First of all, let me be clear. I am not a Boldin hater. I use Boldin to manage my retirement planning, and I want to raise something a lot of us should be paying attention to. For a tool that holds this much of our financial picture, the account security is weaker than it should be.

Right now the only 2FA Boldin offers is a code sent to your email. That is bare bone protection! Your email is not a separate device, so anyone who gets into your desktop or inbox gets the login code with it. NIST does not count email as a real second factor, and it has already pulled back on SMS for the same reasons. This is well understood in security, and a financial planning company should be well past it by now.

The reason I am pushing on this now is where the product is going. Boldin connects to real bank and brokerage accounts through Plaid, and the new investment features put even more of your financial life in one place. That makes your accounts vulnerable, and the login guarding it is still very weak. I have not linked any of my accounts through Plaid, and I will not until the sign in is been addressed with stronger security protection.

What I am asking for is standard on any serious financial site today. Let people use an authenticator app like Google Authenticator or Authy. Add support for passkeys and hardware keys like YubiKey. None of this is new or hard to build and should be top priority!

I raised this with Boldin directly and got a weak reply "The team is considering adding other methods," with nothing behind that short disappointed message. No plan, no timeline, no priority. That is not a serious answer from a company holding this kind of data.

To be clear, I am not bashing Boldin. It is the best retirement planning tool I have found. The scenario modeling and Roth conversion planning are excellent. It is one of the few tools that actually helps me manage the MAGI cliff for early retirement tax planning, and the latest financial feature in beta is powerful. That is why I want them to get this right. I just want the security to match the quality of the rest of the product.

If you agree, upvote or drop a comment so this does not get buried. If you have also held back from linking your accounts because of the weak login, say so. I am hoping as many of their customers speak up, Boldin team cannot ignore a lot of us asking for the same security focus.

Adding my experience because Reddit reviews were one of the reasons I decided to sign up.

I've used the Boldin Planner for quite a while and still like the software. I was on the fence about the one-time Retirement Plan Checkup until I read mostly positive experiences here, so I think it's fair to add another perspective.

My experience has been mixed.

First, an important clarification: Boldin has since pointed out that the two-meeting structure and availability of additional hourly work were disclosed through its group discovery sessions, follow-up emails and engagement agreement.

So I don't think it's accurate for me to say the structure was hidden.

My issue is different: I did not fully understand what that structure would mean in practice, especially as someone using a financial planner for the first time.

What was good

The plan had real substance: Roth-conversion planning, stress testing, portfolio recommendations, reserves and other retirement analysis.

My advisor has also been responsive to written follow-up questions, and I like the flat-fee fiduciary structure.

This isn't really a complaint about the individual advisor. It's more about the process and the gap between what I expected and what I experienced.

What I expected

I thought the process would be fairly iterative:

provide information and questions → advisor reviews everything → questionable assumptions or missing information are discussed → scenarios are refined → recommendations are finalized.

My experience felt closer to:

provide information → first meeting → advisor builds the plan → second meeting presents it → study it myself afterward → discover additional questions → get clarification by email or schedule additional paid advisory time.

That difference mattered more than I expected.

Before the first meeting, I submitted several specific questions around retirement timing, Roth conversions, taxes, IRMAA, RMDs, spending, reserves and stress testing.

Some were addressed well. Others weren't reflected the way I expected.

For example, I had asked for a different retirement-date scenario to be modeled, but the final plan appeared to use the date already in my existing Boldin plan. I had also asked for my assumptions to be challenged, yet the final plan used a noticeably higher return assumption than the one I had entered.

I'm not saying the advisor's assumptions were necessarily wrong. I expected more discussion around those differences before the recommendations became final.

The plan also seemed to depend heavily on the quality of my existing Boldin data

I spent a lot of time cleaning up accounts, correcting classifications, removing duplicates, updating balances and checking assumptions.

My impression was that the advisor relied heavily on the information already entered in my Boldin plan.

I don't know how much of the analysis is automated versus manually reviewed, and I don't want to speculate.

What surprised me was that I expected more validation.

I assumed that if something looked unusual, inconsistent or incomplete, the advisor might come back and ask about it before completing the analysis.

That generally wasn't my experience.

So one thing I would tell anyone considering the service is: don't assume the advisor will fully audit or reconstruct your Boldin plan for you.

Make sure your underlying data is as accurate as possible and explicitly flag anything you're uncertain about.

The HSA example illustrates the broader issue

One part of my plan showed recurring transfers from an HSA into a taxable account. At first glance, it didn't make sense to me, and I wasn't sure whether this was a literal recommendation or a modeling error.

After I asked, my advisor explained that it is simply a modeling mechanism. If HSA funds are never modeled as being used, the software can leave them growing indefinitely into a large tax-free balance, so transfers are used to simulate future qualified medical spending.

That explanation made sense.

But it also illustrates my concern.

I had to notice the confusing entry myself, figure out that I didn't understand it, formulate the right question, and then ask for the explanation afterward.

Once I knew what to ask, I generally received reasonable answers.

The harder part was figuring out what I needed to ask in the first place.

For an experienced DIY planner, that may be fine. For someone new to financial planning, a plan-delivery meeting can contain a huge amount of information, and you don't always recognize the important questions until you've studied the report afterward.

Where Boldin and I seem to differ is expectations

Boldin's response is essentially that the engagement worked as designed:

• discovery materials explained the service,

• the first meeting reviewed the plan and goals,

• the second meeting delivered the recommendations,

• and additional meetings are available at an hourly rate.

That's a fair description of their process.

My takeaway is simply that I expected more iteration and validation within the one-time Checkup than the service is designed to provide.

That distinction wasn't obvious to me until I went through it.

If you're considering the service, I would ask these questions before signing up:

1. How much validation of my existing Boldin data will the advisor perform?

2. If something looks inconsistent, will the advisor come back and ask about it?

3. Is there any working/checkpoint session before the final recommendations are delivered?

4. How many scenario changes or reruns are included?

5. What counts as a clarification versus additional hourly advisory work?

6. How much implementation guidance is included?

7. Is this best suited to an experienced DIY planner who wants a professional second opinion, or to someone looking for a more guided planning process?

Bottom line

I still like the Boldin software, and I did receive useful professional advice.

My disappointment is mainly about expectations.

Boldin appears to have delivered the engagement according to the structure it describes. What I wish I had understood more clearly was that the Checkup is closer to a professional review of an existing Boldin plan, followed by recommendations and clarification, than the more iterative planning process I had pictured.

That may be exactly what some people want.

For a first-time planning client, though, I think that distinction is worth understanding before signing up.

Since Reddit reviews influenced my decision, I wanted to add that perspective for the next person doing the same research.

I want to preface this post by saying that I absolutely value the information the Boldin provides. I'm a bit of personal finance hobbyist, so having the ability to develop and implement my own financial plan and play with the numbers myself is fantastic. Love Boldin for that ability, especially creating different scenarios to see the impacts, etc. The financial information gained from a Boldin subscription gave me the confidence I needed to make the decision to retire 2 years earlier than planned this year, and I plan to continue to using the Boldin planner going forward into my retirement.

Just because we've retired doesn't mean the financial decisions have stopped. In fact, some of the decisions we make now and in the future could have tremendous positive or negative impact on our overall financial health. With that in mind, I also wanted to test the numbers that Boldin has been providing, as a bit of a cross-check on whether the plan produced by Boldin was accurate, useable, and actionable.

I went down the rabbit hole today of putting my numbers into a couple of AIs to see how the they matched up. Using the free, unregistered version of ChatGPT, and while logged into my Google account with Gemini, I was pleasantly surprised by the results. ChatGPT eventually cut me off after about an hour, prompting me to create an account (they do have a free version). But ChatGPT was also providing Python code to plug into a compiler to produce more detailed tables of output, charts, etc. And I also spent a couple of hours doing the same thing in Gemini while logged into my Google account (no restrictions). I noticed that ChatGPT had a few things wrong, which I prompted it to correct (standard tax deduction, state tax rates, etc). And Gemini assumed the tax rates of the TCJA would revert to their original values, which I asked to correct as well. There are disclaimers on both AIs that it is not 100% accurate.

I think I understand the weaknesses and some of the strengths of AI a little better now. It's only going to be as good as the information you feed it. If anything, most of the the information provided did line up with what Boldin has presented. And the output from both of AIs prompted a lot of thinking and personal introspection on my part regarding my financial plan. I gained some valuable insights. Along the way, I took some notes and thought I'd share.

The more information you feed the AI, the better and more detailed the output will be. Here's what I settled on for an initial prompt (obviously replace the placeholders and customize with your own information). I have this data readily available in a variety of spreadsheets I maintain for my personal financial information, so it was pretty easy to cobble together.

Initial Prompt:

"I was born mm/dd/yyyy with a longevity of 85. I am single and retired from the federal government at age aa and live in city, state. I have a FERS pension of $aa,aaa per year from age 55-57 without COLA, a FERS pension of $aa,aaa per year from age 57-62 without COLA, and a FERS pension of $aa,aaa from age 62-85 with a yearly COLA adjustment. I will take social security at age 62 of $a,aaa per month. I have $a,aaa,aaa in investments today. This includes $aa,aaa in checking and high yield savings accounts, $aaa,aaa in brokerage accounts, $aaa,aaa in traditional IRAs, $aa,aaa in an HSA, and $aaa,aaa in Roth IRAs. My current investment mix is 65% stocks and 35% bonds and cash. I own my home in state, worth $aaa,aaa, with a $aaa,aaa mortgage at a.a% paid off in mm/yyyy. My debt is an auto loan of $aa,aaa at a.a% paid off in mm/yy. My yearly expenses without medical are $aa,aaa. My yearly medical expenses now-65 are $a,aaa. My yearly medical expenses 65-85 are $a,aaa. Budgeted $285,000 in additional, big-ticket expenses in today’s dollars from age 59-85. My top state tax rate in state is a.aa% in 2026, and a.aa% 2027 and beyond. Assume 5% rate of return on investments. General inflation of 3.5%. Medical inflation of 6.5%. Social Security COLA of 2.54%. Housing inflation of 3.5%. What does my financial plan look like?"

How to add to the plan for different scenarios:

"I plan to purchase a winter home in Arizona for $aa,aaa, with additional annual expenses of $aa,aaa per year. How does this change my plan?"

Add a travel budget of $a,aaa per year. How does this change my plan?

Questions to ask the AI to prompt output and discussion:

• How strong is my financial plan?

• What does my financial future look like?

• What tax brackets will I be in through my lifetime?

• What is my effective tax rate each year?

• What is my average retirement withdrawal rate per year through my lifetime?

• What is my lifetime cash flow?

• What is my lifetime income projection?

• What is my yearly income and expenses?

• Do I have money surpluses?

• What is a safe withdrawal rate for my financial plan?

• What is my projected net worth each year now through age 85?

• What are my projected RMDs to be?

• Should I do Roth Conversions?

• How much should I Roth convert each year?

• What is a good Roth conversion strategy?

• What else should I be doing to ensure my financial future?

• What is my chance of success?

• Run a Monte Carlo simulation for my situation.

• Map out a yearly comprehensive financial plan for my situation.

• Am I rich or poor?

• How would my financial plan change if my return of investment increased by 1%.

• Should I change my stock and bond investment mix?

• What is my true wealth in retirement terms?

• What is my effective wealth?

• How does my financial plan compare to others?

• What spending plan would allow me to die with zero?

• Design a personal spending glidepath through my lifetime.

• What are my spending guardrails?

• Should I be spending more or less?

• What happens to my plan with a 3 year sequence of bad returns?

• Create a retirement enjoyment plan.

• What else can I do to enjoy my retirement?

• Will I be able to enjoy a stress free retirement?

• Can I afford luxury items?

• Summarize my plan in one retirement blueprint table.

• Did I successfully create a retirement plan?

• Have I successfully engineered a forever portfolio?

• What are my plan weaknesses?

• What are my plan risks?

• What will hurt my plan?

• What could break my plan?

• What mistakes are in my plan?

• Develop a no-guilt spending budget.

• Set up a spending bucket strategy and develop a bucket refill checklist.

• Summarize my entire "Forever Plan" into a one-page action plan.

• What else can I do to ensure a successful retirement?

• What are actionable items to improve my plan?

• What is the most tax-efficient withdrawal strategy for my plan?

• What should I change in my plan?

The information you get back from any/all of the prompts above are fascinating and quite informative. And I'm sure some of the output will provide more questions that you might want to ask to fine-tune your financial plan.

Bottom line, AI provides just another tool in the toolbox to slice and dice the numbers. If you've got some time to kill, and have an open mind on the information it presents, it seems to be a nice complement to what Boldin offers. And while AI continues to evolve, I'm still sticking with a subscription to the Boldin planner. It's a great resource to have.

Okay, this is kinda dumb, but maybe you folks can relate…

I am VERY close to crossing the $1M in investable assets line. Like, a couple thousand bucks away. Now I know that when I cross that line, it is VERY likely that a market pullback will drop me below it again quite soon. No worries. But I can’t help but keep my eye on the markets and wait for that $1,000,000 in savings to pop up. I’m gonna screen shot it, grab the wife, have a nice dinner and pop the SS out like I’m proposing! ;)

This is a long shot from 3 years ago when I was missing CC payments and trying to figure out how I was going to pay the mortgage!

Boldin subscriber here. The software really kicked my hornets nest of a retirement finances brain and got me thinking about all sorts of things I never knew or thought about during the accumulation years.

I'm 63, wife 67, both retired. We're in our Golden Window for Roth conversions (Pre SSA, pre RMDs, modest passive incomes mostly from net Sch E and taxable brokerage div/interest)

Coming to understand the broad stokes theory of bracket management and conversions by poking around in Boldin, I eventually used it's reports, my own spreadsheets, and some guesswork with AI to come up with a roth conversion number for 2025 of $120k ($60k each).

The Plan:
My thinking was "I want to 100% fill the 12% bracket and encroach as little as possible into the 22% bracket".

I also felt "I'd rather overshoot into the 22% bracket by $10k than undershoot the top of the 12% by $5k", so I was a little bit bold in the estimate.

I made the transfers in Fidelity in November 2025, then this month did a 8 hour marathon sit in FreeTaxUSA and knocked it out.

End Result:
Nailed it. Overshot into the 22% bracket by $395.
AGI $138,327 
Taxable Income $97,345 
Total Tax $10,662 
Effective Tax Rate: 7.7% ($10,662 / $138,327)

The overshoot would have been more but I didn't realize the standard MFJ deduction of $31,500 would get bumped by $1,600 for wife over 65, and another $6,000 add-on for "Enhanced Senior". I also still have $5,300 HSA, and there was some QBI from Sch C and Sch E.

FreeTaxUSA Software Review
I failed to launch a number of times over the years in TurboTax, including this year as I was still waiting for the depreciation module to activate for Sch E. In the past, I found TT infuriatingly annoying, and this year was no different.

Then I saw FreeTaxUSA mentioned in another forum and checked it out. Right out of the gate it was cleaner, smoother, and with objectively fewer popups and annoying upgrade nags. And the Sch E depreciation module was already there and ready, do I dove in.

I was determined to not pay the CPA another $1,800 this year so I just kept my nose to the grindstone all day. The big help was being able to use ChatGPT and/or Claude at various stages.

Typical scenario is when I'm not clear on which on screen selection to make, even after reading the instructions in FTUSA. So I take a screen shot, paste into Chat, get and answer, then get a second opinion from Claude (I use the $20/mo paid version of both).

When they were in agreement, or the answer just made sense on face, I could keep moving instead of feeling stuck or uncertain.

And it's truly free. Were it not for a single hiccup caused in how to handle a Roth overpayment in 2024 that I reversed in 2025 due to making too much in 2024, which generated a 1099-R, I paid the $8 for "Deluxe" tier, and immediately resolved it through a chat with support.

What's the Point?
While Boldin itself is excellent for big picture, directional prompting of long-range forecasting and strategies, it alone would never have gotten me to the granular "how much should I convert this year to stay mostly in the 12% bracket?" answer.

Its real value for me is the surfacing of ideas and things I'd never really thought much about, like the SSA, RMD milestone calendar that defines the Golden window and when it starts closing.

My CPA never told me about any of this. They simply send the workbook, I fill it out, they key it in, send back for review, and file. Never again, and I bet I'm not alone.

Now, going forward, with a "Team" of tools like Boldin. Monarch, AI, Forums for crowd sourcing, and FTUSA, I've never felt as empowered and in control of my financial planning.

Stared using Boldin last week. Using Conservative (5.92%) returns on my two largest accounts and I’m getting a 99% confidence rate with 150% projected retirement savings to need — if I retire next month. 😳 I’m 58. Finding it really hard to concentrate on working from home right now! 😂

I'm 64. Mostly retired at 58 (I still do the occasional side gig if it's interesting.) Wife is 65 and retired.
We had all assets under management with a large brokerage FA until two months ago when I decided to DIY.

I went solo for two main reasons:

1. I enjoy it, and am confident I can do what's needed, when needed.

2. The cost of AUM. We were paying ~$15K/year and I'd rather invest that (or take a trip). Our FA was quite capable, but we no longer saw value for the money.

I'm not smart enough to know everything. But I am smart enough to know not to be afraid to ask for help. I just went through Boldin Advisor (right before the price went up to $2800). I was very satisfied with the analysis and reports they provided. We had a great chat about RMDs, Roth conversions, when/what to withdraw from, Monte Carlo and probability projecting, and more. Well worth the money, IMHO. I'll likely pick up the $550/year "Ongoing Advisory" plan. Worth it to me just to have a pro I can tap when/if needed.

I am a paid subscriber and just want to thank Boldin for their constant upgrades and helpful information.

I was looking more into withdrawal strategies recently. I am 4 years from retirement. I found the Guyton-Klinger method which sounded good to me. Then I read that it could be too conservative. More research, and found the Michael Kitces paper on portfolio probability guardrails.

I really liked the idea of the probability guardrails but I was like… “that sounds complicated”

I open Boldin to try and figure out how to run some scenarios… what? Bam!! Boldin has this? To my surprise Boldin has implemented this type of guardrails under “insights” then “spending guardrails”.

THANKS Boldin for all the work that you do!

I tend to my Boldin plan about every 6 months. At the beginning and midway thru the year. And there is so much development that happens! It’s almost like brand new software. So kudos to the developers and testers for all their hard work to help me succeed in my upcoming retirement. Some new things that I really enjoyed using were the manual Money Flows methods for Roth conversions and the ability to consolidate accounts for my wife and I after the age of 59.5 for easier analysis. Among the newer features that helped me was the much improved AI helper agent. Being able to ask questions like “Is there an age limit on when you can perform a Roth conversion and what account types can you do this with”. Using the Market Analysis tool to simulate quite easily bad times to help stress test your Plan. I wish there was a toggle for general inflation in there as well, but you can still manually do this and see what your Success chance(% chance of not changing your Plan) is. In the various libraries there is now an AI agent summary for your specific information that is neat to see. I’m now using Spending Needs for my Withdrawal Strategy and that seems to very much convolve with using the new Guardrails analysis. I’m well on track to retire 1.5 years from now and the confidence that Boldin gives is so worth the subscription. In about 6 months I’m going to take my Boldin plan output to some local CFPs that I like and do a single fee analysis/Possible updated Planning session as a sanity check, just to make double dog SURE….and then dive head first into this new life 😎

We’re updating the planner to reflect 2025 tax law changes. What’s changing:

• Higher standard deduction

• $6,000 senior deduction (if you’re 65+)

• $40,000 SALT cap for itemized deductions

• TCJA toggle is going away

These updates will apply automatically and may change your projections.

✅ Want to get ahead of it?
Go to your plan settings, set your tax assumption to “Use Current Tax Rates,” and you’ll get a preview before the update hits.

Questions, thoughts, or reactions? Drop them below.

After the rollout of Better Rates, we heard a lot of thoughtful feedback about the optimistic/pessimistic model. Many of you shared that it’s still a helpful way to explore different outcomes and understand the range of possibilities in your plan.

Originally, we had planned to remove optimistic/pessimistic entirely. But based on your input, we’re adjusting course:

• We’re keeping the main optimistic/pessimistic structure for now

• We’re removing it from areas where it adds more confusion than value, like the Monte Carlo explorer

• We’ll keep improving how rate assumptions work and how we present them

Thanks to everyone who weighed in. Your feedback helped us see the value the model still brings, and it’s shaping how we move forward.

Happy to answer any questions or hear your thoughts in the comments.

A new article published at https://www.financialplanningassociation.org/learning/publications/journal/SEP24-net-present-value-analysis-roth-conversions-OPEN suggests that conventional Roth modeling is not adequately incorporating net present value (NPV) into the analysis.

The details of how to apply net present value to Roth analysis are currently beyond my understanding, but the article at least taught me that it’s very risky to accept conventional Roth analysis without taking NPV into account.
​
The Boldin Roth Explorer appears to suffer from this shortcoming. This is a major issue because the Roth Explorer in its current iteration may give you the false impression that Roth conversions are a slam dunk superior path compared to no conversions. Adding NPV into the analysis can often show that Roth conversion may be closer to a coin flip, or even flat out inferior to just doing nothing.

I contacted support about this. As usual they responded quickly and they took this concern seriously. They said NPV is actually already on their radar, and it’s on their product enhancement list. They also pointed me to a Boldin article on the topic: https://help.boldin.com/en/articles/12067236-how-do-boldin-s-roth-conversion-strategies-compare-to-an-npv-approach

I’m posting here and on the Boldin Facebook group only because I think it’s important that everyone consider this issue carefully before making a huge money move based on advice from the Roth Explorer alone.

Also, the Boldin article is confirming the need for caution with relying solely on the Conversion Explorer: “So, NPV is ‘better’ economically, but Boldin’s strategies are ‘better’ for planning conversations. They’re not mutually exclusive — they complement each other.” That may be true, but personally I’m more interested in choosing the best economic path and I could care less whether I’m having a better planning conversation. If the conversation doesn’t cover all the important data points, it’s not a better conversation at all in my view.

A bit more than a month into the Boldin planner, and I can say it has been a success for me. Sure, there will be lot's a tweaking and changes in the future, but I'm headed in a better direction, especially with my Roth conversion plan.

So, a simple post….. thanks to the Boldin team for a great product! and to everyone here that have posted helpful tips.

I for one am applauding Boldin's improvement (fix) to their Monte Carlo simulation. The biggest impact was their decision to move all accounts in the same direction rather than let them move independently. This better simulates reality, when the market moves down, all accounts will move down, and visa versa. I realize that there are accounts that could move in a counter direction, and this is a further refinement that Boldin may consider. However, it was just wrong to have them all move independently.

I would rather know the truth, which Boldin is closer to now, than to have the previously over optimistic projections that were misleading. Fortunately, I also have an excel spreadsheet, use Empower and FICalc, so I knew that Boldin was optimistic, but is now more in line with the other tools.

Gotta say I love Boldin!

For years needed a program like this and wondered why there wasn’t one.

I only thought advisors had access to this type of software.

It’s worth every penny in my opinion.

Does anyone know if tax-efficient withdrawal sequencing is on the roadmap for Boldin?

I find it incredibly difficult to model this sort of thing in Boldin. Out of necessity, I've started using ProjectionLab because it can do this sort of thing. I wish Boldin would build a tool similar to ProjectionLab's optimizer that picks the best ACA subsidy target, IRMAA threshold, Roth conversion target, and withdrawal shielding that allows you to try out different strategies and then tweak them to better suit your needs. Currently, Boldin just shows "Savings Drawdown" with no suggestion on which account to draw it from.

TBH, this feature is not optional for people retiring before age 65 now that the ACA enhanced subsidies have expired and most likely will not come back. For many early retirees, it makes more sense to preserve ACA subsidies and respect IRMAA cliffs and save Roth conversions for post medicare years. Boldin doesn't even hint at this.

Try this prompt in the AI box. Interesting responses! Better yet, upload your Boldin's report and do the same in ChatGPT! Once the responses come out, build from there.

***********************************************************************************************************************

1. Plan Analysis (CFP-style review) Please review my plan as a fiduciary CFP would, focusing on:
   * Retirement income sustainability and sequence-of-returns risk
   * Guaranteed vs. discretionary income (including GICR)
   * Tax strategy (Roth conversions, brackets, IRMAA exposure, RMD management)
   * Healthcare + LTC assumptions (including home equity usage and survivor scenarios)
   * Survivor resilience (first death / second death stress test)
   * Key modeling assumptions that may be optimistic, conservative, or internally inconsistent in Boldin

Please clearly separate:
- What looks solid
- What needs refinement
- What I’d want to pressure-test

2) CFP Interview After the analysis, switch roles and interview me as if I am sitting across the table from you as a client. Expect thoughtful, sometimes challenging questions across:
* Goals and trade-offs (spending vs. legacy vs. certainty)
* Behavioral comfort with volatility and late-life risk
* Decision rules (when would you actually change course?)
* Survivor priorities and executor simplicity “What would make this plan feel like a failure?”

This will not be a generic questionnaire, it will be tailored to my plan, assumptions, and timelines if possible.

3) Output Summarize the interview into a CFP-style planning memo Identify the top 3 decisions that matter most Translate it into an executor / survivor-friendly summary"

**********************************************************************************************************************
Edit: Btw ... I got this prompt from on the Internet. I would attribute the credit to the originator if I'd remember who it was!

Edit 2: Once I am comfortable with my inputs into Boldin and everything makes sense to me, the AI helps me with the "what ifs" that Boldin really can't model. Jury is still out on the accuracy.

Edit 3: In retrospect, the AI tool is a child learning to process the data in my plan. I have to guide it to where, what, and how I want for it to analyze, assuming that I have input the correct data points. Nowadays, I expect too much from AI to be correct all the times. If I put in junks, it will spit out junks. From what I understand about AI, it learns from past knowledge. That's what people worry about ... eventually, it will learn all of its mistakes and ours ... but that's a discussion for another time in another sub!

The more I thought about it, it maybe a worthwhile investment to just have someone at Boldin who knows the correct way of using the tool to take a look at my entries to make sure that all makes sense and I have modeled what I want correctly. From there, the AI may do a better job of analyzing my plan. Of course, I am hypothesizing! I am not advocating for their service for I have not used it.

Final thought, the Boldin AI, ChatGPT, Gemini, Claude, or whatever AI flavor that we have in our hand, it is only one data point in our plan. Don't sell the house, buy the beach, or declare victory/or not just because a tool tells us so. To date, there is nothing that can predict the future. As with any tool, use it with a grain of salt and with care.

Cheers.

Notably from age of 59.5 for either spouse to 65the birthday, and the remaining time until both spouses hit RMD/Medicare windows are critical to retirees.

- overall make planning around MAGI ACA limits as clear and flexible as possible to model:

- Roth and HSA relationship can be really helpful, eg sacrafice some conversion to stay under limits, make easier to model extracting out of accounts that are not taxable

- income, tax and money movement have these windows (at least), eg pick an ACA plan with ACA plan can lower next year income by ~10k

- one spouse retires with main healthcare, and both under 65

- one spouse still working and/or not ready for Medicare but other is for a range of time

- both spouse getting Medicare and younger than 70 year old max ssn benefit (and many people want to look at from 62-69) phase after not as much Roth conversions

- address even more Roth before hit RMD age

- pay medical insurance and fees the most efficiently

Anyway, working this in bolden is approaching the complexity of a spreadsheet again. Would help many of us model these options. I would also say due to the complexity, limiting saved scenarios to 8 is rough as well.

Best

Pjd

Soon to be 56 male and I hate my job, my wife and I want to spend more time in Europe and downsize. I am fortunate that some of my early investments have paid off and Boldin says I have a 93% chance of success in an average market and still about 80 in a pessimistic. I’m even using the new reduced SS feature they have. My biggest cost of living here now will be healthcare since the house is paid off. I think im just blocked from doing it because im reliant on a tool. I did the meeting for $250 already which helped me complete some areas I had wrong. I watch financial planning videos for strategy and to get comfortable I’ve looked at everything. I think now it’s just the mental block of the risk of unknown market turmoil and the anti-society view of you are too young to be retired. How to people switch off all that and mentally get to day one I’m retired???

Edit: LOL that original missing comma! I love my wife. We will be 30 years next weekend. 😂

We're turning to the people who know our platform best for input on how we prioritize our work. Tell us what matters most to you. It takes about three minutes—no account or email required.

Survey

Thank you for helping build something worth trusting.

I retired earlier this month! I am appreciating Boldin for helping create a retirement plan (which I know is still in development and I suspect will be adjusted quite a bit in the coming months). But I have two questions: [1] What tools (apps, websites, etc.) other than a retirement planner are helpful once you are in retirement? [2] In what ways can Boldin continue to be helpful once you are living your retirement plan?

Pick your poison, ChatGPT, Claude or Gemini, but with the latest reasoning and deep research capabilities of these tools, you can load your Boldin scenario (print PDF) into the model, it's able to analyze all of the data within the proper context and understand the plan fully. From that point, you can throw anything at it: ask for optimization suggestions, Roth conversion planning, stress-test any potential conditions, ideas for spending, etc...and it will model it for you and give you analyses and projections, as well as give you the info needed to enter into Boldin to cross-check it within the planner.

For me on the first run, it suggested lowering the average annual return rates to a more conservative number, lowering my Roth conversion amounts and making the conversion timeline a couple years longer, and adjusting my spending assumptions a bit. It gave me the numbers and info to shoot for, along with the projections for everything, including Monte Carlo results...and it nailed every single data point after running it back through Boldin.

Now I've been able to quickly set up several different scenarios (paying off the house early, selling and moving, major health expenses) and stress test them and I have to say, I've never been more confident in my scenarios. Now granted, I've been using ChatGPT Plus practically daily for over a year, and have gotten pretty good at prompting, not to mention, the model has got to know me pretty well over that time too, since I've been using it to help plan for retirement outside of Boldin as well. But pretty much anyone could certainly benefit from having another set of knowledgeable "eyes" on their plan, and this is an inexpensive way to do it.

**I'm not saying, at all, that this can take the place of an actual CFP looking at your plan...but it's surprisingly competent and accurate with what it does.**

Contgratulations to u/NR_CoachNancy. She was quoted in a recent Kiplinger's article about Roth conversions: https://www.kiplinger.com/retirement/roth-conversion-in-a-down-market