From Concept to Practice: What an All-Weather Plan Looks Like for Me

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In my last post, The Case for an All-Weather Approach, I wrote conceptually about what it means to build something sustainable, rather than something that only shines in ideal conditions.

So what does that look like in practice?

Today, I’m sharing how I’ve constructed and manage an All-Weather Plan that works for me.  

Today, Dana shares the details on how she's built (and manages) an All-Weather Plan for her investments. Share on X

What An All-Weather Plan Looks Like for Me

For me, a priority in implementing an All-Weather Plan is to use as much autopilot as possible.

The key is to build a plan based on sustainable principles, then execute. That execution happens through automation, intentional tradeoffs, and knowing where human judgment still matters.  

The following are the key elements for how I manage my All-Weather Plan:

Automate as Much as Possible

Each January, I have a recurring calendar task that reminds me to fund any non-payroll, tax-preferred accounts. For me, that means my Health Savings Account (HSA) and a non-deductible IRA.

Let’s take a look at each.

HSA Funding

For 2026, I funded $9,750 into my HSA (corrected from $9,800)

    • $4,400 for me
    • $1,000 catch-up contribution
    • $4,350 for my husband (corrected to $4,350)

We can still add an additional $1,000 catch-up for my husband, but IRS rules require that his catch-up go into a separate HSA in his own name. My contribution and his base contribution can go into my HSA; his catch-up cannot.

Getting his account open is on my to-do list. And if I do it before April 15th, we can fund his catch-up for last year as well.

Non-Deductible IRA Funding

For 2026, I funded $8,600 into my non-deductible IRA:

    • $7,500 base contribution
    • $1,100 catch-up contribution

The key point here is the reminder itself.

I know the decision to fund these accounts will not change unless there’s a major shift in tax law or a significant personal financial change. The short mental checklist goes like this:

“Everything the same?
Yep.
Okay—execute.”

Funding decisions are one thing. How the money gets invested is another matter. Let’s look at the investing side next.

Automated Investing

HSA Investing

My HSA has an auto-invest feature that maintains a required $1,000 cash balance and automatically sweeps the rest into investments. When I set it up, I chose DFAC (Dimensional U.S. Core Equity 2 ETF)—a broadly diversified fund with over 2,500 U.S. holdings that benchmarks to the Russell 3000.

My preferred HSA investment is DFAW, a globally diversified ETF with over 13,000 holdings. For smaller accounts like HSAs—and for accounts that may experience periodic distributions—I prefer broad diversification to help dampen volatility. However, DFAW is not available within my HSA investment lineup. So my portfolio has to adjust.

(This is not investment advice or a recommendation to buy or sell securities. Links above are not affiliated.)

Non-Deductible IRA Investing

My IRAs are managed by our firm’s investment partner, Asset Dedication.

Is it weird to be a financial advisor and choose to have someone manage your assets? I don’t think so. I love what our investment partner does – that’s why we partner with them.

It’s automated. I don’t have to think about it.

And, honestly, when I do have to think about it, I’m prone to behavioral biases—just like nearly every other human being. Knowing yourself is crucial when you’re trying to build an all-weather strategy you can actually stick with.

Knowing myself—and knowing how busy I get—if I can hand this task off, I’m more than happy to do so.

My IRAs and all my retirement investments are currently allocated 100% to equities. Because I’m still roughly a decade away from tapping these assets, I’m comfortable with that risk profile.

My financial plan, not market headlines, will determine when I begin building the safer portion of my portfolio. When my plan shows that I’m within ten years of needing withdrawals, I’ll begin making changes, either by directing new savings toward safer assets or by rebalancing.

Automation as a Behavioral Tool

With my HSA, IRA, and my 401(k), which I’ll cover next, once the money is contributed, the investing happens automatically.

I love this.

There’s no second step where I have to decide when to invest. No wondering if the market is “too high.” No waiting for the next Fed meeting. The plan executes regardless of headlines.

Automation isn’t just convenient. It protects me from myself.

However, the strategy can change over time. The key is knowing when it is time to change.

Here’s how that played out with my HSA.

My HSA: From Emergency Fund to Long-Term Asset

When I first opened my HSA, I kept it entirely in a money market fund. I had limited liquid savings, and the HSA functioned as part of my emergency reserve. I also regularly used it to cover out-of-pocket expenses like dental costs and insurance deductibles.

As my non-HSA emergency reserves grew, the role of the account changed. And so the underlying investments changed.

Today, my HSA is invested 100% in equities (aside from the required $1,000 cash balance), and I don’t plan to tap it until around age 70. I intend to use it to help cover Medicare Part B and Part D premiums.

The role of an account should evolve with your financial situation.

Accepting Tradeoffs: Why I Fund a Non-Deductible IRA

When my income was lower, I made Roth IRA contributions. As that changed, I had to decide whether to fund non-deductible IRAs or direct additional savings to my brokerage account.

Definition: A non-deductible IRA is a traditional IRA funded with after-tax dollars, meaning contributions cannot be deducted from taxable income. While contributions are not tax-deductible, the funds grow tax-deferred. These are often used by high earners who exceed income limits for deductible traditional IRA contributions or direct Roth IRA contributions.

I’ll be honest: I don’t love non-deductible IRA contributions.

There’s no tax deduction going in, and withdrawals will be taxed at ordinary income rates. My accountant has to track basis with an extra tax form each year. If I invested those dollars in a brokerage account instead, I could use tax-efficient funds and potentially pay long-term capital gains rates rather than ordinary income tax.

Part of me cringes at this inefficiency.

So why do I still do it?

Asset protection.

As a business owner, liability risk matters. While I don’t love the tax treatment, I do value the stronger creditor protections available in retirement accounts.

This is a conscious tradeoff:

For me, additional asset protection takes priority over optimal tax efficiency.

Why I Don’t Use the Backdoor Roth

A common follow-up question is: Why not do a backdoor Roth?

The backdoor Roth strategy involves funding a non-deductible IRA and then quickly converting it to a Roth IRA. Because the contribution is made with after-tax dollars—and assuming no growth occurs before conversion—there’s typically little or no tax due.

However, the pro-rata rule complicates this strategy if you already have other IRA assets.

The IRS looks at all IRA balances in your name when determining how much of a conversion is taxable. For example, if I had $95,000 in a pre-tax IRA and made a $5,000 non-deductible contribution, then converted $5,000 to Roth, the IRS would treat that conversion as 95% taxable and only 5% tax-free basis.

If that $95,000 were in a 401(k) instead of an IRA, it wouldn’t count toward the pro-rata rule—and the conversion could be tax-free.

Technically, I could roll my IRA into my 401(k) and use the backdoor Roth.

But I choose not to.

My 401(k) investment options are limited, and I prefer having my IRA assets managed through our firm’s investment partner. And if I want to increase my tax-free savings, I can still make Roth contributions inside my 401(k).

On to my 401(k): Knowing Why You Own What You Own

My 401(k) contributions are spread evenly throughout the year. In 2026, that means:

    • $24,500 in pre-tax contributions
    • $8,000 in catch-up contributions

(Note: if you are ages 60 to 63, your max catch-up limit is $11,250.)

Because my income exceeds the threshold, catch-up contributions must be made to the Roth 401(k) under new rules that apply to earners with prior-year FICA wages over $150,000. While this means no tax deduction on the catch-up portion, I’m happy to have those dollars grow tax-free.

I don’t front-load my 401(k) contributions. Doing so would cause me to miss out on part of the employer match. (Some plans make this up at year-end; ours does not.) I also prefer dollar-cost averaging, which means contributing steadily so I naturally buy more shares when markets are down and fewer when they’re up.

My 401(k) investments are set according to a specific model designed to work in conjunction with my other accounts. It includes a higher allocation to international and small-cap stocks than many traditional portfolios.

That’s intentional. It matches how the rest of my household investments are structured.

This model prioritizes minimizing downside risk in a worst-case market scenario rather than maximizing upside in a bull market.

Managing Cash Is the Hard Part

The final piece of my plan is my after-tax brokerage account, titled in my trust. I love this account for its flexibility, liquidity, and favorable tax treatment.

I think of it in two buckets:

  1. Money market funds, which I’m actively building up for an upcoming home construction project
  2. Diversified equity investments, primarily Dimensional ETFs

The equity bucket is funded largely by minority ownership buy-ins to my business. Partners purchase shares using owner-financed notes and make quarterly payments directly into my brokerage account.

I have calendar reminders set four times a year to invest those payments the day after they arrive.

This part of my system needs improvement.

Sometimes the reminder pops up, and I’m busy. I move it out a week or two. Other times, I hesitate because the market feels “high.” That’s a behavioral bias—and yes, I’m just as susceptible to it with my own money as anyone else.

This is where automation can make an impact.

One solution would be to split the trust into two accounts and turn the equity portion over to our investment partner so it’s invested automatically. Now that I’ve written this down, that option sounds even more sensible.

Cash Management: Time Consuming, but Valuable

Cash management is the most time-consuming part of managing my trust.

Each time money comes in, I have to place a trade to move it into a money market fund. When money needs to go out—say, for quarterly tax payments—I have to:

  1. Sell the money market fund
  2. Transfer the cash to checking
  3. Make the payment

It’s multiple steps every time.

I manage cash this way both personally and for the business. Leaving money idle in checking earns nothing, and with money market yields still north of 3.5%, the effort is worth it.

This cash flow component is also what we find takes the most time during the retirement phase.

Why Retirement Cash Flow Takes More Work Than Saving Ever Did

Accumulation can largely be automated. The distribution phase requires more manual intervention.

In retirement, you’re constantly deciding:

  • Which account to pull from
  • Which asset to sell
  • What will the tax consequences be

We can automate steady monthly distributions. But irregular needs such as taxes, car purchases, home repairs, insurance premiums, and travel… those require human intervention. And those “one-off” expenses happen regularly in retirement.

Conclusions

An all-weather plan is about executing consistently, regardless of headlines, moods, or market conditions.

For me, that means automating as much as possible, being honest about my own behavioral tendencies, being clear about tradeoffs, understanding the triggers that warrant change (and which don’t), and knowing how each decision fits within a larger framework.

The goal of an all-weather plan is simple:

    • Build something you can stick with.
    • Execute it consistently.
    • And know ahead of time what would justify a change.

Clarity is key. It is what keeps me out of analysis paralysis and enables me to execute—for my plan and for clients.

And without proper execution, even the best-designed plan doesn’t work.

Your Turn:  What steps have you taken to automate your investment strategy? If you’re retired, have you found the withdrawal process requires more manual intervention? Finally, any thoughts on how I manage my All-Weather plan?  Let’s chat in the comments.

32 comments

  1. I’m turning 65 and retired 6 years ago – not entirely voluntarily but it is working just fine. I get paid for work maybe 150 hours a year. I’ve dropped all paid investment newsletters, as the advice and buy/sell can be overwhelming with marginal improvements in my portfolio. The cash flow has definitely been most time consuming. Even so, big decisions are only made about once each year. I make a funding decision for the year – which account to use to replenish my “paycheck” account that is used for most spending. This year, the decision will be to surrender a paid up whole life policy (the death benefit rises slightly but the actual insurance amount declines each year as the cash value increases, so it is really a “convert my own money to tax free money after a death” policy). The insurance amount was necessary 20 years ago – not so much now. Cashing out allows another year of IRA deferral, even though I will pay tax on half the insurance surrender value.
    I’m only saving for specific big ticket spending – automated transfers for travel, roof replacement, insurance deductibles, a replacement car. I tweak placement of those funds a bit depending on interest rates (MM, short CDs, short Treasuries) Spending cash already taxed (brokerage dividends, pension, etc) is the new normal.

    1. Kevin, thank you for sharing! We’ve encountered many whole life policies that we had to “repurpose” in retirement. Sometimes they can be used for tax-free withdrawals while maintaining the policy. Other times, as you are doing, it is easiest to just cash them in. And as you are doing, we look at how to “fill” a tax bracket – either with taxable income from cashing in something like a policy or annuity, or from IRA withdrawals or Roth conversions. And I agree about the investment advice newsletters! Too many of those and my brain goes into knots!

  2. That was a good snapshot of how you manage your money. My experience with Non-deductible IRAs is not good. I kick myself for doing them. It complicated a few aspects of my plan. I would do everything you can to not do non-deductible IRAs.

    1. Stan, are there any specifics of how they complicated your plan that you could share? We’ve come across clients that made years of non-deductible contributions but never tracked the basis with IRS Form 8606, so essentially they were being double taxed. No deduction going in and fully taxable coming out since they didn’t track basis. Outside of that I haven’t seen issues, but if there are more complications, I’d love to hear about them.

  3. Dana thanks for the peak behind the curtain.
    2 questions:
    1) my understanding was that the 2026 family HSA contribution was $8,750. How are you able to squeeze the extra $50 ($4400 each) into the account?
    3) when comes time for you to withdraw from your non-deductible IRAs, do you have a plan for separating the basis from the taxable earning?

    1. Ahhh! Re item 1 – You are correct. Typo in my second entry for my husband – should be $4,350. So family max is $8,750 and as we are each 55 or older this year, we can each do the catch-up which would make a maximum upper limit of $10,750. I added a correction to the post. Thank you!!!

      Regarding item 2 – there is no way to separate the basis. It is tracked on IRS form 8606 and it becomes a pro-rata calculation upon withdrawal. For example, if basis was 10% of the value for that year, then 10% of the withdrawal would be tax-free and 90% of it taxable. It is the same pro-rata calculation that applies for the Roth conversion calculation.

  4. I am in my third year of retirement and have the luxury of a good pension to provide steady income for most of my spending needs. This year I anticipate buying two cars and putting a new roof on the house. I won’t need to money right away, but will within six months. I directed my financial planner to sell from my Roth equity funds when the market was high late last year and to stash that in money market fund within my Roth account. It will still earn some interest and be ready for me to transfer to my checking account when I need it in a few months. If the market is down, I won’t have to worry about ‘selling low’. If the market is higher than now, I am still comfortable with having sold shares when it was high enough.

    1. Love that you built up a buffer in your Roth! We have been doing the same for many clients. When markets go up, people spend on extras. And so we’ve been taking gains in the Roths’ and parking it in money market for those same things you mentioned – auto purchases, home repairs, and sometimes so extra traveling or gifting.

      1. I’m doing the same thing. When the market is up near the S&P500 record, I sell equities in my Roth for spending and replenishing the MM fund; when market is down by a fair amount, I pull from the Roth’s money market fund. I’m currently doing Roth conversions near end of year as I strategize for taxes on a real estate sale that hasn’t yet happened. Better to pay around 10% effective tax rate now on Roth conversions than whatever the effective rate will be with the maximum capital gains tax rate on a pricey property.

  5. Great article, thank you. I agree that cash management is more time consuming. I have been retired a year. Since I am in my second marriage it is mildly more complicated. After determining the budget for the coming year, I move a years worth of expenses from my money market/brokerage account to our money market account. Then our monthly paycheck is automated from that money market to our joint checking. Then, I have to remember to move additional funds for extra expenses periodically from our money market. Not hard but time consuming.
    I noted that you have already set up a revocable trust for your assets. Would you consider doing an article on the pluses and minuses of doing that now vs. waiting until death? I have been thinking about that a lot recently especially since I have a wonderful wife and great children from my first marriage. I am also concerned about protecting myself given risks of cognitive decline in the future.

  6. Dana, thanks for your thought process on preparing financially for retirement. I recently retired at the end of 2023 and a bit earlier than planned. Time was just up and need to move on..I was a financial planner so I had some control on the date..Luckily I found a young advisor I could work with to take care of my clients. We worked together for 2.5 years to meet my clients and make the transition as smooth as possible.
    I am fortunate to have a taxable investment account too and it’s important as my tax advisor confirmed in spades. When you need monies for income, vacations, gifts to kids, autos it can provide the source needed without impacting taxes too much. I designed the account to throw off income with an individual bond ladder (mostly corporate, my tax bracket doesn’t really warrant munis) to supplement my income needs before and after retirement. The account also holds dividend paying ETFs and private real estate for a bit of diversification and potential cap appreciation. It has worked wonderfully and allowed me to use the interest/dividends to supplement income needs, delaying social security to 70 and not touching any capital in my accounts. So fortunate….
    I have used an online bank account for my savings accounts for years now. I just transfer automatically an amount monthly to my checking account to pay the bills. Not difficult at all and you get some interest and FDIC insurance.
    When we turn 73 in a couple of years, will use RMDs for either cash needs, investing in taxable account, QCD to local foundation or perhaps gift the monies to my kids.
    Like your HSA idea and I didn’t do enough of that before I turned 65 and started Medicare. Can really help with excess medical bills.
    I also decided to continue to use my succesor advisor to manage investments because I was tired of doing it myself but most importantly my wife and daughter will have someone to take care of things if I pass away first. Too many folks have a spouse do this and then if something happens the surviving spouse is left unsure of what to do…Thanks to you and Fritz for writing this column

    1. Thank you for sharing! Nice to see another financial planner deciding to outsource the investment management. My spouse would be financially lost if something happened to me. It brings me great peace of mind knowing I have a team that would guide him. And so fantastic you found an advisor to serve your clients!!! This has been a key motivation in the structure and growth of my firm – making sure we can serve the clients through various advisor’s retirements, career changes, or health and family challenges.

  7. Great post and very helpful. I love both your content and since I’m tracking close to your timeline, I’m really getting a lot of confirmation on my plans and learning a lot as well. Thank you Dana!

  8. Hi, Your cash management could be simplified, I believe. I have a cash management account with Fidelity. I use a money market fund within this CM account, and all of my bills are automated. Some of my bills go out as electronic transfers and some are issued as checks. In each case, Fidelity automatically cashes out from my money market fund to make these payments.

  9. Hi Dana, great article and I’m so glad you’re writing now for The Retirement Manifesto. I bought your “Retirement Destiny” book a few years ago, and it was superb as well. One question re: the cash management difficulties. You mentioned that you, 1) Sell the money market fund, 2) Transfer the cash to checking, and then 3) Make the payment. Have you considered using something like the Vanguard Cash Plus or Fidelity Cash Management account? I use the former, to which my monthly pension and VA disability flow into, and then all my bills automatically are debited from it. It has a routing number just like a bank, although it’s a savings account so I can’t write checks or have a debit card. I figured you’re already aware of products like this, so I just wondered if you had any thoughts on these, i.e., why you don’t use one? Or maybe you do?

    1. Hi Casey, yes, those are GREAT solutions! I like everything at Schwab, as that is where we custody for clients. I keep my daily checking account elsewhere. And currently I have a higher yielding Money Market option at Schwab than what is listed for those accounts – although truthfully the higher yield may not be enough to compensate me for the time. But if I wanted to keep my cash account elsewhere, those are great options. Thanks for listing them!

  10. As someone in the asset mgmt business, I personally could never live with myself for throwing away a management fee to someone to essentially babysit my investments; who in all likelihood knows less about investing that I do. Crazy. I get it, Dana is in the FA business of convincing people they need to pay for professional advice because investing is so complicated or because people unable to be self disciplined an invest and rebalance. And for some, this might be true. But ask yourself: the $50,000 sitting in the money mkt fund uninvested for some extra time vs the 1% wrap fee on all of your accounts…. Are you really coming out ahead. ~1% of your AUM every single year. What exactly are you getting for that? I’ll take my chances and am pretty confident I will be way ahead.

    1. Throwing money away? Convincing? Lol. We all have different values. And different skill sets. What kind of car do you drive? Do you use a CPA? Ever hired someone to do a home repair? How about change your oil? Landscaping? Ever buy a nicer home, or more expensive clothing? Send your children to private school or a more expensive college? We all have different interests and different values. Good for you for making a decision that helps you live with yourself. Everyone should make decisions that are right for them and their values. I know many professionals in the business that hire other finance professionals – including CPAs, CFAs and fellow CFPS who hire us or other advisors. And, I’m sure, many like you who prefer to do it themselves. This content and blog is about mutual respect.

      1. I think you intentionally missed my point. Not everyone should manage their own money. It’s a personal decision based on a skill set and time. For most money managers, hiring an outside FA- unless you have a complicated situation or are wealthy enough to have multi generational wealth- makes little financial sense.

  11. This is an insightful post. Appreciate the details you’ve shared, thank you!
    I retired in April 2025 and adopted a bucket strategy. Preparing for retirement in 2024, I started simplifying my portfolio and set up a 6 year treasury ladder in my brokerage account. The treasuries fund anticipated annual spending and protect against sequence of returns risk. They mature each December and the proceeds are automatically invested in SWVXX, a Schwab MM account. It’s then set up to automatically sell a set $$ amount at the end of each month which then transfers to my checking account, representing my retirement “paycheck”. So far, it’s working great. And it’s wonderful not to have to stress about the short team ups and downs of the market!!

  12. Gary – We actually hired a fee based advisor for the first time last fall to help focus our withdrawal strategy. I did not learn much (other than to spend more or plan better on how we will gift our assets), but it was useful to focus my wife (she values the opinions of “experts”). He proposed an AUM model for ongoing support. I declined because I don’t see the value. For now. But as I age and mental decline sets in there will come a time when such support is reasonable and appreciated. It won’t be with that guy, but I learned that too. (If you want to know how something works, write a check). And I’ve told my wife to hire someone if should I pass first if it will give her peace of mind. I enjoy mowing the grass, but sometimes the lawn maintenance guy is worth it to me as well, even if he charges as much per hour as I once made.

  13. Dana, great summary! I was wondering if your firm’s 401k allows in-plan Roth conversions. If they did and you have the discretionary funds, it does get money I to Roth accounts and is less complicated than non-deductible IRAs. I understand the benefit of availability of other investments for the outside non-ded IRA. But the Roth option minimizes the potential of RMDs being taxed or causing potential IRMAA problems. I’m interested in your thoughts.

    1. Dan, that’s a great thought and I wish I could make after-tax contributions and convert to the Roth. However, even if the plan allowed it, as an owner and HCE (per the plan definitions a Highly Compensated Employee) there are restrictions that would prohibit myself and firm partners from using this feature.

  15. I got this article via Rob Berger’s weekly newsletter, and I used to watch some of your videos. Good article. You are right. Retirement is definitely more complicated in terms of finances and requires lots of finagling. I retired in 2024 with a pension but still work part time. That income goes into my Roth IRA. I just made the last major Roth conversion to pay for any medical expenses that may come up from there. I also have HSA and a Veba accounts for Medicare premiums, etc. I use my pension (extra taxes) to pay for the Roth conversions. I stayed just under IRMA for 2025 and will try to keep my income low enough next year to qualify for at least some of the extra senior deduction. I am a planner and have always had multiple spreadsheets for any type of scenario, but retirement is definitely another part time job. 🙂

  16. Thank you for an interesting article. Here is why financial advisors we have chatted with tell us there’s nothing they have to offer: Both of us retired at 65 (11 years ago), we each have a small pension $500/750 net/mo, SS is $4500 net/both/mo, our home is paid for, we have zero debt, a $250k HELOC for emergency, $650k saved as mix of broad market stock funds and 1/2 mil in T bills (curr 3.66%) netting about $1000/mo in passive inc. We have never ‘drawn down’ from our portfolio; it continues to grow slightly and we pay for everything from pension/SS. We have a lot of self-discipline and we know where our money goes. We don’t waste anything; I turn off the lights but think nothing of the $400/year we spend on firewood for that evening cocktail together in front of the fire. We live in Marin County, CA, at times ranked as the 3rd or 4th most expensive county nationally. I taught for 30 years and was told by a real estate agent that Marin would not be suitable for someone with my income (my wife averaged $90k year/banker). We spend two months out of every year in Italy, our 16 year old BMWs are well maintained, and we basically buy what we need. A $30 cheeseburger does not fit into our budget, but our morning cappuccini and brioche in our ktichen do. Here’s the secret (in my very very humble opinion): Some people have everything and it is never enough; we have everything, and it’s enough. We have created our own economy.

    1. That’s fantastic and that makes sense. Sounds like you are in great shape. And it’s true, there are plenty of situations where an advisor may not add value. A good advisor will be honest about that – which it sounds like that is what you encountered. And I love your secret philosophy. So true.

  17. I am on two years of retirement and yes making a retirement paycheck takes a little time. Beforehand all was auto deposited in retirement account but now retired, I started out doing the same with my retirement paycheck, but my checking got a little fat. I now auto deposit from bond fund and auto transfer to brokerage account monthly to put it into money market. My adviser rebalances as needed on the part I have them handling and I move money each month to restock my checking account to pay this month’s bills plus a cushion. I have not started Social Security yet and the first year I set what I wanted to convert and then set my paycheck to come to top of my bracket. I found that to limit what you can spend maybe a great idea but at end of first year I was out of funds early. Year two I decided to give myself some room and convert toward end of year when I will have better idea of actual spending. Any excess can stay in brokerage and if that gets too large, I will put some in equities. I am spending about the same but the fear of running out of cash for the year is gone.

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