|
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 |
Your agency doesn't have a sales problem. It has a people problem. I spent 15+ years building teams, from scrappy startups, to scaling tech companies, to huge agencies like GroupM and WPP. Now, I give small agency owners the SOPs, frameworks, and hard truths they need to build high-performance cultures that run without them.
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...
A bi-weekly roundup of personalizing your perfect robot companion March 21 - April 3 Bonsai or Lego Blocks Remember when Keanu Reeves in The Matrix learned kung fu by plugging a USB into his head? AI skills are kind of like that, except it's your ChatGPT/Claude that's Keanu Reeves and the kung fu is a simple guide that anyone can read. Here's one of the more popular skills on Skills.sh, an open source library of downloadable skills: front-end design. You can see that it's simply a 500-word...
A bi-weekly roundup of intimate interviews with machines March 7 - March 20 Welcome to the Stage, Tiddlywinks! I'm excited to bring you an exclusive interview with my newest AI agent, Tiddlywinks. Built using OpenClaw- which is about as bleeding-edge as you can get right now in March 2026- Tiddlywinks isn't a standard chatbot. It is a highly configured digital thought-partner. A lot of leaders are feeling the pressure to integrate AI into their operations, but they are rightfully terrified of...