The resume‑carousel plus humiliation‑interview circuit almost broke me once. I have zero appetite to climb back on in 2025.

I have it good!

Right now I write money and finance blog posts for Quicken. It’s corporate fruit at its ripest.

My manager always tells me to look out for my family first. Work/life balance is a huge thing.

And although I mostly only interact with my boss, the times I have met my colleagues have been brilliant. Truly great people who know they have a great gig.

Nobody worships the little red notification bubble; deep work wins the day.

If they dangled a permanent position tomorrow, I’d sign before the DocuSign animation finished.

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.

Job‑Hunting in 2025: A Quick Tour of the Haunted House

Open LinkedIn. Five minutes, tops. You’ll spot stories like these:

• A friend completes eight video interviews, meets every stakeholder, then vanishes into recruiter silence. The technical term is ghosting and 77 % of applicants report it happened to them last year (Greenhouse Survey, 2024).
• A “remote admin” listing promises $45 k and flexible hours. Onboarding involves forwarding cash through crypto exchanges. The FBI says work‑from‑home scams doubled between 2023 and 2024.
• A sixty‑one‑year‑old CMO shows screenshots of polite rejections: “over‑qualified,” “might not have the energy our startup culture needs.” Translation: age bias. AARP’s 2024 report found workers over 55 stay unemployed 32 % longer than younger peers.

That carnival is brutal enough when you’re 30. I refuse to audition at 60.

The Backup That Doubles as a Lifeline

Here’s the quiet engineering happening behind my webcam:

First: I squeeze every drop of learning from Quicken — AI prompt craft, behavior‑driven content and marketing, SEO that treats readers like humans and LLMs like the authority. I learn more there every day than I have in my last 5 years combined.

Second: Each paycheck fertilizers Second Act Media, the creative business I am building with a few streams of income ready to go. One invoice buys a better analytics tool; another pays for ChatGPT so I can stay at the top of my game.

Third: I’m weaving three slender revenue streams into one strong rope — an expat newsletter and podcast, a bite‑size SaaS called Two Wallets that compares cross‑border banking fees, and an authority-driven blog for people starting a second act in life.

If my boss ever types, “Jason, quick chat?” and it’s that chat, adrenaline will spike — panic won’t.

Why I Drew a Red Line at 57

Fifty‑seven is the twilight zone (I’ll reach it in a few months): too old for bro‑culture startups that call themselves a “family” but only adopt siblings under 35, and too young for Social Security to pick up the tab. I promised myself three things before that birthday:

No ATS (Applicant Tracking System) roulette. Ninety‑seven percent of Fortune 500 companies filter résumés with algorithms (Jobscan, 2024). I’d rather invoice a client than beg an algorithm.

No ageism worries. If a hiring manager craves TikTok‑dancing talent, I’ll be recording a calm podcast from a beach in Iloilo.

No hobby business. Real profit‑and‑loss, real cash flow, a moat deep enough that even recession alligators can’t cross.

What the Grind Actually Looks Like

Most “mornings” start at 4:00 p.m. (I work overnights). I draft for a few hours and schedule LinkedIn posts while my family debates what they want for dinner.

Coffee. The house is loud and chaotic.

Then Quicken hours, starting at 8pm, focused and clean.

Each month I force‑feed myself one micro‑skill.

June: I’m learning more about Quicken’s suite of apps, so I can be a better employee and so I know how to manage my own finances. July: Building an international business without setting my wallet on fire. August is penciled for advanced prompt engineering because ChatGPT isn’t going away.

Every 30 days I run a dry‑run layoff. I imagine the salary disappearing overnight. Which subscriptions die today? Which client can I upsell tomorrow? It’s morbid — and clarifying.

Forty‑five percent of my net income slides into an emergency fund. Six months of life costs is the basement. Ten months is the penthouse view.

Medication and a three‑mile evening walk keep the engine cool. Burnout has vaporized more dreams than bad strategy ever did.

The Shadow Side of a Plan B

A side hustle can become a jealous lover, whispering during family dinner and poking you awake at 2 p.m. when you are trying to sleep the overnight off.

I guard against that by working overnight hours for Quicken like it’s the only gig on earth and doing side‑projects in strict windows.

Quicken is my lifeblood, but these businesses I start as side-gigs are the future.

If You’re Job‑Hunting, Tattoo This Somewhere Visible

Companies ghost because it’s cheap. Recruiters lowball older candidates because churn pads their numbers. The ATS is working exactly as designed, screening humans so other humans don’t have to.

None of that nonsense measures your worth.

While you fire off applications, reserve ten weekly hours to build something you own. A newsletter. An Etsy shop. A Discord server where ninth‑graders learn Python.

It may never pay the rent, but it will pay dignity, and dignity travels well.

Viral Takeaway (Short Enough to Screenshot)

Hire yourself before someone else doesn’t.

Even the juiciest corporate peach can bruise overnight, and the job market will gladly hand you the bill for its broken machinery.

Accountability Corner

By the end of Q4, my newsletter and podcast will already be generating sponsorships. When 57 rolls around, HR’s “We’re restructuring” should sound like elevator music in another building.

If Quicken keeps me? Fantastic — I’ll bring donuts to the office when I go in for the next meeting. If they let me go? Even juicier material for the memoir.

Either way, the plan works — because it’s mine