Barrett Brooks

Writer and coach for mission-driven creators and startup founders

2024 | Week 11

Find new vision after success, map your emotions, and solitude as leadership.

Hey Reader!

Clocks have changed, spring is here, and along with those wonderful events the not so wonderful spring stomach bug arrived at our house. Not my favorite, to say the least.

Still, we made it through the week. The podcast really is still in the works — I’ve been working with my producer to get the trailer right and the edits for first three episodes are nearly finalized. Stay tuned.
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Next week I’m excited to interview Matt Mullenweg, founder of Automattic (parent company to WordPress, WooCommerce, Text) for a future episode of the show. Hit reply and let me know if there’s something you’d love to hear us cover.
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Speaking of podcasts, after almost 10 years since I was last a guest on the show, I joined Pat Flynn to talk about the process I followed to become an entrepreneur again and all that I learned along the way. Listen in here.​
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And here’s a fun overview video of the social impact event I emceed last month, along with an interest form if you’d like to be invited in the future.

Okay, enough prelude. Let’s get to it.

A short essay sparked by my work with founders

One of the most common reasons founders and creators hire me as a coach is because they feel lost. This is never because of lack of opportunity or resources. It’s because they’ve achieved what they once hoped for and now they don’t know what to do.

This happens often in business. When you get started as a founder (or in building a career) you have a motivation or a mission. You’re setting out to earn a living, gain freedom for your family, make a difference in the world, or build a legacy. You haven’t done anything yet and you’re trying to prove to yourself and others that you can.

You create a vision for your company. “Some day, maybe I could ____________.” Maybe I could:

  • Impact 100,000 customers
  • Change the field of education/healthcare/food/energy/AI/etc
  • Become a senior executive of a publicly traded company
  • Hit $10M in revenue
  • Build a unicorn
  • Take a company public
  • Become a CEO leading hundreds of employees

These are the biggest versions of founder hopes and dreams. But there are many that are more approachable too. Make $1M, have a five person team, or become the CXO of a startup.

There are two success states here:

  1. You achieve the full vision
  2. You don’t quite reach the full vision, but you still achieve something great

And then something surprising sometimes happens.

You feel… empty? Isn’t this what I always wanted? Why do I feel lost?

You’ve lost your organizing principle. Up to now, you were trying to make it. You were fighting to get over the hump. Trying to put food on the table. Get out of debt. Get funding. Get profitable. Pay yourself market rate. Earn the promotion.

Now you did it. What do you have to work for?

If you don’t catch it early, your business or career can stall out at this stage. You settle into the status quo. You get lazy.

Then something wakes you up. Revenue drops. People start quitting. You have a a health scare. Go through a divorce.

But if you catch it early, you have options. And the two best options are:

  1. Form an exciting new vision that starts from where you are and forms a new organizing principle for your work
  2. Actively decide that you’re happy at this scale, and work to make your business or career sustainable and defensible while enjoying the accrued benefits

Both are valid. It’s the active choice to do one or the other that matters.

A quote to make you think from a book worth reading

“We’ve found that across cultures, most of us were raised to believe that being vulnerable is being weak. This sets up an unresolvable tension for most of us, because we were also raised to be brave. There is no courage without vulnerability. Courage requires the willingness to lean into uncertainty, risk, and emotional exposure.

In my most recent research on courage and leadership, the ability to embrace vulnerability emerged as the prerequisite for all of the daring leadership behaviors. If we can’t handle uncertainty, risk, and emotional exposure in a way that aligns with our values and furthers our organizational goals, we can’t lead.”

-Brené Brown, Atlas of the Heart​

There are two aspects to emotional intelligence:

  1. Recognizing, interpreting, and reacting to other people’s emotions
  2. Recognizing, interpreting, and reacting to our own emotions

One of the biggest challenges to both is that our emotional literacy as a society is relatively low. We’re not taught to understand the nuance and differences between emotions.

A tool like the emotions wheel can be an effective decoder when we’re in a situation and can’t quite figure out why we’re feeling emotionally stuck. It helps us name the emotion.

Atlas of the Heart takes this a layer deeper by helping us understand the meaning and nuance of these different emotions. Naming them is only as good as our base level understanding of them.

This book is an excellent resource for becoming more emotionally literate — and therefore more effective in leading others, as well as leading yourself.

Three links to encourage deep thought and breakthrough growth​
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1 Solitude and Leadership by William Deresiewicz | Read time: 29min

“We have a crisis of leadership in America because our overwhelming power and wealth, earned under earlier generations of leaders, made us complacent, and for too long we have been training leaders who only know how to keep the routine going. Who can answer questions, but don’t know how to ask them. Who can fulfill goals, but don’t know how to set them. Who think about how to get things done, but not whether they’re worth doing in the first place.”
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If you only read one thing from this week’s newsletter, make it this. I know it’s long, but it might be one of the best essays I’ve ever read on leadership.

This is the essay version of an address the author made to undergraduates at West Point and it is exceptional.

Question to consider as you read: How could you create more solitude in your life to figure out what you think; to form a clear vision for the future? Who are the people in your life you could be in 1:1 solitude with to explore the hard questions and thoughts we must face as leader?

2 Create a Growth Culture, Not a Performance-Obsessed One by Tony Schwartz | Read time: 5min

“In a growth culture, people build their capacity to see through blind spots; acknowledge insecurities and shortcomings rather than unconsciously acting them out; and spend less energy defending their personal value so they have more energy available to create external value. How people feel — and make other people feel — becomes as important as how much they know.”
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Many startup investors and operators will disagree with me on this, but I will strongly stand by my belief that merely hammering away on your people to perform is not the best way to help them reach their potential (or to reach your business goals.)
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People are not performance machines. Our emotions are a much greater source of motivation for and distraction from our work than anything else. Learning to harness people’s emotions to help them grow to reach their fullest potential, giving them roles where they can excel, and benefiting from the results of their work is the best long-term way to build.

Question to consider as you read: Do you have a growth culture or a performance culture? Is it working? What could you do in the next week, in the next quarter, and in the next year to foster a culture of growth?

3 How to Be Successful by Sam Altman | Read time: 17min

“Self-belief must be balanced with self-awareness. I used to hate criticism of any sort and actively avoided it. Now I try to always listen to it with the assumption that it’s true, and then decide if I want to act on it or not. Truth-seeking is hard and often painful, but it is what separates self-belief from self-delusion.”
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Sam Altman if the CEO of OpenAI and former CEO of Y-Combinator. He knows something about being successful — whether you measure success by money, status, or impact.

Like anyone, his formula for success and principles for life will never map directly on to what matters to you. Still, this essay contains thoughtful principles for maximizing your chances for success as a founder.

Question to consider as you read: What is your core metric for success — money, status, impact, freedom, or something else? Which of the 13 principles are you most practiced in? The least? If you had to pick two to grow in, which would they be?

Much love and respect,

If you enjoyed this newsletter, forward it to a founder friend. You can also recommend me to a founder or creator as a coach.