Really good questions

I found an old note recently with a set of really good questions I’d like to share with you. I think most of these came from Seth Godin. He has one of the best podcasts ever made.


What would you do if you knew you were going to succeed?

What would you do if you knew whatever you were going to do you would fail? What is the process you would choose to take, if you knew you were going to fail?

Whatever is causing you stress at the moment, be it a business or a relationship… anything, what might this look like if it were easy? If it had to be easy,  what might it look like?

How far can you ratchet down the scale until you have no more excuses to do something? For example exercise may seem overwhelming, how far down until it becomes easy and you no longer have an excuse not to do it?

Where can I selectively de-optimize activities to promote wellness and optimize myself overall?

Essence of design theory: “Who’s it for?” and “What’s it for?”.

What would matter when you’re 90?

What would you tell your best friend to do in this situation?

What are you getting out of the cycle of [something]? What does it do to add to your life?

What if you stopped looking for new ideas and simply focused on the best idea you have right now?


Sometimes the best advice comes in the form of questions, as they cause us to pause and think about our next steps rather than just telling us where to walk.

Change the thinking to change the outcome

When we do anything, when we think anything, we do so through a lens crafted from a mosaic of our values and beliefs. These values and beliefs influence our thinking and how we perceive the world so much that to us, they have more meaning than the truth. If the truth is at odds with our values, chances are we will double down on what we believe to be true rather than what is objectively true.

This can really get in the way when we start trying to deal with our problems and challenges in life. No matter what we try, we can never break the cycles.

We cannot solve our problems with the same thinking we used when we created them.

– Albert Einstein

Although this quote is generally attributed to innovation and technology, it can challenge a thinker to look at any problem from a different perspective. If pushing doesn’t work, try pulling.

Einstein’s quote highlights a key truth: the thinking that created a problem won’t be the thinking that solves it. It calls for a shift in mindset. Real solutions require us to challenge old patterns and embrace change.

To do so will feel very strange at first. In fact it will feel down right wrong. We will need to completely go against what we’ve “always” felt to be true and what we’ve connected to our very identities.

Change starts with action, and it happens incrementally. It happens so slowly we barely notice. Taking action and d”oing something” will eventually help you get more comfortable with the new way of thinking. The more you engage with the new approach and stay aware of it, the more it begins to shift your old thought patterns. Over time, this new perspective becomes part of how you think. Either you’ll start seeing different results, or your expectations will shift enough that the issue no longer feels like a problem.

The mindset that built it won’t fix it.

Our beliefs shape how we interpret experience

David Foster Wallace told a story during his 2005 commencement speech at Kenyon College about two guys sitting in a bar in Alaska:

There are these two guys sitting together in a bar in the remote Alaskan wilderness. One of the guys is religious, the other is an atheist, and the two are arguing about the existence of God with that special intensity that comes after about the fourth beer. And the atheist says:

“Look, it’s not like I don’t have actual reasons for not believing in God. It’s not like I haven’t ever experimented with the whole God and prayer thing. Just last month I got caught away from the camp in that terrible blizzard, and I was totally lost and I couldn’t see a thing, and it was 50 below, and so I tried it: I fell to my knees in the snow and cried out ‘Oh, God, if there is a God, I’m lost in this blizzard, and I’m gonna die if you don’t help me.’”

And now, in the bar, the religious guy looks at the atheist all puzzled. “Well then you must believe now,” he says, “After all, here you are, alive.” The atheist just rolls his eyes. “No, man, all that was was a couple Eskimos happened to come wandering by and showed me the way back to camp.”

– David Foster Wallace

This “didactic little story” as Wallace called it shows how our beliefs shape how we interpret our experiences. The same event can be seen as divine intervention or random chance, depending on the lens through which we view the world. But where did we get the lenses? Were we born with them or given to us by our parents, our communities, or peers? Can we ever change them and see things differently?

The meaning we assign to events is often less about truth and more about the stories we’re inclined to believe.

Maybe it was God. Maybe it was chance. Maybe it was both; A world created by God filled with chance. Maybe it was neither… but I’m not quite ready to get into determinism yet.

Maybe it doesn’t matter which lens we’re looking through, so long as:

  • we are aware that lenses exist,
  • we know other lenses are out there,
  • and we use this knowledge to choose which lens we look through, or at least be aware that during any experience, we are in fact looking through a lens.

It’s is not about choosing what to think, but choosing how to think. Wallace called this lack of awareness the “default setting”. To begin to override it is to become aware, to pay attention, and to recognize that our default settings may blind us to other perspectives.

We are what we eat; and what we once ate, we were fed.

Obstacles don’t block the path, they are the path

Life is filled with annoying things, annoying people, and annoying responsibilities. There’s too much to do, not enough time to do it, and at every step; an obstacle. Our default is frustration. We get mad at these obstacles. We blame them for keeping us from our goals. “Why do I get all the obstacles when that other guy gets it so easy?”

“Obstacles don’t block the path, they are the path.
– Zen Proverb

Maybe we should recognize that these obstacles are unavoidable features of life. Through them we change and grow. Maybe we can see them for what they truly are; opportunities.

The times we learn are the times when we struggle. If we choose to view obstacles as puzzles, challenges or simply as more experiences that we pass along our way, we might just relieve the pain we think they cause.

“The impediment to action advances action. What stands in the way becomes the way.”
– Marcus Aurelius

Obstacles aren’t bugs, they’re features.

Burn ships, not bridges

The phrase “don’t burn bridges” originates from a military tactic where armies would build bridges to cross rivers, then burn said bridges behind them; either to prevent retreat (forcing troops to fight onward) or to stop enemies from following.

“When your army has crossed the border, you should burn your boats and bridges, in order to make it clear to everybody that you have no hankering after home.”
― Sun Tzu, The Art of War

This tactic of “no going back” can also be linked to Julius Caesar, Alexander the Great, Tariq Ibn Zyad, and of course the Spanish Conquistador Hernán “burn the ships” Cortés a la my last post. Although an effective motivator, I doubt the soldiers were happy their leadership team chose this over the promise of a victory pizza party or the implementation of Casual Fridays. While these generals were literally burning bridges, they were figuratively burning them with their troops. What happens to the relationship after the crisis?

The phrase has evolved to mean: “don’t destroy relationships or opportunities you might need in the future”.

When making major life or career decisions, “burning the ships” can be an effective way to stop procrastination and puts you “all in” on the path you chose. However, what happens when that burning ship floats under a bridge and you start spreading flames all over everything in your life? In Summary:

BURN THE SHIPS = Commitment = 🙂
BURNING BRIDGES = Potentially harming others = 🙁

Here are some ideas to retain connections when making changes in your life:

  • Be clear and respectful
    Explain your decisions with honesty without blame or criticism. Express appreciation for past opportunities or relationships.
  • Give Proper Notice
    If you’re leaving a job, give notice and offer to help with the transition.
  • Stay professional
    Even if you’re frustrated, avoid venting or speaking negatively.
  • Leave doors open intentionally
    Let people know you’re open to future connections, partnerships, or referrals.
  • Do handovers cleanly and document
    Finish strong. Ensure others can pick up where you left off. This shows reliability and respect.
  • Don’t publicize the split
    My dudes, avoid the dramatic announcements on social media. Keep the focus on what you’re moving toward, not what you’re leaving behind.

It’s hard to commit, it’s easy to blame. Burn ships, not bridges.

Burn the ships

Burn the ships

The story goes that in 1519, Hernán Cortés arrived on the coast of what is now Mexico with a small force of Spanish soldiers. They were about to face down the powerful Aztec Empire, vastly outnumbered and in completely unfamiliar territory.

To prevent retreat, Cortés ordered his men to destroy their ships. The idea was simple; there was no turning back. The only path was forward; either conquer or die. “Burn the ships” means to eliminate any option of turning back, forcing full commitment to a course of action or choice.

When faced with a big decision in life (career, relationships, investing) it’s natural to want a safety net. Having a backup plan feels like the smart move. The presence of a backup plan could be the very thing keeping us from being fully committed to a choice. We waffle, we procrastinate, we stall.

Backup plans offer comfort, not clarity. They make the unknown feel manageable. That comfort often leads to delay, distraction, and diluted effort. When a Plan B exists, Plan A becomes optional. It’s easy to convince ourselves we’re making progress when really, we’re just going in circles.

“Burning the ships” eliminates the easy way out. It forces action and focus. You can only go forward, so get going. It’s not about being reckless; it’s about commitment.

If there’s something important you’ve been putting off, ask yourself: what would change if there were no way back? Maybe it’s time to burn the ships.