Barrett Brooks

Writer and coach for mission-driven creators and startup founders

Be honest with yourself (2024 | Week 27)

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Hey Reader!

I’m back! My family and I took a fantastic 2+ week trip to Singapore, which is where I took the opening photo for this week’s newsletter. We stopped off in San Francisco for a few days to see friends on the front end then spent two weeks seeing extended family, exploring the touristy stuff and eating so. much. good. food.

My wife was born in Singapore, so it was a bit of an unfair advantage to have my first trip to Asia be a bit like going home. But even without that being the case, I’d highly recommend it as a travel destination. I even got to meet up with a couple of awesome creators while there:

Ok, enough preamble. Thanks for caring about me as a human in addition to the leadership advice I share here.

One more thing: read to the end for a fun ask! I’d love to hear from you. (No, I’m not selling anything)

Mini Essay: Be Honest With Yourself
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The beginning of every coaching engagement I do starts with what I call a commitment. A commitment might be as direct and logical as “Grow my company to $10M a year in revenue” or as deeply personal as “Share my true feelings with the people in my life, including my spouse, family, and team.”

The creator-founders that make up the bulk of my clients are highly “successful” in conventional terms. Their businesses are usually earning at least $1M a year in revenue. They have reached goals most people who aspire to be entrepreneurs hope to one day reach.

Many Successful Founders Have Negative Internal Narratives

It might surprise you to know that many of these founders have negative internal narratives about who they are, what they are capable of, and whether they can achieve their goals going forward.

One of the most common commitments I work on with clients is a category that includes things like:

  • Trust myself
  • Believe my own experience of life
  • Be honest with myself
  • Create alignment between my inner and outer lives

What powers us to overcome the obstacles necessary to “make it” as entrepreneurs are what holds us back as we hit new stages of scale. Entrepreneurial survival is a hell of a drug.

But abundance and growth require a new set of skills because skills based in stress, cortisol, and workaholism quickly turn into liabilities at scale.

You Have to Be Honest With Yourself to Keep Growing

The first key to turning the corner and becoming the leader the next stage of your business needs is to be honest with yourself. You have to tell yourself the truth.

That sounds like a negative thing. Because most entrepreneurs have relentless inner-critics, “honesty” is often misinterpreted as “beat the shit out of my soul with criticism until it wants to cry.”

That’s not honesty. That’s a broken pattern based on old stories and experiences.

Being honest means admitting things like:

  • I’m hitting the edge of my financial understanding of this business
  • I don’t know how to grow from $1M to $10M in revenue
  • I feel overwhelmed by the amount of work on my plate
  • I need help

It also means being honest about the skills and expertise you’ve built. You have to be willing to admit the ways in which you’re world class too:

  • I’m in the top 1% of the world in understanding [topic]
  • I have more social media followers than 95% of humanity because I understand what people want
  • My last product launch did $600,000 in revenue and that is remarkable
  • I am an exceptional storyteller, as evidenced by [projects/campaigns/books/content]

If you’re going to be honest, you need to be honest about the full picture. You can’t just beat yourself up and say that’s “honesty” because in fact that is a way of lying to yourself. Telling yourself a falsely negative story keeps you small and prevents you from reaching your potential.

Name Your Silent Thoughts and Filter Down to Your Real Beliefs

What follows from a commitment to telling yourself the truth is a greater willingness to admit what you actually think. Once you admit to believing you’re world class at something, you become more willing to say other things you’re “not supposed to say.”

Repressing the things you think gives them more power. When they are spoken out loud, they lose some of that power. When you admit to the weird, scary, or embarrassing things you think but don’t say, you allow them to occupy less space in your heart and mind.

Here’s an exercise to practice this:

I’m not advocating you walk around saying all of the things you think to everyone you know. Moderating your thoughts before sharing them is a necessary skill to maintain good relationships and practice responsible leadership.

I AM saying you should admit what you think to, for example, a spouse, a therapist, a coach, a close friend, or someone else you trust. These are people who can help you process what you have held in silence for too long. They can help you filter down to what you really believe.

At minimum you should write these silent thoughts down so you can stare at them outside of your own head, even if you feel the need to burn those thoughts out of existence afterwards.

Knowing What You Really Believe Gives You Permission to Say No

Being honest with yourself — fully honest — enables you to admit what you think. And when you can admit what you think, you gain a greater ability to filter for what matters to you. When you know what matters, you can much more easily say no to things.

As your income and business grow, there is much more risk in the things you say yes to than the things you say no to. Scaling a business means finding what works, cutting what doesn’t, and building systems to scale the things that work. That will require a lot of saying no.

Too many entrepreneurs have convinced themselves that they must say yes to things they know in their hearts they shouldn’t do. Why? Because if they say no, “the opportunity may never come again.”

I Say Yes to Things for The Wrong Reasons Too!

This happens to me too! Just a few weeks ago I said yes to doing three podcast interviews in one week even though I knew it would cause me to work far too many hours. Why? Because I was scared I wouldn’t get to interview a guest if I proposed dates that worked for me.

When I said this out loud to my own coach, the false narrative became obvious.

I said, “I booked three podcast interviews last week. I felt overwhelmed and worked too much.”

My coach replied, “And what made you feel that you had to say yes to so much?”

…

…

“Well, I guess I was scared I’d never get the chance to interview that person again,” I said with decreasing conviction with each passing word.

But that thought was buried in my head and heart. I had not admitted it to myself, let alone said it out loud. As soon as I said it, the idea lost all power over me.

Learn To Say No and Make Counter Proposals

Entrepreneurs making millions of dollars a year say yes to things they don’t want to do all the time because they aren’t being honest with themselves. They aren’t admitting what they actually think.

“My time is more valuable than that. That doesn’t work for me.”

You don’t have to say it that way to the other person. You can say, “No thanks, that doesn’t work for me.”

Trust Yourself

Above all else, you have to trust yourself. You have to trust that you’ll be ok. You have to believe the full truth about who you are and what you’re capable of. You have to admit what you actually think. And you need the courage to act on it.

So be honest. You probably need to grow if your company is going to grow. And you’ve become world class at a number of things along the way. The things you think but haven’t said out loud have power over you right now. Write them down. Speak them to a trusted person. Act on what you know to be true.

Trust yourself.

A Few Tweets to Make You Think

​What you consume is what you think.

Solving seemingly impossible problems is sometimes just math.

I write for founders, but you don’t have to be a founder to lead. You also don’t have to be a founder to build substantial wealth.

A thought about July 4th in the US that applies to anything that matters.

An Ask: Write Me a Letter!

My essays in this newsletter are based on real coaching conversations with founders. This is a fun way to write, but it’s largely sharing lessons from the founders paying me to work together. I’d love to be able to help you directly!

My wish for this newsletter is that it might become something like a “Dear Abby” or “Dear Sugar” column for founders and creators working to become the leaders their teams and customers deserve.

So I have an ask: if you’re a founder would you write me a letter?

Here’s a quick format you can follow:

Dear Barrett,

I’m a founder of a company that: [what your company does].

Here’s the situation at my company: [relevant details and context to what’s going on]

I’m struggling with: [what’s challenging you the most as a leader given the situation]

My core question is: [what question(s) do you have about how to move forward]

Thanks!
[Name]

It would be awesome if this newsletter could become a series of letters between you and me, published for others to learn from. I don’t know the answer to every question, but I have the coaching skills and plenty of my own experience to offer perspective that may be helpful.

Plus, it’ll make this entire enterprise more fun for all of us, and hopefully more helpful to you.

So, write me a letter! Let’s make this something special together. (And if no one writes, I’ll keep doing what I’m doing and ask again later)

Much love and respect,

PS: Things to do next:

  1. Listen to my podcast conversation with Nathan Barry about everything we learned building ConvertKit to $30M in annual revenue over five years
  2. Forward this newsletter to a friend who would enjoy it
  3. Refer a founder friend to coaching and I’ll pay you $1,000 if we start working together