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$83B on the Side Is a Signal Employers Can’t Ignore

Amazon cuts 16K, LinkedIn adds AI skill certs, and $83B/month side hustles show how to build a portfolio career in 2026.

"The question isn't who's going to let me; it's who's going to stop me." -Ayn Rand

👋 Welcome, Jobseekers

Big Tech is still cutting (Amazon and friends) while AI pulls money and hiring toward power, infrastructure, and the pick-and-shovel builders. LinkedIn is turning AI tool usage into official skill signals, and Anduril is literally making hiring a contest. Meanwhile, $83B a month in side hustles says “portfolio career” is the new baseline, and bachelor’s filters depend heavily on your ZIP code.

  • 📆 Event: Build AI workflows with GTM folks over sundowner

  • 🧑‍✈️ Career CoPilot: $83B/Month in Side Hustles: What Tech Should Learn

  • 🔈️ Signals of the Week: LinkedIn is adding AI skill certificates tied to real tool usage

  • 📉 Layoff Report: Amazon axes 16,000 jobs as it pushes AI and efficiency; Pinterest, Oracle, Autodesk with big cuts as well

  • 📈 Trends & Data: The Bachelor’s Degree Isn’t Dead.

    It’s Regional.

  • 🔧 Jobseeker Tools: Relay.app, KIN

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Top Signals of the Week

Tech is in whiplash mode: the giants are still cutting to get leaner, while AI is lighting a fresh money fire under everything that powers it, from data centers to nuclear fuel. The takeaway is simple: chase the AI gravity wells and the pick-and-shovel builders, and be extra skeptical of “generalist” roles sitting far from revenue or infrastructure.

Amazon laying off about 16,000 corporate workers in latest anti-bureaucracy push 

Source: TrueUp

Amazon said Wednesday it plans to eliminate about 16,000 corporate jobs, marking its second round of mass job cuts since last October. In a blog post, the company wrote that the layoffs were part of an ongoing effort to “strengthen our organization by reducing layers, increasing ownership, and removing bureaucracy.” That coincides with a push to invest heavily in artificial intelligence.

$83B/Month in Side Hustles: What Tech Should Learn

Side hustles are not only not going away, but they’re evolving into “portfolio careers.” More people will mix full-time work with freelance, fractional roles, and paid projects to reduce risk, keep skills current, and create options in a market shaped by layoffs, high costs, and rapid AI change. The big shift isn’t just having a side hustle. It’s treating multiple income streams as a normal, intentional strategy.

The data

  • 73% of Americans say side hustles are a financial necessity.

  • One-third of Americans have a side hustle.

  • Side hustlers collectively earn $83.1B extra per month.

  • 51% started their side hustle within the past year.

Why this matters for tech jobseekers

Hiring managers are increasingly comfortable with non-linear careers (if you can show proof of impact). Experts predict that gig work will be more recognized in career progression (“gig portfolios”), and that side hustles will become part of mainstream financial planning. Translation for tech: shipped work + measurable results can carry as much weight as titles, especially when companies are cautious about full-time headcount.

As AI rapidly changes the game, the safest posture is building resilience: upskilling, testing new domains, and stacking small wins that make your next role easier to land.

What to do with this: treat your job search like a portfolio. Keep a main track (full-time roles) and a second track (contract/fractional/project work) so you’re building recent, verifiable outcomes while you interview. The candidates who win in 2026 won’t just say they’re adaptable. They’ll have receipts.

The Bachelor’s Degree Isn’t Dead.
It’s Regional.

“Skills-first” hiring is growing, but bachelor’s degree requirements are not disappearing. Indeed data shows the share of US job postings requiring a BA+ rose meaningfully from late 2023 to late 2025, and even when you control for shifting job mix, degree requirements have been inching up since March 2024. Where you live matters a lot: some states and metros still screen heavily on degrees, even for similar job titles.

The numbers

  • 19.3% of US Indeed job postings required a bachelor’s degree or higher in Nov 2025, up from 16.6% in Nov 2023.

  • 51% of postings listed no formal education requirement (meaning 49% listed some requirement).

  • After adjusting for job-title mix, BA+ requirements hit a 5-year low of 18.5% (Mar 2024) and ticked up to 18.6% (Nov 2025).

  • State raw BA+ share: Washington, D.C. 43.7% vs Mississippi 11.3% (Nov 2025).

  • Adjusted by identical job-title mix: D.C. 22.4% vs Alaska 10.6% (Nov 2025).

Why this matters for jobseekers

  • Treat “skills-first” as a messaging trend, not a guarantee. Expect degree filters to persist, especially in policy-heavy, regulated, and professional-services hubs.

  • If you are non-degree or career-switching, target geographies and employers where BA+ requirements are lower, then use proof packets: portfolio, work samples, shipped projects, certs, and references.

  • In degree-heavy metros (DC, Boston, NYC, Chicago), assume tougher screening. Lead with keywords that match the JD, and add a “Comparable experience” line near the top of your resume.

  • If a posting says “BA required” but the work is practical, try a backdoor entry: referrals, contractor-to-hire, adjacent titles, or teams with more skills-based managers.

  • For recruiters: ask directly, “Is the degree a hard requirement or a preference?” The methodology notes many ads mention degrees but accept lower levels.

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