I Made Over $56K A Month Working 4 Tech Jobs – Then I Walked Away

Originally published by Mike Westbrooks on Medium.

“I didn’t get into tech to make money. I got into tech to learn how to build and design my freedom. The money came when I realized I could build for myself.”

Before the Breakthrough: Learning Over Luxury

Before I ever saw $56,000 in a single month, I was just a young man with a marketing degree from Morehouse College and a stubborn belief that I could teach myself how to build apps. I didn’t come from a CS program. I didn’t have a mentor in Silicon Valley. What I had was curiosity, Udemy, and a daughter who would one day ask me what I did with my shot.

Before I ever stepped into a Fortune 500 office, I started building for people around me. So I launched my own company — RedRooster Technologies — focused on helping small businesses turn napkin ideas into real products. I didn’t have funding or a big team. I had questions, code, and a drive to figure things out.

Some of my first clients were local. A valet trash startup called Tydee. A bidding app for a fashion influencer. Then came bigger names — a travel agency project for a well-known actor from the Fast & Furious franchise, and eventually, Cox Communications, known for TechStars and Kelley Blue Book.

RedRooster became my personal bootcamp. I learned how to ship fast, break things, fix them, and move on. Every build made me sharper. Every failure made me faster. But at some point, I knew I needed something more. To grow in this career and become the best, I needed to learn how the best teams in the world build — at scale, with process, with polish.

I sought the answer to these questions:

• How do the best teams in the world build?
• How do you fit into a system that big?
• And how do you take those lessons and one day build your own?

So in 2019, I joined a major airlines as a junior iOS engineer. Later, I landed at one of the largest tech companies in the world and built apps that landed on their biggest stage at major conference for dreams they host every year— not through some perfect resume, but through grit and growth.

Back then, I wasn’t chasing money. I was chasing mastery.

At the time, I was living at home with my daughter, my parents, my brother, and two dogs — under one roof in the suburbs north of Atlanta. Financially, I was fine. I wasn’t trying to ball out. I was trying to become dangerous.

Then Came the Pandemic — and the Window Opened

COVID hit, and the world shifted.

Companies were scrambling to go digital. Remote work became normal overnight. Roles started popping up everywhere — and staying open longer. Recruiters were reaching out like clockwork.

And I started to wonder…

“What if I didn’t just take one of these jobs… what if I took two?”

That curiosity turned into action.

I was already working remotely at one company. So I accepted a second full-time offer from a multinational financial technology company — both teams based on the West Coast. The hours didn’t conflict much. They were both in iOS but executed differently. My performance didn’t suffer. And the income? It doubled.

That experiment opened the floodgates and soon after, I started stacking:

• Full-time roles at the tech company, the financial technology company, a short stint with an electric vehicle (EV) charging and media company, I spun the block back at one of my first roles, and had a 2 year run at a now public company specializing in family safety and connection services.
• I also sprinkled in a 3 year contract with another major fin company, a mid-west based grocery chain, a bank that actually provided my loan for my car, and then the company with whom I purchased that vehicle from. (Thinking about it now, that was very crazy).

Each job had its own hardware. Its own time zone. Its own system.

And I became the system.

I Built a Control Room — Not a Desk

My setup looked like something out of NASA.

• Laptops were grouped by time zone: East Coast, Central, and West
• Monitors stacked. Chairs positioned. Devices always on.
• Headphones in both ears, plus Bluetooth on top — so I could juggle up to three meetings at once
• Status lights green across platforms. Screens active. Calendars synchronized by instinct.

It was intentionally designed and curated for success in my endeavors at the time. I wanted a clean system that facilitated the context switching while also supporting flexibility. For me, it wasn’t chaos. It was choreography; it was a beautiful mess.

At any given time I was doing 4 roles. The kicker was that I was still receiving interview requests and as I was deciding if a role was no longer serving my end goal, would I actually explore the opportunity.

When determining what to add or swap out, I had a very strict set of requirements and if the role didn’t align with some of the criteria — fully remote, time-zone balanced, Swift-based, and high-paying — I passed on it. Every job had to fit the machine I was maintaining.

This wasn’t about getting rich quick. It was about becoming impossible to ignore.

Hitting $56K/Month: What It Felt Like

The moment I crossed $30K/month, I got serious — bought life insurance, set up Stash, dabbled in Fundrise, Masterworks and more. I wasn’t a financial wizard, but I was trying to be responsible.

However, when I hit $50K/month, I got emotional and my mindset shifted. I bought things. I went out more. I felt lighter. One of my most fondest memories was for my 33rd birthday, I flew my mom, aunt, brother and 6 of my closest friends to Vegas — all lodging, dining, leisure expenses paid.

“Don’t worry about a thing. I got the rooms. I got the dinners. I got the parties. Just show up.”

That trip cost nearly $30k. And I smiled the whole time. Because it meant more than money. It meant I had become the person I used to dream about being — someone who could not only earn, but share.

Someone who could give freely. Move freely. Live fully.

But Then… Burnout Came For Me

At first, I stayed ahead of burnout by moving. Going out. Treating myself. Treating others. Gym at 5AM. Focus blocks from 2PM to midnight.

But by mid-2024… I started fading.

• My attention slipped.
• My work ethic cracked.
• I showed up to meetings, but not presently.
• I stopped being excited about the next sprint and started dreaming about my next step.

“If I can do this for other people’s companies… I can do this for myself.”

So in October 2024, I did the unthinkable. I walked away. From every job. Every paycheck. Every laptop.

The Pivot: Building My Way Forward

When I stepped away from those roles, I didn’t do it with bitterness. I did it with gratitude. Because the truth is, I didn’t get here alone. From my parents who gave me a place to regroup and rebuild…

To my daughter who reminded me what this is all really for…

To every mentor, recruiter, teammate, and friend who opened a door or offered encouragement when I needed it most…

I’m here because people showed up for me.

So this next chapter? It’s not about proving anything. It’s about giving back and betting on myself. It’s about turning my experience into something useful — something that helps others who are trying to figure it out the same way I once was.

One of the ways I’m doing that is through a platform I’m quietly building called RezuMate — a space designed to help people tell their stories, close their skill gaps, and step into careers they might’ve thought were out of reach. I modeled the system after the system I used in 2023 to aquire the last 3 full-time roles.

But honestly, whether it’s through tech or a conversation, my mission is simple:

Use what I’ve learned to make someone else’s path a little clearer.

Because if there’s one thing I’ve learned from all of this — it’s that success hits different when you share it.

If You’re Still Reading…

Let me leave you with this:

You don’t need permission. You just need a plan.

If you’ve got hunger, clarity, and the willingness to work, you can build a version of success that’s yours. Maybe it’s not $56K/month. Maybe it’s $5K/month with time freedom. Maybe it’s a product you believe in. Maybe it’s the ability to fly your family out and cover everything — just because you can.

Whatever it is:

✅ Get clear on it

✅ Align your decisions

✅ And don’t let anyone tell you it’s not possible

Because I did it.

And now I’m doing it again — this time, for me.

Originally published by Mike Westbrooks on Medium.