05.26.22

10 Lessons from 10 years of freelancing

Today, I celebrate a decade of freelancing/self-employment.

Something funny happens when you give notice at a job: people ask you what you’re going to do next. So when I put in my notice at Groupon a decade ago, after burning out twice, I did it because I was on the edge of a third burnout. I had enough saved up at the time and very few expenses so I was able to leave without thinking of what I’d do next. But because people kept asking, I ended up scrambling for an answer and blurted out, “I’m starting a business! I’m going to do coffee crawls!”

Wow, I was so naive. Fast forward through creating and ending that business, part-time jobs, a “full-time” client that paid me as a consultant, and offering and stopping services, here I am.

One decade is a long time. If you’ve been following along in my journey, you’ll know that I like to celebrate the wins, no matter how small. My freelance-versary is a big win: it’s marked in my calendar, I usually do something to celebrate it, and I write one of these posts to mark where I was in the journey. You can read my 9-year post from last year here.

Here are 10 lessons I’ve learned from 10 years of freelancing:

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11.24.21

To pay or not to pay

If you’ve been in the business of providing services long enough, you’ve likely grappled with this question. “Should I charge for this X thing?” And even if you’re mostly a product-oriented company, you probably offer some services like classes or tutorials.

I do not have an easy answer for you, as it’s something I am also struggling with. Expertise comes with experience built on labor, whether physical or mental. When you reach a certain level of expertise, people start coming to you with questions. This isn’t about how to set your rates or prices, it’s about whether you should or not.

I am a believer in both not gatekeeping valuable information and paying people what they’re worth. It is unfortunate that we tie money with value but it is what it is. When you pay for something, you want to receive something back. This is an easy enough concept for physical goods but not so much about digital ones or intangible ones.

If you pay for a cooking class, you expect to learn how to cook that meal. The more you pay, the more detailed, personalized, and valuable experience you expect to have. Yes, you can watch a free recipe video on YouTube but maybe you want more.

And this is the hazy line that I’ve settled in. Generalized information and advice, like this newsletter, is free. Once you start veering into the personalized advice territory (i.e. “What should I do with my Instagram account for this specific goal I have in mind?”), it becomes a paid service. Digital worksheets could be both as long as the free one has some clear goal. It could be brand awareness or leading customers to a paid worksheet.

Likewise, you could offer free video tutorials on how to brew coffee with a certain method (there are so many of these out there). AND you can offer paid small group classes or 1:1 home barista training.

I’d love to hear your thoughts on this, especially if you’ve drawn a different hazy line than I have.

07.29.20

So you want to pick my brain

Disclaimer: this is not about you. I have received many pick-your-brain emails through the years. I also volunteer a lot of time to community efforts and provide free content (like this newsletter and blog) because I believe giving back is important for sustaining an industry.

So you want to pick my brain about what I do and how I got here. Before the pandemic, you probably wanted to grab a coffee, now it’s video chats.

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