Why I left the Corporate World to Build Comara
- Ginny Armstrong
- Jul 13
- 4 min read
For most of my working life, I was the person who made other people's plans work.
Executive assistant is a title that undersells the job. What you actually do is hold a hundred small variables in your head at once and arrange them so that someone else walks into a meeting and everything is already handled. The meetings are scheduled - and rescheduled. The hotel is arranged for that last minute business trip. The dietary restrictions are noted and communicated to catering. Organizing chaos. Done well, the work is invisible.
I was good at it. I AM good at it. Between working at a large tech firm and then a startup, I started noticing that the only thing I wanted to plan were the business trips.
My father owned a travel agency, back when that meant a storefront, a wall of brochures, and a phone that rang. I grew up understanding travel as something you arrange for people, not something you simply buy. Done well, it is a craft — the difference between sending someone somewhere and getting them there ready to actually see it.
My father led the trips. My grandmother took me — she was the one who let me witness a way of living other than the one I knew. Comara is named for her.
And then there is my other grandmother, Ginny, whom I am named after. She had a habit that I did not recognize until I was old enough to miss it. She saved you a seat. At the table, at church, at whatever crowded room she had arrived at first. She did it without ceremony and without making you thank her for it. You just arrived, and there was a place, and it had your name on it in the way that unspoken things do.
Combined, they are the building blocks for Comara. Come along. We saved you a seat.
Here is the part I did not expect to have to explain as often as I do.
When I travel with my wife, I always wonder how our relationship will unintentionally become the subject of questions. Will the hotel give us double beds instead of the king bed that was booked because we must be friends and the booking must have been a mistake. Is the guide going to say and your friend in a tone. How will be perceived if we show any affection.
Most of the time everything comes out fine. That isn't the point. The point is that I did it, and others did not, and the cumulative cost of running that calculation across a lifetime of travel is taxing.
When I went looking for group travel that would let me set that all aside, I couldn't find exactly what I was searching for. I wanted my own room at the end of the day, I wanted a long, lingering lunch. I wanted to meet the person who made the olive oil I was tasting in front of me, and I wanted to share a common understanding with the people I'm sharing with.
That did not exist at the size and shape I was looking for. So I stopped waiting for it.
People ask why Portugal, and the honest answer is that Portugal is the right scale.
I don't mean that it's small. I mean that the distance between a producer and the person eating their food is short enough that you can walk it. In the Alto Alentejo, I will sit with a family who produces olive oil on their olive grove which the family has worked for generations. There will be no gift shop at the end of it. Portugal still permits that kind of encounter, in a country where I can hold my wife's hand.
The two flagship trips came out of this desire. The Awakening, in May, moves between Lisbon and the Atlantic coast. The Harvest, in October, sits inside the olive harvest in the Alto Alentejo.
Why small groups is the easiest question to answer.
Fourteen is the most people who can still share one dinner. Above that, a group splits into sub-groups and the thing you came for stops happening — the table becomes tables. So the number is never more than fourteen, and usually closer to twelve. Small enough that by the last night, there are no strangers left. That is the entire methodology.
Everything else follows from the table. Two properties per stay so you settle in rather than pack and repack every night. Programming that works whether or not you drink. Small producers instead of the branded version of the same experience. And me, present, on every trip.
That last one is not sentiment. It is structure. A new travel company has no reviews. It has nothing to point at. The only trust mechanism available to me is that I show up, I am accountable in person, and if something is wrong I'm onsite to fix it right away.
Why now.
I left my tech job in May. I am aware how this will come across. I know a lot of other women have done the same thing. Woman leaves corporate role. Woman finds meaning. Woman is now, conveniently, selling you something.
So let me be clear. I am selling you something. I've spent a year building the unglamorous parts of it — the entity, the insurance, the participation agreement a lawyer marked up twice, the vendor contracts, the emergency protocols nobody wants to read and everyone should. I did that work first, before the photography and the launch and this essay, because the difference between a company and a feeling is whether anyone thought about what happens when a guest gets sick in a country where she does not speak the language.
I did not leave executive work to escape logistics. I love the logistics. I just wanted to point them in a direction led by passion.
The first Comara trips begin in 2027, and I've had the same question in my head which has been a guiding thought of Comara.
When was the last time a trip left you with people, not just photos?
For me, that has been the scouting trip I took in May — sitting at tables in Portugal with people I'm building this with so you can meet too. And if you can't remember your own answer, or it's the same as mine, I saved you a seat.
Comara's inaugural Portugal season opens in 2027. Limited seats per trip. Request a seat.