Stay Comfortable and Underpaid or Seek Growth?

As we wrap up the year, I’ve been reflecting on my career and where I’m headed. Here’s my situation:

I’m a mid-30s male working as a Business Analyst, making about $88k total compensation with solid benefits. I’ve been with the same company for over 10 years and my background is in Data Analytics. The work environment is super chill—real work only takes a few hours a day, and my boss is incredibly laid-back. This has allowed me to maintain a great work-life balance and even focus on a side hustle, which was very profitable two years ago but has slowed down since.

However, there’s a flip side to this comfort. I feel like I’ve become complacent. My work isn’t challenging, and I’m stuck working with obsolete technology. Earlier this year, I tried applying for Senior BA and Product Owner roles. While I had a decent number of interviews, nothing panned out. It’s made me question whether I should keep looking for new opportunities or stick with the comfort of my current role.

I know I’m underpaid for the market (especially given my experience), but the chill work environment make it hard to leave. Realistically, how much could I expect to earn if I pursue new opportunities? And would you prioritize happiness and stability or push for growth and higher pay?

Would love to hear your thoughts, especially if you’ve been in a similar spot.