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I might be very lucky that I didn’t join Google before the summer as I’m not stressed about potential layoffs… but on the other hand i do feel unlucky to finally fulfill my dream and make it through the recruitment process, only to get stuck in the team-matching stage. And then the freeze.. how long can people stay on the list until they get hired? Or does your place on the list ever expire?Google
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Honestly I'd stay at the big company for the cash in hand. For stock you have to wait for it to vest and pray that it keeps/grows its value. It's just that the boss is in my face daily and they're a pain in the butt. I'm waiting for final stock amounts and if the $$$ is compelling I'm thinking I might jump.
I accepted job 2 today, it felt amazing to have the support of my future manager. I'm inspired again and can't wait to start the new role.
Why does no one consider the most important issues? if you aren’t watching any news, AI is literally going to tear through the business world and decimate jobs. Which company do you think will better survive that. Which one will open up opportunities for you to ride that wave?
Well you can’t really know what is going on inside the other company without an insider you trust, frankly if I had comfort with the survivability where I was, I wouldn’t jump into a situation about which I knew nothing or had info that wasn’t from a trusted inside source, fyi, people trying to hire you will not tell you the truth cause there’s no upside or downside to lying to you.
Depends how old you are? Do you have dependents? How miserable are you? How close to retirement are you? How is the job market for you?
I'm 52, I been struggling for 4 years to make the salary i once made and be in a good environment. Saving is burned.
I'm close to your age, and am the only income supporting family of 5. Oldest kid couple of years away from college. I'm saving a ton right now.
As for AI, it's hard to say who will survive it better. Both companies are embracing it; legacy firm has a much larger footprint so if all goes well, much higher opportunity. New company is public, also embracing AI, but more limited scope of services, more competition in the space.
Smart move is 1. Dumbass move is 2. Literally do more work for less money and more stress. Bit my boss is nice? Ni e doesn't pay bills and student loans. So much brainrot
Bosses come and go. The “seems nice” boss can quickly be replaced by someone you don’t like as much, especially in a smaller high growth company. Another thing I’ve seen happen is your boss’ boss can get replaced by somebody more aggressive who pressures your boss to make tough changes, and suddenly your nice boss isn’t so nice anymore. 
I wouldn’t use the specific current boss as much of a deciding factor compared to the more permanent factors. 
2nd one! Mental health and feeling valued causes less stress and anxiety. Especially if you plan to commit yourself to a company for years and be content and productive. Instead of angry, dejected, and miserable. I’ve been there. Felt like I was losing my sanity. Couldn’t even sleep through the night and definitely couldn’t concentrate on being productive at work.
As someone who has recently found a job that is excellent for mental health, I’d take the second. Money is nothing if you don’t have the time to use it.
Mental health is very key.
Job 2. Life is too short!
Stay put, I promise you.
Choose the nicer boss.
Is Job 2 already public? If so, what’s the vesting schedule?
Personally, I’ve worked at a company like Job #1 and I loathed it. I can’t stand a process-centric company where it takes forever for anything to see the light of day. So I’d be tempted to move to Job #2 just because it aligns so much better with how I prefer to work.
You’re in a great spot (lucky to have 2 options) it really depends on your personal circumstances and what you want in your career and progress. There’s pros and cons with both.
My take is go with #2. Having a bad boss is the worst thing, it can drain you physically, mentally and emotionally.
Choose one and put forth effort in making work for YOU!
Good luck!