• I did marketing design from 2000-2010 and then dove headlong into product design which I still do at a fairly high level in a large city
• I've worked at a handful of already successful startups in which I didn't really identify with the mission for one reason or the other
• Since Mar 2017 I've been working as Employee #1 at a startup on a moderately interesting enterprise workflow kind of tool. The company is 12 people and we will pursue Series A early next year. I have 120,000 options, half of which have vested.
The downsides? I'm 10+ older than anyone there. We work in a really crappy dirty warehouse. I've asked for either more design hires (it's just me), a bonus, a raise, or some kind of ramp-down of the sheer number of features and requests made on tight deadlines which, after 2.5 years, still seem relentless.
We're going live to the public as a SAAS/self-serve kind of product in January and it's comparable to Slack or Notion in terms of ease of use. Business-wise, I could see it being moderately popular, but who knows. All I know is I'm totally exhausted and just want to play music and travel for awhile. But we haven't technically launched yet.
What's keeping me? FOMO. Fearing I'm leaving at "the wrong time." Fear of resentment. Fear of not knowing what the next move is as a 44 year old designer. Fear they'll hire a mediocre replacement, the app experience will suffer, my equity will be worthless...
Any advice?
Best of luck :)
At this point, I think it's reasonable to ask for a real vacation. Yes, it will be tough if you don't have backup but surely the founder can risk you burning out and/or leaving. Is it possible to arrange something at a relatively less busy time in the next six months?