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
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:
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 $9,800 into my HSA:
$4,400 for me
$1,000 catch-up contribution
$4,400 for my husband
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.
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.
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.
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.
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).
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.
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:
Money market funds, which I’m actively building up for an upcoming home construction project
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 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:
Sell the money market fund
Transfer the cash to checking
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.
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.
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.
