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Based on the most helpful WSO content, here's what you need to consider:

1. Your Long-Term Goals: If your ultimate aim is to become an entrepreneur/investor, both paths—staying in high finance or transitioning to insurance sales—can lead there, but they offer very different experiences and skill sets. High finance (IB to PE/HF) provides institutional knowledge, deal experience, and a network that can be invaluable for buying and scaling businesses. On the other hand, insurance sales can offer immediate high earnings and entrepreneurial exposure, but it may limit your ability to pivot back into institutional finance later.

2. Private Equity Transition: If you're serious about transitioning to PE, especially LMM, your current IB experience is a strong foundation. PE roles will teach you how to evaluate businesses, structure deals, and institutionalize operations—skills directly aligned with your entrepreneurial goals. However, this path requires patience and persistence, as off-cycle recruiting can be competitive and time-consuming.

3. Insurance Sales Opportunity: The success of your friends and family friend in insurance sales is compelling, especially with your prior sales experience. If you’re confident in your ability to replicate their success, this could be a faster route to financial independence. However, as you noted, this path may "lock you out" of institutional finance, making it harder to return if you change your mind.

4. Risk vs. Reward: High finance offers a more structured career path with a clear progression, but it can feel like a grind, especially in roles like IB. Insurance sales, while lucrative, is more entrepreneurial and comes with higher risk—your income will depend on your ability to sell and build a client base.

5. Hybrid Approach: One potential compromise is to stay in IB for another year while actively recruiting for PE roles. This keeps the door open to institutional finance while giving you time to evaluate the insurance sales opportunity further. If PE doesn’t pan out or you remain dissatisfied, you can pivot to insurance sales with a stronger financial cushion and more clarity.

6. Networking and Mentorship: Regardless of the path you choose, having advocates and mentors in your desired field is crucial. In PE, this means networking with professionals who can guide you through the recruiting process. In insurance sales, it means leveraging your connections with successful brokers to learn the ropes and hit the ground running.

Ultimately, the decision comes down to your risk tolerance, financial needs, and how much you value the institutional finance experience versus immediate entrepreneurial exposure. Both paths can lead to your end goal, but they require different sacrifices and commitments.

Sources: 30 and a bit lost in career - Advice Appreciated, Newbie Financial Advisor: How To Be Successful., Transitioning from tech to a serious finance job (yes, you read that right), https://www.wallstreetoasis.com/forum/wealth-management/qa-a-bored-financial-advisor?customgpt=1, Switching from IB to AM/WM in undergrad?