Why do we constantly underestimate how long something will take in the short-term? In other words, we tend to over-estimate just how much we can achieve right now. Then, when we think long term, the reverse tends to happen: we actually UNDER-estimate what we're capable of achieving over time.

Today, we want to know more about the promise of a popular trend, the creative streak, and whether they can help us overcome our constant battle with planning our time and achieving something greater.

This week, Grant Faulkner, Executive Director of the world-wide phenomenon NaNoWriMo (aka National Novel Writing Month) gives us a peek into the power (and potential pitfalls) of creative writing streaks. Meanwhile, Giorgia Lupi, an information designer and partner at the firm Pentagram, reflects on her famous, collaborative creative streak, Dear Data, with Stefanie Posavec -- a year-long journey of sketching personal data-based postcards, which eventually led to exhibitions, book deals, critical acclaim, and internet fame.

Can we change our relationships to deadlines? How might we banish our inner editors holding us back during crucial early stages in the creative process? And how might we reconcile both the short-term and long-term work we do?

Let's go streaking.

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💌 Playing Favorites is the newsletter from Jay about resonance, storytelling, differentiation, and getting off the content hamster wheel to make things that matter more (because when your work matters more, you can hustle for attention less).

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WORK WITH JAY:

✅ If you're an expert/entrepreneur looking to develop and differentiate your personal brand, podcast, speaking, newsletter, or other pillar project, learn more about Jay's coaching.

👋 Or you can book Jay to speak to your organization or event.

📚 You can also explore Jay's books.

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ABOUT JAY ACUNZO:

Jay Acunzo helps business leaders develop more original premises — the big ideas they become known for publicly. His work focuses on his core belief in prioritizing resonance first, not reach.

After starting his career in media and marketing roles at Google and HubSpot, Jay authored the book about questioning best practices, Break the Wheel, toured as a professional speaker, giving keynote sin 25 states and 3 countries, and cofounded the mastermind for business storytellers, the Creator Kitchen.

As an advisor, he’s worked with more than 200 individuals and teams to help them differentiate through the impact of their ideas, not the volume of their content. Past clients include Salesforce, GoDaddy, Wistia, Drift, and Help Scout, as well as hundreds of individual thought leaders and experts, including the author behind Google’s innovative employee training program and the performance coach who helped Kobe Bryant develop his Black Mamba persona.

Jay is a proud New England resident, a troubled Knicks fan, and an obsessive grilled pizza chef. His grandest aspiration (though he’d say delusion) is to be the Anthony Bourdain of business storytelling.

💛 Keep making what matters!

The Devil Wears Intifada (1/27/25)