April 2026
From the Field
Where do birds go to vacation during Spring break? Somewhere cheep.
Happy April Fools Day! And better a dad joke than a reminder that the tax filing deadline is less than 15 days away. I'm assuming that anyone reading this already knew that and has one, already filed their taxes or two, hasn't filed their taxes, but works better under pressure. In any case, once filed, this is one my favorite and nerdiest times of the year - when I get to look at tax returns. There's a treasure-trove of information on each one and they are mostly as unique as your fingerprint. Take a close look at yours this year and see what you glean from it - you might be surprised. Just don't feed it to AI...
The BLUF
I know you'll want to read the entire newsletter, but here's a preview of what's included in this month's edition.
✅ Feel Good Moment. The reality of retirement.
✅ The AI Boom Keeps Booming. What am I using it for?
✅ VGLI. Overlooked or undervalued?
✅ Investment Rebalancing. When should you actually act?
✅ In plain site. Some of the other places you'll find my musings.
Feel Good Moment
This month is less a moment and more a reminder of a realization. The further I get away from military retirement and into life 2.0, the more ironic I feel my life becomes. I have found this strange tension between living my best life, which I 100 percent am doing, and an undercurrent of this thought; "should my life feel so... relaxed and balanced?" Among the financial advisors I hang around, there isn't one who preaches anything other than to know & control your expenses, know how your guaranteed income meets those expenses, and then find (through exploration and curiosity) a purpose-filled line of work that covers the gap. This is the ideal life I'm living. It feels both wonderful and weird at the same time, as if I am getting away with something. Is life meant to be this good, this rich, and this meaningful? Perhaps living with 25 years of continuous pressure to deliver mission success had more of an impact than I thought. Today, delivering mission success, (i.e. advising clients in the most responsible way I know how), while still weighty, doesn't consume my life the way the military used to. I was reminded of this fact yet again as I spoke to a friend recently, still active duty, who was really struggling to maintain his physical fitness level given all of the other responsibilities he had. I imagine that his fitness level was only one area of his life he was struggling to maintain balance in. The great news though is that this isn't a problem when you leave the military... unless your next profession makes it a problem. I'm here to tell you, this lifestyle works and is wonderful. Weird, but wonderful!
Artificial Intelligence: Yes, 'artificial'.
It seems that artificial intelligence is finding its way into every crack and crevice of our world, much like a spilled cup of coffee finding every critical component of your computer. That probably comes across poorly. I actually do like AI, but within reason.
Having a healthy respect for what AI is and is not good at, I thought it might be beneficial to invite you into how I use it for a few moments.
Creating Images
Case in point, scroll up. That image was generated just for this newsletter based purely on the prompt from my Feel Good Moment. If you follow any of my work on LinkedIn, Facebook, or Instagram, those images are AI-assisted as well.
What used to be a challenge in finding military-centered visuals is now just a well-written prompt away. Where does it go wrong? This image is version eight after removing an extra piano and a few other oddities. AI is powerful, but it is not perfect.
Notetaking
If you have met with me or another advisor in the past year, you have probably noticed an extra participant in the Zoom room, the AI notetaker. This is not just for advisors. Notetakers are now common across boardrooms, classrooms, and financial planning meetings.
A good notetaker can identify who is speaking, summarize key points, assign tasks, and organize follow-up items based on how it is prompted. For me as an advisor, this allows me to focus on what matters most, active listening.
Previously, there was always a balance between listening and writing. Pausing to take notes meant risking missing something important. With AI assisting in the background, that tradeoff is reduced and conversations can stay more focused and productive.
Parsing Large Amounts of Data
AI’s main strength right now, in my opinion, is its ability to take a large volume of information and summarize it quickly. Tasks that would take hours or days can now be done in minutes.
Think Partner
Personally, this is where I find the most value from AI. If I am working through an idea, I can ask AI to challenge it, improve it, or point out what could go wrong. If I am stuck, I can use it to generate options or approaches I may not have considered. Used correctly, it is less of a replacement and more of a second set of eyes.
What Am I Missing?
While AI is an incredible tool, given its popularity and interaction with humanity for the foreseeable future, we must evaluate how to interact with AI in our personal and professional lives that doesn't sacrifice our security and privacy.
Privacy
Free versions of AI can be useful, but they are not where I would ever put personally identifiable information (PII). Think of it this way - if it's free, you ARE the product. AI models / Large Language Models (LLM) are being trained from whatever information is provided and there's nothing quite like openly sourced (or openly given) information from the internet.
This is how OpenAI will begin advertising to you - it's based on how you've interacted with their free version. Simply paying the $20/mo in subscription fees can do a lot to keep your information private, and OpenAI has stated that they will not advertise to you there...yet. (Emphasis added by me with current evidence of different entertainment subscription services having varying levels of payments for varying levels of ad exposure).
Even still, I remain skeptical of the privacy of even paid versions of ChatGPT, Grok, Gemini, and Claude. So what can you do? The practical takeaway is the same guidance many of you have seen in cybersecurity training; Do not freely give away your personal information. Keep prompts general. If you have a specific situation, do not tie it directly back to yourself or anyone else.
Security
This area requires more diligence, especially in financial planning. The use of AI with client data demands a clear understanding of how that data is handled, stored, and protected. In my own practice, that evaluation happens before any tool is used. Client confidentiality and fiduciary responsibility do not change just because technology evolves.
This kind of evaluation is no different than what the government has done with Anthropic and OpenAI to certify that even controlled unclassified information, or a higher classification of data, is safe and not accessible to anyone else but the intended party.
Moving Forward with AI
My intent is not just to leave you concerned about AI. The goal is to emphasize the level of respect this tool requires, just like any other tool we rely on.
Once you understand where AI can go sideways, you can begin to use it in more effective and intentional ways.
Veterans Group Life Insurance: What's the Deal?
VGLI. It tends to get a bad reputation, and not entirely without reason. But that does not mean it is a bad solution. Before getting into the details, it helps to understand where VGLI actually fits.
The Scenario Where VGLI Matters Most
First, there needs to be a real need for life insurance. Not everyone requires coverage, and that evaluation should always come first. Life insurance is meant to protect against financial loss, not exist for its own sake.
Assuming there is a clear need such as income replacement, family support, debt obligations, or future goals that depend on you, let's press ahead.
You are separating or retiring from the military. You had SGLI in place, so coverage was handled. Now that coverage is going away. At the same time, life is changing quickly. New job, possible move, adjusting to civilian life, and a long list of financial decisions that all seem to hit at once. Life insurance changes being on that list, you do what you are supposed to do; you beginning shopping around.
And then you hit a wall.
A medical condition, something in your records, or even just elevated risk factors make you ineligible for private coverage, or the cost is far higher than expected.
That is where VGLI becomes relevant.
What VGLI Actually Does Well
Veterans’ Group Life Insurance is designed to provide continuity of coverage during your transition period out of the service. It also helps to provide some amount of life insurance coverage if you are unable to be insured privately.
If you apply within 240 days of leaving service, you can obtain coverage without any medical underwriting. No exams, no health questions, no risk of being declined.
After that 240 day window, you can still apply, but you may be required to provide medical information, which introduces the possibility of denial or higher costs.
That initial window is what makes VGLI valuable. It guarantees that you are not left without coverage at a time when your life is likely the most in flux and perhaps you are struggling to find needed coverage.
The Structure and Limitations
VGLI is not meant to be a perfect, long-term solution, and this is where most of the criticism comes from.
- Coverage is capped at $500,000. For many families, that may not be sufficient on its own.
- It is also structured as a five year renewable term policy. That means the policy continues, but the cost adjusts as you age.
The Cost Reality
Yes, premiums increase over time. By the time you reach your late 40s and beyond, the cost can become significant.
But this is often overstated as a unique flaw. Any term policy that renews as you age will reflect increasing costs. VGLI is not unusual in that regard.
The difference is that level term policies lock in pricing for a specific, usually long-term period, while VGLI adjusts every five years.
Where VGLI Fits in a Plan
VGLI works best as a backstop, not a permanent strategy. If you are healthy and have time to shop, a private term policy will often be more cost effective and offer higher coverage amounts.
But if you cannot qualify medically, or if timing does not allow you to secure private coverage before your SGLI ends, VGLI ensures that you still have protection in place. From a planning standpoint, the goal is simple. Maintain coverage first. Optimize it second.
You can always revisit your options later. What you cannot do is go back and add coverage after something changes with your health.
The Bottom Line
VGLI is not perfect. It is not meant to be. But in the right situation, it is an incredibly valuable safety net. Like most financial tools, its effectiveness comes down to how and when it is used.
Investment Rebalancing: Timing or Discipline?
Rebalancing sounds simple. You adjust your portfolio back to its intended allocation. In practice, however, it raises a harder question. When do you step in, and when do you leave things alone?
Markets do not move evenly. Over time, certain investments will outperform others. Left unchecked, that drift can push your portfolio into a risk profile that no longer matches your plan.
Why Rebalancing is Necessary
Take this scenario. You start out your with 80 percent of your investments in stocks and 20 percent of them in bonds. If the stock portion of your portfolio performs well, it can grow into a much larger percentage of your overall investments, unintentionally changing your allocation to 85/15 or 90/10. What started as a balanced allocation can become significantly more aggressive without you realizing it.
The opposite can happen in down markets, where risk is reduced unintentionally when your bonds perform well and stocks do not, moving your allocation to 70/30 or 60/40.
Rebalancing keeps your portfolio aligned with the level of risk required to achieve your goals, not whatever the market happens to deliver.
So what is the tipping point?
There are two common approaches.
Time-Based Rebalancing
This is the simplest method. You review and rebalance on a set schedule, often quarterly, semi-annually, or annually.
It is easy to follow and removes emotion from the decision. The downside is that it may trigger changes when they are not really needed, or miss opportunities when markets move quickly between review periods.
Threshold-Based Rebalancing
This approach focuses on how far an allocation has drifted from its target.
For example, if your target for equities is 60 percent, you might set a threshold of 5 percent. If that allocation drifts to 65 percent or down to 55 percent, it triggers a rebalance.
This method is more responsive to actual market movement, but it requires more attention and discipline. There is a risk here that given too narrow a threshold, you might find yourself rebalancing at every headline. If this is the case, you may consider changing your threshold to something more significant such as 10, 15, or even 20 percent.
So which approach is better?
In most cases, the answer is not one or the other. It is a combination of both. A structured review schedule paired with clear thresholds creates a framework that is both consistent and responsive. More importantly, it removes guesswork.
What About Target Date Funds and TSP Lifecycle Funds?
If you are invested in a target date fund or a TSP Lifecycle fund, rebalancing is already happening for you behind the scenes.
These funds are designed to maintain a specific allocation and gradually shift that allocation over time as you approach retirement.
That does not mean they are automatically the right fit for you, but it does mean you are not responsible for manually rebalancing within that fund.
The key decision with a target date fund or TSP L 20xx Fund becomes whether the fund’s allocation and timeline match your actual goals.
Your Takeaway
Rebalancing is about maintaining the level of risk you have already determined you are comfortable with. It forces a simple but often uncomfortable discipline. Trimming what has done well and adding to what has not.
Whatever approach you choose, decide now, (not when the market is jostling), and put the systems in place to follow through with your approach such as adding a calendar task or an alert on your investment account.
In Plain 'Site'
Check out my latest articles:
Check out the Fiscal Foxhole podcast with myself and Rob Moore - we're out every Wednesday morning!
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Disclaimer: This newsletter is provided for educational, general information, and illustration purposes only. Nothing contained in this material constitutes tax advice, a recommendation for purchase or sale of any security, or investment advisory services. I encourage you to consult a financial planner, accountant, and/or legal counsel for advice specific to your situation.
