Real Time Creator | A Career Break Diary
I spent years chasing success and money while shelving my creative dreams. I was a $200K+ earner in tech and a secret weapon inside of a 7-figure creator business. Then EVERYTHING changed.
I decided to give myself a minimum 1 YEAR career break and creative sabbatical to reinvent my life.
I'm Alison Kinsey, and each week I share a raw and unfiltered glimpse into my career break, money transparency after getting laid off, and the messy work of creative reinvention. I also share the stories of other inspiring women who have built a portfolio career after a career pivot.
If you've been asking yourself, "is this IT for my life?!" this is your weekly voice note to inspire you through the in-between.
New here? Start with Episode 1: "I Lost My $200K Tech Job... and Everything I Thought I Wanted."
Connect with me on Instagram: @alisonkinsey
Or email me: alison@alisonkinsey.com
Real Time Creator | A Career Break Diary
After 300+ Nights, Airbnb Invited Me To Their HQ
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
I’m still REELING over this. Airbnb invited me to fly to San Francisco for an all expenses paid experience at their headquarters for their 2026 Summer Release.
This is far from a play-by-play. I’m taking you behind the scenes of the most interesting aspects of this trip, what surprised me the most, the people I met, and why this brand activation meant SO much more than a free flight.
In This Episode:
- A reality check that had me questioning everything and feeling defeated
- How the Airbnb team caught me off guard (in a good way)
- The 2 Airbnb stays (out of 100) that didn't exactly go as planned
- What Airbnb got right about hospitality, community, and making people feel seen
Resources & Links:
Watch the 2026 Airbnb Summer Release Event on YouTube (I was in the audience!)
Let's Connect:
Follow me on Instagram: @alisonkinsey or send me an email: alison@alisonkinsey.com.
Connect with Alison on LinkedIn.
I also help entrepreneurs and thought leaders launch and grow their podcasts through my boutique podcast editing agency, Podcasting for Creatives.
You better believe I was screaming on the inside, like, what? All expenses paid. Flights, Airbnbs, meals, Uber credits, you name it. I didn't know a soul. I had no idea who was going to this event. Hi, friend. Welcome back to the Real Time Creator Podcast. I had a pretty off day earlier this week. What happened was I got hit in the face with a financial reality check that was embarrassing, disappointing, and it ultimately left me feeling defeated, to be honest. It was like a big spotlight on me that was screaming out, Allison, you don't make enough money. Which is what makes what I'm about to tell you hit even harder. Because even though I've been riding some ups and downs lately, there was a moment a few weeks ago where I felt chosen. And I specifically want to call this out because if you're dealing with the aftermath of a layoff or you're feeling like you're invisible, this is proof that things can change quickly. So if you tuned into my last episode, I was in San Francisco recording from my hotel room, but I didn't really tell you why. I was a little secretive. Now I can tell you, I can give you the full scoop. On April 8th, I got the craziest, most unexpected email of my life. The subject line was special invitation from Airbnb. And in that email was an invitation to fly out to their headquarters in San Francisco, all expenses paid, flights, Airbnbs, meals, Uber credits, you name it. And when I read it, I just kind of sat there in shock processing this email. And you better believe I was screaming on the inside, like, what? Me getting an invite like this? Because I have spent so many months just feeling squirrely, feeling like I'm not doing enough. I'm still trying to figure out my life as a 30-something. And then getting that invite, it made me feel so seen in that moment by a brand that I've been extremely loyal to for many years. And my loyalty runs deep with Airbnb. I'll give you the backstory. I've been on Airbnb for 12 years. And in that span of time, I have completed a hundred stays and over 300 nights. 99% of my experiences have been positive. There's really only been a couple of experiences that had some issues. The first one was seven years ago. We booked an Airbnb in Salt Lake City and it ended up being in a really sketchy area. And when we got into the Airbnb, the mattress was super lumpy and sunken in to the point that I literally rolled into the dip of it. And I just could not get comfortable. It was more of just like, ugh, kind of annoying. The second experience was another place we stayed that had a serious sugar ant problem, those teeny tiny ants where there's always a million of them. And they were actually coming out of the light fixture on the ceiling. So I think they were like nesting in the roof of the place. But again, none of these issues were Airbnb's fault. And nearly all of my stays have been absolutely incredible. And I know for me, a lot of the reasons I choose Airbnb over other options is because we have three dogs. And it's really difficult to stay in hotels if you have multiple pets. But in all of this time frame, even with all the stays, all the dollars that I've spent, I had never once been recognized by Airbnb for my loyalty until that email. Obviously, within seconds of processing the invite, it was like, yeah, there's no way I'm turning this down. It felt like a once-in-a-lifetime invite. So immediate yes. So last month I got on a plane to San Francisco. And I want to tell you just a few things that surprised me, what delighted me about the experience. And the way they had structured it was they had given us a rough itinerary of what to expect. So I had a schedule. There were places I needed to be at certain times. And the first event was a welcome party at this beautiful space in San Francisco called Progress. I remember stepping out of my Uber, feeling just all the usual nerves and butterflies in my stomach because I didn't know a soul. I had no idea who was going to this event. And a couple of members of the Airbnb community team were standing outside to greet me. So I get out and they just went in for hugs right off the bat. No handshakes, hugs. I remember feeling so caught off guard in a good way, just getting a hug. In my mind, I figured Airbnb is a massive Fortune 500 company. It's going to be all corporate vibes. And I love that I was proven wrong. And it wasn't just those two people that were part of the community team. It was every single employee that I met. And there were several, and all of them were just so warm and genuine. There was this woman, Amanda, who was telling me about her obsession with the Real Housewives of Rhode Island, and Linda, who gave me her undivided attention at the welcome party. And she met me with such curiosity when I told her about my tech layoff. And any tension or nerves that I felt just melted away. And I felt so instantly welcomed. And it's amazing how something as simple as a hug can just break the ice when you're at an event. Next, oh my gosh, you guys, the people. Every one of us who got this mysterious invite was just curious, friendly, diehard, passionate about traveling. And what was interesting is that they mixed us up. So there were people like me who had a profile of being an Airbnb guest. And then there were about 25 folks who identify as Airbnb hosts. So they run properties or experiences on Airbnb. By the end of the two days, we were exchanging phone numbers and Instagram handles, taking selfies with one another. It was a whole thing. And it kind of made me think of the bonds that people make when they're on a reality show together, but obviously not to that degree. But it's like we all went through this cool experience together. And the people that were there, I mean, there was this older woman named Marianne who had to have been around 70. She's been to 80 countries and she's about to go to Kazakhstan. And I was just so impressed with her. And then there was Anne. And let me just say, we all need an Anne in our lives in these kinds of situations. She arrived the same time as me at the welcome event. And she was like my emotional support animal throughout the whole thing. Like she was my person. And we hit it off, and we had such a great time hanging out together. And when I look back at this whole thing, and there were other moments too. Like we sat in the audience for their summer release keynote, which is kind of similar to what Apple does when they announce a new iPhone. They just do this huge stage event and, you know, their slides and all the things. They did that too. And I know you're not here for a feature rundown. So I'll keep this super brief. But one thing I am giddy about is that they're launching a travel map. So sometime this summer, you'll be able to see where your friends have stayed. I assume you have to opt in for the feature, but how convenient. Like if I in the future plan a trip to Italy or Croatia, I can see which of my friends have been to those countries and maybe get recommendations from them. I feel like that will be so useful. I guess when you think about this whole thing, I mean, this was a major activation for Airbnb. I mean, they probably spent six figures on this thing. If you count all the people they had to fly out, the stage setup, because they made a stage inside of their HQ. They like brought in cameras and lights and all kinds of things. They put serious intent behind this. And I have a lot of respect for brands that are masters at creating that sense of community and building belonging. And that's exactly what Airbnb did over those two days. And I have to say, I was always loyal to Airbnb. Like, if anyone asked me on the street what I think of Airbnb, even before this, I always have been like a positive megaphone for the brand. But now I'm even more loyal because of this. I feel like it's really rare and special when a brand can make you feel like a human, you know, like rather than just a number or a user or a transaction. It's just really, really cool. And honestly, this invitation just feels like it came at the right time in this whole phase of life that I'm in right now. I don't doubt if I had received this exact invitation while I was working at my tech job last year, I would have felt so guilty for even asking to get time off because this event took place midweek. I would have second guessed going because the event fell towards the end of the month. And in sales, end of month is always a big push. I feel like I would have tried to justify going, but simultaneously feeling so guilty about it. And I didn't have to argue with myself. It was an easy yes. I could just go and feel untethered and just take the experience for what it was. And now, the day that I'm recording this episode, I am packing my suitcase again. I'm so excited. I am going to be in Boise, Idaho this entire week for a two-day mastermind style event. And then I'm heading to Craft and Commerce, which is one of the best creator conferences. It's put on by kit. It is so worth going. If you identify as a creator or a service business or an entrepreneur, it is like the best conference to go to, primarily because of the people, but even just the quality of the event. Boise is adorable. So if you happen to be there, say hi, find me, let's do something. I can't wait to fill you in on more and more of this squiggly career break journey that I'm on right now. So I appreciate you so much, and I will see you next week.