I'm a designer who turned into a writer who turned into a startup CEO. My mission is to help creators earn a living. Subscribe for essays on building an audience and earning a living as a creator.
5 questions that make hard decisions easier
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Hey Reader, The hardest decisions you have to make are rarely between good and bad options. They usually feel like choosing between two good options. When I was talking with my coach, Dan, about everything I’m trying to balance, he told me to imagine myself 10 years in the future. He asked: which one would I regret most if I didn’t accomplish it? I thought I’d say growing Kit to $100M. But the answer surprised me: publishing my book. If Kit hit $100M and I never published another book, I’d be disappointed. If I published one book but Kit only reached $60M or $70M, I’d be satisfied. So I prioritized my book, The Ladders of Wealth. I finished writing the manuscript and I’m publishing it later this year. That’s not to say Kit is taking a backseat, there’s an incredible team working tirelessly to improve and promote the platform, but that I need to prioritize my daily writing habit to bring this book to life. That conversation clarified something I’d been doing intuitively: I use a series of different questions when making difficult decisions. Here are 5 lenses that will reveal something different about the choice you’re facing: Lens 1: What's the most fun?It’s easy to dismiss fun as something that doesn’t belong in serious business decisions. But if you’re the type who optimizes too heavily for metrics or outcomes, asking “What would I actually enjoy doing?” might be exactly what you need. The work you enjoy is the work you’ll keep doing. And doing something consistently over time is how you get results. Lens 2: What furthers the overall business goals?When you’re stuck between two good options, return to your broader strategy. What are you actually trying to build? Which option moves you closer to that vision? This lens helps you avoid chasing shiny objects that don’t serve your larger ambitions. Lens 3: What drives the most revenue, profit, or cash flow?Sometimes the answer is straightforward: you need money now. In those moments, set aside the long-term and focus on what generates income today. There’s no shame in choosing short-term cash flow when that’s what your business needs to survive or grow. Lens 4: What makes the most of existing commitments?You’ve already invested time, energy, and resources into certain projects. Which new opportunity creates multiplier effects with what you’ve already built? Look for choices that leverage your existing momentum rather than starting from zero. Lens 5: What would I regret not doing?Use this lens for decisions that will shape the next several years. Fast forward a decade. What would disappoint you if you never pursued it? Regret will show you what you actually care about. For me, it’s writing. I want the book to have a big impact, but I’m also writing for my past self—it’s the book I wish I had as a teenager. That I want my kids to have as they become adults and navigate the worlds of money and business. It’s focused on people I deeply care about—not just on what’s most profitable. You don’t need to use all five of these lenses for every decision. Most choices are simple enough that one or two questions will give you some clarity. It helps to simply know these questions exist. Because once you’re aware of them, you’ll start noticing which one would be most helpful for the decision in front of you. — These five lenses have helped me work through dozens of hard decisions. What questions do you ask yourself when you’re stuck between two good options? PODCASTMillion Dollar Coach: How To Be A Great LeaderMeet my business coach of more than 7 years. Dan Putt has coached thousands of leaders and he’s been instrumental in my success with helping me lead and grow Kit. A month ago, he interviewed me on my podcast. But today, he's back for an episode where I interview him. He shares his coaching philosophy, tools for overcoming imposter syndrome, and explains why he rarely gives advice. Here’s what we cover:
Watch or listen to episode » X POSTReplacing a 10-Person Sales Team with AIMy friend Lenny Rachitsky interviewed Jeanne DeWitt Grosser, former Chief Business Officer at Stripe and current COO at Vercel. He wrote an X post with his top 10 takeaways from the interview. Here are a few excerpts: A single engineer at Vercel built an AI agent that replaced a 10-person sales team. "The agent costs $1,000 per year to run versus over $1 million in salaries for the sales team." Wait until $1 million in revenue before hiring your first salesperson. Most customers buy to avoid risk, not to gain opportunity. About 80% of customers purchase to reduce pain or avoid problems, while only 20% buy to increase upside. THE NATHAN BARRY SHOWWant to come on my podcast?I have a couple spots left for our upcoming podcast recording event in February. We’ll have a group come to Boise to batch record some episodes with me over two days at Kit Studios. If you’ve wanted coaching with me, this is a great opportunity. Bring a business challenge, and I’ll help you map it out on the board. Or if you have something you’d like to teach, we could do a regular interview or use the board to teach a masterclass. You’re also welcome to record any other content you want at Kit Studios while you’re here. Have a great week! —Nathan |
Nathan Barry
I'm a designer who turned into a writer who turned into a startup CEO. My mission is to help creators earn a living. Subscribe for essays on building an audience and earning a living as a creator.
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