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.
Why I embrace being a delusional optimist
|
Hey Reader, The other day someone called me a delusional optimist. I wasn’t sure if it was an insult or not—being called delusional usually is. But throw in optimist and I think the combination describes me well. It’s something I’ve come to recognize about myself over the years. I genuinely believe that almost anything is possible. You’ll have a hard time convincing me that something can’t be done. There’s a quote I love: “The reasonable man conforms to the world. The unreasonable man expects the world to conform to him. Therefore, all progress depends on the unreasonable man.” This mindset serves me in significant ways. People want to be part of something big. They want to follow a vision. When you set audacious goals and communicate them with conviction, you rally people to join you. This has been essential in building Kit. But there’s a downside too: you can build a reputation for being unreliable or not grounded in reality. If I cast big dreams and miss too many times in a row, people start saying, “There goes Nathan again,” and roll their eyes at my latest ambition. But as a delusional optimist, it’s the only way I know how to operate. It might come with missing deadlines sometimes as a rule of dreaming too big, but the point is that it makes me chase big things. I’m often too optimistic about how quickly I can get something done. But given enough time, I’m able to bring ambitious dreams to life. Realists would never try certain things. They’d calculate the odds, determine it’s too risky, and move on. Sometimes that’s wise. But often, the most worthwhile pursuits look impossible at first glance. With that said, there’s another trap to be wary of: Confusing patience with procrastination. Sometimes you tell yourself, “I’m just being really patient with this project” when in reality, you’re procrastinating. It’s important to recognize the difference. You might say, “I’m being patient in this sales process,” when you’re actually avoiding making necessary calls. I do this with book writing. I’ll say I’m patiently developing ideas when I’m really just avoiding the hard work of putting words on the page. The key is recognizing when your optimism is pushing you toward important goals versus when it’s simply helping you avoid difficult work. Being a delusional optimist means believing in possibilities others don’t see. But actually accomplishing those big things requires pairing optimism with honest self-assessment. Consistent action is what will bring those possibilities to life. Next time you catch yourself saying, “I’m just being patient,” ask yourself: “Am I truly being strategic, or am I using optimism to mask inaction?” PODCAST$100K Passive Income Strategy for 2025Want to add $100K in creator income to your existing services business? Today, I coach Ali Schwanke on how to build profitable, scalable offers without cannibalizing her core services. We cover how to:
Watch or listen to episode » EVENTCraft + Commerce 2025Join us in Boise, Idaho this year for Craft + Commerce: a conference for serious creators like you—where top online creators gather to grow their businesses and build meaningful connections. At Craft + Commerce, you'll experience: → Keynote talks 20-minute main stage talks where diverse creators share real stories of building sustainable online businesses. → Intimate workshops Learn practical strategies for building teams, scaling systems, and leave with the confidence to take your business to the next level. → Direct access to Kit experts Get your email marketing questions answered and set up the systems you need to scale your business. → Extended Kit Studios access Book time in our professional video and podcasting studios. Kit Studios is free for all creators attending the conference. → Parties + meetups Connect with like-minded creators throughout the event—from our opening night party to coffee breaks and creator-led meetups, ending with a dance party. BOOKFour Thousand Weeks: Time Management for MortalsMost productivity books focus on getting more done, but Oliver Burkeman takes a different approach in Four Thousand Weeks. Instead of telling us to squeeze more into our days, he encourages us to embrace the finite nature of time. The title comes from the sobering reality that the average human lifespan is only about four thousand weeks. When you look at it that way, time management becomes less about optimization and more about making conscious choices. I find this perspective refreshing in our productivity-obsessed world. Rather than trying to hack your time, accept that you can't do everything and prioritize what's essential. 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.
Hey Reader, There are opportunities hiding in your email list right now that you probably have no idea are even there. And that’s because while your audience may know you, at scale it’s difficult for you to know them. Until now. Last week was the biggest product week in Kit’s history. From the stage at Craft + Commerce, I announced a new Kit feature I’m really excited about called Subscriber Signals. It’s audience research done for you automatically. It was my favorite announcement but far...
Hey Reader, My worst business name ever was Unattended Media. The logic made sense to me at the time since I was building websites and software that ran automatically even when I wasn’t sitting in my desk chair. I laugh when I look back on it now, but the logo I made was actually an empty chair. The name meant freedom to me, but to a potential customer, their impression was that nobody worked there. Imagine a conference put on by “Unattended Media”. Kit used to be named “ConvertKit”, which...
Hey Reader, Have you noticed people seem to be outsourcing their thinking more lately? Clear writing used to be a good indicator of clear thinking. To produce clear writing, you had to go through an iterative process that involved reflection and refinement. Amazon famously required six-page memos before every meeting. They banned slide decks because they masked poorly thought-through ideas. The point of the memo was never the words on the page, but instead that rounds of thinking and...