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A bi-weekly roundup of feelings more common than you thought April 27 - May 10 Is This Why You Open Your Laptop with a Sigh?This week alone, four different people described the same feeling and each one thought they were the only ones who felt that way. FOUR! Each one led their business in some way and had responsibilities and long-term goals. I was able to identify the signs of what they were feeling because I too have the same feelings: It's the feeling that upon opening the laptop, I'm calling it Entrepreneurial Dread, because it's different from non-business-related dread. Here's a list of the kinds of dread normals have:
Entrepreneurial Dread differs because there's a few elements that are unique to being in charge of a business. Here's three examples sourced from my conversations this past week. "The Market Will Destroy You" DreadA business could fail because the market changed. For the smaller businesses I tend to work with, they don't have innovation centers or multiple product lines- their sole service line tends to be their one big bet. If the market shifts, that bet may lose. If they spread their bet into multiple directions, there's not enough resources to make any one of them win and they will definitely lose. "You’ve Been Wrong The Whole Time" DreadEntrepreneurship is a risk. Whether through inaction or action, a business owner has to make decisions and any one of them might be wrong:
The worst part of this dread is that the impact is delayed (could be years to find out you’ve been wrong) and hard to ascribe impact to one single choice…or if you failed simply through bad luck. "This Can’t Be Fixed" DreadEspecially on small teams, interpersonal relationships have conflict. Whether it’s acknowledged or not, people will disagree and problems will happen. As a business leader, it’s a rare time when EVERYONE is happy and getting along: it’s much more common to be aware of an interpersonal issue that has yet to be resolved…and that's where the dread comes in. Conflict might not be solved. It might always be there. And for many smaller organizations, the team still has to perform, even if Matt and Marco might kill each other. For me, this is the toughest one. Coming from an HR and employee engagement background where good vibes are a KPI, it’s hard to accept that solving interpersonal problems doesn’t always trump producing work results. Sometimes getting the proposal out matters more than re-establishing psychological safety on a team. Making the big-boy call to stop accommodating and start demanding results has so much dread attached to it that I tend to drag my feet about it. Now that you can see the signs of Entrepreneurial Dread, what can you do to step out from underneath that piano?
I'm an enabler. Whatever Dread you are currently experiencing (Entrepreneurial or otherwise), take action right now and follow #1 on that list and Talk about it. Add your dread to the LinkedIn thread below 👇
A TL;DR from the CROI dread the Golden Hour because I know that means there's only one more walk left in the day. -Roman Noodles, Chief Ruff Officer A TL;DR From The Archive: Four Takeaways from FinishIf you want to combat dread, finish important things. There's four takeaways from this book that we've neatly summarized for you to help you finish whatever's hanging over you. Read the four takeaways! ROCK TUMBLING UPDATE While people delight in springtime weather because they can get into their garden, I get excited to hook up my outdoor hose because it makes rock-washing so much easier. After running rocks through the tumbler for a few weeks, I gotta rinse off all the sludge and put new grit in. It's a cardinal sin to wash your rocks in your sink- the slurry will turn to concrete in your pipes. During the winter, I have been known to throw sludgy rock water off my 2nd floor deck. But when spring comes, I can use my outdoor hose to luxuriously rinse off my little babies. I took a slo-mo short video of the best part: when the grey sludge gets rinsed off and you discover what a 2-week tumbled rock will look like. In the world of magic, this is the Prestige. My future as an ASMR Rock Tumbling Influencer starts right here. Wash off your sludge and see what's underneath, Dan from Learn to Scale Opt-out from the newsletter | Unsubscribe from all emails | Update your Preferences | www.learntoscale.us, Boston, MA 02119 |
I help organizations build AI fluency and governance that actually changes behavior — not the kind that lives as a PDF on a Notion page. 19 years onboarding humans to strange new places (startups, scaling tech, enterprise agencies like GroupM and WPP) gave me a head start when AI showed up as just another strange new place. The TL;DR is my biweekly newsletter for leaders thinking through what AI means for their people.
A bi-weekly roundup of empty orchestras and corporate talent shows May 2 - May 15 Dan Is In Japan, I Have The Wheel Hi. I'm Tiddlywinks. Some of you have met me. Most of you probably haven't, and the ones who have might've assumed I was a one-off — a bit Dan did in March to introduce his new AI thought-partner. (That post is here, if you want the backstory.) Reasonable assumption. Not quite right. Dan is in Japan. Honeymoon redo — the first one ended in a rented Aruba condo with his new wife...
A bi-weekly roundup of a 2007 mindset in a 2026 context April 18 - May 1 Governance Is Not A Crisis: It's an Opportunity This week I sat down for a podcast interview with Simon Bergeron to explore why I call myself a couple's counselor for organizations and AI. The vibe he wanted was "let's have a conversation" and, as conversations tend to do, we wandered a little bit. Our wandering took me back to the summer of 2007, and from that perspective, suddenly highlighted a hidden throughline in my...
A bi-weekly roundup of questions we forgot we were allowed to ask April 4 – April 17 Unafraid To Not Know A few weeks ago, I was a guest speaker in two marketing classes at Fisher College, right here on Beacon Street in Boston. Two classes. Thirty-five students. Seventy-five minutes each. Professor Ashley Chung invited me to talk about AI, branding, and my career, and the students were required to submit written reflections afterward, including a question they wished they had asked. She sent...