Welcome back to Little Leadership Lessons, my weekly newsletter of short, but powerful lessons to help you become world class at what you do.
Welcome to all of the new folks who joined us after Ali Abdaal shared a partial transcript of a recent coaching session from our work together in his newsletter yesterday. Here’s something similar Ali shared last September that’s available publicly if you’re curious.
A Beautiful Photograph of the Natural World

Little Leadership Lesson: Your Brain Wants Certainty
“We are designed to try and reduce uncertainty as much as possible. Our brains are pattern-matching machines that are trying to understand a signal in the middle of the noise[…] trying to make the best predictions possible. Really, that’s how we survive. We evaluate risks.”
— Anne Laure Le Cunff
Author of the newly released Tiny Experiments (highly recommend!) and guest on E42 of Good Work
My Take: Retrain Your Brain to Handle Uncertainty By Defining the Alternative
Anne-Laure is a PhD in neuroscience and a trusted resource on topics like why our brains love certainty. She is, of course, correct on this. We create safety and comfort by matching patterns to get more of what feels good and less of what doesn’t.
When our goal is to stay safe, pattern-matching makes sense. When our goal is to maximize upside, pattern-matching often limits what is possible.
We are constantly faced with choice as entrepreneurs. Do I do this or that? Do I take this big client project or do I create a new course? Do I hire my first employee or do I keep doing it all myself?
The default will always be to choose the more certain option that matches past experience. If you could take a job making $250,000 a year or you could build a business that doesn’t exist yet… you’re more likely to take the job simply because it is more well-defined and therefore certain.
The key is to try your best to define the alternative, even if you could choose anything. If you could build any business, then give it a shape. Choose a timeline. Choose a customer base. Choose a product offering. Set a revenue goal.
Now the choice becomes:
- Take a job for $250,000 a year
- Build a business that will be making $175,000 a year within 18 months by offering social media and content management to outdoor influencers
Now rather than choosing a job that is well-defined or a business that is undefined, you are choosing between two clear options with obvious upside and downside.
Perhaps the job will require 50 hours per week, does not allow side projects, is in office, and allows three weeks of vacation. It also guarantees your income.
The business comes with much more uncertainty and increased responsibility. You have to create every dollar you earn. You have to sell. You have to deliver on services. Do climbers, cyclists, sailors, windsurfers, and skiers have the budget to pay you? How many clients do you need to hit your numbers?
Do you see how the choice changes when you define the shape of the alternative? Now we’re talking about whether this particular business idea has legs rather than choosing the job by default.
Next time you face an uncertain decision because one option comes with infinite choice, give it a shape. Reduce the uncertainty. Make it so that your brain optimizes for the future you want, not just certainty.
From Burnout to Balance: How Tina Tower Built a $2M Business—Without Breaking Herself

On Episode 43 of Good Work, I talk with Tina Tower, founder of Her Empire Builder, a membership community helping women start and scale online course businesses. Tina’s journey to success has been anything but straightforward. She launched a tutoring center at 20, built a franchise that nearly broke her, and sold it in a deal that taught her some tough lessons about business and burnout.
We dive into what she learned from scaling too fast, how to avoid the potential pitfalls of selling a company, and how she transitioned from a high-stress business to running a wildly profitable $2 million-a-year company—with less stress and more joy than ever before. If you’ve ever wrestled with balancing wealth, meaning, and a lifestyle you truly love, this conversation is for you.
Thanks for Being Here
Thank you for being part of my crew. I spent a lot of my life feeling misunderstood, underappreciated, and sometimes actively bullied for who I am.
Knowing that you choose to spend a little piece of your time with me through this newsletter, my podcast, and my coaching work means a lot to me.
You are proof that there really are plenty of kind, ambitious, and thoughtful leaders and entrepreneurs out there who want to both build a better world and create beautiful lives in the process.
Much love and respect,
