It takes a lot of confidence to forge into unknown creative territory, telling yourself you’ll figure it out along the way. But there’s another kind of confidence.

Public speaking is like driving a car full of people. For the next few minutes, you’re going to take them somewhere. How you do it matters. 

When I was 21 years old, I found myself in Washington D.C. for a day alone. I wandered around, looked at some stuff, met a friend for lunch, and scalped a ticket to a baseball game. In the middle of it all, my father told me to meet a colleague of his who ran a recruiting firm. 

Can you call a business a success if it closes its doors? Can you say you are successful if your small business isn’t growing? If you have to shut down or sell or leave a business, can you really call that successful? 

I think you can. 

The things I’ve failed at in the past are better indicators of a future path than new things. If I’ve failed at them before, that means I’ve already gotten far enough to fail. 

Building a business takes time. Not because it takes a lot of time to create all the things that a business needs to run, (like a product or a service or a website or a marketing campaign) but because every business is built on trust, and you can’t rush trust. 

This self-focused view made my upcoming talk nerve-racking. As I prepared for the talk, I had a third-person imagination of myself, thinking about how people would view me, how I would sound, and if I would come across as cool and smart.

Every aspect of Martha Stewart’s life came together to make her empire possible: gardening, hosting, modeling, Wall Street, publishing.

In my years producing commercials, I’ve been involved in countless creative builds. This required me to digest the brand, understand the product, learn the audience, and create something that speaks to all of that. Now, I do something way easier. 

Jarred always played with an intensity. Watching him take his at-bats, you could see a stern and determined brow. When he struck out, he walked back to the dugout with a look of pure disgust, flabbergasted that he didn’t get a hit. 

When you find yourself in a moment of stress, there are two prevailing pieces of advice. Some people will say, “just be present.” Other people will say, “this isn’t going to matter in five years, so stop worrying about it.” Neither one feels particularly helpful when you’re in a moment of stress.

When I started my career, I didn’t even know the rules. I made simple mistakes, stepped on toes, and missed easy opportunities. This was just the path I had to take to learn the “rules.”

Trust takes time to build with clients, especially as a freelancer. Early in your career, people hire you as a band-aid; someone to “patch up a hole in the business real quick.” Clients look for someone who seems like they can fix their problem, and who doesn’t cost too much, and they hire them. 

They were both selling their paintings for thousands and thousands of dollars. They both had commissions from wealthy buyers, and were working hard to keep up with demand. Every artist’s dream. So what changed?

To be in business is to take a risk. In a capitalistic society, success is not guaranteed, or even likely. 

Little things can add up over the course of a year. Especially if they’re mostly automated. 

Baseball has a truncated outcome distribution. When you swing, no matter how well you connect with the ball, the most runs you can get is four. In business, every once in a while, when you step up to the plate, you can score 1,000 runs.

My friend started a disc golf company that creates discs from 100% recycled material. Anyone who knows anything about plastics knows that this is a difficult thing to do. It’s a good thing my friend didn’t know anything about plastic.

There’s a tipping point in many decisions. If you’re wondering whether or not to do all the startup work for a new project you’re testing, just don’t. Get a few dry runs under your belt. It’s okay if it’s not a perfectly clean process.

I became aware of the idea of the $100,000 salary in 2005, and have held that number in my mind since then as a benchmark. Here’s the crazy thing. 2005’s $100,000 only has the equivalent buying power of $66,000 in 2023’s money.