I am thinking of retiring or figuring out how to find a way to semi-retire this year. I have had this plan for a while but I was targeting for when I turn 55. Retiring this year is 3 years earlier than I planned. I have been working full time since I was 22 with over the last two decades working for one of the big tech companies. It is not important which big tech company - they have all turned into pretty terrible places to work in the past few years as they look to fire (without severance) their long term FTEs to make room in the budget for AI. I have not been fired - yet - but at this stage of life and career I do not feel like spending every day looking over my shoulder and waiting for some random hammer to drop on me. This is not how I envisioned the end of my career would be, but here we are.
So onward and upward. The below is a breakdown of my assets and net worth. I did my best to follow the template on the forum.
Debt: Primary Mortgage: $230K Principal. Year 5 of 30-year fixed at 3%. Credit cards all paid in full every month. No other debt.
Tax Filing Status: Married Filing Jointly (wife is 49) with 3 Dependent children (15, 18, and 20).
Tax Rate: 22%-ish% effective Federal rate, ??% State. I reside in a fairly 'moderate' income/capital gains tax state.
State of Residence: rather not say but somewhere in the middle...
Age: 52
Desired Asset allocation: 80% stocks / 20% bonds
Desired International allocation: 0% of stocks
Cash Portfolios:
Cash Account #1: $1.3M (90% of which is one single stock - yeah, I know I need to do something about this)
Cash Account #2: $1.2M ($650K VTSAX, $130K VITAX, $120K VIMAX, $100K VWALX, $200K, VMFXX)
Retirement Accounts:
401K: $1.85M ($880K S&P Index Fund, $500K Russell 2K Index, $365K Bond Index Fund, $100K BigTech Single Stock, $9K Russell 10K Index)
IRA #1 (mine): $400K ($320K VTSAX, $80K VBTLX)
IRA #2 (mine - inherited): $25K ($19K VTSAX, $6K VBTLX)
IRA #3 (wife): $6.5K ($6.5K VTI)
HSA: $47K ($22K S&P Index fund, $22K Megacap tech fund, $3K cash)
Checking Account: $35K
Farmland:
Tract of land (crops) - cash rented: $1.2M approximate assessed value (could be more or less - assessed in 2017 at about $1M)
Private Land Investment:
Land Fund investment: $70K (probably my biggest regret - money is locked and illiquid. May take decades to see a return on principal and hopefully some sort of profit)
Variable Life Insurance Policies: $50K
One for me and one for my wife. Anticipate combined value will be about $50K when the policies go to term which will happen when I turn 55 (3 years). Current money invested in what I am sure are high-load funds that I was forced into. Like the private land investment, I regret these investments as well. Was younger and dumber then...

I have been tracking my cash flow and expenses closely for the past 7 or so years. In 2024, my total expense was $214K. $37K of that was paying for two kids in college (funded via their 529s) and $28K of that was paying excess income taxes due to bonuses and extra income generated from the farm cash rent and dividends collected from the case brokerage accounts. Expenses include all out of pocket medical expenses - that is, I do not use my HSA for these as I am building it up for when I am not employed. Medical expenses were about $7,700 in 2024. I did NOT make any major purchases like a car nor did we take any extravagant vacations in 2024 although we did take a few small trips which would be in that total.
On the income side, my investments across all accounts (retirement and non-retirement) equated to about $48K which for the most part I simply reinvested. The farm cash rent yielded about $32K in income. So about $80K in income generated from my portfolios and land as they stand right now.
If I were to retire, my biggest worry is health insurance. Currently I pay into an HSA and have to meet my deductible for the year but my job takes care of the rest. For at least the next 2-5 years I will need to provide coverage for 5 people. Looking beyond COBRA, ACA for an OK plan seems to be horribly expensive - like $35K - $40K/year unless I can play the subsidy game to bring that down. But - as we all know healthcare in this country is one big sh*tshow and is probably only to worsen in our lifetime.
I THINK I would need to draw about $240K starting this year to pad my need to pay for healthcare and to maintain (maybe somewhat improve) my current standard of living. I assume once my kids are graduated and out of the house with their own healthcare and stuff that will certainly help, but that is several years away so need to plan for the current reality.
If you have read this far, I would really like to know any opinion or recommendation you have with the above such as:
- Does this seem doable or do I need to keep working for another couple years?
Any suggestions as far as current investments - that is, a need to change things? And yes, I am very aware of my very large single stock exposure - any ideas on how to efficiently divest that such as direct indexing are welcome!
Healthcare - I mean, I have done a fair amount of research on this - anyone have a magic bullet here, please let me know!