For many of us, financial success is defined by “margin”—the breathing room between our income and our obligations. In 2017, my family reached a milestone that felt like the ultimate finish line: we paid off $87,000 in debt, built a six-month emergency fund, and bought our home. We were intentional, goal-driven, and, quite frankly, proud of the fortress we had built.
But life has a way of shifting the ground beneath your feet. Since that “win,” our family has grown to include three young boys—ages five, three, and nearly one. My husband faced a mass layoff just two weeks after returning from parental leave, and while he found a new role quickly, it came with a lower salary. Couple that with the relentless grind of inflation and the mounting expenses of three children, and that once-robust “extra buffer” began to evaporate.
Even with a solid foundation, the feeling of a shrinking margin can be visceral. It creates a quiet panic that whispers you aren’t doing enough. It was that whisper that led me to accept a new job—and a profound realization that led me to quit just six days later.
Understanding the “Messy Middle”
There is a specific season of life that the Money Guy Show aptly calls the “Messy Middle.” It is that grueling stretch where your financial responsibilities—mortgages, childcare, and the sheer cost of living—are at their absolute peak, yet you haven’t yet reached your peak earning years.
Even for those of us who have “done everything right,” the Messy Middle feels claustrophobic. You are no longer in the adrenaline-fueled phase of aggressive debt payoff, but you are miles away from the finish line of financial independence.
“Honestly, sometimes in this season I felt discouraged, like we’re not doing enough… [The Messy Middle] is like this season of life where you have a lot of financial responsibilities but you’re not in your peak earning years, and it can just be a stressful financial time.”
In this season, the drive to “do more” often clashes with the reality of a finite resource: our time.
The 1099 Trap: When “Flexible” Hours Aren’t Truly Free
When I applied for a remote content creator position, it looked like the perfect solution. It was a 1099 contractor role promising “flexible” hours between 5 and 20 per week. I told myself I could find an extra 10 hours.
However, the reality was a stark departure from the promise. I wasn’t starting from a place of total availability; I was already a stay-at-home mom juggling two other side hustles—social media and a virtual bookkeeping business—which I carefully managed during naps and after bedtime. My “capacity” was already a delicate ecosystem.
The new job’s training was intensive and required business-hour calls that immediately fractured our daily rhythm. Suddenly, my husband was having to take time off from his own job to handle preschool pickups because I was stuck on “unmissable” calls. To keep up, I found myself leaning on the television to babysit my children for hours at a time. I quickly realized that “flexible” work is an illusion if it requires you to be mentally and emotionally unavailable during the hours your family needs you most.
The “Play With Me” Moment: A Reality Check
The breaking point didn’t come from a spreadsheet or a budget review; it came from my five-year-old son. After a day of intensive training where I had been physically present but emotionally distant, he looked at me with a simple, heartbreaking request.
“Mom, can you just play with me? Can we play?”
When my response had to be, “Buddy, I wish I could, but I can’t because I have to do this work,” something shifted. I realized I was trading the irreplaceable present for a future that isn’t guaranteed. I was sacrificing the magic of these fleeting early years just to see a slightly higher number in a retirement account.
Money as a Tool, Not a Master
In the heat of the Messy Middle, it is easy to let money become the master of our decisions rather than the tool it was meant to be. I felt like an absolute idiot for taking the job and then quitting so quickly, but the experience was a masterclass in priority alignment.
When I look through the lens of my 70-year-old self, the perspective changes. That version of me won’t look back and wish I had squeezed in five more hours of contractor work to slightly increase a 401(k) contribution. She will, however, cherish the memory of playing on the floor with three small boys who actually wanted her attention. If the life we want to live is one where I am present for my children, then the money must serve that goal—not the other way around.
The Power of the Financial Foundation
I want to be clear: the ability to quit a job after only six days is a luxury. But it is a luxury built on the back of years of discipline. I wasn’t trapped in a misaligned job because of our “previous hard work.”
Our Financial Foundation Checklist:
- The $87k Debt Payoff: Eliminating high-interest debt years ago meant our “survival” expenses remained low.
- The Fully-Funded Emergency Fund: This safety net removed the desperation that often keeps people in toxic or ill-fitting roles.
- Consistent Investing: Even without this extra job, we were already maxing out two Roth IRAs and contributing to my husband’s 401k.
Because we had done the work early, we had the “freedom to quit.” We weren’t losing what we already had; we were simply choosing not to pursue “extra” at the cost of our peace.
Choosing Your Sacrifice
In the Messy Middle, something always has to give. You cannot maximize your income, your time with children, and your rest all at once. You have to choose your sacrifice.
For me, for this very short season, the sacrifice is the extra income. I am choosing a smaller margin and a slower path to wealth so I can soak in these years. I want to be clear that I support all paths to motherhood—I have friends who work full-time and use daycare, and I support them 100%. For them, that is the alignment that works. For me, the “best of both worlds” is my bookkeeping and social media work that truly fits into the fringes of my day.
Conclusion: A Question for the Reader
The Messy Middle is temporary. In two short years, my youngest will be in preschool, and the “margin” of my time will naturally expand. But until then, I am giving myself permission to move at a walk instead of a sprint.
As you navigate your own financial journey, I encourage you to look past the spreadsheets and ask yourself, “What am I currently sacrificing in the pursuit of ‘more,’ and is it a trade my future self will thank me for?”
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