This is my first post, so please forgive me if I do anything that's outside of the accepted format.
Basic info -- I'm 34 yo living in the midwest. I'm married and we have a young child, which is part of why I'm presenting this question...
Our financial situation: I'll lay out my salary info below, but basically I'm in the "getting out of debt" phase of my life. My husband is debt free aside from a mortgage on a rental property, which he's working to pay off. I have consumer debt and student loans, but I'll be out of all of them by mid-2019 (based on my current budget/payoff rate). I have two mortgages -- one on a rental property and one on a family vacation property (which is very unmustachian but for now, I'm considering it an investment and would likely live there when FI). My husband and I both owned duplexes when we got married and we haven't sold them, hence the mortgages -- mine makes 3x the mortgage monthly. Our finances are separate because of his ex/child-support (for the next 6 years), so I'm asking this question without really considering his income. We have no mortgage on the house we live in. Based on my forecasting, I can have everything paid off (including my mortgages) by 2025. At that point, we would take in $85K+ in passive income annually from rental properties. I wouldn't have much invested at that point, but I think we could slow down and worry less about working constantly (semi-FIRE). My husband will also have a military pension that will be paid out starting in 2032, so we're in pretty good shape as long as I get out of debt and get that mortgage paid off.
My situation/question:
I founded and lead a nonprofit organization. I make $110K and while my job isn't necessarily low-stress, its fairly straightforward and I can keep it for as long as I want it (barring some major upheaval of my board, etc). I work from home on Fridays so I have more time with the baby. My husband travels for work so Mon-Thurs or Fri I'm "single parenting" which gets old. I lead a team of 13 people, so I do deal with a lot of managerial crap that makes me not want to be a "boss." I wish I had more flexibility in both WHERE I work (because that way I could actually travel some with my husband for work) and WHEN I work (I.e. not being tied to a desk in an office from 9-5). The income is steady and likely won't go up much, but also won't go down. We have 8 weeks paid maternity leave as a benefit.
BUT...
I've recently started thinking about leaving my job and going out on my own to consult. I have some national recognition in my field and several people I respect have told me that I could easily get work this way. I'm experimenting with it right now and I'm able to charge $150/hr without anyone batting an eye (my rates could likely be higher if this became my "full time" gig). Right now, I just got my first "side hustle" contract of 5-20 hours a month (so $800-3000/mo). If I left my job and did this, I'd have flexibility of time and location. We have benefits through my husband's military service, so I don't need to worry about that. Everyone I've talked to who is doing similar work is making more now than they were when they were in salaried jobs.
I guess I'm looking for advice on taking a leap like this when I'm still paying off debt. If it goes well, I can pay it off faster -- I'm guessing I could make closer to $150K or so, but that's not guaranteed and its dependent on me getting the contracts. If I were FI, I'd obviously just do it. But when you're still trying to work through debt, is it bad to take the risk? We also want to have more kids so I'd have to build in maternity leave for myself (timing projects to work around baby/leave). I'm not under the illusion that consulting is a cakewalk. I'm trying hard not to have romantic notions of leisurely workdays spent in coffee shops. I know it'll be work, and there will be (some) travel, and I will get super stressed at times--maybe more than I am right now (or at least a different kind of stress).
MMM's post yesterday was PERFECT for me, because it reminded me that if this didn't work, I could just get another job...in theory it could slow down my debt payoff if I'm not able to replace my income, but I'm not worried about starving or defaulting on my debt.
So, any thoughts on doing this given where I am in my financial journey? Should I suck it up and recognize how lucky I am to make 6 figures at a fairly easy (though sometimes stressful) job and just focus on it being a means to an end? Or should I take the risk with the potential of doing even better (financially and lifestyle) than I am right now? Thank you!
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