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.

The Schedule That’s Keeping My Second Act Alive

People ask me how I manage it all. Job, projects, writing, life.

The truth? I don’t always.

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.

Here’s what a typical day looks like:

8PM — 5AM: I work my full-time contract job.

It’s overnight. It pays the bills. It’s not glamorous, but it’s consistent. And right now, that consistency is the foundation everything else is built on. When I clock in, I try to stay present. I put in the work. But as I’m doing it, a part of me is always thinking about what I’ll build when I’m off the clock.

5AM — 8AM: I write.

This is my creative window. The rest of the world is asleep. It’s quiet. My brain is tired but oddly clear. This is when I write essays, draft social content, and publish blog posts. Not because I have a huge audience, but because I have something to say, and writing keeps me alive.

AI helps me here. I bounce ideas off ChatGPT and Claude. I brainstorm structure, rewrite hooks, and talk through blocks. Not because I can’t write without them, but because they help me write faster, and sometimes better. I still edit every word. But the support matters.

It’s still my own voice. My own blood on the page.

8AM — 2PM: I sleep.

This is the hardest part to protect. Life doesn’t stop because I work nights. The world doesn’t care that I just went to bed. There are knocks at the door, deliveries, noise. But I try. I use blackout curtains. I silence my phone. Because without sleep, I fall apart.

2PM — 6PM: Family time, errands, real life.

This window belongs to the people I love. My kids. My wife. My real world. We shop, talk, handle logistics, exist together. I’m not always energetic. But I show up. I’ve missed too many years of connection already.

6PM — 8PM: I build.

This is the sacred window. Just two hours to work on whatever project I’m bringing to life. A newsletter system. A SaaS tool. A piece of my second act. I don’t scroll. I don’t waste it. I focus. Deep work is key.

And then I go to work again.

The Truth About This Schedule

It’s brutal. Let’s not sugarcoat it.

I’m tired. I don’t rest enough. I don’t have much space for fun. There’s no Netflix bingeing. No weekend getaways. No long walks just for the hell of it.

But there’s movement. There’s purpose.

This schedule is keeping my second act alive.

I don’t get balance. I get momentum. I get shit done. I get small wins. I get a little closer to freedom each week.

Some people wake up at 5AM to build.
Some people quit their jobs to go full-time.

That’s not my story. I’m building in the cracks. In the in-between. In the hours most people don’t see.

Because I’ve already had one heart attack. Because I lost decades to mental illness. Because I’ve had enough of letting time slip through my fingers.

What Keeps Me Going

  • The idea that I can build something that lasts.
  • The thought that maybe I’m not too late.
  • The knowledge that I’m showing my kids what persistence looks like.
  • The community I’m slowly finding, other people building, burning out, and still trying.

And yes, there’s hope in the tools.
AI helps me work faster. Not because I want shortcuts, but because my time is limited. My energy is finite. I’ll use whatever helps me make it count.

If You’re in This Too

If you’re building something after hours, f your calendar looks like chaos and your goals feel miles away, I see you.

You’re not doing it wrong. You’re just doing it real.

This path isn’t easy, but it’s worth it.

Some days I fall behind. Some days I question everything. But I keep showing up. One hour at a time. One post. One tool. One page.

Because I believe in the thing I’m building.
And I believe in who I’m becoming as I build it.

You don’t need a perfect schedule.
You just need a reason.

And this is mine.


Jason Weiland - Quicken | LinkedIn
I’m a late bloomer, and I’ve never felt more in bloom. After decades of wrestling… · Experience: Quicken · Location: Tucson · 500+ connections on LinkedIn. View Jason Weiland’s profile on LinkedIn, a professional community of 1 billion members.