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How I Built a VA Business After 40, And Why It Was the Best Decision I Made

Writer: Chastity Cortijo
Chastity Cortijo
Aug 4
3 min read

I spent over a decade inside some of the biggest names in finance and media, Salomon Smith Barney, Prudential Securities, Citigroup, Credit Suisse, GroupM/Mindshare, CafeMom. I learned how big organizations actually run: the systems behind the systems, the processes nobody sees, the follow-through that keeps a massive operation from falling apart. Later, I managed a 25-person remote team at CafeMom, which taught me something different, how to keep people organized, accountable, and moving in the same direction without being in the same room. And then they let me go - corporate lay-offs it's called.


That's when I knew I was done letting a company decide what my future looked like.

But I was a single mom with two kids to feed. I had to figure it out.


What I found when I looked at the VA industry


I didn't know I was a VA when I was looking for my very first clients. I just needed an income. In doing that, what I actually found was a huge, underserved gap: contractors, property managers, HOAs, small local businesses, the kind of businesses that run on relationships and paperwork, not funnels and content calendars — desperately needed help with the boring stuff. Scheduling. Inbox management. Document tracking. Vendor coordination. The unglamorous back-office work that keeps a business from quietly falling apart.


Most of the VA industry is pointed at solopreneurs and online coaches. Nobody is building for the guy running a window treatment install business, or the HOA board drowning in meeting minutes, or the property manager juggling six vendors and zero systems. That's where I went.


Why the corporate background actually mattered

Here's what I didn't expect: everything from Salomon Smith Barney, Prudential Securities, Citigroup, Credit Suisse, GroupM, Mindshare, and CafeMom translated directly. I wasn't starting over, I was applying the same skill set to a different scale. I know how to build a process and make it stick. I know how to manage up, down, and sideways. I know what "professional" actually means when a client is trusting you with their operations, not just their to-do list.


That's the difference between a VA who can send an email and a VA who can run the parts of a business the owner doesn't have time for. My corporate years weren't a detour from this work - they were the reason I'm good at it.


Why I built Do The Boring Work

I built DtBW because I know I'm not the only woman sitting on a stack of admin skills from a corporate career, wondering if any of it transfers to something more flexible, more hers. It does. The scheduling, the systems thinking, the client management, the "keep it running while everyone else is putting out fires" instinct - that's not a corporate-only skill. That's a sellable, buildable business.


DtBW exists to help women take the skills they already have and turn them into a sustainable remote VA business - without pretending they need to become social media experts or influencers to do it.

It's retainer over hourly.

Consistency over hustle.

Real client work over vague hustle-culture noise.


What's possible from here - Building a Business After 40

If you've spent years in a corporate role, running projects, managing people, keeping things organized so nobody upstream had to think about it, you already have what you need to start. You don't need a certification. You don't need a niche figured out on day one. You need to see that the skills are transferable, and you need a place to figure out how to package them.


That's what DtBW is for.


If any of this sounds like your story, come do the boring work with us.


Join Do The Boring Work and let's build something that actually fits your life. https://www.skool.com/dotheboringwork

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