I Quit My Six-Figure Job to Live the 90/10 Life

It was February 29th, 2016. Leap Day. I did not know it that morning, but it was the day I finally took the leap I had been circling for over a year. This is the real story behind the 90/10 Life - not the highlight reel, the actual one - and why I walked away from the best job I ever had.

At the time I was a project manager for one of the most valuable brands in the world. The work was challenging and genuinely rewarding. I am wired for high-stress roles - there is something magical about walking into a hopeless situation and turning it into a win, and I got to do that a lot. In 2012 I had packed up my life and my seven-months-pregnant wife and moved to uncharted territory outside Portland, Oregon to manage projects across five states in the Pacific Northwest. Honestly? I loved it. If the events I am about to describe had not stacked up the way they did, I might still be doing it today.

The Side Project That Became a Company

I am an overachiever, and I have always been hungry to grow in every direction at once. I was named one of the top five project managers in the company nationwide in 2013, and again every single month through the first quarter of 2014. But even working ten-plus hour days for my career, I had a hobby that most people would call a second job: I built virtual teams for fun.

Some people play video games or join a league. For me it was project management. I would spend two or three hours a night on freelance platforms, hiring people to help with my own side projects, charging ten to fifteen dollars an hour and experimenting with how to deliver great work at a profit. I learned fast that pure freelancers were rough to work with - the second a project ended, they were gone. So I started building my own team. Social media management first, then web design, and then I found the real sweet spot: virtual sales assistants. Most quality sales operations paid account managers six figures, and then watched them waste their most expensive hours on the lowest-value task in the job - finding leads.

I stepped into that gap and landed contracts in 2014 on four-to-six-thousand-dollar retainers, which let me triple my team. The wild part was how little of my time it took. On my "vacation" from work I flew to the Philippines and trained the team to manage themselves. To this day they do not have a manager. They are self-managed, onboarded with a standard operating procedure for every role. Clients have flown from the US to our Philippines office to build SOPs with me and fine-tune the team. It ran without me. That was the point.

Then Life Threw Everything At Once

Things were smooth, and then they were not. My father found a softball-sized tumor in his abdomen. He was in his mid-fifties. It turned out to be late-stage lymphoma that had spread through several lymph nodes and into his chest. Around the same time, my grandfather got sick - he lost over a hundred pounds and was getting blood transfusions almost daily. We all knew he did not have much time.

My marriage was strained, held together mostly by our young son, who barely knew his extended family because we lived hundreds of miles away. And right as all of this hit, I got "promoted" to Project Manager III. Except it was a reclassification, not a raise. Same five states, now also mentoring the rookie PMs, with the extra work landing outside my paid hours.

Then, just before Christmas, my wife and I learned she was pregnant again. We were thrilled. We built a little snowman family in the yard - her, me, our son, and a small snowman baby - and sent it out as our holiday card. A week later, around nine weeks in, we lost the baby. The congratulations were still rolling in on Facebook while I quietly took the photo down and messaged people to explain. For weeks afterward, word kept reaching folks who had not heard, and the congratulations kept coming. It gutted my wife. I spent weeks doing damage control while traveling so much that her mother had to take emergency leave to be there, because I had business obligations and no one to cover for me. I had asked to relocate to California to be near family three separate times. Each request was denied, because there was no one to replace me.

From 8 PM to 3 AM, Finger Over the Send Button

I remember writing the resignation letter. It had to be perfect. It had to thank the people I loved and respected, show grace and gratitude for every opportunity I had been given, and stay respectful even though I felt undervalued and unappreciated after running an entire region through turnover after turnover. I went through eight managers in four years there. I trained eight project managers, and only three stuck it out.

So there I was, torn between the best job I had ever had and the worst feeling of not being there for my family. I hovered over that send button for hours - from eight at night until three in the morning. Broken and excited and crying and laughing all at once. My wife reassured me that we could not keep doing this to ourselves. I thought about the people I would miss most: Wally, a mentor who had my back from my first interview onward. The two Jims, who talked me into the role and showed me the ropes. And Shannon, my tag-team partner who planned nearly every project with me, sometimes from the library on a Sunday because she was getting worked to the bone too. Those people were the hardest part to leave.

The Freedom to Do Both

I hit send. I quit because I had to start valuing my time the way my employer no longer did, and because it let me move back near my grandfather and the rest of my family. I could not sleep that night, imagining what people would say about the one who had toughed it all out finally walking away. But I also knew something else was calling me. I had managed enormous teams in the corporate world and proven I could build my own on the side. Everything I did inside that company - the systems, the delegation, the SOPs - could be taught to anyone who genuinely wanted to build a business and get their life back.

That is what the 90/10 Life actually means. It is not just golf and travel, though that can be someone's 10%. It is working from home, or anywhere, and having your kid wander in to ask if you are meeting with clients today. We moved back just a few months before my grandfather passed. If I had not taken that action, I would never have gotten that time. I got to truly say goodbye to him, and to be there for my dad through his cancer the same year. After those final months, I left for the Philippines with my family to go build the thing my grandfather always believed I could.

You Do Not Leap Blind

You have seen the ads that tell you to just jump off the cliff and it will all work out. I am here to tell you the opposite. Taking a leap of faith does not mean skipping the part where you study how to land. It means honestly examining the talents and systems you actually have faith in, and building a net before you jump. I had spent four years building mine without fully realizing it.

When the accountant handed me my numbers later, the headline for 2016 wrote itself: I had built a virtual army that made me over five thousand dollars a week and left a six-figure day job to travel the world with my family. That virtual army became VA Staffer. Years later, when ChatGPT arrived, I flew back to the Philippines and retrained that same team into AI Operators - which is a whole other story I tell in Yes, AI Will Steal Your VA Job. The tools changed. The principle did not.

That is the system I have spent the years since teaching. If you want the framework underneath the story - how to find your 10% and offload the rest - read the 90/10 Rule. The leap is real, but it is not a gamble when you build the thing that catches you first.