The Unfireables - Jason Weiland

04/08/2026

𝗠𝗲𝗲𝘁 𝗧𝗼𝗼𝗹𝗶𝗲: 𝗙𝗿𝗼𝗺 𝗖𝗹𝗮𝘀𝘀𝗶𝗰𝗮𝗹 𝗠𝘂𝘀𝗶𝗰𝗶𝗮𝗻 𝘁𝗼 𝗠𝗶𝗰𝗿𝗼𝘀𝗼𝗳𝘁 𝘁𝗼 𝗕𝘂𝗶𝗹𝗱𝗶𝗻𝗴 𝗛𝗮𝗽𝗽𝘆 𝗛𝘂𝗺𝗮𝗻𝘀.

Most people don't go from concert halls to coding. Toolie did.

She wasn't born a geek. She was a classical musician. Working on computers was her day job until Microsoft recruited her. Ten years there. Then 9 years running her own business. Then back to corporate: Agile contracts with Boeing, Amazon, Disney, Expedia, Starbucks, JPMorganChase.

Then 2025 hit. Laid off.

"I've been secretly wanting to return to entrepreneurship for years but didn't have the financial cushion. Well, so much for that plan! Being laid off pushed me back into it whether I was ready or not."

Sound familiar?

𝗛𝗲𝗿𝗲'𝘀 𝘄𝗵𝗮𝘁 𝗺𝗮𝗸𝗲𝘀 𝗧𝗼𝗼𝗹𝗶𝗲 𝗱𝗶𝗳𝗳𝗲𝗿𝗲𝗻𝘁:

After 14 years in Agile software development, she noticed what's broken. Nobody trains the people who actually lead the teams — Scrum Masters, Kanban Managers, Product Owners. They lead by influence, not authority. Way harder. Nobody teaches them how.

So Toolie's building what's missing.

𝗪𝗵𝗮𝘁 𝘀𝗵𝗲'𝘀 𝗰𝗿𝗲𝗮𝘁𝗶𝗻𝗴:

YouTube videos teaching Agile leadership. A mentorship program for Agile leaders working alone in their companies. A free chat community for real-time help. Certification classes teaching Agile practices that actually work.

𝗛𝗲𝗿 𝗺𝗼𝘁𝘁𝗼: "𝗛𝗮𝗽𝗽𝘆 𝗛𝘂𝗺𝗮𝗻𝘀 == 𝗕𝗲𝘁𝘁𝗲𝗿 𝗦𝗼𝗳𝘁𝘄𝗮𝗿𝗲™"

While everyone obsesses over AI, Toolie focuses on the humans writing the code. Because if developers aren't empowered to push back when things aren't working, they'll produce crap whether they're using AI or not.

𝗪𝗵𝘆 𝘀𝗵𝗲'𝘀 𝗶𝗻 𝗢𝘃𝗲𝗿 𝟰𝟬 𝗮𝗻𝗱 𝗨𝗻𝗲𝗺𝗽𝗹𝗼𝘆𝗲𝗱:

"The Community provides accountability and the chance to share information that benefits everyone. It's not the kind of accountability that makes you feel guilty, you feel uplifted when things don't happen as expected."

And this: "Entrepreneurship is really a combination of zig-zags and sidesteps before you achieve a rhythm that propels you forward. The Community and Jason's coaching help you find that rhythm."

Toolie® Merchant, SPOC®, SMC®, SAMC®, SCT®, SAC® gets it. Entrepreneurship is scrappy. It's building something because the system pushed you out whether you were ready or not.

Welcome to the community, Toolie.

— Jason

𝗧𝗼𝗼𝗹𝗶𝗲'𝘀 𝗟𝗶𝗻𝗸𝘀:
Certification: https://www.remotescrumstudy.com
Chat & Support: https://www.practicalscrum.com
Corporate Agile: https://www.rsscorporateagile.com
Leadership Content: https://www.youtube.com/

𝗝𝗼𝗶𝗻 𝘁𝗵𝗲 𝗰𝗼𝗺𝗺𝘂𝗻𝗶𝘁𝘆 𝗲𝘃𝗲𝗿𝘆𝗼𝗻𝗲 𝗶𝘀 𝘁𝗮𝗹𝗸𝗶𝗻𝗴 𝗮𝗯𝗼𝘂𝘁. 𝗜𝘁'𝘀 𝗳𝗿𝗲𝗲!
https://www.skool.com/second-act-ai-3035/about

04/01/2026

I sent over 800 job applications.

No offers. No callbacks. A lot of silence.

I'm 57. By every measure the job market uses, I'm done.
Except I'm not.

We started Over 40 and Unemployed because we needed a place for people like us. Not a job board. Not a networking group full of toxic positivity and resume tips that don't work. A real place.

Where you can say "I've sent 300 applications and I'm losing my mind" and someone actually gets it.

We have almost a thousand members on Skool right now. People building freelance businesses, monetizing their writing, landing consulting clients, making their first dollars outside traditional employment. People who were written off. Building anyway.

This page is an extension of that. A place to share what's working, what's not, and what the job market will never tell you about your own worth.

And there's something else coming.

Something bigger than a community. Bigger than a course. A movement for workers the system forgot. People who've been employees their whole lives and now need to be more.

It's called The Unfireables.

I'm not ready to say everything yet. But it's coming. And if you've been shut out, written off, or told you're overqualified one more time this year — it's for you.

For now: follow this page. Join the free community: https://www.skool.com/second-act-ai-3035/about. And if you've sent 100+ applications with nothing to show for it, drop a number in the comments.

Let's see how many of us are out here.

03/26/2026

Read it on Substack:

https://jasonweiland.substack.com/p/the-unfireables-why-im-building-a

03/25/2026

Become...

04/27/2025

Starting over after 40 isn’t a setback. It’s a strategic advantage.

I’m seeing more and more professionals walk away from careers that no longer fit — and step into businesses, projects, and creative work that actually matter to them.

They’re not crazy.
They’re not reckless.
They’re ready.

Because after 20, 30, 40 years of experience, you know exactly what deserves your time and energy.

🔥 You spot distractions faster.
🔥 You choose wisely.
🔥 You create with purpose.

If you’re thinking about a second act, you're not behind.
You're right on schedule.

This week’s Second Act Letter dives into why starting something new after 40, 50, or 60 might be the smartest move you’ll ever make.

➔ [Read the Sunday edition here]
https://jason-weiland.beehiiv.com/p/starting-over-at-40-or-50-or-60-isn-t-crazy-it-s-courageous
➔ [And if you believe second acts deserve support, check out the Second Act AI Indiegogo here]
https://igg.me/at/secondact/x/32741061 #/

Your next chapter isn’t waiting for permission.
It’s already inside you.

Sometimes all we need is a little boost

04/26/2025

You're not too old. You're just getting started.

I've been thinking a lot lately about how we treat aging — and how wrong so many of those old ideas are.

They told us success had an expiration date.
That if you didn't "make it" young, you missed your chance.

But the truth is... some of the greatest success stories happened later in life:

🌟 Colonel Sanders founded KFC in his 60s.
🌟 Dara Torres won Olympic medals in her 40s.
🌟 Eddie Brocklesby completed an Ironman at 74!

They didn't stop. They didn’t give up.
They started again, stronger than ever.

And so can we.

I wrote about this in my latest article:
Age Is Just a Number: Embracing Success at Any Stage of Life
https://medium.com//age-is-just-a-number-embracing-success-at-any-stage-of-life-506720c08ad7?sk=4620f8fdc0b7531a6c710a62c98f5a78

I hope it reminds you that your next chapter can be your best yet.

If this resonates with you, I’d love for you to also check out the project I’m building — Second Act AI, a creative companion designed to help people rediscover their voice and build their second act with confidence.
👉 Support Second Act AI on Indiegogo
https://igg.me/at/secondact/x/32741061 #/

Thanks for being here. Let’s keep dreaming. 🖋️✨

Redefining Aging and Unlocking Potential Beyond the Conventional Timeline

04/22/2025

I used to think a longer to-do list meant I was getting closer to my dreams.
Turns out, all it did was pull me further away from myself.

✅ More tasks.
✅ More hustle.
✅ Less clarity.
✅ Less joy.

When I finally started my second act, I didn’t need another list.
I needed a new story.

Second Act AI is built for those of us ready to stop measuring life in checkboxes — and start creating something meaningful.

Not faster.
Not bigger.
More true.

💬 If that resonates with you, I’d love for you to join me:
https://igg.me/at/secondact/x/32741061 #/

04/19/2025

✨ It's never too late to chase the life you dreamed about. ✨

I'm building something special for all the late bloomers, second chancers, and dreamers who still have stories left to tell — even if life got in the way for a while.

It's called Second Act AI — a creative companion built for writers, founders, artists, and anyone ready to start their next chapter.

Not to replace your creativity, but to walk beside you as you build something meaningful.

🎯 Organize your goals
🎯 Capture your ideas
🎯 Get encouragement when you need it most

If that sounds like something the world needs, I’d be honored if you checked out the project — and maybe even helped us bring it to life.

👉 igg.me/at/secondact/x/32741061 #/

Let's show the world that second acts are just getting started. ❤️

04/18/2025

🌟 Your Story Isn’t Over — It’s Just Getting Good. 🌟

Introducing Second Act AI — a creative companion for dreamers, writers, founders, and late bloomers.

Whether you're starting a new business, writing your first book, or simply ready to chase a long-held dream, Second Act AI is built to support your next chapter — not replace your creativity.

✅ Stay organized
✅ Capture your best ideas
✅ Get a little encouragement when you need it most

Because it’s not too late.
It’s your time.

👉 Join the movement: https://igg.me/at/secondact/x/32741061 #/

Let’s build your second act together.

07/12/2024

Sometimes, I like to send questions out to my network, for things that stump me, hoping I can get some insight from people who may have been in a similar situation.

I'm worried about my health.

When I couldn't control my mind, because of severe mental illness, I did something to change it and now I live a much better life.

While searching for meaning in my life, I returned to God, and now I see hope where I only saw pain and uncertainty before.

I know I need to fix my health situation. I have heart problems, diabetes, HBP, and neuropathy, and I'm overweight and unhealthy.

I try like I did when I started the plant-based diet, but nothing ever sticks and still I gain weight. Part of it is the medication I take, but the other huge part could be controlled if I put the work in.

I thought the heart attack would shock me into changing my health, but it didn't. I feel like I am being given a chance for a full life but I am destroying it because I am too weak to do something about my health.

I want to travel, explore entrepreneurship, and figure out my own ways that I can serve God and do some good in this world, but if I don't get my health in order, I am going to die early.

For those of you who have made great health changes in your life, what was the thing that was the impetus? What got you started? You would think impending death would do it for me, but still, I put off what can be done today.

The more weight I gain, the more hopeless I become.

Do you have any advice?

06/12/2024

My first blog post published on Quicken . Many more are coming. I worked hard to get a byline on Quicken.com, but here I am!

https://www.quicken.com/blog/market-research-on-a-shoestring-budget/

Raise your market research game without breaking the bank.

06/10/2024

I wake in the morning with the realization that I have so much love in my life.

It's time for me to step up and find some balance, to show my family that I can be the person they need.

I need my wife to see that I am better than the man she married

In times like these, alone, I pray and everything feels right in the universe.

Just right...