Let’s imagine you’ve been facing a big decision for a long time. 

Perhaps you’re thinking about starting a business or changing careers or moving across the country. You’ve worked hard to gather information to make the right choice, researched all the alternatives, talked to people you trust, reflected on what you really want. You’ve asked all the questions you can think of and gotten decent answers.

Your gut and your heart are telling you to go one way, but the Voice of Doubt in your head is still freaking out. You don’t want to fuck this up. You don’t want to make a choice that you’ll later forget. 

What to do?

First thing, once you’ve gathered all that information, it’s time to stop looking for more.

Comparing and analyzing all the options can work well with straightforward decisions like picking a restaurant for dinner. But when we face complex choices like whether to change jobs or start a business, our conscious minds can have a hard time juggling too many variables. 

According to the law of diminishing returns, at a certain point, doing more of something good starts to have a negative effect. One ice cream cone is delicious, but you don’t really want to have more than that. At a certain point, you’ll have prepared as much as is necessary. Adding more information can confuse you, keep you mired in analysis paralysis, or even lead to a worse decision. Trying to predict all the potential pitfalls can waste time and prevent you from seeing solutions that are right in front of you. At a certain point, you’ll need to close the computer and go to bed. 

The moment of opportunity is like fruit on a tree. You must wait for the fruit to ripen. And you must not wait too long. 

When faced with highly complex decisions, the decisions we make quickly are often better than ones we make cautiously and analytically. When something feels right in our bodies, but our minds don’t know why, there is often a great reason, even if we don’t know what it is. It’s often far better to make a quick decision and come up a bit short than to take no step at all. 

So how do you know when you’ve prepared enough? As Tim Brown, renowned designer and founder of IDEO writes in Change By Design

“You just have to know when to stop, and that is an art that can be learned but probably cannot be taught.” 

Now, I know you might be thinking: But what if I make the wrong choice? 

The bad news is that it’s true: At some point, things won’t go the way you hoped or planned. You can show up with your whole heart, take all the steps to prepare yourself, and things can still go downhill. You can be super experienced, well-trained, and successful and still fall on your face. Most paradigm-shifting ideas are initially dismissed or discouraged by others. No great story is devoid of danger.

Now for the good news: Even though you cannot control the outcome, you can still do your best to make a smart decision. As Nobel Prize winner Daniel Kahneman writes in his book on decision-making, Thinking Fast & Slow, the quality of a decision is not determined by what happens after you make the decision. The quality of a decision is determined by how you made it. Kahneman writes that to make a good decision, you must get the “outside view”: gather information about what happened in similar cases. 

I have no precise formula to let you know with certainty when or how to decide. What I can say is that the more you practice making little decisions that meet your needs, the more you will be able to trust yourself to make the bigger decisions in life. 

For now, listen to your gut and your heart. If they say you still need to prepare, trust that. Ask them what steps you need to take to prepare. Take those steps. And if your gut tells you to move forward, listen. 

If this pandemic has taught us anything, it’s this:

Someday, you will face the ultimate gate: the Gate of Death. 

I invite you to think about a choice you’re facing now, a choice between two options. Now, pause and imagine that you’re at the end of your life, looking back. 

Imagine that you’ve chosen one path. How do you feel?

Now imagine that you’ve chosen the other. How do you feel? 

There is likely one choice that, from the perspective of the end of your life, resonates more (even if it makes you scared). If so, that is probably the way to go. 

Like a distant drumbeat, you can ignore your heart’s call for a long time. Many people stay home their entire lives. But those who don’t make the journey face a spiritual death and are cursed with what Campbell called a “dull case of the call unanswered.” 

The hero finally chooses to answer their call when it’s harder to stay home than it is to move forward. 

Don’t die with your song still in you.

Please share your thoughts in the comments section below.

Much love,



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