One of life's difficult crossroads. What would you do?

Question

Long story short (as I can make it):

I'm 39, and still just trying to get my life in order. I have been enlisted in the Navy for 7 years. The opportunity to pursue becoming a Navy pilot has recently presented itself. I'd be making ~$80k-$140k/yr for the rest of my career and have a decent retirement in 13 years. Flying is my dream, and I got a bachelor's in it, but never had a job flying. The Navy keeps me away from family WAY too much and we'd have to move every 2-3 years, worldwide. Civilian aviation pays peanuts for the first 5 years, FYI (~$20k-$40k/yr), and once pay gets good, it'd keep me away from home just as much as the Navy.

On the other hand, my wife is a successful real estate agent and is opening her own brokerage (the Navy would make this near impossible to sustain). She has suggested that I could become a loan officer or contractor, and has connections who could train/hire me. We could bounce referrals to each other and potentially be very successful. Neither seems very interesting to me, but I'd be able to stay home with her and my 3 wonderful kids, I could still serve in the Reserves, could MAYBE fly on the side if we become successful enough, and I feel it could really help us become successful real estate investors.

We currently have one decent investment property and have done one decent flip. I have been wanting to aggressively grow our rental portfolio for the past few year, with the intention to achieve financial freedom and primary retirement income My wife is very pessimistic/conservative, wants to focus solely on paying off ALL debt first, and hates the thought of even acquiring "good" debt. We're both stuck in the rat race, but have different strategies to get out, but neither of us thinks the other's strategy will work... As much as I love aviation, I think working in the RE industry would expose me to a lot more possible opportunities that could help change her mind and align with my financial freedom goals.

I have 3 years until my current enlistment contract is up. Just trying to get some input from people that have grown a rental portfolio as a primary income. Thoughts?

Chris Levarek · Answer

@Joel McKinney Why not both? The salary of an officer in the military can very easily assist with real estate goals. Cutting off one stream of income for another is not always as efficient as two streams of income, one from rentals and one from military. Of course that is the financial logical decision.

The other choice is choosing to follow ones passion of flying OR putting the time with family before anything else. That's more the emotional decision. Perhaps talk to some pilots? (DM and I can refer) Get to know the life and see if it is worth the efforts.

Craig Anderson · Answer

I like your idea of finding other asources of income, than what ties directly into the real estate business. The trouble with this business, is that it tends to be cyclical, in which everyone in it, at some point, is doing poorly, in certain years, with income, which puts who is invested in real estate, at risk. And if you have other avenues for income, then you might be best to pursue them, in addition to incomes available in real estate. If you have a Rental portfolio, you will best, also, have some form of income. And in 3 years, you leave the Navy, hopefully to some new career.

One of life's difficult crossroads. What would you do?

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