When someone leaves behind a handwritten will, they probably had good intentions. They took the time to write something down. They put their wishes in their own words. On its face, that can feel like enough. But creating a will isn’t only about intentions, there are legal hoops that must be jumped through.

Howard Hughes is a well-known example of how that can go wrong. After his death in 1976, a handwritten document surfaced that appeared to outline how he wanted his humongous estate distributed. It quickly became the center of national attention. Where was it found? When did he write it? Was it even authentic?

Those questions weren’t easy to answer. The document was challenged, scrutinized, and ultimately rejected by the court. Despite the existence of a handwritten “plan,” Hughes was treated as though he had no valid will at all. His estate fell back on the state’s default rules, and what followed was years of litigation and uncertainty.

Why Should I Care?

Most estates don’t involve mysterious documents or national headlines. But handwritten wills still show up in everyday situations:

• A note written at home and kept with personal papers 
• A document started with good intentions but never finalized 
• Instructions written down without much thought to legal requirements 

In Idaho, a handwritten will can be valid but only if the material portions are in the person’s handwriting and it’s clear they intended it to function as a will.

Even when those requirements are met, a handwritten will doesn’t avoid probate and doesn’t eliminate uncertainty. It still has to be located, accepted by the court, and interpreted if questions arise.

What feels simple to write can be complicated to carry out. A handwritten will sits in an uncomfortable middle ground. It’s not the same as having no plan, but it doesn’t provide the clarity of a well-structured one either.

If it doesn’t meet the legal requirements, it may be ignored entirely. If it does, it can still leave room for interpretation, delay, and dispute. Either way, the outcome may look very different from what was intended.

The Bottom Line

Writing something down is a good instinct. But for that will to work, it must do more than express intent. That means following the legal requirements, making sure the document can be found, and understanding how it fits into the probate process.

Without that, even a handwritten will can lead right back to the same place as no plan at all.

A Practical First Step

If you’ve written down your wishes, or are thinking about it, the next step is making sure those instructions will actually work when they’re needed.

Taking that extra step now can prevent a lot of uncertainty later.

-Jane Powell

Now that tax season is behind us, most business owners are ready to move on. And honestly, that’s understandable—filing is stressful, the deadlines are real, and getting it done feels like an accomplishment in itself. (And if you filed an extension, well, you’ve got to hang on a little longer). But before you close the folder and set it aside until next April, it’s worth pausing for a moment.

Your tax return isn’t just something to file and forget. It’s actually one of the most useful documents your business produces all year—a concrete record of how money moved, how your business is structured, and where decisions were made proactively or reactively. Reviewed the right way, it can surface opportunities you may have missed and flag issues worth addressing before they compound.

Here are a few things I often look for when reviewing a return with clients.

How Your Business Is Structured

The form your return was filed on—Schedule C, Form 1120-S, Form 1065, or Form 1120—tells me immediately what your tax structure is. What it doesn’t always tell me is whether that structure still makes sense for where your business is today.

Entity and tax choice have real consequences for how you’re taxed, how you’re protected from liability, and how your business can grow or be transferred. A sole proprietorship might have been the right call when you were just starting out, but as revenue grows and complexity increases, the calculus often changes. Similarly, an S corporation maybe seemed like a no-brainer at one point, but the business now has different goals and aims.

If you haven’t revisited your entity structure in a few years, your return is a good prompt to do so.

How Money Is Flowing Through the Business

One of the first things I look at is how the owner is being compensated. Are you taking a salary, distributions, or some combination? That distinction matters—both for tax purposes and for long-term financial planning. Reasonable compensation requirements for S corporation shareholders, for example, are an area where there is a lot of interest and differing opinions.

The return also shows whether profits are being retained in the business or distributed to owners, and how expenses are being categorized. Sometimes there are legitimate deductions that aren’t being taken. Other times, I see deductions that are being stretched in ways that could attract scrutiny.

Owners often focus on the bottom-line tax number without looking closely at the story the income and expense lines are telling. That’s where a lot of the useful information lives.

Whether You’re Planning or Just Reacting

There’s a difference between a return that reflects deliberate decisions made throughout the year and one that reflects a scramble to produce a number in late March. Both can produce a similar tax bill—but only one of them is actually building toward something.

Patterns I look for: Were retirement contributions made, or was that opportunity missed? Were major purchases timed thoughtfully, or just made without considering the tax impact? Is there evidence of quarterly estimated payments, or does the return show underpayment penalties?

Proactive planning doesn’t always mean paying less tax in a given year; sometimes it means accepting a higher bill now in exchange for a better outcome later. But it should always be intentional. A return that reflects reactive decisions is a signal that the planning conversation needs to happen earlier next year.

What’s Not Showing Up on the Return

Some of the most important observations from a tax return aren’t about what’s on it, it could also include what’s missing.

No retirement plan contributions? That’s a missed opportunity that compounds over time, both in terms of tax savings and long-term financial security. No evidence of a health insurance deduction for a self-employed owner? Worth a closer look. A business that’s been profitable for several years but still hasn’t addressed estate planning or succession? That gap tends to matter more than people expect, and later than they’d like.

After tax season, I wish more clients would ask: “What can we learn from this?” and “What should we be thinking about for next year?” Those are the conversations that tend to produce more value than any single filing decision.

A few questions worth asking after reviewing your return:

• Is your current entity still the right fit for your income level and goals?
• Are you taking money out of the business in the most tax-efficient way?
• Were there planning opportunities available to you this year that you didn’t use?
• Are you set up to make better decisions next year?

Using Your Return as a Tool, Not Just a Requirement

A tax return is more than a filing requirement—it’s a snapshot of how your business is operating. Reviewed thoughtfully, it can tell you whether your structure is still working, whether money is moving efficiently, and whether you’re making decisions proactively or just responding to circumstances.

The goal isn’t just to minimize taxes in a given year. It’s to make sure your structure and decisions are aligned with your long-term goals so that each year builds on the last, rather than simply closing out. The period right after tax season, when the details are still fresh, is actually one of the better times to have that conversation.

Ready to Talk Through Your Return?

Now is a good time to take a step back and look at what your return is actually telling you. If you’d like to talk through your situation or think more proactively about the year ahead, feel free to reach out.

In law school, we learned legal principles by examining real cases and hypotheticals. We saw how the law works through the lens of what happens when things go wrong. In estate planning these cases often read like a soap opera script, with secret families, coerced will changes, hidden assets, and murder for money. But most estate problems don’t arise from dramatic circumstances. They come from something much simpler: no plan at all.

One of the most well-known examples is the estate of Prince. In 2016, the death of pop-rock icon Prince shocked the music world; his lack of any estate plan soon shocked the legal world.

With no will, trust, or any clear expression of his wishes, his $200+ million estate went to probate. The court was left to apply the state’s default rules for inheritance. When you die without a plan, the court doesn’t try to guess what you would have wanted. It applies a one-size-fits-all set of default rules. And as anyone who has ever bought a ‘one-size-fits-all’ item knows, it rarely fits anyone well.

What followed were six years of litigation, administrative complications, and public disputes among family members. Most of this could have been avoided with basic estate planning.

What Would a Plan Have Changed?

If Prince had created even a simple estate plan, it would have allowed him to:

• Decide who would receive his assets.
• Appoint someone he trusted to manage his estate.
• Provide clear instructions for handling his music rights and business interests.
• Avoid unnecessary conflict among family members.
• Significantly reduce the time and cost of administration.

Instead, those decisions were made by statute and enforced by the courts.

And Why Should I Care?

This situation is not unique to celebrities. If you don’t create an estate plan to memorialize your wishes, state law determines who receives your assets, when, and how.

In Idaho, those laws are based on legal family relationships.

If someone is married, their spouse may receive all of their estate. If there is no surviving spouse, the estate typically passes to their children. And if those children are minors, someone may need to be appointed to manage their funds until they reach adulthood. Then, at eighteen, they would receive their entire inheritance.

If you were making a plan yourself, you might make those same choices. But the law’s one-size-fits-all rules tend to fit poorly in less traditional family situations. Your wishes for a blended family, unmarried partner, or estranged relative often don’t align with how the default rules actually work.

Additionally, assets may need to go through probate before they can be distributed, which adds time, cost, and administrative complexity.

The Bottom Line

Estate planning gives you control. It’s about making decisions now, so your wishes are clear, your family has direction, and the transition is as smooth as possible.

Without a plan, the law steps in and makes those decisions for you.

A Practical First Step

If you have been putting off estate planning, the first step is simply to start the conversation.Understanding your options and putting even a basic plan in place can make a significant difference for your family in the future.

-Jane Powell

The Internal Revenue Code requires that business expenses be ordinary and necessary to be deductible. Those words can sound like jargon, but the concept is practical: the expense should make sense for your type of business, and it should have a real business purpose.

The Two-Part Standard: “Ordinary” and “Necessary”

An expense is generally ordinary if it is common and accepted in your industry. It does not have to be something you pay daily, and it does not have to be something every competitor pays for. The point is that the cost is a normal type of expense for a business like yours.

An expense is generally necessary if it is helpful and appropriate for running your business. “Necessary” is often misunderstood. It usually does not mean “absolutely required.” Instead, think of it as: would a reasonable business owner see how this expense helps the business operate, earn revenue, or reduce risk?

Put together, the standard is meant to separate true business costs from personal spending dressed up as business activity.

Common Examples of Potentially Deductible Business Expenses

Context matters, but many routine operating costs are frequently deductible when they are truly connected to your business. Examples include:

• Advertising and marketing, such as online ads, website hosting, print materials, sponsorships, and promotional costs
• Employee wages and other payroll-related expenses
• Rent for office, retail, storage, or other business space
• Supplies and day-to-day operating purchases
• Professional services, such as accounting, legal, bookkeeping, and other outside help
• Software subscriptions and technology tools used to run the business
• Utilities and communications, like business phone and internet
• Travel that is directly tied to business purposes

Where Deductions Get Tricky: The Gray Areas

Some expenses are more likely to cause confusion because they can be partly personal, they can feel “optional,” or they can be hard to connect to a business purpose without extra explanation. These expenses are not automatically non-deductible, but they often require clearer documentation and better judgment.

Common gray areas include:

• Vehicle expenses when a car or truck is used for both business and personal driving
• Meals tied to business discussions or travel, especially if the “who, what, and why” is not documented
• Travel that mixes business and personal time (for example, a conference plus a vacation)
• Home office costs, depending on how the space is used and whether it is truly set aside for business
• Clothing that could be worn outside of work

A helpful way to think about these categories is: if someone unfamiliar with your business looked at the expense, would they immediately understand the business purpose? If not, you may need stronger documentation, or you may want to think more about how it is reported.

Documentation: The Part People Underestimate

Even a legitimate expense can become a problem if you cannot support it. Good records help show:

• The expense was actually paid
• The amount is accurate
• The expense was connected to business activity

Practical documentation usually includes:

• Receipts and invoices
• Bank and credit card statements
• A brief business purpose note for anything that is not self-explanatory
• Logs or tracking for mixed-use items, such as mileage tracking for vehicles

One simple habit can save a lot of time later: when you make a purchase that could be questioned, write a short note the same day with the business reason (for example, “met with vendor about supply contract” or “travel to job site to oversee installation”).

A Quick Self-Check Before You Deduct an Expense

Before you decide a cost is a business deduction, ask yourself:

1. Is it primarily business-related, rather than personal?
2. Is it the kind of cost that is common in my industry or in businesses like mine?
3. Is it helpful to the business in a clear way?
4. Is the amount reasonable for what I received?
5. Do I have records that show what it was and why it matters?

If the answer is “I’m not sure,” that is usually a sign to take a closer look before filing. Often, the issue is not the expense itself, but whether it is documented well enough or categorized consistently.

If You Want Help

If you are trying to clean up your bookkeeping, decide how to handle borderline expenses, or build a documentation routine that holds up over time, professional guidance can help you make decisions with more confidence.

Dean Business & Tax Law works with business owners on practical tax planning and documentation questions, including how to think about business expenses in a way that is clear, consistent, and supportable. If you would like to discuss your situation, you can call (208) 248-0800.

I’ve worked with businesses throughout my entire legal career. I’ve spent time inside a Fortune 100 company, and I’ve also helped individuals set up small businesses that started as side gigs. I’ve always been fascinated by businesses and energized by their journeys—watching how ideas turn into something real. 

What’s interesting is that I didn’t come from a family of entrepreneurs. For a long time, I assumed business ownership was for someone else. 

A couple of years ago, a light bulb went off. I have spent years helping businesses form, grow, scale, and sell. I understood the legal, strategic, and practical issues that show up at every stage. At some point, I asked myself a simple question: why not put that knowledge to use and build something of my own? 

Working at other law firms and companies was a great experience. I learned a lot and worked with talented people. But I also realized I wanted more. I wanted to be more entrepreneurial. I wanted to be more entrenched in the decision-making process and to work side-by-side with fellow entrepreneurs and business owners. 

I missed the variety and challenge that comes with advising people who are building and running businesses. And candidly, I wanted to see if I could do it myself—not just help others do it. So, I took the leap and started my own firm. 

What 15 Years of Practicing Law Taught Me 

In May 2026, I’ll reach the 15-year anniversary of graduating from law school. Over that time, my practice has taken me around the country and involved matters touching issues across the globe. It’s been very different from what I imagined when I started—and rewarding in ways I couldn’t have anticipated. 

One lesson has come up repeatedly: it is almost always easier to address problems sooner rather than later. 

Clients who seek legal advice early generally have better outcomes. Those who wait until the last minute often end up paying more and dealing with far more stress than they expected. I’ve said to many clients over the years, “You can pay me $5,000 to do this now, or $50,000 to fix it later.” In my experience, that sentiment is almost universally true. 

My Approach to Legal Advice 

My goal is to be a trusted advisor to my clients. That phrase can sound like a cliché, but I take it seriously. 

I want to understand the full range of challenges my clients are facing—not just the narrow legal question in front of them. I aim to be proactive and to connect dots that clients may not see because they’re busy running their businesses. 

Legal advice shouldn’t exist in a vacuum. Business decisions involve risk, timing, relationships, and practical realities. My role is to help clients understand those risks, weigh their options, and make informed decisions that align with their goals. 

What Clients Can Expect When Working With Me 

At the core of my practice is a focus on building meaningful relationships. I want to work with people I like, and I expect clients to want an attorney they like as well. 

That said, liking someone isn’t enough. Too often, I hear stories about attorneys who are unresponsive or difficult to reach. My goal is to provide a better legal experience. 

I return calls and emails. I communicate proactively. I don’t want clients to feel that nothing will happen unless they follow up repeatedly. When a client engages me, I see it as my responsibility to follow through on what I promise—and if circumstances change, to communicate that clearly and promptly. 

Who I Work Best With 

My clients are typically individuals who own or operate one or more businesses. Most have multiple business interests that they juggle and need help quarterbacking those legal issues. 

The clients that tend to be the best fit are those who understand and value legal services. They see legal advice as an important part of running and growing a business, not just something to turn to when there’s a problem. 

I work best with people who are entrepreneurial-minded and seeking growth. These are clients who value professional services and have a team to support them. They appreciate expertise, speed of delivery, and clarity in the legal advice they receive. 

Issues I Wish Clients Would Call About Earlier 

I wish all clients would seek legal guidance before setting up a legal entity. Sometimes it seems “easy” and straightforward. But I deal with clients almost weekly where the problem could have been avoided with early intervention. 

Over my 15 years of practice, I’ve seen a lot of partnerships start strong and later go south, often because there weren’t clear agreements in place from the beginning. 

Many people don’t fully understand the nuances of entity selection from a state law perspective, or the federal tax implications that come along with that choice. And if they have a partner, they assume that the good relationship they have will never sour. Unfortunately, it often does, and having good agreements in place up front can save a lot of headaches and disagreement down the road. 

Why Local Relationships Matter to Me 

I was born and raised in Ohio, I live outside of Boise, and my wife’s family is in Utah. I have a presence in all of those places. 

Even in a world where Zoom meetings are the norm, getting to know people on a personal level—clients and other professionals alike—matters to me. I value face-to-face relationships. I want to understand the people I work with, not just their businesses. 

While running a law firm is certainly a way to support a family, I’m not building a practice solely to maximize short-term profit. I’m focused on long-term relationships and sustainable growth. I’d rather work with fewer clients and provide excellent service than try to take on as many matters as possible. 

A Bit About Me Outside of Law 

Outside of practicing law, I enjoy traveling, following sports, and spending time with my family—ideally all at the same time. 

So far, I’ve traveled to 47 states and 16 countries, with plenty more on the list. Travel expands my perspective and worldview, and I genuinely believe it makes me a more thoughtful and empathetic attorney. 

A Note to the Reader 

The goal of this blog is to provide practical insights and guidance for individuals and business owners. The law can be dense and difficult to navigate, but my aim is to make it more accessible and useful. 

If that sounds helpful to you, I’m glad you’re here—and I hope you’ll stay tuned.