Second Act - Jason Weiland

Jason Weiland

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Second Act

A collection of 11 posts

The Schedule That’s Keeping My Second Act Alive

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.

Building a Business at Midnight

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.

Your Second Act Won’t Be Handed to You — You Have to Build It

Your Second Act Won’t Be Handed to You — You Have to Build It

Building your second act means getting your hands dirty. It means taking drastic action, trying things that might not work, learning new skills, and being willing to start small and imperfect.

You’re Not Overwhelmed — You’re Under-Supported

You’re Not Overwhelmed — You’re Under-Supported

I’d written prolifically for so many years, but somewhere along the way, between 20-page essays and programming classes, I lost my will to write. It wasn’t that I didn’t have anything to say, it was that my voice got lost in the shuffle.

Second Chances Aren’t Given — They’re Taken

Second Chances Aren’t Given — They’re Taken

For too long, I kept waiting for my life to restart itself. I thought there would be a sign, a shift, something external that would shake me awake. But the truth is, there was no sign. Just silence. And eventually, I realized nothing was going to change unless I did.

The Tool I Wish I Had When I Started Over at 42

The Tool I Wish I Had When I Started Over at 42

For weeks, I had barely left my bed. Depression hung over me like a wet blanket. The silence in my apartment was deafening. I was sleeping too much, eating too little, and telling myself I was just “resting.” But I was unraveling.

You Don’t Have to Know the Whole Plan — Just the Next Step

You Don’t Have to Know the Whole Plan — Just the Next Step

We’re told these days that we can’t start anything unless we’ve got a polished five-year plan, a business strategy, or some perfect vision. I bought into that for way too long. I held off on dreams because I thought I wasn’t ready.

AI Isn’t Replacing My Voice — It’s Helping Me Find It

AI Isn’t Replacing My Voice — It’s Helping Me Find It

There’s this unspoken stereotype floating around the tech world: that if you’re over 50, you don’t “get it.” You’re too old to understand AI, not adaptable enough to use the tools shaping the future.

Late Bloomers Don’t Need Permission — But Here’s Mine Anyway

Late Bloomers Don’t Need Permission — But Here’s Mine Anyway

Somewhere around 50, many of us start to believe the lie that our best years are behind us. The body aches more. The afternoon nap isn’t a luxury, it’s a survival tactic. And suddenly, those voices whispering “Great things only happen in youth” start sounding more convincing.

A Life That Took Its Time: Notes from a Late Bloomer

A Life That Took Its Time: Notes from a Late Bloomer

From a young age, I was told college wasn’t meant for me. God had a different plan, and higher education would only fill my head with “worldly” ideas. If I wanted college, I’d have to betray the very beliefs I was raised on, and figure it out alone.

From Voice to Page: How AI Helped Me Remember How to Write Again After 50

From Voice to Page: How AI Helped Me Remember How to Write Again After 50

Eventually, I stopped writing for fun. I stopped starting anything. I let go of entrepreneurial dreams. I abandoned Medium, Substack, even my personal journals — except for a few hastily scribbled notes.