May 28, 2022

Doing It Afraid


kay, this leadership thing…it’s hard. Don’t cry for me. I am lucky to have these problems. Zero complaints. Okay, well, maybe a few to Princess Buttercup from time to time. Thanks for the support, B.

I wanted to share this because I don’t think I’m alone. Maybe I am, but I doubt it. Before I got this fancy title, I thought, “What’s so hard? It’s just the next level? It’s just more responsibility. How hard can it be?”

Ah, the ignorance of inexperience.

First, it’s not all bad. There are some extraordinary highs. Mine usually revolve around finding out our aspirational culture is real, at least a little. Or when I watch someone grow. It’s like a time-lapse of a tree growing. They get bigger and stronger. They bear fruit. The ecosystem starts relying on them more. Immense joy. It makes it all worth it.

Conversely, there are low lows. If it reaches ‘your desk,’ it’s not usually good or easy. If it were, it would have been solved already. The days are filled with those. Stay strong.

Do It Afraid

I met a guy the other day, Corey. He had "Do It Afraid" stitched on the inside of this jacket. I LOVE THAT.

It got me thinking about some hard times I was going through late last year. Hard decisions on ‘my desk.’ There were two paths, one hard and one easy. I desperately wanted to take the easy path. Fear was creeping in, but I ended up leaning into hard.

I remember how hard it was and I saw the easy way out. I wanted to bow down and let it own me. My training said, “Don’t give in. People rely on you to take the hard right instead of the easy left. Take the long view. What will you do, sarge?”

I made a decision not to give in. I’m sharing this not to be boastful because who knows if I was right. Only time will tell. I’m sharing so that you see this guy questions himself too. For this decision, I let fear be my arrow.

My Take Away:

Do it, afraid. Fear points us in a direction that keeps us alive, not just breathing, but alive.

10 Thoughts Inspired by The Hard Thing About Hard Things

When things get hard, I think about one of my favorite business/leadership books—the Hard Thing About Hard Things, written by Ben Horowitz. Here are a few thoughts inspired by quotes I like. Ok, let’s get into it.

First, each chapter leads with a bit of poetry from the likes of DMX and others.

This here is all about My wife, my kids, the life that I live
Through the night, I was his, it was right, but I did
My ups, and downs, my slips, my falls
My trials and tribulations, my heart, my balls.


1. Don’t Worry, You Have Choices

If you don’t like choosing between horrible and cataclysmic, don’t become CEO.

That about sums it up. When it gets hard, lose yourself in the service of others. And when you want to break, remember nothing is permanent. This too shall pass and you will be okay - worse things are happening to better people.

2. Plant Good Seeds, Get Good Plants

By far the most difficult skill I learned as CEO was the ability to manage my own psychology.

Fear, Uncertainty, Criticism & Doubt (FUCD) - make sure you know those are just voices in your head. Thoughts are the one thing you can control. And yes, the acronym is intentional.

3. It’s Not About You

Truly great leaders create an environment where the employees feel that the CEO cares more about the employees than she cares about herself.

Make the right decisions for the team, regardless of what happens to you. Leaders sacrifice.

4. You Won’t Always Be Popular

Being CEO requires lots of unnatural motion. From an evolutionary standpoint, it is natural to do things that make people like you. It enhances your chances for survival. Yet to be a good CEO, in order to be liked in the long run, you must do many things that will upset people in the short run. Unnatural things.

So much to unpack. They laugh at my jokes. Why would I do anything to upset that? Because it’s the right decision for the organization. Period. It’s not about you. It’s about the team. Great leaders will consistently do things that people don't like in the short run. If all leaders did were things people like, everyone would lead.

5. The Mission Matters

Nothing motivates a great employee more than a mission that’s so important that it supersedes everyone’s personal ambition.

People want to do things that matter. Some want commas in their bank account, but everyone wants what they do to mean something.

6. Choose An Action Culture Vs Status Culture

There are two kinds of cultures in this world: cultures where what you do matters and cultures where all that matters is who you are. You can be the former or you can suck.

This. Gosh. Do things that matter or suck. What if we all spent less time worrying about what people think? Up, down, or sideways. Just do good work and let it speak for itself.

7. Know The Situation: Wartime Vs Peacetime

Peacetime CEO knows that proper protocol leads to winning.
Wartime CEO violates protocol in order to win.
Peacetime CEO focuses on the big picture and empowers her people to make detailed decisions.
Wartime CEO cares about a speck of dust on a gnat’s ass if it interferes with the prime directive.
Peacetime CEO builds scalable, high-volume recruiting machines.
Wartime CEO does that, but also builds HR organizations that can execute layoffs.
Peacetime CEO spends time defining the culture.
Wartime CEO lets the war define the culture.
Peacetime CEO always has a contingency plan.
Wartime CEO knows that sometimes you gotta roll a hard six.
Peacetime CEO knows what to do with a big advantage.
Wartime CEO is paranoid.
Peacetime CEO strives not to use profanity.
Wartime CEO sometimes uses profanity purposefully.
Peacetime CEO thinks of the competition as other ships in a big ocean that may never engage.
Wartime CEO thinks the competition is sneaking into her house and trying to kidnap her children.
Peacetime CEO aims to expand the market.
Wartime CEO aims to win the market.
Peacetime CEO does not raise her voice.
Wartime CEO rarely speaks in a normal tone.
Peacetime CEO works to minimize conflict.
Wartime CEO heightens the contradictions.
Peacetime CEO strives for broad-based buy-in.
Wartime CEO neither indulges in consensus-building nor tolerates disagreements.
Peacetime CEO sets big, hairy, audacious goals.
Wartime CEO is too busy fighting the enemy to read management books written by consultants who have never managed a fruit stand.
Peacetime CEO trains her employees to ensure satisfaction and career development.
Wartime CEO trains her employees so they don’t get their asses shot off in the battle.
Peacetime CEO has rules like “We’re going to exit all businesses where we’re not number one or two.”
Wartime CEO often has no businesses that are number one or two and therefore does not have the luxury of following that rule.

I do love these. Especially the comment about fruit stands…though that is a good book too. Also, there is a time and a place for each and generally don’t believe in absolutes - including this one.

8. Embrace It

If you are going to eat shit, don’t nibble.

It’s gonna suck. Embrace it. It makes you stronger. But head the advice, never eat alone. Lean on your humans and take in the experience. Lessons don’t come from the experience, they come from reflecting on the experience.

9. Don’t Make Excuses

All the mental energy you use to elaborate your misery would be far better used trying to find the one seemingly impossible way out of your current mess. Spend zero time on what you could have done, and devote all of your time on what you might do. Because in the end, nobody cares; just run your company.

Just focus on what you can control and do the next best thing. Coach Wooden would add: Don’t whine, don’t complain, don’t cheat, and don’t steal.

10. It Should Be A Struggle

The struggle is where greatness comes from.

If it’s not a struggle, you are probably not trying hard enough. Leading is hard. The world is counting on you to lead. All good things take time and require leadership.

Lead on, my friend. Lead on.

Take care - Kelly

PS - This weekend is Memorial Day. This is when we make it a point to take time and remember those who have died in our country's service. This is a special holiday for me. It is where I remember, honor, and celebrate those incredible humans. Rest easy, brothers and sisters.

PPS - As you celebrate them this weekend, please make sure you hug your humans. Especially the little ones. Not everyone gets to do that this weekend. When will this stop?

One More Thing

A very good friend is building a business (which is very hard). I will share more details later, but please check it out at They make getting your knives sharpened easy. So, remember this photo of them laying down a sweet edge when you take out that knife you got 12 years ago as a wedding gift to slice / smash your Memorial Day tomatoes. And to the crew at Vivront - keep at it, friends, proud of you.

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