If You Don’t Push Back, They’ll See You as Junior

Tommy Chan
4 min readOct 16, 2019
Photo by Kaleidico on Unsplash

It’s funny how honest coworkers get with each other when someone is about to leave a company. I had worked for a startup for just shy of two years and was leaving my full-time role at the company, transitioning into a remote consulting relationship with them. People knew I was gone for good, so as I was having my goodbye lunches and drinks, we exchanged a lot of advice and reflections on the things we experienced.

I’d be lying to you if I said that I did not vent about frustrations as a part of these reflections during my last few weeks with my closest coworkers.

The biggest thing I vented about, and the biggest factor that made me leave, was the culture.

It’s completely true what people say about culture in organizations. If you have good culture, your company will be successful in retaining the employees you want to retain. If you have bad culture, the opposite will likely happen.

Culture is a vague word that embodies many things within a workplace. When one of the organizational leaders stands in front of the rest of the company and says, ‘We have great culture here at X,’ what does that exactly mean?

So, what about the culture specifically drove me away?

It was that almost everyone was perceived as a yes-man. This is not exactly a bad thing, but when coupled with the organizational structure it became a talking point among many circles. Organizational leaders were much older than those at most other startups and therefore had more experience, knowledge, and connections within the industry. In general, they know where the direction of the industry is going, so they called the plays and we ran with them.

In the beginning this was smooth. As time went by, not so smooth. As in most other startups, many pivots happened, and the graveyard of dead projects grew sizable over a short period of time.

We followed marching orders, knowing that something was not going to work, but going through the motions of analyzing and building it anyways. As the desire to find something that sticks increasingly grew, we ended up throwing more at the wall.

We continued to follow marching orders, working hard, sacrificing personal time, building things brick by…

Tommy Chan

Writing about technology, business, and work culture. Subscribe to my Web3 newsletter at https://stillbuilding.substack.com/