Deciding between 2 different paths?

[kev014]

I am trying to decide between two different paths professionally. One is 100% remote and allows me to take off as much time off as I want whenever I want (completely unpaid time off, this is 1099/self-employed - don't work, don't get paid). The other is in person W2 for the first 2-3 years, then remote potential, but most likely always unable to take off more than a few weeks a year.

Being 100% commission based/self-employed doing retirement planning (selling financial products) vs. being a W2 employee working in commercial insurance. I have been doing the retirement income planning on and off for the past few years and have had some serious challenges with previous business partners (mentors to teach me the business). Previously it was not profitable or sustainable.

I am now very recently (last 2 weeks) with a good mentor who has thus far shown to have everything to run a sustainable, highly profitable business - good marketing, spending enough on ads to generate sufficient lead flow, good sales process and products, etc. I don't think this is what I would spend the next 30+ years of my career doing; I would get bored, but assuming it all goes accordingly, it would allow me the ability to go travel while I'm young (27) and don't yet have any kids. It would also provide the flexibility to pursue other entrepreneurial ventures should I become curious (which I'm sure I will in the future).

I have done very little travel in my life, but have wanted to since I was 21/22. Have tried to pursue entrepreneurial ventures for years to enable this desire, but haven't been able to make it work yet financially.

The W2 commercial insurance work, however, seems more intellectually stimulating (different customers, complex products/solutions, far more technical) and relationship based. It's an industry with a lot of entities/individuals involved, so it's highly relationship based - many have said their customers/coworkers genuinely become their friends (and I can tell this isn't BS).

Also, commercial has the potential to build an actual business (start as an employee, but eventually build your own individual 'book of business'). Meaning, not just being 'self-employed' where income starts at 0 every year + is tied directly to hours worked. 'Actual business' = Recurring revenue + able to build a team that operates independently + able to potentially be sold in 10 plus years. Simply put, much more upside longer term in commercial insurance, but I believe I'd make more in the next 2-3 years in the retirement income planning.

If I could go travel for 3, 6, or 12 months and 'scratch the itch' I think the decision would be much
easier. I'd be much more okay with working in person. Thinking about being full
time in an office right now though definitely makes me feel trapped.

Ideal scenario would be I could work in the office most of the time, but go work remote for a month or so while traveling/living abroad. Not sure how to make this decision truthfully.

Any suggestions?

[Dauntment]

Meh, seems alot of rationalizing and calculating. I'd say to consider more of: Intuition & Aligning with your values.