Hey everyone — looking for some outside perspective on my current situation and what I should be thinking about next.
I’m 38M, married, and my wife is 41. We have one daughter who is 8. I work in a high-pressure and extremely high stress finance / M&A career. I generally like parts of the work, but the intensity, stress, and constant deal pressure have me thinking more seriously about financial independence and what “enough” looks like.
Current financial picture: $2.5M cash/investments and $65k budget
- Primary home / acreage is paid off, estimated value around $700k
- Rental home is paid off, estimated value around $300k
- Rental generates about $1,600/month gross rent
- Taxable brokerage / cash: approximately $1.5M
- Retirement accounts: approximately $500k
- Private investment: approximately $200k in a privately held biotech company
- No personal debt
- I just closed a large transaction and expect approximately $300k net in cash that I can invest
- We live in Nebraska, so cost of living is relatively reasonable
- My wife currently works and makes approximately $100k/year, and her job provides our family health insurance
- My job varies, but I gross $500k - $700k per year - average 50 - 60 hour weeks, which is fantastic considering other firms in investment banking.
One wrinkle is that I could see us putting $300k+ into our acreage over time for a new shop and home upgrades, such as a new deck, bathroom remodel, and other improvements. These would be lifestyle / property improvements rather than necessities, but they are real things we’d like to do.
Big picture, I feel very fortunate and am thankful every day for our financial situation and know we are in a strong position. That said, I’m trying to be thoughtful because we are still relatively young, have a child, healthcare is a major unknown, and I don’t want to make a reckless career decision just because I’m tired after a big work push.
A few things I’m wrestling with:
- One major hesitation I have is career re-entry risk. If I step away now, I worry it would be difficult to get back into my current career because of licensing, deal flow, and the perception within my network that I’m no longer “in the game” or fully dedicated.
- I’m also at a possible inflection point professionally. My boss is considering stepping down next year and wants me to take over our small firm of 5 employees. On paper that could be a great opportunity, but honestly I’m not sure I have the ambition right now to take on more work, stress, leadership responsibility, and pressure. Also, I'm assuming I'd have to spend money for payroll, etc. as our firm is heavily project-based - taking this on is also a financial risk.
- How close are we realistically to FIRE? From an expense standpoint, I think we could live very comfortably on around $65k/year, especially with no mortgage or debt. That said, for planning purposes, should I be using something closer to $100k/year to be more conservative and account for healthcare, taxes, home projects, travel, inflation, and lifestyle creep?
- I’m not sure how much to budget for health insurance if we ever had to buy it ourselves. My wife has lupus, so healthcare coverage and out-of-pocket costs are a major consideration. What would people realistically budget for health insurance in that situation?
- Since my wife currently earns $100k and provides health insurance, does that change the analysis materially? Can we both retire early or should one of us before the other?
- Would you count the rental property as part of the FIRE portfolio, or only count the net income after taxes/maintenance/insurance/property taxes?
- Should I keep grinding for a few more years while income is high, especially with this potential leadership opportunity, or start designing a more sustainable life now?
- What would you do differently if you were in my position?
Lifestyle-wise, we are not huge spenders, but we do enjoy a comfortable life. I’d like to spend more time with my wife and daughter, nieces and nephews, get healthier, work out more, spend more time outdoors/on projects, spend more time with all of my hobbies (I have a lot), and not feel like work is constantly consuming my attention. I also want to be realistic that some of the things we’d enjoy — property improvements, a shop, home upgrades, travel, and healthcare security — may mean our true planning budget should be higher than our current “bare minimum comfortable” spending.
I’m not necessarily looking to quit tomorrow; I’m more trying to understand whether I’m already financially independent, whether I’m close but should keep going, or whether I need to keep my head down for several more years. I’m also trying to balance the financial math against the softer career/life questions around identity, ambition, stress, and whether stepping away from a high-income career too early could be hard to reverse.
Would appreciate any thoughts on:
- Safe withdrawal rate assumptions - especially where to draw from initially - I'm assuming the brokerage account? but at what %? 4%?
- Whether to plan around a $65k annual budget or closer to $100k
- How to think about rental real estate in the FIRE calculation
- Health insurance assumptions before Medicare age and with my wifes condition
- Whether I’m underestimating taxes/healthcare/college costs
- Whether a fee-only financial planner would be worth it at this stage
- Whether career re-entry risk is a good reason to keep going longer
- Any blind spots from people who have been in a similar position
Thanks so so much in advance; this is a daily struggle for me these days!!!