Financial Frustration

Financial frustration is probably one of the most common emotional themes throughout my life. As a kid, my family got in some trouble, filed for bankruptcy, firesale’d one house and moved a family of six into a house less than half its size, briefly survived on food satamps and food banks, all that good stuff. I grew up giving the lunch lady my yellow ticket, a kind of scarlet letter for poor kids. I also grew up, from roughly the ages of 8 to 14, waking up at 5am every day, no exceptions, to deliver the local newspaper by bicycle for a nickel a paper. If I wanted to have a sleepover at a friend’s house, I either needed to wake up, ride home, and do my job, or try to convince someone else to do it for me that day. Long story short, my experience as a child was deeply affected by money, and specifically a lack of it.

Looking back at my upbringing and ensuing choices over the years with regard to career, education, etc, it’s easy to see that financial security was always within the top 2-3 criteria for whatever line of work I would pursue. I never seriously considered vocations or lines of work that were inherently financially insecure. Initially, I wanted to be a lawyer, and then I wanted to learn business so wanted to be a management consultant, but then got the opportunity to work on Wall Street so nearly became a financier, etc etc.

One choice I did make that wasn’t affected by a drive for financial security was going to China to teach English for a year, and ironically that period was by far the most financially secure of my life, which was part of the reason one year ballooned into four.

Growing up on the early internet, and in many ways growing up alongside the internet, I always knew whatever I did would be deeply impacted by technology, whether I worked with it directly or not. Coming back from China, I was hoping to get an MBA and work at Google Ideas. Instead, I got pulled to San Francisco to work at an early-stage startup.

After paying $5000 to defer school and moving to the most expensive city in the world, I was out of a job, and would be homeless as soon as my brother left the city along with his company. I drained all my savings from China and took out a loan from my parents to cover cost of a $12k accelerator program that basically was like a paid social network. Questions of value-add aside, it did help me get a job making $60k per year working 12 hour days, and I moved into the converted mudroom of a Mission row house (housing built for the poorest of poor workers, recall) paying $1250/mo for rent. And I had a really great time doing all of this (!), exhilarated by the challenge, learning, new experiences, and promise that with enough grit, perseverance, and growth, the short-term toil and volatility would pay off with the financial security I had been seeking my entire life.

Wow, was I wrong.

I spent the next 3-4 years grinding at two startups, building my own plane having jumped off the cliff myself. Unfortunately, I did not account for the sort of detritus I would need to navigate while trying to put the pieces together - laziness, pettiness, maliciousness, and most often sheer incompetence. Dealing with my managers and coworkers became so infuriatingly exhausting that I decided to become an independent consultant and contract as a way to redefine my relationship to work. Today they call this “fractional” work and people make great careers out of it, but when I started, it was just consulting. Still, I was able to make enough money to live and since I was paid probably 75% of market rate at both my previous stops, which was up from the maybe 60% market at my first job, it didn’t feel like that bad of a tradeoff.

After this point, a lot of other things started to happen in my life and work became much less important to me relative to dealing with other shitstorm detritus that maybe I’ll someday write about. But long story short, the next period of my life was even less stable and financially secure than those first 4 years in SF.

Fast forward to the last couple years and I’ve been able to come up for air a bit more mentally and emotionally, and this has allowed me to work a bit more. I’ve spent a good amount of my energy on personal projects, but every now and then clients come through and it feels Groundhog Day all over again: the same patterns and behaviors, from both myself and my clients, bubbling to the surface over and over again.

I’m not sure where I’m going with this, really. This is more just a mental dump to get things out of my head. I recently asked a client for a 10 day break from our engagement because I found myself raging against them for the tiniest of perceived slights. While I could make a compelling argument that they should do better with regard to how they communicate/interact with me, I’m too exhausted to do so, and moreover, being an asshole because someone is an asshole to you isn’t a good way to live.

I recently reviewed my invoice history, and since May 2017 when I started consulting, I’ve invoiced for $350k. That’s $43k per year, on average, and doesn’t take into account any expenses like health insurance or the $100k or so I subcontracted to my sister as a favor. That’s about $21/hr. In Portland, where I live, a 16-year old kid work at Chipotle for $18/hr plus benefits.

I guess what I am getting at is that I find it incredible that someone with my skills and experience, much less my education — not the degree, but the actual education from both school and life — is valued roughly the same as a child with no experience, work or life, whatsoever.

Perhaps the way to tie this back into something that a reader can understand or relate to is that my experiences of trading my time, dignity, and emotional well being are not new to this country, much less this world. Nor is my experience of being misled to believe that grit, persistence, and growth would lead to financial security. We used to call that The American Dream, but wow, were we wrong.