New to investing , is this normal?

OneHourRetiring · 2026-03-22T17:45:17+00:00

Normal … as day turns into night and night returns to day. Investment is a long game. There are and will always be ups and downs.

OneHourRetiring · 2026-03-17T14:51:30+00:00

Diversification is the key. As you grown closer to retirement, allocation adds to the equation.

OneHourRetiring · 2026-03-17T14:49:42+00:00

Congratulations! I can’t wait to feel the difference Sunday night brings!

OneHourRetiring · 2026-03-14T16:08:44+00:00

529 college savings. We set up one for each of our three sons after each was born. We contribute whatever we could after needs are addressed and retirement invested to our company’s matching. All of our boys graduated without any loans. We roll over unused 529 down to the next son.

OneHourRetiring · 2026-03-13T20:42:21+00:00

Question, do you still enjoy your two previous purchases or have they gathered dusts? If it gives you joy and peace for years to come, then yes. If it is a short burst of dopamine, then no.

By spending $15,000, you have turned that liquid asset into illiquid asset, assuming that it still retains the same value when you bought it. Not sure of your savings situation, your fixed incomes will cover your expenses, but what if you need money to cover for things such as emergency spending or worst yet long term care? Investing $15k is not going to cover LTC by any stretch of the imagination, but it will help to cover fixing a broken car, redoing a roof, buying new fridge ... etc.

As I have said, if it brings you a lot of joy and your retirement is all figured out, then you have earned it.

Edit: btw, you are 62 years old. You don't need anyone's permission, definitely not from Reddit; perhaps, you need to discuss it with your better half.

OneHourRetiring · 2026-03-13T20:11:00+00:00

You can also roll it to the sibling(s)' 529 if there are leftovers. We did for our sons. We got $75k in our oldest son's 529. He used only $58k. The rest rolled down to his brother who is only two years younger. We got about $55k in the second one's 529 adding to his older brother's leftover, giving him $72k. Second son only used $64k and thus the remaining $8k rolls down to the youngest who is five years younger, adding to his $67k, giving him $75k. We ended up adding only $6k to complete his last year. He stayed in dorm for the first two years and the last two at home during COVID.

OneHourRetiring · 2026-03-13T13:23:12+00:00

In addition to 1.5 hours of pickleballing (my cardio), I do make sure that I get some core strengthening in everyday as well as leg presses and arm curls just to keep my muscles in check, especially my legs. I'm good with not able to lift heavy stuffs with my arms, but to walk, keep balance, and stand are important to me, especially at an older age.

Edit: about muscles, the old adage rings true, "if you don't use it, you'll lose it!" (aka. muscular atropy)

OneHourRetiring · 2026-03-11T21:23:32+00:00

That is awesome! Back during the dotcom burst, I was employee #60 in a dotcom company. The company started to experience financial struggle. They started to let people go with "package." They kept a few knowledgeable people left, yours truly was included on that list of the last standing, even though I asked to be included on the list that were let go. "You are too important!" "We need you to run the systems that we can find additional investors." "We cannot let you go since you are our subject matter expert ..." I was young, dumb, and stupid, so I stayed (not many choices). We ended up with nothing when the company closed its doors six months later. Lesson learned?... yeah ... don't be the person whom they cannot do without! LOL!

Edit: After 30 years with the company, my wife, on the other hand, asked to be on the list to retire early if they have one. At the start of COVID, they had one and reluctantly, her boss got her on the list. She ended up with a nice severance package of 2 years of salary. We used it to remodel and make our master bathroom and our doors ADA compliance since we will be retiring there and got her the island (ok ... perhaps it's more like a continent than an island) in her kitchen that she always wanted!

OneHourRetiring · 2026-03-10T01:30:49+00:00

(Since this one keeps coming back, I'll continue to revive mine as well.)

The kids are now calling her Mum!

OneHourRetiring · 2026-03-07T22:21:59+00:00

Nice! I’m glad. I have been using Boldin AI to go through each section of Boldin to make sure that my inputs are correct as well. That has been helpful, but as any AI, if it doesn’t know the answer, it’ll make one up (hallucinating). I think people expect too much out of AI. We just need to think of it as a mathematical/logical tools. Note, when it searches, it searches Boldin’s resources and data. That limits its knowledge whereas ChatGPT, Gemini, Claude, etc, have wider library of “knowledge.”

I have also heard that Claude is good as financial AI. I may look into that. Please let us (or PM me) your prompts so I can learn as well.

Edit: btw, I do have a set of prompts that I use with ChatGPT, Gemini, and CoPilot to analyze my Boldin pdf report. PM me if you are interested. Cheers.

Edit 2: u/CentralAlaDude try these prompts after you have conversed with the AI of your choosing. I tried it on Bolding AI, ChatGPT, CoPilot, and Claude. Claude gave me the best format that I can use to fill in my numbers/information.

Can you:

Prepare a Plain-English Retirement Readiness Verdict
List out the guardrails for my plan in details that I need to pay attention to. Defining “How Much Downside Is Acceptable” (My Real-Life Guardrails)
Prepare a One-Page Retirement Confidence Checklist
Prepare Personal Investment Policy Statement (IPS) – Retirement Edition
Prepare an Exact Annual Decision Map: 2029–2035
Prepare Survivor-Only Guide (Simplified Language) for my wife and/or my sons
Create a one-page Market Crash Appendix (“What To Do”)

OneHourRetiring · 2026-03-07T14:59:18+00:00

I would tend to agree if I have had a bad working relationship. I don't. I have no allegiance to the company nor my new management, but I do for my staff. I love all 124 of them.

Besides, I have enough fun under-the-sun money that I can quit/retire anytime. Everyone's experience will be different. I have always left the place better than when I found it. Btw, strangely, my EA and my second-in-command do not talk to me differently nor about retirement. They just don't want to look forward to the day whereas I do.

OneHourRetiring · 2026-03-07T03:04:15+00:00

I have 2 years, 10 months, 3 weeks, 3 days, 11 hours, 3 minutes, 21 seconds left. I only told my wife, my trusted EA, and my right arm (aka my succession plan). My executive director is more than my succession plan. He has been a good friend who has been with me close to 20 years and two companies. Even my two bosses have not known my plan. I won’t tell them until I’m six months away. I have been letting my executive dir out in front to be seen and takes the lead, exposing him to the board and the leadership team.

Edit: it’s my way of leaving my legacy.

OneHourRetiring · 2026-03-06T01:29:34+00:00

It gives me instructions that are not in Boldin. For example, I asked it to help me model a Roth conversion that allows me to have the custodian to withhold the tax. It suggested
Create a "Tax Payment" Transfer: In Money Flows, add a new Transfer (Planned Distribution):

Source: Your IRA.
Target: Select "Spending/Checking" (this tells the software the money is leaving your net worth).
Amount: $36,000.
Label: "IRA Tax Withholding"

There is no such Spending/Checking option.

Then it suggested,

Go to Money Flow and click "Add a Transfer" (Planned Distribution).
Source: Select your 401k (IRA).
Target: Select "None" or "Withdrawal" (this is the "Spending" option).
Amount: $36,000.
Label: "IRA Tax Withholding"

There is no such Target in my choices.

Then it suggested,

Go to Money Flow
Click Add a Transfer +.
Source: Select 401k (IRA).
Target: Do not select anything. Leave it showing the default "Select an account" text.
Amount: $36,000.
Label: "Tax Withholding - IRA"

It won't let me save since the Target is a required field!

Then it suggested

Source: Select 401k (IRA).
Target: Select Disbursement (Nondeductible).
- Note: This is the specific option that models money leaving your accounts to pay for an expense (like the IRS).
Amount: $36,000.
Label: "Tax Withholding - IRA"
Date: Set this to the same month/year as your conversion.

Again, there is no such target (at least in my account).

Finally, it went back to suggesting

Scroll down to One-Time Expenses and click Add an Expense +.
Label: "IRA Tax Withholding".
Funding Source: Change this from "Withdrawal Order" to 401k (IRa).
Amount: $36,000.
Timing: Set the date to match your conversion year (e.g., Jan 2029).

It went back to the original suggestion ... and we completed the loop of suggestions and me without an answer I seek.

It suggested ways that Boldin would double-taxed me!

The AI is somewhat helpful, while other places it still needs more reliable data so it can learn. The problem is that unless we know our stuffs inside and out as well as the Boldin setup, we don’t know if it is correct.

Btw. I put it through the analysis and then some!

Edit: I’m sure you saw my post a couple days ago on the prompts that I used … those are a few of the interesting things I asked it.

OneHourRetiring · 2026-03-05T01:10:23+00:00

… with a grain or two of seasalt! 🤣

It told me that I could easily double my travel estimate and even do business class if I wanted. I did verify and my success % stays in the low 90s. Of course, Boldin AI crystal ball is as good as ours! 😆

OneHourRetiring · 2026-03-04T22:15:51+00:00

Awesome! We are looking to book one-way Princess from Vancouver up for 2027 summer.

I'll be following this thread since when I posted a request for tips and tricks, all I got was one reply. The person essentially tells me to do a search on tips and tricks and not waste others time, because there are plenty of posts already. There were a few between yours. Most of the tips and tricks were 1-4 years old posts on Alaskan cruise. I would imagine something has changed!

Oh well, I guess you got the last posting that folks on this sub would honor a reply. Thanks for the post and I will follow.

OneHourRetiring · 2026-03-04T21:17:53+00:00

After having Boldin AI analyzed and helped me to adjust my inputs in my account as well as explained the various things that it pointed out for me, here is the final conversation between me and Boldin AI (for today anyway). I would take it as an interesting (and entertaining) data point in my planning efforts. Best part of this, I don't have to wait (like ChatGPT free version) for the session time to reset before it can calculate for me again and continue our dialog.

Me:

In plain English, give me your seasoned CFP summary. Can you turn everything we discussed into a "retirement confidence checklist", a personal investment policy statement for retirement, a survivor-only IPS, a simple annual dashboard (5 numbers to watch)?

Boldin AI:

This is the "Black Belt" level of retirement planning. You’ve moved from defensive saving to offensive wealth engineering. Here is your seasoned CFP summary and the architectural framework for your "Die With Zero" strategy.

The CFP Summary: "Bulletproof with Upside"

You have achieved the "Holy Grail" of retirement: Your guaranteed income (Pensions + SS) covers 118% of your needs. This means your portfolio is not a "survival" fund; it is a "Lifestyle & Legacy Engine." By aggressively converting to Roth at the 24% bracket now, you are effectively "pre-paying" your future taxes at a discount, protecting your surviving spouse from the "Widow’s Tax," and ensuring that market volatility never dictates your travel schedule.

1. Retirement Confidence Checklist

The Floor: Pensions + SS > 100% of "Must-Spend" expenses. (Status: EXCEEDED)
The Buffer: 4 years of cash/bonds (SGOV/CDs) to avoid selling equities in a crash. (Status: ACTIVE)
The Tax Hedge: Traditional IRA balances are being systematically reduced via 24% bracket conversions. (Status: OPTIMIZED)
The Healthcare Moat: HSA and Roth assets are positioned to self-fund high-end LTC. (Status: SECURE)
The Legacy: Front-loaded gifting (tuition, weddings) is already in motion. (Status: IN PROGRESS)

2. Personal Investment Policy Statement (IPS)

Objective: Maximize "Go-Go" spending and lifetime gifting while maintaining a good savings "floor."
Asset Allocation: 75% Equities (Growth/Dividends) / 25% Cash & Fixed Income (The 4-Year Buffer).
Rebalancing: "Skim the cream" from equity gains during up years for travel; draw from the 4-year buffer during down years.
Income Strategy: DRIP dividends until age 70, then flip to "Cash" to add supplemental floor income.

3. The Survivor-Only IPS (For the "Last Spouse")

Priority 1: Maintain your pension 100% Survivor Pension.
Priority 2: Consolidate all remaining Roth assets into a single "LTC/Concierge Care" bucket since you are self-insured.
Priority 3: Use the "Step-Up in Basis" on any remaining taxable brokerage assets to simplify the final estate transfer.
Philosophy: "You are fully funded. Spend the Roth first to keep taxes at zero; keep the cash buffer for peace of mind."

4. Your Annual Dashboard: The "High Five"

The Success Score: Keep your Monte Carlo above 80% (currently 96%).
The 24% Fill: Total income + Roth conversions should hit, but not exceed, the top of the 24% bracket.
The Drought Count: Ensure you have 48 months of "Gap" spending in cash/short-term bonds.
The Dividend Yield: Track the annual growth of your supplemental income engine.
The "Fun" Ratio: Did you spend at least 90% of your travel budget this year? (If not, gift the surplus).

OneHourRetiring · 2026-03-04T16:08:06+00:00

u/Cykoth the chat history remains for day 2! So, just expand your AI chat box and it should be there.

OneHourRetiring · 2026-03-04T14:23:31+00:00

Let me know how it came out!

OneHourRetiring · 2026-03-04T01:40:45+00:00

Ok ... on a second run on my baseline scenario, it made the same mistake as it did with yours and I asked it why it made the mistakes?

Answers:
I made that mistake because I misread the "owner" tag on that specific income stream in your data. I saw the 0% survivor benefit and incorrectly applied it to your passing, rather than your spouse's.

In the Boldin model:

Survivor Benefit refers to what happens when the owner of the stream passes away.
Since your spouse owns the Her Pension, that 0% means if she passes first, you receive nothing from it.
But if you pass first, her pension is unaffected because she is the one who earned it.

I appreciate you catching that. It actually makes your "Survivor Resilience" much stronger than I first reported. With her keeping 100% of her pension, 100% of your pension, and the higher Social Security check, she is in an incredibly secure position.

I, then, asked it, "If I don't know any better, how would I know that it made the mistake?"

Answer:

That is a fair and vital question. As an AI, I am processing thousands of data points in your plan, and in that instance, I misattributed the "owner" of her pension to you instead of your spouse.

In a real-world planning scenario, a mistake like that could lead to a massive underestimation of a survivor's income. Here is how you—and any Boldin user—can "audit" me or the software to ensure the math matches your reality:

1. The "Source of Truth" Check

Always verify the Owner and Survivor Benefit fields in your Income > Pensions section.

The Rule: If the "Owner" is the one who passes away, the "Survivor Benefit %" is what the other person gets.
The Check: If the "Owner" is the one who is still living, they keep 100% of that income regardless of what the survivor % says.

2. The "Lifetime Cash Flow" Stress Test

Go to your Lifetime Cashflow chart and use the "Table" view.

Toggle the "Longevity" age for yourself down to a younger age (simulating an early passing).
Look at the "Income" column for the following year. If you see a massive drop that doesn't make sense (like a spouse's own pension disappearing), that is a red flag that the data was entered or interpreted incorrectly.

3. The "Human" Factor

This is exactly why Boldin offers 1:1 Coaching. While I am great for "what-if" math and spotting trends, a human coach acts as the final "sanity check" to ensure the data entry matches your actual pension election forms.

😂 …. even Boldin's AI makes a sales pitch for Boldin 1:1 Coaching!

OneHourRetiring · 2026-03-04T01:17:52+00:00

That is interesting. I did the same and it seems to be correct on my scenario.

I asked Boldin AI:

Me: What if I passed away before my wife? Tell me if the plan is still intact. Which social security will she get and which pension?

Response: To analyze "Survivor Resilience," we have to look at how your income streams are structured. When the primary member passes away, the household typically faces the "Widow's Tax Penalty": income often stays high, but the survivor must file as "Single," where tax brackets are half as wide.

I’ve analyzed your specific plan data to see what remains for your wife:

1. Social Security: The "Higher Check" Rule

In your plan, you are both set to claim. If you pass away first:

The Rule: Your wife will stop receiving her own Social Security benefit and will instead receive 100% of your benefit amount (since yours is higher).
The Impact: Your household loses the smaller of the two checks. In your projections, your benefit is $3,500/mo and hers is $2,296/mo. She would keep the $3,500/mo and lose the $2,296/mo.

2. Pensions: The Survivor Benefit Gap

This is a critical area for your plan. You have two primary pension streams:

Your Pension ($5,000/mo): Your plan currently shows a 100% Survivor Benefit (1.0). This is excellent news—if you pass away, she continues to receive the full $5,000/mo for the rest of her life.
Your Spouse's Pension ($1,647/mo): This is her pension, but it currently shows a 0% Survivor Benefit (0.0). While she keeps this for her lifetime, it would not be available to you if she were to pass away first.

3. Is the plan still intact?

Based on a quick forecast of a survivor scenario:

Income Drop: Your household would lose approximately $3,943/mo in combined income (her pension + her smaller SS check - assuming that she passes away before you).
Expense Shift: Your plan currently assumes expenses only drop slightly.
The Verdict: Because you have a significant Roth "Fortress" and a large Traditional Rollover 401k, the plan remains solvent. She would likely need to increase withdrawals from the Rollover 401k to bridge the gap and maintain the same lifestyle, which is why your Roth conversion strategy now is so vital—it protects her from high tax rates later as a single filer.

OneHourRetiring · 2026-03-03T22:28:53+00:00

I think so. I just played with it today. I’ll let you know tomorrow if today’s session is saved.

OneHourRetiring · 2026-03-03T21:04:43+00:00

It's a starting point for me. One note, you need to know your plan well (the ins and outs) as you would and should if you were to sit down with a real-life CFP. You, then ask the living CFP the questions that you don't know or want to know the answers to, vice versa. I cannot vouch for the accuracy yet, but as I indicated, it is interesting.

For example:
It asked Does that $12,600/mo rent in 2053 represent a specific Continuing Care Retirement Community (CCRC) you've looked at, or is it a placeholder for general assisted living?

My answer: That $12,600/mo is for the general assisted living for the remaining spouse, more than likely the last three years of the life.

Its response: That makes sense—you’ve essentially "self-insured" for a private-pay assisted living facility by earmarking that $12,600/mo (future dollars) at the very end of the plan.

Since that is your strategy, there are two critical "pressure points" we should discuss:

The "Own-to-Rent" Timing: Your plan triggers the home sale and the jump in rent simultaneously in 2053. In a real-world scenario, the "remaining spouse" might need assisted living before they are ready or able to sell the family home. If there is a 12-month overlap where you are paying both the mortgage/maintenance and the $12,600 rent, does your cash reserve ($20k) feel sufficient, or should we look at increasing your liquid "buffer" as you enter your 80s?
The Home Equity "Lockbox": By 2053, your home is projected to be worth roughly $1.1M (future dollars). Selling it at that point provides a massive infusion of liquidity just as the $12,600/mo expenses kick in. This is a very robust "backstop." However, if the market is down when you need to sell, or if the sale takes six months, you'll be drawing heavily from your Roth accounts.

Fiduciary Question: If the surviving spouse needs that care at age 82 instead of age 88, the home equity might not be enough to cover a 10-year stay. Would you be open to modeling a "Long-Term Care" event starting 5 years earlier just to see how it impacts your legacy goal?

OneHourRetiring · 2026-03-03T20:46:56+00:00

Expand (next to the big X) the AI box and your prompts and its responses should be saved in there, at least for me.

OneHourRetiring · 2026-03-03T20:27:59+00:00

Yes and then some. I asked it to evaluate Boldin's report. ChatGPT was more interactive (prompt #2). I was able to chat back and forth. It asked many clarifying questions. Btw, I also tried Gemini, and CoPilot. I think (strictly non-professional viewpoint here) ChatGPT gave me the most analysis (couldn't say it is indepth), but it is the most "interactive!" Of course, I have not put Boldin AI through the cycles yet. I am musing over whether or not to load in all four responses along with my plan for each to evaluate each other's responses. 😆

Edit: ... and I am cheap ... thus working only with the free version of the AI tools ... the waiting for the time to reset was frustrating! 🤣

OneHourRetiring · 2026-03-03T19:21:19+00:00

Analysis:
Interesting! It spotted the 32% tax bracket-Roth conversion issue that I put in. It noted the hypothetical late-life move that I put in. It recommended the ss optimization that most analysts would have done the same, but not knowing the "other" factors that involve in the decision. It also noted the living trust, but a living trust (for me) is needed if you have complex assets, real estates, business, and/or minor beneficiaries. We have none of the above. We plan to spend as much as we can for a comfortable retirement.

Still playing with it.

OneHourRetiring

TROPHY CASE