This transcript was generated from the episode audio and may contain minor errors.
[Music]
My life as a proposal planner. That's what you're gonna hear about today. Well, not my life specifically, but one Bay Area event planner. She turns suitors dreams into carefully choreographed reality complete with hidden photographers and heartfelt surprises. And of course she gets paid for this.
This is side hustle school. It's not just fun hobby school. It's all about how you can take a passion or a skill even better and transform it into something that is helpful to other people and also profitable for you. Now this is part of our first $1,000 segment. We do it every Monday.
It's all about how somebody makes their first $1,000, how they get going, how they in fact go from idea to income. So with that in mind today, we're gonna hear from Haven in San Francisco. They've got this business. I don't know if it's full time yet, but it's definitely a good recurring side of business. And how do they in fact get started?
How did they do that? That whole process of making their first $1,000 and beyond. Let's hear it from Haven. I'll come back at the end with a quick wrap up. [Music]
I'm Haven and I earn my living by planning marriage proposals in the San Francisco Bay area.
It all started when a close friend asked for help popping the question in Golden Gate Park. She was worried about everything from the perfect vantage point to how to stash the ring without getting caught. I stepped in with the idea of a Twilight picnic, a hidden path lined with berry lights and a snapper photographer named Jenna waiting behind the scenes to catch the big moment. The photos ended up on social media and it wasn't long before a friend of her friend contacted me to set up his own perfect proposal. I quickly put together a website, calling it a proposal planning package.
My pitch was simple. I'd scout the location, coordinate the details and bring in vendors if needed. Jenna, the photographer offered a separate rate, but we collaborated whenever possible. Our synergy was great. She captured heartfelt visuals and I organized little surprises no one ever thinks of until the day of.
My first four bookings brought in 3,000 over a few weekends. That was the moment I realized I'd found a real idea. Every couple wants something different. A cityscape with the Golden Gate Bridge in the background, an intimate restaurant reveal or a quiet ocean overlook in Half Moon Bay. I keep track of potential locations, best sunset times, local musicians and even dog friendly spots for those who want pets involved.
Some suitors want me to hide a vocalist in a bush. Others want friends and family to rush in right after the yes. There's always a flurry of last minute requests, like sourcing balloons at dawn or pulling off a quick pivot when a park randomly shuts down for maintenance. One suitor wanted to use an extravagant flash mob that took a bit of negotiation with city permits. No matter the request, it's my job to keep the moment stress free for the couple.
Meanwhile, Jenna has become brilliant at blending in, pretending to be a casual passerby until the rain comes out. The monthly income quickly grew, mainly because they introduced tiered packages. Some couples want an elaborate storyline with custom props while others prefer something minimal and discreet. Every successful proposal adds new photos to my portfolio. When people see those emotional reactions captured on camera, they grasp the value of orchestrating these details.
I don't rely on cliche gimmicks like sparkly confetti cannons in every scenario, though that's on my list of last resort emergency props, just in case. The real selling point is giving couples the right balance of romance and realism. If all goes well, no one's the wiser that half my job involves texting multiple parties from the bushes to confirm we're still on track. [Music]
I always love hearing interesting different kinds of stories. That's what we're all about here on the podcast.
Let me know if there's something we should hear about from you or someone you know. Thanks of course to Haven for telling us about their first $1,000. Listeners, I hope you found it encouraging. Much more is coming up. The show is completely free for nearly 3,000 days in a row, 3,000 consecutive daily episodes.
You can find the entire archive of episodes on the website, sidehustleschool.com. You can subscribe to all new episodes in Spotify, Apple Music, or wherever you prefer to get your podcasts. That's how it works. You know the drill. My name's Chris Guillebeau.
This is "Side Hustle School." [Music]
From the "Onward Project."
