As business owners, we are often so focused on the daily grind of running our companies that we ignore the big-picture protections we actually need. We build our businesses with passion and grit, but many of us leave a massive blind spot when it comes to safeguarding what we’ve created.

One of my favorite things about hosting the Not Your Typical Business Podcast is the opportunity to sit down with incredible business professionals I meet through networking. I wanted to bring their unique journeys and industry-specific expertise to a wider audience, because there is so much we can learn from others’ paths.

In our latest episode, I sat down with Jane Wilcom of Eskay Law Group. Jane is a personal family lawyer who specializes in estate law and trust planning in a deeply personal, relationship-first way.

We dove into the uncomfortable truth about why estate planning for business owners is actually a foundational piece of business protection, how changing tax laws affect your operations, and why human empathy remains irreplaceable in a tech-driven world. Whether you are running a high-growth trades business or scaling a creative agency, these are the key insights and lessons from Jane’s journey that every business owner needs to hear.

1. Reinvention is a Season, Not a Mid-Life Crisis

One of the most inspiring parts of Jane’s story is her career evolution. Before training in estate law, Jane spent over 30 years in big-firm litigation and working in-house for family-owned corporate entities. She eventually reached a point where she realized her work wasn’t directly helping people in the way she wanted to. So, she stepped back, went back to school to learn a brand-new practice area from scratch, and completely pivoted her career.

I can completely relate to this. My college degrees are actually in animal behavior and human psychology! If you had told me years ago that I would be running a boutique accounting and advisory firm, I would have laughed. But life is made of different seasons.

As entrepreneurs, we aren’t locked into a single path forever. You have the freedom to reinvent yourself, your role, and your business workflows. Recognizing that your current setup might only be right for “this season” of your life gives you the permission to change direction, delegate, and focus on what truly fulfills you.

2. Estate Planning is Business Protection (Not Just a Will)

Did you know that 59% of adults in the United States do not have an estate plan? It is the ultimate “I’ll deal with that later” task because nobody wants to talk about their own demise. But if you are a business owner, ignoring this is a massive operational liability. Estate planning isn’t just about what happens after you die—it’s about protecting your business, your partners, and your family while you are still living.

Jane highlighted several critical areas where business owners must take action:

• The Reality of Incapacity: Estate planning heavily involves planning for temporary or permanent incapacity. If something happens to you in a car crash or medical emergency, who has the power of attorney to access your business bank accounts, approve payroll, or sign legal documents? Without these protections in place, your business operations will grind to an immediate halt.
• The “Specific is Terrific” Rule for Minor Children: If you have minor children, a will is the only place to legally name their guardians. If you don’t do it, a judge—who has never met your family—will make that decision on paper. They won’t know your personal values, family dynamics, or who is actually equipped to raise your children.
• Stipulating the Future: When setting up a trust, you don’t have to blindly hand a massive lump sum of money to an 18-year-old. You can write highly customized stipulations. For example, in my own family’s trust, I wanted to make sure my daughter could use her inheritance to go to a trade school or start her own business, rather than restricting it strictly to a traditional four-year college.
• The Three-Year Rule: An estate plan is not a “one-and-done” binder that sits on a shelf forever. Jane recommends reviewing your estate plan every three years or after any major life event (marriage, divorce, new children, buying property) because your assets change, your relationships change, and tax laws change.

3. Shifting Tax Tides and Regulatory Changes

We also discussed how critical it is for business owners to stay informed about changing laws and regulations. As an example, Jane and I talked about the massive compliance shifts coming from recent legislative updates, like tax exemptions on overtime and tips.

While these changes are designed to benefit workers, they will introduce major operational hurdles for employers:

• Overtime Disputes: Under the Fair Labor Standards Act (FLSA), classifying employees incorrectly as “salary-exempt” to avoid paying overtime has always been a risk. Now that overtime pay is tax-exempt, employees will push back harder to be classified as hourly so they can bring home tax-free time-and-a-half cash.
• Tips Reporting: In industries like hospitality and restaurants, cash tips have historically gone underreported. With tips becoming tax-exempt, employees will likely report more of their tips because showing a higher legal income on paper helps them qualify for mortgages and car loans.

As business owners, we don’t need to know every single legal or tax rule inside and out. But we do need to build a network of trusted professionals—lawyers, advisors, and CPAs—who can flag these compliance shifts and help us navigate them before they turn into major headaches.

4. Why AI Can Reconcile, But It Can’t Empathize

We hear a lot of noise about AI taking over professional services, from legal document generators to automated accounting software.

But Jane and I agreed on one fundamental truth: technology cannot replace human relationships and empathy.

A computer program can generate a generic, cookie-cutter will, but it won’t ask the nuanced questions about your family dynamics, your business succession goals, or your fears. It can’t look you in the eye, listen to your story, and help you make hard personal decisions.

The same applies to the financial world. Software can auto-categorize bank transactions, but it can’t understand the heart behind your business, translate your numbers into a stress-free growth roadmap, or act as a supportive, judgment-free sounding board when you are facing a cash-flow crunch.

At the end of the day, people buy from people, and they partner with people. Empathy, listening, and real human connection are what make a business truly sustainable.

Listen to the Full Conversation

If you want to hear more of Jane’s incredible career journey, the details of estate law, or our full discussion on navigating business shifts, check out the full episode!

Listen on Spotify | Apple Podcasts | Amazon Music

The Not Your Typical Business Podcast is all about real conversations with real business owners sharing the honest lessons behind their work. Want to stay updated on future episodes or share your own business journey? Visit nytbpodcast.com to learn more!

Want to connect with Jane?  You can find her here:  Website | LinkedIn