As I stared at my journal with scribbles that even I have a difficult time reading… I thought it would be worthwhile to write about quitting after 2.5 weeks. 

Other than my family, a handful of close friends, and avid subscribers of my newsletter, no one knew I had taken on a new job after a long (some 2 years?) search. Given how picky I was and how long the journey was, the pressure for the opportunity to be ‘just right’ compounded. 

I ended up joining a media startup in a writing and research role. 

From a rational lens, many things added up. The role seemed to let me get paid to do something I was already doing for free (reading + thinking) and I could work under someone who was a well-connected investor in Silicon Valley. I could also work remotely and be an early hire to a well-funded startup. It checked many of the boxes. 

But I didn’t feel the excitement about the role. I could never put a finger on it but it just felt wrong. Those close to me noted the rational arguments and it looked like an opportunity where there was no downside for me. Hence, it only made sense to take the job. 

Once I did, I learned so much. Things like what it meant to be a full-time writer, and the anatomy of startups. As I think through the process of how I made the decision to leave, I want to play the hard game of not criticizing anyone or the company specifically. I think it’s probably easy to name the cons when one leaves something (a job, a relationship, a city), etc… because we default to justifying the decision we made. 

In many ways, my decision could’ve been naive, short-sighted, and impatient. But, when facts change, one needs to be able to change their mind. For me to stick around for a ‘future’ with an organization, the present and past need to give me some indication that gives me hope for the future. If it doesn’t….then it seems prudent to assume the base rate of failure for the venture in question. 

That was one factor I considered in making the decision. Sure I had stock options. Sure, startups having growing pains. Sure, I could try to create new roles and projects for myself. But learning about the history, speaking to some veterans in the company, and merely observing the day to day…. It seemed clearer to me that I could not see a future with the company. 

I admit I may have been biased in that view. That view may have been impacted by the sheer amount of anxiety I felt every day. I’m not sure if it was because I had such high hopes for my next job given how much I had given up to search for the ‘right’ opportunity. 

Call me a hopeless romantic or maybe even a fool to believe there are ‘right’ opportunities. But as far as any of those positive confirmations was concerned…. I felt negative confirmation, which is just as valuable. 

I also think the vast amount of data I had collected from working in many diverse jobs in the past gave me the conviction that what I was feeling wasn’t right. Kahneman says System 1 thinking is unreliable but when it comes to the super-computer (i.e. our brain) analyzing all the career data I have… I think this is where the gut feeling is quite reliable. The anxiety I felt from Day 1 just couldn’t be ignored. It’s as if the relationship was doomed from the start. I actually wondered if that was how most people felt when they joined a startup. I don’t think so. 

Maybe it was because I spent the last few years focusing on building life doing things I love but I knew this feeling of anxiety, stress, and misery was not normal. Every day's journal included elements of feeling anxious about my job. Naturally, it didn’t make me a fun person to be around. I also noticed how much I would write about looking forward to the weekend or just for the clock to hit 6 pm so I could report my hours (I had to report how many hours each newsletter took… the purpose may have been for data collection but to me, it brought up the sickening feeling of micro-management). 

One might wonder why I was feeling so anxious. The wonderful thing was that my colleagues weren’t mean. They were all nice and kind. But you can still have a poor culture even with nice people. It became as clear as day for me that the root of the problems lay in the systems and the leader who approved the systems. My highest moments of anxiety were when I had to interact with the founder because I disagreed with everything related to company strategy and management style. Naturally, this killed one of the most important rational factors for taking the job. Working with a well-connected founder. 

I also realized the job of a full-time writer who churns out 10,000 words a week on tight daily deadlines took away the one part of writing I loved - the ability to sit and think. My daily life was reduced to regurgitating news and condensing any chance for insight into fast quick hits where I felt I was saying nothing and asking people to pay for such nonsense. It actually brought on shame to see my name next to such writing. The flip side represents the wonderful thing about putting your work out in public. There’s some consideration for accountability when your name is associated with it. Even if you know you are just learning.

It was also revealing that I learned I did not care so much whether I got to write or not. I did care if I got to think but I didn’t have to be writing all day for that. The issues that plagued my mind - aside from business/content strategy - were all the things related to people. Everything from hiring, interviewing, and developing people. 

Those were the issues that were so clear to me. I wasn’t sure how to solve it but they were the problems that bothered me the most. It kept on being the things I got frustrated about every night. This became an indicator that a role in content production wouldn’t be an interesting one for me in the future. 

It sometimes gets frustrating because I told myself I wanted to find work related to developing people…. And after two years…. It seems I finally have the conviction that I only want to do work related to human performance. So, even if it was short…. I did gain valuable knowledge. 

What’s also been fascinating is the physical reaction I had while at the job as well. I’ve long been a believer in the ‘mind-body’ connection. It’s one of the key reasons why I think strength training is essential for any kind of mental development. 

Cognizant of the body, it was evident that my heart rate would skyrocket frequently while at the job. Call it stress or panic, I was hitting prolonged heart rate levels similar to when I’d be training at the gym and this was nowhere close to as enjoyable. Inclusive with this was a consistent drop in the quality of my sleep as well. 

And this isn’t conclusive but I ended up getting a skin infection that resulted from a confused immune system and the first thing the doctor asked was if I had been under any kind of immense stress. Not a cause/effect but I’m sure the job factored in. 

Ultimately, it simply came down to a journal entry where I wrote life was too short to plow through such misery. I had embarked on this weird journey of mine with a purpose and it was getting clearer that I would not actually get to do the kind of work I wanted. 

Even weeks after I made the decision, I do wonder if I made it too lightly. It also happens that I made this decision after having heard about a friend who so badly wanted to quit his job but just wasn’t able to do it. Though I recorded these thoughts in numerous daily entries… I thought it would be valuable to write this thought out in full here. 

I think the hope is that I can look back on this decision fondly.