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Life & Work with Jen Robinson

Today we’d like to introduce you to Jen Robinson.

Hi Jen, can you start by introducing yourself? We’d love to learn more about how you got to where you are today?
I grew up in a suburban town, just north of Los Angeles. I didn’t realize it at the time, but there wasn’t a whole lot to do, so my friends and I hung out around the neighborhood or in the local shopping center. Even as a teenager, I really enjoyed novel experiences, but at a time when there was no internet or social media, I would have to create my own adventures. I remember hosting murder mystery parties, creating video montages and designing scavenger hunts. A family friend told me that I could make a business selling my scavenger hunts.

I moved to San Diego in 2006 and was immediately blown away by the amazing food, places to hike, gorgeous beaches and unique neighborhoods that offered something for everyone. In 2013, I became a mom and started a playgroup that met every week. Instead of just going to parks, our playgroup was different. We took the ferry to Coronado, we toured fire stations and we biked with our babes around the bay. One time I created an Amazing Stroller Race, where the moms raced around Liberty Station to complete challenges, with their kids in strollers. My mom friends told me that I could make a business selling my playgroup ideas.

Some years later, I got a divorce but eventually I started dating again. I have been with my boyfriend for 2 years now, but when we first started dating, I would plan our outings. Part of the reason I did the planning was because I enjoyed it, and the other part of the reason is because it came naturally to me. On some of those first dates we went on amazing adventures. We rented electric scooters, cruised around Shelter Island and shared a Mai Tai at the Bali Hai. We dined in the convertible at Buona Forchetta and then saw a Dive-In movie at The Pearl. We sipped wine at Cordiano and spent time with the owner in his private tasting room. My boyfriend told me that I should make a business that shares my outing ideas with others. This time, I said, “I should, and I am.”

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Gather San Diego has only been around a few months, but so far it has been going really well. I am also a teacher, so when school starts back up again, I will be challenged to balance my job with Gather San Diego. My hope is that my followers will start taking me along on their outings so that the ideas I share, come from all of us. Writing blog posts and sharing outings on a daily basis has been a lot of work, but I am enjoying it so much, and I told myself in the beginning, if I can even help just a few people, then it’s worth it!

Alright, so let’s switch gears a bit and talk business. What should we know about your work?
In May of 2021, I sat in my garage, pondered over a name, and within five minutes, Gather San Diego was born. After a year of not being able to gather, this name felt extra special and I became so excited to launch a website and Instagram page that would share San Diego County outing ideas for couples, friends and families. What makes Gather San Diego different is that I plan complete outings that generally include 3-4 stops or components.

For example, couples may choose to tap into their mysterious side with a Convoy District date that will require some teamwork and spontaneity. They would enjoy dinner in a unique sushi bar, work together to overcome a series of puzzles and challenges at an escape room, and celebrate their triumphs (or failures) at a nearby speakeasy.

I also have a series of “Would You Rather?” outings. One of these experiences takes you shopping, dining and drinking in North Park after answering three “Would You Rather?” questions:
1. Would you rather peruse an airy home gift shop OR stroll to an eclectic store for vintage clothing?
2. Would you rather eat a taco with a modern spin OR grab a cut of Roman-style pizza?
3. Would you rather savor a homemade beer in an industrial-chic tasting room OR sip on a craft cocktail in a retro space?

A series of outings that I am really excited about follows a “Choose Your Own Adventure” theme. Couples can choose their own sporty adventure, families can choose their own dining adventure, and friends can choose their own speakeasy adventure. After making a choice, the adventures can be extended through paired activities.

The goal of Gather San Diego is to share curated outings that are creative and fun, and that take little effort to execute. Just visit my site, pick your adventure, and go!

Contact Info:

  • Email:
  • Website:
  • Instagram: gathersandiego
  • Twitter: gathersandiego

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