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My Whole Life Actually Did Prepare Me For This

  • Writer: Olivia Allen
    Olivia Allen
  • Apr 29
  • 3 min read

I was told your whole life prepares you for the very moment you're in. Sitting here, I'm realizing how all the pieces of mine actually did come together.


Like when I was little, I would pretend to be the hotel front desk agent. Or an airport ticket counter rep. Or store clerk. Or when I would go to my mom's work with her and I'd pretend to be the office manager. Or sometimes her.


I watched closely. Learned quietly. And fell in love with the idea of building something of my own.


I was offered 3 options after high school: go to college, start a business, or go to work on my own. Funny, I ended up doing all 3.


I went to college. My major was preparing me to be an actuary. I was good at math. I wasn't ready. Apparently I still had adventuring yet to do.


I worked in the restaurant industry and fell in love with food, but mostly the people. I managed the most prestigious inn in Princeton — serving a full range of cultures and economic statuses, from the maids to the wealthy, ambassadors and dignitaries from other countries. I learned so much about what it meant to deliver good, honest, well-intentioned hospitality. For guests. For my staff. Even for the owners. Until they didn't want that kind of management anymore. The good kind that served people. I could no longer sacrifice the integrity of a staff that daily delivered excellence and memorable experiences — for less cost, less care, less respect.


I wasn't let go. I quit.


I left there to become a financial advisor. I got my licenses (life/health, Series 7 & 66) and gave it 1000%. Yet I struggled, because of the pressure to meet sales quotas with no real structure to care for the accounts I was bringing on. So lopsided. Just left to fend on my own.


I found myself in a Kitces.com rabbit hole and uncovered a way to bring my licenses and operational experience to the flipside — providing support and managing operations for RIAs instead — through a VA firm. I accepted and eventually transitioned to a competitor firm.


In both roles, I found myself as a CSA managing operations for multiple RIAs simultaneously. And the longer I did it, the more I noticed the same problem playing out over and over again. New hires were getting thrown into the deep end with no real training — not because firms didn't care, but because no formal training resource for CSA-level operations work existed anywhere. The knowledge lived in someone's head. When those people left, it walked out the door with them.


So I started modeling my own way. I spent hours, days, weeks, months building and testing workflows, client communication standards, internal knowledge systems — and servicing clients with them. In a short time, I was creating raving fans. Clients requested me as their support. I was asked to teach others, even as the company didn't prioritize the resources those people would need to succeed.


Oh, by the way — I was also expecting a baby.


I gave birth to Kaeson on March 22, 2024 — on my birthday — and three months later in June, I found myself thoughtfully still, sitting in front of my computer.


My son was in one arm. My screen in front of me. On one hand, I'm feeding a human being I am about to rear. On the other, I had been rearing a whole new standard of excellence in an industry hungry for it.


Looking at Kaeson. Looking at the screen. Good at math. Passionate for doing the good work. Day by day building a future as a mom, influencing how he shows up in life. Moment by moment, influencing how I show up. Everything counts now.


And honestly, if I could give birth, naturally at home, I could do anything.


All those pieces did come together. My whole life actually did prepare me for that moment.


Because then, just me — a single mama, with my baby in one arm, the trust of one client in the other, and the encouragement of my business coach (my mom) — I walked away from a system I didn't believe in and gave birth to Village Financial Services LLC.


By December 2024, I hired my first employee. Today I have a team of 12 and we've served 48 RIAs so far.


It was always going to be this. I just had to live the whole story first.




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