After nearly five decades in business, and after working with family-owned companies, entrepreneurs, and organizations of every size, I've learned that every year brings a new set of challenges. Some years it's the economy. Some years it's technology. And some years it's simply uncertainty.

As I look around in 2026, these are some of the issues we're seeing most often.

Rising Costs Continue to Put Pressure on Margins

We've watched businesses absorb higher costs for labor, insurance, materials, and services. Add tariffs and inflation to the mix, and many owners are finding that yesterday's pricing models simply no longer work.

Most business owners I know aren't afraid of hard work. But trying to run uphill while carrying heavier and heavier expenses can be exhausting.

Artificial Intelligence Is Creating New Opportunities - And New Risks

Our team has been thoughtfully embracing AI tools, and we've seen firsthand how much they can improve efficiency and reduce repetitive work. At the same time, we've become increasingly aware that these tools require oversight.

AI is capable of making mistakes. It can expose confidential information. It can create liability. And perhaps most concerning, it can give people confidence in information that simply isn't correct.

Like any powerful tool, AI works best when guided by responsible human judgment. Every AI transaction that is intended for consumer consumption must have a human in the loop.

Cyber Threats Continue to Evolve

We've seen cyber risks become more sophisticated every year. Criminals now use AI just as aggressively as legitimate businesses do.

Phishing attacks, ransomware, fraudulent wire transfers, and social engineering schemes are becoming increasingly difficult to recognize. Smaller businesses are particularly vulnerable because they often lack dedicated security teams.

Finding Great People Is Still Difficult

One challenge we hear repeatedly from clients is finding qualified young people with the work ethic and common sense to step into available opportunities.

In some industries, it isn't that applicants don't exist. It's that finding individuals with the right skills, attitudes, and work ethic has become increasingly difficult. We've also found that technology and outdated systems, a condition that plagues the world of P&C insurance, often create unnecessary friction for younger employees entering the workforce.

Uncertainty Makes Planning Hard

Business owners can adapt to almost anything - provided they know the rules.

What makes planning difficult today is the constant change. Regulations shift. Markets fluctuate. Political headlines create uncertainty. Supply chains change. Business owners are left trying to make long-term decisions in an environment that often feels very short-term.

Borrowing Money Isn't Cheap

For many businesses, access to capital has become more challenging. Higher interest rates have changed the math.

We've seen owners become much more disciplined about debt and far more cautious about using borrowed money simply to maintain operations. Growth financed by strong fundamentals feels very different than growth financed by desperation.

Technology Is No Longer Optional

Whether it's AI, automation, CRM systems, or communication platforms, businesses are under pressure to modernize.

We've experienced this ourselves. Implementing new tools is rarely as easy as the sales presentations suggest. Training people, changing processes, and getting adoption takes patience and persistence. But ignoring technology altogether will lead to a dramatically shorter business lifespan.

Customers, Clients, Carriers, Expect More Than Ever

People expect fast responses, personalized communication, and a seamless experience.

What used to be considered exceptional service is now viewed as normal. We've found that investing in communication and the client /carrier experience often creates advantages that our competitors struggle to replicate.

Politics and Regulation Affect Everyone

Whether we like it or not, business doesn't operate in a vacuum.

Changes in regulations, taxes, tariffs, labor laws, and political priorities all influence how companies operate. The challenge isn't predicting every change. It's building organizations that are resilient enough to adapt quickly when change inevitably arrives.

Attention Has Become Scarce

Perhaps the biggest change we've witnessed is how difficult it has become to capture and hold people's attention.

Everyone is marketing. Everyone is emailing. Everyone is posting. Everyone seems to just be kicking the can further down the road.

We've found that authenticity still matters. Relationships still matter. And in an increasingly automated world, genuine human communication is increasingly more valuable, not less. 

Final Thoughts

Every generation of business owners has faced its own set of challenges.

Looking back, we've lived through recessions, technological revolutions, labor shortages, market crashes, and more than a few surprises. Yet entrepreneurs continue to adapt, innovate, and move forward.

Maybe that's the real story.

Not the challenges themselves, but the remarkable resilience of the people willing to build businesses, employ others, and keep showing up every day despite the uncertainty.

That's something I've always admired, and something that still gives me hope.