To Boomerang or Not

I spent around 2.5 years (first job out of school) as a software engineer at a large company in a pretty separated robotics project. The job was really fun and engaging, but ultimately I left and even moved states because a) I felt my growth in the team had stagnated b) I always wanted to try working at a small robotics startup.

Around 5 months ago, I dropped everything and moved states to work at a 20 person startup that addressed an industry that I later discovered I don't have as much passion in. The leadership within the startup is actually some of the best and most knowledgeable I have seen, however I've been struggling to become involved with the product and break into the culture since everyone else had previously worked with one another and has very different interests outside of work. I also don't see myself being in the state I've moved to long-term or at this company long enough to see the project to an exit.

I am now considering going back to the same company I was originally at, on a different project and team. The TC is around 280K for the first year and it's a completely remote opportunity (per my request since I have realized I value the work/life flexibility with my hobbies) they are offering covered travel to visit the team, but also limited vacation days. Right now, the startup I work for has a TC of 220K where 60K was the valuation of the equity when I signed the offer several months ago, and the job is primarily in person with unlimited vacation that has been a significant change in lifestyle for me.

I am interested in working remotely in my future endeavors and I'm also interested in the project at the bigger company. However, I hestitate that going back to the large company is going to be bad for when I pursue other startups in the future or that 5 months isn't enough time at the startup with all the changes that have happened in my life. I also feel diengaged with my work currently and don't think I will grow as much as I had hoped since I've felt less involved.

I have interviewed at other places, only to get rejections. So at this point, I think my options are to go back to the company I worked at or wait a year before looking again. Is it bad to go back to a previous company? should I wait until a year is up at the startup before looking again? Is 5 months at a startup enough to evaluate whether you enjoy working there? Any advice that could make this decision would be appreciated!

I've seen lots of folks be very successful boomeranging back to a previous company. In my experience, that is most successful when you've been away a few years and gained experience that you can bring back and be very impactful with. I usually advise people to stay a year unless the job is completely different than it was described, there are ethical issues or mistreatment. You mention how great and knowledgeable the leadership team is. Do you feel there is enough value learning from them, even if you aren't psyched about the product? It can be hard to break into a group that has a work history and common interests. Can you find one or two people to build a relationship with? Hope that helps!!
There might be a chance to learn some of the considerations and such when it comes to running a startup. But that would be from just witnessing what’s happening within the company.I feel as if I have very little to contribute to decisions and in company meetings which makes me feel as if It’ll be really hard for me to grow here. I’m not sure how to get myself to feel more engaged.Is there a particular reason you recommend staying a year besides the bringing back new experiences part?
My thought on a year is it usually takes 6 months to learn the ropes and another 6 to feel the full extent of the value you are bringing and getting from it. My experience with start-ups is they are often made up initially of people who have worked together and as they bring in new talent, people are able to break into the group but it take time.The advice Sherie25 shared is also good. That all said, only you know if you feel you've given it enough time to know and tried all the avenues. Good luck!
First I would share openly with your current manager that you are feeling a bit disconnected- use that word and share that its because of the teams previous work relationship and that you want their guidance on how to fit in or get into the inside circle. If that does not help the situation in 30 days then I would start to look. Boomeranging is fine but before you decide to go back really tell yourself why. Is it the devil you know? or is it the passion for the work? Money isn't everything but happiness and growth is. Find your soul and plant it there. Don't worry about future startups and whether they will consider you. When the time is right a good engineer will find a home in the right place. Good luck!