I started in the dish pit.
New York City, washing dishes, which is where almost everybody starts and where most people stop. I did not. Twelve years later I was running kitchens as an executive chef, having worked most of the jobs in between, front of house and back.
Restaurant work teaches you things that do not sound like skills until much later. You learn to work with people who do not share your first language. You learn that a plan survives right up until 7pm on a Friday. You learn that the person who tells you something is broken is usually not the person who can explain why. And you learn to keep going when the night has already gone wrong, because there are still ninety covers left.
I did not think of any of it as transferable. It took me years to notice that most of the things I am good at now, I learned standing up.
Then I did two jobs at once.
In 2011 I helped launch a franchise group, and for the first time I was doing two jobs at the same time. I ran the kitchen, built the menu and trained the staff. I also worked on the marketing: the brand, the advertising, who we were actually trying to reach.
That is where the second career started, without me planning it. I was working in Spanish all day, across teams where half the room spoke one language and half the other, and being the person who could talk to everybody turned out to be its own job.
It also put distance between me and the industry I had been in since I was a kid. From there, going back to a line was never really on the table.
Working remotely, before anybody called it that.
I went out on my own in 2015. That is roughly five years before the world discovered remote work, and at the time it was not a lifestyle or a movement. It was a thing you had to explain, usually more than once, to people who assumed you were between jobs.
What I actually did was run a small business. The work was digital marketing, and it was genuinely varied: SEO and analytics, managing content across a client's CMS, paid campaigns on Google and Facebook, email programs, funnels, the writing, the social accounts. Clients ranged from people starting something in a spare room to established businesses with real budgets.
The part nobody talks about is everything around the work. Contracts. Scoping something before you know how long it takes. Rates, and holding them. Invoices that go out on time and come back late. Deciding whether to chase a client who owes you or let it go and keep the relationship. Saying no to work you can technically do but should not take. Being the entire company, including the part of the company that has to have the awkward conversation.
Ten years of clients teaches you something an office does not. If you are wrong about what somebody needs, nobody carries it for you.
Having no boss did not mean answering to nobody. It meant answering to six or eight people at once, any of whom could leave at the end of the month. That turns out to be a harder manager than an actual manager.
It also meant nobody was going to send me on a course. If the way people expected a page to behave changed, or a platform half a client's business sat on moved the rules, or a tool everybody used got replaced by a better one, I had to know before they did. Staying current on design, on tools, on where things were actually heading, was not professional development. It was how the invoices kept going out. Ten years of that is why picking up something new does not feel like a risk to me.
Some of that work stayed in one place and some of it moved. I have spent years working from wherever I was, in time zones that did not always line up with my clients, which mostly taught me to write things down and stop relying on being reachable.
Inside other people's companies.
Not all of it was freelance. For two years I was a senior project manager at a web and marketing firm, running ten to fifteen client projects at a time and coordinating designers, writers and a development team spread across time zones. Marketing sites rather than complex software, and the useful part was not the projects. It was learning to stand between somebody who wanted something and the people who had to build it, and to be careful with what I promised on their behalf.
Then several years with software companies. At Salesbox I onboarded B2B customers onto a done for you sales service, and worked alongside the teams building each client's outreach. At OpenBOM I ran the marketing for a SaaS product and ended up on the phone with people who were mid trial, asking what they were trying to do and where they got stuck. Nobody hired me for that part. The scope just kept widening until it was mine.
Those years are the reason I care about the difference between what somebody asks for and what they actually need. I heard the gap between those two things several hundred times before I ever built anything.
Now I build it myself.
I am not an engineer. I use AI to build working software, which means I can put a real product in front of a real person instead of stopping at a wireframe and hoping somebody else picks it up.
There are three of them so far. A restaurant operations platform with paying customers, which exists because of the twelve years. A habit tracker in Spanish, which exists because of the ten years and the language. And a learning product, which exists because I got tired of not understanding what engineers were telling me.
The through line is not obvious from a resume. Everything I have done for twenty five years has been some version of the same job: figuring out what people actually need, and then being responsible for whether it works.