Picking a place to start

The other day, I suggested to a friend that they should start a business. Their reply was, “What would I do though?”

I listed a bunch of ideas that included a dog poop scooping business, lawn care, shoveling snow, reselling used cell phones and patching drywall. That was just in the first five minutes of conversation.

The problem isn’t finding a good idea. The problem is having the guts to start something that might not work. There is no shortage of good ideas out there in the world. Ideas are everywhere, especially if you are looking.

Of course, it is easy to point to where we feel deficient. “I don’t have enough education/experience/resources/good ideas…” And on, and on, and on.

It makes me wonder what Lin-Manuel Miranda was thinking before producing Hamilton. Let’s do a broadway show on a lesser known founding father, while casting historically white characters as black, latino and asian, and use heavy influences of hip-hop for the lyrics.

Doesn’t sound like a good idea on paper until you see it. Most good ideas look terrible in the ether until they are done in real life.


No one just wakes up at rock bottom. You get there incrementally. It isn’t until later on we realize that we’re in over our heads. Ernest Hemingway wrote:

“How did you go bankrupt?”

“Two ways. Gradually, then suddenly.”

Doesn’t all bankruptcy follow this same pattern?

Whether we are talking about spiritual bankruptcy, emotional bankruptcy, physical bankruptcy…”Just this once” quickly forms a habit. Habits drive our decisions. Decisions over time make up who we are.

The good news is the hole you’ve dug isn’t so large that you can’t escape. Every problem has a solution otherwise it would be a situation. An unfortunate one at that. It’s likely that you have a choice to make here, just not one you are happy about.

Raising the floor

We can choose to focus our work on raising the floor or the ceiling.

Most of us opt for the latter. We want more status, artifacts, title, money, time, stuff.

The reality is there are many out there who are in far worse positions and would trade for our situation in a heartbeat. Do you honestly believe there is no one else in the world who is suffering more than you are right now?

What we need is to appreciate what we have. That isn’t to say it’s a bad thing to want more. But this whole western mindset that, “Greed is good” isn’t bringing us the joy and happiness we seek.

In a world where people couldn’t care less, be someone who couldn’t care more.


We are all falling and falling.

The bad news is there is nothing to hold on to.

The good news is that there is nothing to land on.

We try so hard to establish a platform of predictability, reliability and safety but there is nothing to stand on. Life is always changing. We can’t predict what happens next and there is always something that happens next. That hope to establish something that can never be brings us so much suffering. We lose sight on what is actually happening to us, right now, in the moment, while trying to escape the feelings we have.

When something we perceive as “bad” happens, perhaps instead of creating all this drama we can ask ourselves:

What happens next?

HT When things fall apart.

Faking it

Have you ever noticed that in order to fall asleep, you have to start by pretending to fall asleep?

Creativity follows the same practice.

In order to be creative, at first you have to fake it. We fake it while we practice, while finding our voice, while we develop good taste.

It’s okay to feel like a fake. That’s the starting line.

Freedom of choices

It’s easy to be seduced to believe that you need to have more freedom in your choices.

And it is certainly true, particularly people of color and women and those without enough means, are limited in their choices because of racism, sexism, income inequality and other factors out of their control.

For everyone else, however, we can be convinced that a boss or a teacher or a parent won’t let us do the thing we want to do in the moment, then we must not have enough freedom.

Having an infinite amount of choices and the time on our hand is nothing without discipline. The paradox of choice is very real. The more choices we have, the more unhappy we feel about the choices we make. Because we imagine the other alternatives, we think the grass is greener on the other side.

What we are actually looking for is the ability to choose which constraints to make. Ironically, constraints are nothing but a human invention. They are made up. There is no rule that says you have to use Facebook in order to promote your idea. You can simply choose ignore it or not. You can choose to be vegetarian and now you have invented a constraint about what it is you eat.

We can choose where we are going to set the boundaries and play the game we see fit. Whoever you answer to may not let you choose which project to work on during work hours but last I checked, after 5 o’clock you are free to do what you please.

Get good at the autonomy you do have. Otherwise, what is the point of having more time if you already are wasting the time you’ve got.

What’s a better name for France?

I played a game with some friends over Zoom the other day called Quiplash. The game is really simple. Players answer a wide away of funny prompts (like the title of this post). It’s all made up and you sorta just say whatever comes to your mind.

Most players, however, trip up trying to think of something funny to say. What usually happens is people don’t think the answer that they first come up with isn’t funny enough.

The irony can’t escape me. We have no problem having an opinion, using our voice in settings where we are comfortable. But when we step on stage, we hesitate.

Take a look at Google and obviously you will see it’s a simple search engine. We can fill that box with anything we want. All the collective information for the entire world is right at our finger tips. Except we don’t know what questions to ask.

It’s apparent when you go to a conference and the speaker asks, “Are there any questions?” Of course, we think of questions to ask after the conference is over because we are in a safe space where no one can judge us.

The same thing happens when we load students up in the van for work and I ask someone to pick one of their favorite songs to play. “I don’t have any favorite songs.” Really? You can’t name one song that you like? Of course, you can. But what happens when we pick a song that people don’t like? What does that say about us?

There is a real need for each of us to feel accepted. To fit in. To be like everyone else. I don’t want people to think I’m not funny. I don’t want people to think the question I asked was stupid. I don’t want people to judge my taste in music.

Not everyone is going to like everything about us. We like to complain that people won’t listen to what we have to say but when we have the opportunity to speak up we are quick to let someone else take our turn. If you have something to say, believe that it is important enough that it needs to be heard.

Discard pile

No one is sad about discarding cards in a game of Poker.

We don’t fret about chucking junk mail into the trash can.

Then why are we saddened when our work didn’t resonate with someone and we have to put it in the discard pile?

Because of our effort, we think we deserve specific outcomes. Which causes us to lose focus on the work.

Be proud of your discard pile. Be happy for the fact that something hasn’t worked yet.

That’s the key. Keeping working until it does resonate with the people you seek to change.

Your discard pile should be a mile long. Chock full of mistakes and lessons learned that have been used to make the work better.

Another rejection means you are one step closer to breaking through.


It’s a tricky word. We often fool ourselves into believing that in order to be creative it must be authentic. Something totally new, real, a stroke of genius.

Yet, most ideas don’t follow this pattern. Just walk down the milk isle and you will see whole milk, skim milk, 2% milk, chocolate milk, oak milk, soy milk, almond milk, milk in a jar. Endless variations of the idea of milk.

Every good idea is borrowed and then changed. Rarely, if ever, do we see something that has never been done before.

It’s worth noting, the Greeks have two words for authentic. They have Authentikos which means original and genuine. The definition we are most familiar with. They also have Authentes which simply means, “one acting on one’s own authority.”


All you need to be authentic is to pick yourself. Do creative work. Aren’t you tired of pretending you don’t have greatness in you?

The haves and have nots

We are living in a time of chaos and unrest.

Politics, the pandemic, climate change, racial inequality, minimum wage, healthcare, taxes, education…every single area of our lives needs radical reform.

It’s easy to say, “I don’t want anything to do with this.”

Convenient if you are in a position of power. I mean, why would you want to change a world that suits you?

Those without are thirsty for reform. The Haves, on the other hand, want to maintain the status quo and keep things as they.

Opting out is a sign of privilege.