Ask HN: Should I take a downgrade to work in a better company?

If I were you, yes.

But a question to ask is... Are you willing to sacrifice?

It might be a short term sacrifice. Because maybe after few months or a year, the startup will be acquired or became a hit. We don't know.

Also, do you have family? If you have, maybe consider to ask them first.

When joining a startup, I always said to myself that it's not about the money. It's about the value (experience, learnings, etc.) you will get.

The most important consideration is your future. Does this job open up new opportunities, new skills, new connections?

If you see yourself rising up the ladder in your current place, and it interests you, stay.

But all in all, the other opportunity looks good.

The short answer is: Yes.

But what really should matter is the market -- i.e., your options. Learn what your opportunities are, and take the best. Did FiveYearItch send you some other offers? How do they compare? Did you look for options elsewhere?

I wouldn't.

If you were able to receive one offer without looking then surely you can get another offer if you were specifically looking for another job in SF.

Though it's good to love your job, it's also important that your time in your job is financially providing something more than just a paycheck. You should be able to put money away and enjoy the time that you aren't working as well. Getting paid just enough to cover your cost of living is no fun and stressful. What do you do if they go under? If they really recognize the value that you are bringing to the table, then they should be paying you enough to make this an easy question.

It sounds to me like this offer has perked your interest for moving on and that perhaps you haven't considered this before. Perhaps you should look around for other opportunities and at least get some competing offers. Maybe you could even do something as a remote developer (just don't apply to Yahoo!) somewhere.

ETA: If you want to scratch an itch, start a side project or find an open source project to contribute to.

If it only covers the cost of living in SF I would suggest that you do not take that job. Also if you are working now as a Team Lead try to find another job that does not bust you down.

Don't forget the challenges that you may find in your current job. Maybe in your current team, they're just phoning it in, but in a large organization there are always new challenges to be found.

In your FiveYearItch.com signup, did you specify the crucial requirements that you need to succeed: Top colleagues, flat hierarchy, passing the Joel Test? If so, and if they can guarantee you that, go for it!

I just took a pay cut for a new job and I'm loving it (however, the pay cut is more about the region I moved to having lower pay overall). If you spend 8+ hours a day in the place, you should really enjoy it. However, as another poster said, think hard about whether the new job is good for your future, especially if you are taking a less important position.

Go for it! If there's nothing holding you in the Midwest, take the offer, learn, grow, and come back later if you want.

Such a small percentage of the industry rocks like most hot SF startups rock. Take the opportunity.