Jason Weiland
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business

A collection of 4 posts
When Life Shifts: My Second Act and the Search for Collaboration
jobs

When Life Shifts: My Second Act and the Search for Collaboration

I’ve been freelancing off and on for more than 20 years. In that time, I’ve written about everything from mental health and finance to technology, expat living, and business strategy.
20 Aug 2025 4 min read
Dear Job Market: please lose my number
business

Dear Job Market: please lose my number

Yet, at 56, I’m old enough to hear the trapdoor click somewhere under my rolling chair. I want the next five years (or however long they’ll have me) to feel luxurious without pretending the hatch isn’t there.
10 Jun 2025 4 min read
The Schedule That’s Keeping My Second Act Alive
business

The Schedule That’s Keeping My Second Act Alive

But I do what I can, because I’m trying to build a second act that actually matters. I’m trying to be financially successful by 60. Not just for the internet. Not for clout. But for me. For my family. For the version of myself that almost gave up.
28 May 2025 4 min read
Building a Business at Midnight
Second Act

Building a Business at Midnight

I finish work when most people are waking up. And then I try to quick-change from “employee mode” to “founder mode.” Some days, I manage a little. Other days, I crash and burn.
22 May 2025 3 min read
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