Episodes

July 5, 2022

EP 389: Context Clues: Does everyone need a personal brand?

How has our relationship with ourselves changed since we started to put so much effort into emphasizing the most marketable parts of our identities?

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June 28, 2022

EP 388: Extra Context: Not Getting Paid

Can work be valuable even if you're not making money with it? What role do hobbies and personal pursuits have in our lives outside of work?

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June 21, 2022

EP 387: Context Clues: Is there hope beyond positive thinking?

Vibe check: does positive thinking get in the way of recognizing real limitations and structural challenges?

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June 14, 2022

EP 386: Extra Context: Getting Paid

How can we think more strategically about the way we get paid as business owners & independent workers?

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June 7, 2022

EP 385: Context Clues: Who do you work for?

Do you spend more of your time working for internet companies than for yourself or your clients?

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May 31, 2022

EP 384: Context Clues: Do you love your work?

Is loving your work all it's cracked up to be? And is the work you love meeting your needs?

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May 24, 2022

EP 383: Extra Context: Rugged Individualism

Has individualism made it harder to navigate the 21st-century economy?

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May 17, 2022

EP 382: Context Clues: What makes for a fair refund policy?

Does your refund policy help you make sales... or do right by your customers?

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May 10, 2022

EP 381: What happens when you take a 4-month break from business as u…

At the end of 2021, I stepped away from my business: left our community, off-boarded my employee to another company, and focused on my mental health. Over the next 4 months, I wrote a book and thought about what might …

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April 5, 2022

EP 380: When does overdelivering become overcompensating? with Alliso…

I’m sure you’ve heard it before: underpromise and overdeliver. But is that really the best way to do business? Or does it just give us a permission slip for self-exploitation? When does overdelivering become overcompensating? And when does being ge

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March 29, 2022

EP 379: Why do we choose squeezing more in over taking time off? (Tim…

I’m bringing our Time & Money series to a close this week by exploring why we choose squeezing more in over taking time off. I share how The Squeeze works, why work gets more intense over time, and some of …

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March 22, 2022

EP 378: How much time do you work? with Anne Ditmeyer (Time & Money 7)

A lot of the work we do today doesn’t much look like “work.” The divide between work-life and life-life is flexible and porous. So what does that mean for the way we spend our time? Or how we earn a …

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March 15, 2022

EP 377: What game are you playing? (Time & Money 6)

The systems we operate in all have different incentive systems: our business models, the social media platforms, our economy, the culture at large… And many of these incentive systems have become simplified and gamified—changing the way we view the

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March 8, 2022

EP 376: What Is Our Time Worth? With Keina Newell (Time & Money 5)

Most of us learn the value of our time in our first jobs. Even as we get more experience and our hourly jobs turn into salaried jobs or freelance projects, the specter of selling your time for a particular wage …

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March 1, 2022

EP 375: Is this really a new economy? (Time & Money 4)

I’ve been talking about the “new economy” since about 2010. But more and more, I recognize that the economic possibilities created through the internet aren’t nearly as new or innovative as I’d first thought (and hoped). It seems that the …

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Feb. 22, 2022

EP 374: How do you measure quality time? with Elisabeth Jackson (Time…

There’s more than one way to measure success—and there’s more than one way to measure time. How do you account for the time you spend working? And is it really the most effective—for you—to spend it? In other words, what …

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Feb. 15, 2022

EP 373: Should we lower our expectations? (Time & Money 2)

We spend money on lots of tools designed to save us time and work. But all too often, those tools just end up raising our expectations. Why do work in less time when you could do more work in the …

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Feb. 8, 2022

EP 372: What Is Money? with Paco de Leon (Time & Money 1)

“Time is money.” Ben Franklin gave us that chestnut in 1748—and ever since, we’ve been trained to think of our lives as opportunities for making a buck. This week, we start a series exploring the “time is money” construction. But …

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Feb. 1, 2022

EP 371: How does emotional labor impact our work?

Emotional labor is an under-appreciated, under-compensated type of work. But it’s essential for navigating the 21st-century economy. Entrepreneurship almost always brings with it a need for managing our emotions to lead and care for others. And thi

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Jan. 25, 2022

EP 370: What is the creator economy? with Gina Bianchini

What is the creator economy? And why are so many creators… miserable? Mighty Networks founder Gina Bianchini was the first person I knew talking about the creating economy. She’s passionate about helping entrepreneurs, organizers, and creators see

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Jan. 18, 2022

EP 369: Do your goals make you a better person?

The way we set goals often invites a load of comparison and competition. We can even create a moral hierarchy of more and better. In this episode, I explore the roots of moralizing around the goals we set, borrowing from …

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Jan. 11, 2022

EP 368: What Does Growth Without Striving Look Like? with Rita Barry

“What does growth without striving look like?” Rita Barry posed this question 3 years ago, and it’s stuck with me ever since. In this episode, I talk with Rita about the journey she’s been on to answer that question as …

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Dec. 14, 2021

EP 367: Moving Into A New Chapter with Darden Creative Founder Tamera…

In This Episode: * Why Darden Creative founder Tamera Darden decided to shut down her business at the end of 2022—and how that decision evolved* How she wrestled with the practical, emotional, and financial questions around this big decision* The

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Dec. 7, 2021

EP 366: Unpacking Business Grief with Charlene Lam

In This Episode: * Creative grief worker & curator Charlene Lam shares how grief impacts us—as humans, leaders, and business owners* How she discovered a passion for understanding grief and helping others process after the death of her mother* The

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