Author: Neil Gulino
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What to Do With Your 401(k) When You Change Jobs After 50
Changing jobs after 50 comes with a weird administrative side quest nobody asked for. One day you’re cleaning out a desk or setting up a new laptop. The next day you’re staring at an old 401(k), four competing options, and a pile of rollover jargon that sounds like it was written by a committee that…
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What Middle Managers Need to Know About AI Before Their Teams Do
If you’re a middle manager, the weird part about AI isn’t the technology. It’s the social timing. The people above you are asking strategic questions they barely understand, and the people below you may already be using the tools quietly because they don’t need permission to shave 40 minutes off a report. That’s why AI…
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Wordable Review: Is Content Publishing Automation Worth the Investment?
If you’re publishing from Google Docs and still spending part of every week fixing WordPress formatting, this Wordable review will probably feel uncomfortably familiar. Content publishing automation sounds like a fancy way to avoid boring cleanup work. That’s because it is. And for anyone pushing out articles regularly, boring cleanup work has a nasty habit…
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A Boy and His Bot: What I Learned Building with AI
I need to tell you about my relationship with an artificial intelligence. It’s complicated. Not complicated in the way people use that word on social media. Complicated in the way that any relationship is complicated when one party is capable of genuine brilliance and the other party keeps forgetting it’s not a person. I’m the…
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It’s Not a Warning Anymore: The AI Job Cuts Are Here
I started Durable Earnings with a simple premise: AI was going to change the math on millions of careers, and most people wouldn’t see it coming until after it arrived. I wanted to be wrong about the speed. I wasn’t. On May 20th, Meta cut 8,000 jobs and forcibly reassigned another 7,000 employees into AI-focused…
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Morningstar’s Portfolio Risk Analyzer: A Guide for Retirees
Retirement portfolio advice gets fuzzy right when it needs to get specific. “Stay diversified” sounds responsible until you’re five years from retirement, taking withdrawals, and trying to figure out whether your actual holdings are built to survive a bad sequence of returns instead of just looking respectable on a pie chart. That’s why Morningstar’s Portfolio…
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How to Identify Transferable Skills for a Career Change After 50
You can spend 25 years getting good at work and still freeze when someone asks what else you’d be qualified to do. That’s not because you lack useful skills. It’s because most people were trained to describe their jobs, not the capabilities underneath them. That gets expensive after 50. A January 2025 AARP survey found…
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Portfolio Careers: How to Combine Multiple Income Streams After 50
A lot of experienced professionals are staring at the same ugly math. One paycheck used to feel solid. Now it feels like a single point of failure wearing business casual. That doesn’t mean the answer is to become a hustling internet goblin with six apps open and a ring light in the spare bedroom. It…
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Interviewing After 50: How to Address Age Concerns with Confidence
You can walk into an interview with 25 years of results behind you and still feel like you’re being quietly judged for the date on your driver’s license. That’s not paranoia. That’s pattern recognition. When you’re interviewing after 50, some employers see judgment, steadiness, and scar tissue in the useful sense. Others see a pile…
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How to Write a Resume That Highlights Experience, Not Age
Job searching after 50 often means squeezing thirty years of work into a document built for shallow screening. The problem is not imaginary. Employers say they value experience, then quietly filter for youth signals when a resume lands in the pile. That does not mean experience stopped mattering. It means packaging matters more than it…
