behind.

All these factors would inevitably come back to haunt me in a big way. After the novelty of the job, the title, and the pay wore off, all that was left was the drudgery, repetitiveness, and meaninglessness of my work.

My days consisted of sitting through one of the worst commutes in America for three hours a day. Sitting in my windowless office, building spreadsheets, and writing reports that no one would read. Having lunch at my desk alone. Being too drained to make myself a decent dinner. Surfing Facebook until I fell asleep. Everyday felt like a rerun of the day before. I felt like a robot programmed to turn inputs into outputs as efficiently as possible. I remember in the middle of the night wondering if I was wasting my life by conforming to society's conventional standards, instead of living an authentic life based on my own unique values.

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My windowless office

I found it difficult to focus on and finish my work, which led to working even more hours. Late nights turned into all nighters. Working every other weekend turned into working every weekend. An unrelenting feeling of guilt about unfinished work occupied my mind 24/7.

Outside of work, I had no significant other to confide in, my friends stopped calling me, my house was usually empty. I had no way to unplug.

Everything came to an ahead one dark and rainy Friday night. I was working late to get the week end reports out. I remember looking around at my office, I was by myself, in a windowless room with artificial lighting, looking at a spreadsheet. I started having an existential crisis and thought to myself, "This place looks like an insane asylum!", "What am I doing here?", "What am I doing this for?", "Is this all there is to life?"

I sent out the report and was making my way through a rainy evening commute, when my phone rang. It was my boss calling about a huge amount of money missing from a customers account. I immediately made a U-turn and headed back to the office to figure out what was going wrong. I found out that my spreadsheet didn't pick up a balance. I didn't catch it because I was in such a rush to get home. I deservedly got chewed out by my boss.

It was on my second attempt driving home, that I reached my breaking point and had a mental breakdown. The exhaustion and stress broke down my mind's ability to fight the loneliness, sadness, and pain. I just sat in my car and cried. I had never felt so alone in my life.

Luckily, it happened just as my two week vacation was coming up. I told myself, all I had to do was hold it together until my vacation came and I could rest and recover.

The vacation helped a little but it didn't solve my fundamental issues. My mind had already gone into self preservation mode and checked out. I was still doing all nighters. One time after pulling an all nighter to finish a deal so I could fly out to spend a weekend with friends. I boarded a plane and the close quarters of the cabin triggered a major panic attack. I was forced to leave the plane. After that, the panic attacks continued, often times while I was still at work.

The best way I can describe a panic attack is feeling an overwhelming sense of terror and a need to escape. Once the panic attack is over, you feel a crippling sense of isolation and despair.

Up until then, I had been reluctant to quit my job because I was scared. Scared of not having money, scared of what people would think, scared of leaving the security of my bi-weekly paycheck to venture into the unknown.

But after the panic attacks, I knew I simply had no choice. So in April 2015, I emailed my resignation letter and two weeks later I quit. I had no job lined up. I didn't need another demanding job in a different cubicle. I needed time to rest, recover, and reflect. I needed to go on a sabbatical.

Immediately after quitting, I felt two things that surprised me:

I was surprised by how little I thought about my old job, something I obsessed over for the past two years of my life. It was unsettling knowing that I could jedi-mind trick myself into devoting my life to something that, at the end of the day, I didn't really care for that much. It was like my career hijacked my identity. I was mainly interested in my industry because I was surrounded by it all the time. I'm glad I came to the realization while relatively young than on my death bed.

I was surprised by how alive I felt. Once I realized the bi-weekly direct deposits weren't coming anymore, my dormant survival instincts kicked in like a captive animal being released back into the wild. I literally felt my mind and senses sharpening. I felt a sense of urgency and became acutely aware of the opportunity cost of my time. Every week I wasted, was a couple hundred dollars disappearing from my bank account. I was no longer being fed by my corporate masters, I had to learn how to hunt.

My initial plan after quitting was to end my lease and backpack across Southeast Asia. However, I had just moved to the San Francisco area and never had time to explore. So I decided to stay and explore the area before beginning my travels.

In order to do that, I needed to find a flexible low commitment job to pay the rent. I felt like Kevin Spacey in American Beauty, when he quit his job in advertising to flip burgers at Mr. Smiley's.




I thought about bartending or serving but decided I needed something with a more flexible schedule. I ended up joining the "on-demand economy" by driving for Uber and Lyft. Knowing that time was literally money, I quickly signed up, got my car ready for the inspection, got the sign off, and was on my way.

After the first few rides, I found the experience to be profound:

It was flexible. I literally worked whenever I wanted. I worked as little or as much as I wanted depending on my need for time or money. I had no boss and could utilize my own strategies to increase efficiency. I could stop and start work by tapping my smartphone. It literally was an on/off switch for work.

I was able to completely separate life from work. No more sleepless nights worrying about deadlines. I was able to be present when spending time with family and friends without a looming deadline in the back of my mind. Without work on my mind, I was also able to rediscover, explore, and cultivate my innate interests in philosophy, culture, travel, and art (especially writing, which is what I'm doing at this very moment).

Instances were I randomly decided to hangout with friends and family.

It paid enough. Considering the skill level involved (know how to drive, work a smartphone, and talk to people) and stress level (close to zero) the pay was pretty good. It has a lot to do with driving in San Francisco, where the majority of people don't own cars and the fact that the companies are heavily subsidizing rides to grow, but I'll save that for another blog post.

It was spontaneous. No day was ever the same. I never knew who I was going to meet or where I would end up.

Everyday had the potential to turn into an adventure. A stark contrast to the rigid repetitive routine of corporate life. If you do the same thing day in day out (e.g. sit in traffic, sit in your cubicle, talk to the same people), how can you expect anything new or exciting to happen in your life?

It was social. If you know me, you know I love meeting new people, learning new things, and having stimulating conversations. I remember telling myself, the perfect job would be if someone paid me to sit around and have deep conversations with people. Turns out, this job let me do exactly that!

Going from being isolated in my office most of the day to being surrounded by new and interesting people all day was a huge contrast. I was meeting people from all walks of life, hearing new and different perspectives, having deep meaningful conversations, learning new things, and making new connections. The feeling of human connectivity was profound, if not sometimes spiritual.

Great passengers and great conversation!

Was the job perfect? No. From the lack of benefits to drivers bearing all the risks (car accidents, tickets, repairs, unruly passengers), the downsides have been covered extensively by the media. However, for this use case, as a temporary means of employment, I find the positives outweighed the negatives (if you're strategic about it). Oh yeah, being a single guy living near a major city with no kids or mortgage helps a ton as well.

After driving for a few months, I eventually became aware that this was the beginning of the revolution of work.

I'm convinced people stay at jobs they hate because they feel they need the job to survive. Given today's ridiculous cost of living (especially in the Bay area) even the most thrifty of savers would only last a few months before running out of cash. This keeps people trapped with making short term career decisions. As opposed to taking the time to think deeply and thoroughly about their careers (something that will occupy the majority of their waking hours), people hastily jump from job to job because they need to pay the monthly rent or mortgage.

The "on demand" economy changes all that by allowing people to leverage their existing assets (car, spare room, talents, etc.) to generate income to cover living expenses while they find or transition to a new career, pursue a passion, reassess their life goals, or recover from burn out. The days of doing the same job for 40 years so you can retire comfortably are over.

Once I realized I didn't need to stay at a job I hated to survive (or move to a job I hated a little less), it empowered me to take risks and pursue goals that were meaningful to me. Imagine if the whole of society, stopped working to merely survive and started working on things they found meaningful, it would unleash a tsunami of pent up human potential. Everyone knows workers that are engaged are more creative and productive.

At first, I thought these ideas were unique to me until I began meeting people that were doing the same thing. People using Rideshare driving to quit their jobs to find more meaningful careers, to pursue their passion for food sustainability, to focus on their music, to found a startup incubator, to raise their young children, or to travel the world.

It was at that point that I realized this phenomenon was bigger than me and that I had to begin documenting it. Hence, the creation of this blog, where I'll be sharing my insights and experiences. My goal is to show those of you who feel trapped in your soul crushing careers that there is a way out. That work isn't something that we just have to bear to survive. That life can be more than punching in, punching out, and paying bills. That it's okay to move in and out of the work force to facilitate your personal growth outside of the professional realm.

In the coming posts, I'll be documenting my experiences (positive and negative) as well as the trials and tribulations. Hopefully, if you choose to go on a Rideshare Sabbatical (or should I call it Steemit Sabbatical now?) of your own, my blog will help you avoid the pitfalls I've experienced, so you can find whatever it is that you're looking for. Especially those of you reading this in your cubicle right now, instead of working...you know...like you're "supposed to."


Be honest... you're always looking for ways to bring up crypto during conversations during Uber rides. I do that as a passenger hah.

Good story! Upvoted! Keep hustlin!

Keep an eye on www.arcade.city - peer to peer ride sharing.

I had the SAME exact thought! I think Steemit's model can be applied to ridesharing i.e. the blockchain paying out rewards to drivers and passengers. Instead of a centralized middle man like Uber taking a 25% cut of every ride. What are your thoughts @dan and @ned?

Totally agree at the same time Uber can and I’m sure will get with the program and do it themselves at some point. Maybe even airdropping to its total customer and driver base. That would be a huge community

Okaliedokie, time to migrate a post over from Medium.....

My goal is to show those of you who feel trapped in your soul crushing careers that there is a way out. That work isn't something that we just have to bear to survive. That life can be more than punching in, punching out, and paying bills. That it's okay to move in and out of the work force to facilitate your personal growth outside of the professional realm.

Inspiring post man. I'm also 28 and in the exact situation as you were... I'm not depressed though but I'm stressed, and burnt out, and I'm sick of the corporate world. I want out too. I know there's much more to life than spending most of it in a slave-job and I always fantasize about how much happier I'd be if I didn't have to work... if somehow I made a few million bucks so I can live life the way I really want to live.

Unfortunately I don't have the balls to walk out just yet. Although, if bitcoin has another rally and hits $3K, I may just pull the trigger. But your post did inspire me and I hope you are successful.

Bitcoin hits 19k

Great post and a gutsy move man!
I wish you all the best with your self-driven (haha) future!

Haha, I see what you did there ;) But I don't think fully autonomous cars (or rideshare service) will be viable for years. My evidence? The guy who got decapitated by a semi because he fully trusted Tesla's "autopilot."

God I know... seriously though, WTF was he thinking?

He thought he could trust fully autonomous machines. Kinda like investors in the DAO did. lol

I'm convinced people stay at jobs they hate because they feel they need the job to survive.

I couldn't agree more. I am friends with a few whose job absolutely defines them. It's hard to socialize because all they are talking about is their work. We are worth so much more than our work, which is a point you make extremely well. Chasing paper dreams takes you away from your reality. Chasing your passions is what makes you real. Thank you for sharing your story!

I can empathize with them. If all you do is work, what else would you have to talk about? At the end of the day, making money fulfills the bottom levels of Maslow's Hierarchy of Needs. Once you make enough to satisfy that, you need to address the higher levels of the pyramid to be happy :)

Nail on the head with the intrinsic motivation thing. Nothing is more rewarding than achieving something you do for genuine enjoyment, be it something challenging, something creative, or even something pointless. Extrinsic motivation on the other hand is very fragile, superficial and transient.

and with innovations like Steemit, hopefully you can earn money (extrinsic reward) to allow you to keep on doing what you find intrinsically rewarding :)

in fact it is a very cool article made ​​me think about many a man !

Thanks @maximkichev! Perhaps if everyone takes a year or two off to travel the world, the world would be a more open and understanding place :)

Come over to my instagram - and we will be friends there man 8-) https://www.instagram.com/maksimakichev/

you're absolutely right , I'll have 2 years living in travel, @kevinpham20

I live in Japan. Thank you for the very beautiful photo

Right on, now live off steem!

Totally get it and good on you man. Taking care of your mental and physical health comes first.

Great post, thanks for your honesty that many have felt but rarely make public. "I was motivated by extrinsic rather than intrinsic rewards." This statement is most important to help us all see/contemplate what it is we are all here for and why it's important to understand/know that about ourselves.

Life is a journey of choices and experiences that create the most wonderful or awful story, but it's is our story. Once you know/accept that it is up to you leaps are more acceptable and become adventures rather than things to be feared.

Congratulations on your 'leap' and much success on your new path. ~ljl~

WOW, That was a brave but needed choice. I can see where you are coming from. Having a chance to interact with people and work with crypto is great. I would do it too, but I like my job and the people I work with so far. I was lucky enough to get in on Steem kinda early, but not lucky enough put in the time and money to be a whale. But if the Steem grows like it should, I will be do pretty good. I just might join you. Ha!

very good, I think this post will eventually lead to me to drop out of college.

To me, as the great Peter Thiel said, college is good "insurance policy." College isn't for everybody, especially when considering the financial burden. I went to a community college and state school and can say that I don't regret the experience. It gave me a great foundation in my understanding of business, finance, and economics. But at the end of the day, the only one that knows what's right for you is you.

Great post about leaving the corporate ball and chain and becoming an Entrepreneur..I actually just posted about my journey...just haven't pulled the corporate plug yet due to said House, kids etc..Following your journey!

Greetings Kevin! If you're in the SF Bay Area we're holding a meetup on Aug. 25th: https://www.meetup.com/steemitsf/ Will announce it soon.... hope you can make it!

@kevinpham reading this post I cry you put to words exactly how I feel about being in my job