Over the past few years I've been an employee, either at startups or mid-sized stable organizations. When negotiating the job description, I've always requested from the founders/managers to chip in in various ways -- PM, design, engineering, etc. They always were enthusiastic to have employees with diverse interests, but reality sometimes proved otherwise:
- Some startups gave the flexibility, but it just felt worse than working on my own. I had the same long hours and work pressure, but a fraction of the ownership and was working on someone else's vision - Other startups really just needed engineering muscle. I was evaluated on pure engineering output, and any other mechanisms I had of contributing were viewed as distractions from my core responsibilities and were actively shut down. Doing one thing with my life wasn't very pleasurable after wearing all the hats, and I wasn't rewarded for being a generalist - The one mid-sized org I work for tends to value me more; they needed engineering work, but also had growing pains and needed existing employees to step up and fill in the gaps. Having a willingness to do that was eagerly accepted
Some general impressions that I currently hold loosely: - having a stable income is nice and I can afford most everything I want, but it's not enough. I miss having the startup belief that my reward is proportional to my output - company perks (food, learning reimbursement, commuter benefits, etc) are usually deterrents for me now. Colleagues feel more sedated than energized when life is too good. I miss working with hungry (figuratively) people. - I care a lot about the mission. I have the good fortune of working at an org that actively seeks empathetic, passionate people out. I don't think I can go back to normal jobs where I just need to do a thing. This includes even my own startups (which had, in hindsight, little value-add to society) - the slower pacing actually feels more conducive to personal growth, but to a point. It helps now to be on a team where we constantly try to improve and iterate, as opposed to just being a resource-strapped feature shop. I'd avoid teams that move too slowly though, or don't have the pressure to introduce something new. - both startups and large companies can have diverse employees, or can have monocultures. Turns out I like the former infinitely more; didn't get that at most startups I've worked at - leaving silicon valley for a job actually gave me a lot more perspective on the world than struggling as a founder in SF. Turns out there are a lot of big problems people are trying to solve that don't get talked about in silicon valley, and the diversity of people trying to solve it seems a lot larger.
All these impressions, however, are loosely held because I've come to think of my career as consisting of phases in no particular order: take chances, invest in personal growth, make money, hustle, have predictability and work-life balance, give back, etc.