whimsy is in the eye of the craigslistmaxxer

If you’ve talked to a Zoomer lately, you’ve likely heard one of us declare our efforts to become more whimsical.

Whimsy is the essence of curiosity and creativity that made the average childhood experience so self-reliantly amusing. It helped us enjoy the world and all it had to offer before the baggage of "real world" problems started to weigh us down. Ultimately, I've found that it is something that many young adults are hoping to reintegrate into their lives despite being more busier and tired (at least compared to the ones we led 10+ years ago).

A few years ago, I felt depraved of whimsy. I recently saw this Thread (I know, nobody uses Threads) that summarizes how I feel most of the time. When you're someone as Type A as me and just have to get shit done (or die trying), you need to operate on deadlines, timelines, and calendar invites - all of which are the exact antithesis of childlike wonder.

For context, between 2023 and 2024, I finally faced the music of my post-grad blues: I was not happy because I could no longer rely on the bubble of youth to serve me my social life, education, and passions all on a single silver platter. Yes, I acknowledge that I’m privileged to even have had those experiences as part of my reality, but that didn’t make the adjustment period any easier.

Whether we like it or not, each of us are solely responsible for our own happiness and growth in this world. We’ve got to find a way to take advantage of the time AND ENERGY we have - even it feels like we never have enough of either of these things.

So one day I decided to pump my schedule full of stuff that would force me to get out there socially and creatively, regardless if I had a buddy to face these new experiences with or not. And the more that I did this, I became emboldened to become someone who builds these opportunities for other people. I believe that this shift in mindset led to me to the idea for Club Rambutan.

I became hungry to increase MY surface area of luck, and I wasn't going to wait for anyone else to feed me.

Anyway, flash forward to now, in the great year of 2026 A.D., and my life is a lot more chaotic (in the best way). I recently started a new job (I switched from being in nonprofit for 3 years to an operations role at a start up a little under two weeks ago), am committed to making progress in my fitness journey, having a number of amazing relationships to grow, and I am of course still running Club Rambutan. I got exactly what I worked for.

But regularly being at the mercy of whatever my Google Calendar says has worn me out a bit. And again, I don't mean to sound ungrateful for having to tend to these amazing things, but I realize now that I need to grant myself a little bit more flexibility and open ended opportunities to feel more grounded once again.

So, although this sounds SUPER counterintuitive, my effort to become more whimsical is to do more. Specifically, more random and non-committal stuff. Enter: Craigslist. Hello, gig economy!

Is the website sketchy looking? Sure. But if your sense of discernment is strong and you’re brave enough to look past the outdated user interface that practically hasn't been updated since the 2008 recession, you are bound to find a side quest that will expand your worldview. Don’t believe me? Here’s a brief timeline of my most recent gigs once I started treating CL like it was the morning paper. 

August 2025: Brand Ambassador (Kali Uchis - $200)

This was my first time truly delving into the world of CL. Around this time, I was looking for ways to offset the costs that went towards putting on The Pyres of Desire, which was Club Rambutan’s first-ever fashion show in September that year. Although CR has a separate bank account for all its expenses (which I think is worth mentioning that I’ve single-handedly built up over the last 2.5 years, partially out of my own pocket before we started selling event tickets and merch), TPD was the most expensive event we’ve ever put on. I was worried that our expenses would be too much in the red, so that’s when I turned to CL in hopes for some quick cash. 

I really lucked out when I applied to an extremely vague listing for a Brand Ambassador at Chase Center. On that very same night, I got a voicemail saying I’d be working at Kali Uchis’s brand activation booth during her San Francisco show on the Sincerely, Tour, namely to sell body oil and butter from her lifestyle brand, Homebody by Uchis.

At first I thought it was a scam! I was convinced that because they requested a picture of me in the initial application, they saw that I was a girl and made up a fake opportunity attached to a popular female celebrity in order to lure me somewhere and traffic me. I even tried searching up the name of my CL contact who was ~allegedly~ working with an event staffing agency, and even though no solid results turned up, I still trusted my gut and showed up to where they told me to go anyway. And lo and behold, it was the most fun 5 hour shift I’ve worked in a while (and I had just come from my actual job!). 

Additional Perks: Going backstage during Kali Uchis’ set, free makeup and clothes from the brand, and being complimented by many lovely women while working the activation. I ended up using this money to reserve a private room at a local bar in Oakland for the TPD after party.

October 2025: Earring Model (Yellow Owl Workshop - $200)

At this point, I had fully caught the CL bug and the only remedy was to secure another cool gig. Transparently, between the Uchis gig and YOW, I learned that it was crucial to be consistent in checking Craigslist (basically on a daily basis). People in the Bay Area STAY posting on CL and so there’s usually always a new flow of opportunities that are posted (but consequently are quickly claimed). 

At Yellow Owl Workshop, I sat in a very roomy photo studio for 4 morning-time hours in the Mission District (before I went to my actual job) and hung out with a very hip, very cool millennial photographer and product manager (shoutout Aya and Eric!). You can see my right ear modeling a variety of enamel earrings on their website today, although my lobe was definitely sore after wearing 30+ pairs.

Additional Perks: Free lunch, free merch (I got a cute printed reusable grocery bag that can hold up to 40 lb), cute dog to entertain me, and two (2) free vintage tin type portraits of myself (courtesy of Eric and his vintage large-format camera and dope red room set up!)

December 2025 - February 2026: Research Participant (Misc. Companies - on avg. $25/hour)

Over these last few winter months, I’ve committed to more boring gigs as a research participant. I found that if I don’t have an immediate goal to spend a couple hundred bucks on, I’m less inclined to get out there because there isn’t a pressing need to make money. However, I did decide to book a last ish-minute trip to do my first ever solo vacation in Vienna and Copenhagen, so these gigs have been coming in clutch. For this purpose, I’ve gamified Craigslist; I’ve already paid for my plane tickets and other related accommodations, so I track how much everything costs and try to treat these gigs as a way to “discount” the overall price of everything by making as much of that money back.

The main gigs I did were:

• Talking to a computer for 2 hours by typing in a dark cubicle with a heavy spiky helmet strapped to my head (I can participate up to 10 times, and I’ve completed this 6 times already and always between 7:30 and 9:30 AM)

• Reading (sometimes aloud, sometimes silently) a very boring series of passages on a screen while wearing headphones even though nothing ever plays on them (I can do this unlimited amount of times; I’ve completed this twice because the research facility is far from my apartment)

• Go to a rental house in Mission Bay and walk into different rooms doing miscellaneous actions while wearing a vest of wires for 30 minutes (this was a fun one; I got a $150 giftcard of my choice in exchange for my time) 

I should mention that these RP gigs are usually offered at different time frames throughout the day, so I would choose the early morning slots before I went into my actual job. Am I crazy? I’d rather use the word “dedicated”. Some of them also let me choose how many hours I wanted to participate, usually from 1 to 4 hours at a time. 

Now, I will admit that money was definitely an incentive for me to get out there and do these things. However, I also chose to see these as silly opportunities to lean into the unknown and sometimes LARP with strangers (main example: I’d ask to be addressed as “Angela”, which is my second name, instead of my first name that I’ve always gone by). For me that felt extremely whimsical. 

Unfortunately, I foresee my CL adventures being put on pause for the time being (I got a new job so yay! But also boooooo), but I could not recommend this website enough for people who are dying to try something new. So if any of this resonated with you, I wish you the best on your journey [back] to whimsy – I’m confident that you’ll achieve it!