The Midlife Escape Plan

Ditch the 9-to-5 Forever

Photo by Nick Fewings on Unsplash

For years, I believed in making employment better. That employees should be able to express themselves at work, that paychecks and taxes should be easier to understand, and that toxic workplaces should be a thing of the past. I wanted to help fix the system, make it more transparent, and empower employees to take control within it.

But here’s the truth: it’s not fixable.

Salaries aren’t keeping up with inflation. Retirement is increasingly a fantasy. Workplaces are too unpredictable for employees to stake their entire livelihood on. The idea that a stable job and a steady paycheck will carry us comfortably into the future? It’s a lie we’ve been sold for generations.

And for us midlifers, this realization is even more urgent. If you’re in your 40s or 50s, you don’t have the luxury of waiting for employers to “do the right thing.” It’s time to escape the hamster wheel.

Why Employees Need to Break Free

Employers are unpredictable (and indifferent to your future)

The idea that you can rely on an employer for long-term security is outdated.

• Layoffs are gutting whole industries, and company loyalty means sh*t. You could be the best, most dedicated employee in the company, and one bad quarter later, you’re “redundant”.

• Employers are optimizing for profit, not for you. Not your families, your benefits, or your well-being. Sure as hell not your freedom, or “work/life balance.”

• That means wages stay stagnant while costs rise, and your retirement plan? If your employer even offers one, it’s not their problem if it doesn’t pan out.

The only person responsible for your future is you.

Salaries are losing the battle against inflation

Even if you get a decent salary, have you noticed that it buys less and less every year? The cost of living keeps climbing, but annual raises (if you even get one) are barely keeping up. The “good job” that used to provide a middle-class lifestyle now barely covers the essentials.

If you’re not building your own income streams, you’re painting deck chairs on the Titanic - losing ground, and fast.

Retirement is a pipe dream for most

My parents retired together 2.5 years ago. They were supposed to have their golden years together.

Mom died a year ago, and now my dad stares at Fox News all day. But yay retirement, right?

Retirement used to mean working for 40 years, collecting a pension, and enjoying your golden years. Now? Pensions are almost extinct, 401(k)s are unreliable, and Social Security is a question mark.

Many people in their 40s and 50s are realizing they don’t have enough saved and never will if they stay in traditional jobs. They’re going to have to work longer, and the scariest part? Their industry may not even want them by the time they’re in their 60s.

Photo by 🇻🇪 Jose G. Ortega Castro 🇲🇽 on Unsplash

The Midlife Escape Plan

If the 9-to-5 is a sinking ship, the smartest move is to build our own sailboat. (Or fishing boat, if that’s your thing.)

Here’s how we can start transitioning out of employment and into self-sufficiency and control.

1. Shift your mindset: from employee to owner

The biggest barrier to breaking free isn’t financial—it’s mental. Most of us have spent decades being conditioned to think like employees:

• We wait for someone else to give us a paycheck.

• We expect external validation for our work.

• We trade our time for money instead of leveraging assets.

To escape, you have to start thinking like an owner. You need to see money as something you create, not something you’re given. You need to stop thinking in terms of “jobs” and start thinking in terms of systems, businesses, and assets.

2. Start a side business (without quitting yet)

If you’re in your 40s or 50s, you likely can’t just quit tomorrow—you have responsibilities. But you can start building something now that becomes your escape route.

Start with a side income stream that fits your skills:

• Freelancing (writing, consulting, design, marketing, tech, etc.)

• Coaching or teaching (leveraging your experience in a profitable way)

• Selling digital products (courses, e-books, templates)

• E-commerce or a service business (leveraging automation to scale)

The goal isn’t instant wealth—it’s to prove to yourself that you can make money without an employer. Once that switch flips, everything changes.

And you - YOU - can do this.

3. Cut dependence on a single paycheck

Financial independence isn’t just about making more money—it’s about needing less. Most employees are trapped because they’re completely dependent on one source of income (their salary). If it disappears, they’re in free fall.

To escape, start diversifying:

• Build savings so you have an emergency fund.

• Invest in income-generating assets (stocks, real estate, small businesses).

• Create multiple income streams (your side hustle, investments, and other revenue sources).

Freedom comes when losing one income source isn’t catastrophic.

4. Leverage skills you already have

You don’t have to start from scratch. You have decades of experience, knowledge, and skills—that’s an asset.

• If you’ve worked in management? People pay for leadership coaching.

• If you’re good at marketing? Businesses need consultants and copywriters.

• If you know a specific industry well? You can teach others how to break in, or how to pitch to those companies.

The fastest way to start making independent income isn’t learning something new—it’s monetizing what you already know. I

It’s never too late to learn new things, explore new possibilities. But don’t let that become procrastination from banking on the skills you’re sleeping on right now.

5. Know when to quit the 9-to-5 for good

The best exit strategy is gradual. You don’t have to take a blind leap. Be smart, you can plan it:

• Phase 1: Start a side income.

• Phase 2: Grow it until it covers your essentials (for me, this includes paying off my debts). Stay here as long as needed to ensure this income is sustainable - don’t let a seasonal fluke convince you you’re golden.

• Phase 3: Quit when your job becomes optional.

When you no longer need the job to survive, you’ve won. Even if you don’t quit, you can practice your 2-minutes-notice letter.

Photo by Austin Schmid on Unsplash

The future belongs to the self-sufficient

My parents used to fantasize about winning the lottery. All the money and time they’d have. As they got older these dreams shifted to retirement, so they reasoned they’d be more or less broke, but still have all the time in the world together.

Retirement, lottery winnings…these are both faces of magical thinking. Dreaming something is going to save us one day. One day…

But the job market isn’t getting better. Salaries aren’t suddenly going to catch up to inflation. Employers aren’t going to become more generous. If you’re waiting for conditions to improve, you’re wasting time.

The only real security comes from owning your time, skills, and income streams. For f*cks sake, bet on YOU.

Midlife is the perfect time to take control—because you have the experience, the wisdom, and the urgency to do it now.

The question isn’t if you should leave the 9-to-5 mindset behind. The question is: How soon can you start?

***What are you doing to become your own boss? Drop a comment, and let’s support each other!