27 is still pretty young all things considered. If you don't have a family to support then I say take the risk and go where your heart takes you

Op, I've been in your shoes. If you don't have a wife and kids, take the risk and follow your heart. You'll be glad you did.

just to give an argument for the option most folks are not choosing.

I work for a huge old company and here are some of the benefits:

• Good pay
• Great work/life balance. putting in over 40hrs/week is unheard of, no crunch time
• Size of the company allows for movement to different tech areas
• Very stable, great job security

Now granted, we are totally WFH, don't think I would be willing to do an in-person job with a suit every day, but there is an argument to make for making more money when you're younger that you can start investing early.

The lack of bleeding edge tech could also be used to your advantage if you could spearhead leading a more modern initiative.

I'm not sure how large the pay difference is, but it sounds like your heart is leaning towards the start up.

In the end, you'll just have to weigh the positives and negatives and figure out what you truly want.

It's really up to what you value most I would say. Personally I work to live, and all of my passions are outside of work, even if they are programming-related. I get paid ridiculous money doing BS work at some corporate company doing nothing for the world, and I'm okay with that. If you would rather do something cool and innovative for a company and put in a lot of effort that would potentially only be compensated by the knowledge and experience that you gain, that's also an option. It all depends on what you want your career to look like.

Semi-related, please learn about Boglehead investing while you're young and stuff all your phat programmer money into the right places. You could retire by the time you're ~40, and that may shape your expectation of what you want your full career to be.

You're 25, unless your dream job is social media manager, you have 10+ years before anyone starts using your age against you. No matter which job you take, you can always pivot, just spend a few minutes crafting a narrative.

You can learn at any company. The financial company is going to give you a lot of space to learn process and compliance, and probably be infuriatingly slow, but you'll probably come out with a different opinion about risk. The IoT start up is probably going to let you have more independence and playing with rando tech, and you will learn more about work life balance and your own working habits there.

If you've never worked remote, take the contract and see how much that flex is worth to you monetarily. You might be surprised. I would rather rub shit in my hair than wear a suit to an office everyday. But then again, maybe you love volley ball that much.

Make a SWOT analysis for each option. Quantify EVERYTHING you can into personally objective and subjective values. Then A/B all of those values against each other. Then sleep on it, ask other people, and then return to the SWOT tables and try to add and simplify.

If you still have troubles after that, try to figure out what about either choice you don't know, and work to find it out with footwork and socializing, asking pointed questions, and paying attention to the things you want in life about people.

If that still doesn't tip the scale, it's probably because you don't know enough about something else, probably yourself.