I believe in reading the tea leaves and sensing when industries are at a critical juncture, with your leadership job on the line. Businesses hit strategic crossroads, and startups reach pivotal moments.

There were two other points in my career when I experienced cross-industry tipping points: the dot-com bust in the late 1990s and the financial crisis in 2008.

Turning points also impact people in their roles and lives. I told some of my turning-point stories in Digital Trailblazer. The one I am sensing now is impacting many of my readers, supporters, colleagues, and career friends.  

Many Digital Trailblazers I speak to are sensing an inflection point and feeling angst about their jobs, focus areas, and careers.

The trigger points impacting transformational leadership

There isn’t a single trigger point, and here are four drivers.

• The release of the AI models at the end of 2025 with improved coding capabilities raises many questions about how Digital Trailblazers should lead software development and build AI agents.
• Investor reaction to AI’s advancing software development capabilities drove a selloff in shares of publicly traded SaaS companies, which can impact how Digital Trailblazers select platforms and experiment with AI.
• Fundraising for U.S. venture-capital firms dropped 35% in 2025 to $66 billiion, and globally it was “exceptionally weak” at $118 billion. Additionally, 50% of the total deal value went to just 0.05% of deals, and AI firms captured 61% of global venture capital in 2025.
• World events, and there are several, are creating uncertainties that can sometimes paralyze business leaders around strategic decisions and investments.    

These four data points will drive shifts in business, technology, and AI strategies. It means roadmaps and investments may be impacted. And for some, it may also trigger job cuts and reassignments.

Weak employment is driving alternative careers

Here’s a more tangible trigger point that may impact your leadership job. There’s been a lot of depressing labor-related data published in the last week.

• The Labor Department reported that employers cut 92,000 jobs in February, and the unemployment rate rose to 4.4%. 
• The WSJ reported that, “Nationally, there were 532,319 new-business applications in January, according to the Census Bureau, 36.8% more than a year earlier. On LinkedIn, the number of people listing themselves as founders is 69% higher than a year ago.”
• The WSJ also reported that, “About one CEO in nine was replaced last year across 1,500 of the biggest publicly traded companies. It’s the highest rate since at least 2010, when the U.S. was emerging from the financial crisis.”
• Jack Dorsey blamed AI and cut over 4,000 people, 40% of Block’s workforce. Morgan Stanley laid off 2,500, 3% of its workforce.
• Layoffs. fyi reports 35,650 tech employees laid off and 50 tech companies with layoffs in 2026, outpacing 2025’s total.

When layoffs are in the news, other companies often follow suit. When large enterprises flip CEOs, it often drives trickle-down leadership changes. Leaders who are out of work aren’t finding new roles, and so entrepreneurship and solopreneurship are on the rise.

But going it alone isn’t easy when the market is flooding with new consultants and companies are shedding employees. And the VC route looks tighter, unless you have a highly scalable AI business seeking investment.    

Leadership job opportunities for Digital Trailblazers

I recently recorded a new Driving Digital Standup video titled AI Leadership Opportunities: Successful Strategies When Jobs Are at Risk. This video is for Digital Trailblazers in one of these situations:

• Employed leaders who want to drive AI impacts
• Employed and unemployed leaders who want to position themselves for new AI opportunities.
• Leaders who are considering entrepreneurship, solopreneurship, or joining startups.

Watch the video below for insights on the AI leadership opportunities.

If you are out of work, thinking you may be soon, or want a better opportunity, you are not alone. I want to hear from you.