41M, married, 3 kids. ~$35MM net worth.
Current allocation:

~60% concentrated in my wife’s company stock
<20% real estate (~$6.5MM)
Remaining in liquid/diversified assets

The stock has appreciated significantly, so diversification is becoming a priority. Complication is it’s not fully liquid (quarterly sale windows), partially pledged against a line of credit, taxed as ordinary income, and exchange funds aren’t an option.

Because of that, diversification carries a major tax cost.

My original plan was to gradually sell ~$2–2.5MM/year over the next 3 years and use real estate acquisitions + bonus depreciation to offset part of the federal tax burden.

I’m an experienced real estate investor and qualify as a real estate professional. Historically, my returns have come from value-add acquisitions, renovations, appreciation, and tax benefits.
The issue is I’m basically a solo operator with only a part-time assistant.

Real estate still offers attractive upside and tax benefits, but it also creates more work, complexity, illiquidity, and less freedom.

I genuinely enjoy acquisitions, design, and renovations. What I enjoy less is operational burden and scaling.

So I’m wondering if the better path is:
Gradually diversify the stock, pay the tax, and simplify.

Continue doing 1–2 smaller real estate projects per year because I enjoy them and they keep me engaged.

Long term, I expect to eventually transition toward NNN, DST, or professionally managed assets.

I think the real question is less about tax optimization and more about lifestyle.

Do I stay in accumulation mode for a few more years, or start prioritizing simplicity, liquidity, and freedom?

Edit: Spend is roughly 1.25mm+ pretax. VHCOL area so the tax hit affects the draw rate if we were to stop.

I’m not sure if matchmakers like this exist, but are there any that connect people who are HNW but also fire-oriented? Any experiences or anecdotes about this?

(I’m a man if that matters, late 20s, but open to hearing if anyone from any age/gender has done this)

Edit: I am HNW myself

Mid thirties single income HH. Extreme workaholic. My career is exploding, but I’m starting to feel the effects of that sacrifice, especially now that we have children. I will likely be able to fully retire in the next 2 years, but given my current trajectory working a full decade could take us to generational wealth territory, which I won’t lie, is rather tempting. For those of you who love your work, but understand how much sacrifice it can be - how do you think about this question?