u/No_Effort591

Apologies for the formatting, I’m on my phone.
35M attorney in California trying to figure out whether continuing the grind is actually necessary anymore, or whether I’m just psychologically attached to maximizing income/career progression.

Current snapshot:
~$3.6M net worth
~$3.1M index funds
~$170k cash
~6 rental properties that are cash-flow positive after debt service (about $3k/mo net profit on average). $330k in equity
~$700k total mortgage debt across properties
No kids
No spouse

One important nuance: I currently live with my parents, and the household expenses are around ~$12k/month post-tax. That figure is not really “my personal spend” — it’s more of a worst-case assumption that I may eventually need to fully support the household financially.

So I’m trying to analyze this conservatively:

1. assume I cover the entire household

2. assume continued market volatility

3. assume I don’t want to rely heavily on selling assets

4. Career-wise, I’m at a crossroads between:

6. moving in-house / lower stress / more normal hours.

7. Continuing to grind in biglaw

The strange thing is that mathematically it feels like the portfolio may already compound faster than our spending over the long term, especially given my age (35). But emotionally it still feels risky to step off the gas while I’m in prime earning years.

Questions for the sub:

Would you consider this already ChubbyFIRE?
Does the leverage/rental portfolio materially change the equation?

If you were me, would you:

1. retire,
2. coast,
3. go in-house,
4. or keep maximizing income?

For people who left high-paying/high-stress careers around this level, how did you know it was “enough”?

How much should I value future earning power at 35 versus current freedom/time?

I suspect the harder part here is psychological rather than mathematical, and I’m curious how others navigated that transition.

35M attorney in California trying to figure out whether continuing the grind is actually necessary anymore, or whether I’m just psychologically attached to maximizing income/career progression.

Current snapshot:
~$3.6M net worth
~$3.1M invested assets
~$170k cash
~6 rental properties that are cash-flow positive after debt service
~$700k total mortgage debt across properties
No kids
No spouse

One important nuance: I currently live with my parents, and the household expenses are around ~$12k/month post-tax. That figure is not really “my personal spend” — it’s more of a worst-case assumption that I may eventually need to fully support the household financially.

So I’m trying to analyze this conservatively:
assume I cover the entire household
assume continued market volatility
assume I don’t want to rely heavily on selling assets
Career-wise, I’m at a crossroads between:
staying on a high-intensity legal path (biglaw-type trajectory), or
moving in-house / lower stress / more normal hours.
The strange thing is that mathematically it feels like the portfolio may already compound faster than our spending over the long term, especially given my age (35). But emotionally it still feels risky to step off the gas while I’m in prime earning years.
Questions for the sub:
Would you consider this already ChubbyFIRE?
Does the leverage/rental portfolio materially change the equation?
If you were me, would you:
retire,
coast,
go in-house,
or keep maximizing income?
For people who left high-paying/high-stress careers around this level, how did you know it was “enough”?
How much should I value future earning power at 35 versus current freedom/time?
I suspect the harder part here is psychological rather than mathematical, and I’m curious how others navigated that transition.

35M attorney in California trying to figure out whether continuing the grind is actually necessary anymore, or whether I’m just psychologically attached to maximizing income/career progression.

Current snapshot:
~$3.6M net worth
~$3.1M invested assets
~$170k cash
~6 rental properties that are cash-flow positive after debt service
~$700k total mortgage debt across properties
No kids
No spouse

One important nuance: I currently live with my parents, and the household expenses are around ~$12k/month post-tax. That figure is not really “my personal spend” — it’s more of a worst-case assumption that I may eventually need to fully support the household financially.

So I’m trying to analyze this conservatively:
assume I cover the entire household
assume continued market volatility
assume I don’t want to rely heavily on selling assets
Career-wise, I’m at a crossroads between:
staying on a high-intensity legal path (biglaw-type trajectory), or
moving in-house / lower stress / more normal hours.
The strange thing is that mathematically it feels like the portfolio may already compound faster than our spending over the long term, especially given my age (35). But emotionally it still feels risky to step off the gas while I’m in prime earning years.
Questions for the sub:
Would you consider this already ChubbyFIRE?
Does the leverage/rental portfolio materially change the equation?
If you were me, would you:
retire,
coast,
go in-house,
or keep maximizing income?
For people who left high-paying/high-stress careers around this level, how did you know it was “enough”?
How much should I value future earning power at 35 versus current freedom/time?
I suspect the harder part here is psychological rather than mathematical, and I’m curious how others navigated that transition.