Great news! Not all the headliners skip San Diego on their way up to the valley. This past week, I was fortunate enough to attend San Diego Upwork Expert Evening, hosted by WeWork Aventine in La Jolla. A beautiful space offering knee-buckling views of Nobel Drive and Interstate 5.

As with most gatherings of the professional ilk, I entered and promptly transgressed. “Beer is members only,” a WeWorker kindly reminded me.

It was going to be a great night.

Some background

According to San Diego Upwork Ambassador Dana Rowley, Upwork Expert Evenings are only currently hosted in four cities: San Diego, Austin, Los Angeles, and Philadelphia (suck it, New York). They’re an opportunity for freelancers of all skill levels to learn how to be more successful on the Upwork platform.

Dana also shared some interesting statistics about the freelance economy. Here’s two tidbits to nibble on:

  • Content Strategy is #7 on the list of top 20 trending skillsets in the Upwork freelance ecosystem
  • All freelancers fail at least one hundred thousand times on their way to stunning six-figure years

Okay, I made that last one up. Still kinda true.

More on that later.

Key takeaways from esteemed Upwork experts

All three San Diego Upwork experts met my litmus test: they are all Upwork members with legitimate profiles and earnings above three, four, five large. None have been on the Upwork platform terribly long (I think two years was the high water mark?); but two years is a lot more than some of the people trashing the platform without ever having won a single job.

We heard from:

Stephen Fogle, Pro Automotive and Financial Writer & Editor

Stephen’s easter
egg: Find your niche! A common call to action for freelance writers, but an important one nonetheless. What was nice about Stephen’s advice was that is was backed by his own successes as a writer specializing in auto and finance.

Josh Isaacs, Professional Music Producer

Josh’s easter egg
: Follow up! This might have been my most actionable takeaway from the entire night. Honestly, I hadn’t thought to follow up with both current and prospective clients. Check in. Be professional and service-oriented. This was Josh’s message, and I applied it that very night. Heard back from some clients I wasn’t expecting to hear back from, too.

Gia George, Meditation Writer

Gia’s easter egg
: Signs you’ve fallen out of balance! Leave it to a creative working in the field of yoga and meditation to get all metaphysical. What those signs are will depend on the freelancer; for me, the harbingers of imbalance are testy client interactions, dollars before quality, and total and complete ennui. Apathy, even.

Things we didn’t talk about

There were some Upwork topics I was hoping to hear about, namely:

  • Job Success Score – I brought this up during the wind-down and it felt like I was speaking a different language.
  • Upwork profile and portfolio strategy – Portfolio items were touched on in passing; profile optimization wasn’t mentioned at all. In my experience, these are two crucial areas of winning jobs on Upwork, especially early on.
  • Other irons in the fire – Come on, now. Let’s not beat around the bush: most—if not all—freelancers have multiple streams of both income and clientele.
  • Race to the bottom – This has to be the elephant in the room for any Upwork event. Every freelancer forum, LinkedIn group, and Upwork blog I read has at least one freelancer complaining that Upwork is overrun by low-paying, high-hassle jobs.

My thoughts on the San Diego Upwork event

Overall, I found this event to be quite informative. If nothing else, the San Diego Upwork Expert Evening provided some much needed perspective.

Yes, fellow freelancers, we can earn worthwhile money on Upwork. We just have to be smart about how we go about doing business.

Off-platform freelancing is no different.

And no, we don’t have to find our niche. At least not yet. If you’re earning money and leveling up, forget the term generalist a moment. We’re goddam copywriter green berets.


There’s nothing wrong with generalism if you’re good—if you deliver quality each and every time. Hell, I don’t have any discernible niche, yet I’ve managed to subsist on the platform to the tune of over $20,000 since 2017.

I’ve had some epic fails, too. These fails wounded my pride, my credibility. While I appreciated that each of these presenters shared some Upwork fails, I wish they touched on the consequences of failed Upwork contracts.

Consider this: none of the presenters have 100% JSS scores.

The myth of perfection on the Upwork platform is just that:

A myth.

All things considered, the San Diego Upwork Expert Evening was definitely worth my while. I learned a lot. I gained some perspective.

I thought about all the subtext that goes unsaid.

I’m looking forward to the next opportunity to rub shoulders with other Upworkers.

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