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Daily Inspire

Weekday encouragement and weekend insights for rebellious, big-hearted entrepreneurial spirits.

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Daniel Pink on the power of regret

SPONSORED BY KIT Hey Reader, Three years ago, I met Daniel Pink in person while he toured for his book, The Power of Regret. He talked about how the mentality of "no regrets" is bullshit, but not in the sense that takes away from the sort of divine imperfection of all our lives. Instead, he meant if you don't regret anything, you probably didn't learn anything (and that's the problem). Regret has the power to incite new action: Maybe you didn't go to that conference last year, but say yes to...

SPONSORED BY KIT Hey Reader, Some of you know this about me because I'm a Feng Shui energy geek, but I see colors around people. It's not like light blasting from the crown of your head; it's more of a subtle visual in my mind's eye. Sometimes it's one soft color, sometimes two or three together––they change depending on the person's mood and the moment, and I've always used them as a way to explore how someone might be feeling. I use it with myself, too, especially on days when I can't quite...

SPONSORED BY KIT Hey Reader, When I was in Paris in 2017, I took a live nude drawing class. Before we started, the instructor told us it was going to be extremely taxing, and that people often underestimate how much mental energy it takes to focus on a subject for hours. I relished in this. Who doesn't love a challenge? First we had to focus for 5 minutes while the model held different poses. Then 15 minutes. Then 20 minutes. Then an hour. Midway, the instructor came around to see our...

SUPPORTED BY HALF-OFF HOSTING Hey Reader, When I was a kid, I had a junk drawer full of random springs and metal parts and scrap pieces I found in my Dad's garage. It was the bottom drawer in my nightstand and every evening I'd open it, sit on the floor cross-legged, and see what I could make. One time I made a Home Alone style door knob trap. It worked. Another time I made a perfectly usable slingshot. Ask my brother if it worked. But perhaps my favorite invention was a pulley-system basket...

SUPPORTED BY SHOUTOUT.IO Hey Reader, Are you self-critical? Or are you one of those weirdos who has radical self-acceptance? (In which case, can we hang out?). Because one thing I notice about self-critical people like me is we've got a funny little wound around acceptance. Someone, somewhere said we were weird or different or too much or not enough and we made the mistake of internalizing it––of using every experience we could to justify why they're right. And oh boy, does that take its toll...

SUPPORTED BY SQUARESPACE Hey Reader, One of my favorite creators right now is Katelyn Bourgoin, the founder of Why We Buy, and one of the most empathy-driven entrepreneurs I've ever seen. Katelyn digs deep into buyer psychology and I recently saw how she (automatically) adjusts her language and product recommendations depending on the buyer's specific problem. She asks a multiple choice question in her emails, assigns them custom tags, and based on that tag will send a dedicated welcome...

THANKS TO POCKET-SIZED COACHING Hey Reader, Yesterday, my business coach made an observation about the way I work that was both amusing and accurate (if not a little bit vulnerable). He said, "The thing that excites you and the thing that makes you feel guilty are the same thing." I'd mentioned how I love working in sprints which ultimately requires significant rest to recharge––and I feel guilty about that, but there's something about the urgency of sprints that just gives my brain the...

SUPPORTED BY STUDIO Hey Reader, When I was 14, my aunt said very plainly said to me: "Do you think I'd be in this relationship if I could support myself?" I was shocked. Partly because she admitted this to me but also because I didn't realize anyone could feel this way––like they couldn't figure something out. Color me naive, but I believed that come hell or high water, figuring things out was the thing we could all do. But I was wrong and lots of people don't believe that at all. When I...

Procrastinating, clearly

SUPPORTED BY SQUARESPACE Hey Reader, Have you ever felt like you know exactly what to do, but are scared to actually do it? Even when something's good for you, change is scary. The trick for overcoming that fear and doing the thing you want is this: You can either make the thing less scary OR make the scary matter less. Make it less scary This is possible by priming our brain, and there's only two ways I know how to do that: Take on little bits at a time. Have a public talk coming up? Make a...

SUPPORTED BY SQUARESPACE Hey Reader, What do you get when you put 40 extremely generous creative entrepreneurs in a room with unlimited coffee, curated dinners, and prompts for sharing best practices, personal blocks, and underrated opportunities? You get The Lab IRL. This in-person event by Creator Science takes its online community offline for an opportunity to collaborate, share, and connect in an industry which is more lonely than any of us care to admit. We met in a boutique hotel in...