“God, grant me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference.”

You may have heard this prayer, you may have said it, hung it up in your house, or even gotten it tattooed on your back. However, I don’t think we put as much effort into actually understanding it as we should. I love this prayer. When I see it or hear it, I can’t help but connect it to that Kenny Rogers song

I interpret this prayer as knowing when to hold and when to fold. Knowing when to believe in something and continue fighting the good fight vs. knowing that the good fight has been fought. This applies to love, friendships, businesses, investments, everything. This applies to everything. Knowing when to hold and when to fold is something that, I believe, is essential to creating the life that you want. Like most philosophies, it’s easier said than done, but it can be done through learning from experience and a strong sense of self.


Knowing When to Hold & When to Fold

It’s difficult to understand the disparity between the things you can and can’t change, the choices you can and can’t make, and the consequences you may or may not face. Let’s say you’re holding onto a relationship with somebody who is intrinsically flawed in ways that you couldn’t predict when you first started dating—ways that heighten your own flaws and insecurities. But this person manages to give you the consistency and dependability you’ve always craved. Should you leave them in the hopes that the next person’s flaws are more palatable, or do you stay and assess which of the flaws between you could be worked on together? Alternatively: you meet a charismatic person with a business proposition for you. It has all kinds of holes in it but the upside could be unlimited. Do you trust in your ability to tighten up the proposition and their ability to overcome obstacles with their charisma or do you believe that the charisma is flawed and the proposition is ultimately too risky?

It’s not always easy to know the answer. The only way you can know when to hold and when to fold is by seeing the situation for what it is and assessing the variables that you might not be able to control.

Getting into the game is not hard to do. The hard part is once you’re all in.

Let’s consider the poker roots of the analogy. When you’re in the game, it’s not about how you actually get in the game. Starting something is relatively easy. It’s easy to go on dates but it’s not easy to get into a meaningful relationship. It’s easy to write down ideas but it’s hard to build a successful business. Getting into the game is not hard to do. 

The hard part is once you’re all in—when you’re entrenched in the game, and you’re about to devote yourself to the cards that are currently in your hand. When the time has come to decide whether you should hold or fold (or even press harder), that’s when you have to take a step back and assess what’s in your control. What are the potential consequences of how you play your cards? Which move gets you closest to the results you were hoping for? What cards are already on the table and, besides that, what kind of players are there? To get good at knowing, not only do you need experience, but you need to learn from your experience.

The right place you should start is with yourself. Before the game even  begins, you have to know who you are.

Sense of Self & Accountability

In any game, you have to be able to go in knowing your strengths, weaknesses, and how you deal with certain situations. Nevertheless, the malleability of your sense of self dictates your ability to know when to hold and when to fold. If you’re the type of person who believes “I’m a winner, and winners never quit,” aren’t you setting a potential trap by putting yourself into such a rigid box? How will you know when to quit if you never do? Would you refuse to quit even if the situation became harmful or detrimental to you or those around you? Is winning always worth the sacrifices that follow?  Your core values should be cultivated with care and consideration, but even those must have wiggle room in order for self-evolution to take place. Without self-evolution, you won’t be receptive to the lessons that come with experience.

To allow yourself the opportunity for self-evolution, you have to know who you are and be aware of your limits by holding yourself accountable. Are you the one holding yourself back? Have you really tried to the best of your abilities? What if you’re the toxic one? Would success still be guaranteed if the situation changed? Are the signs there, and are you just choosing to ignore them? Is what you’re doing right now in line with your goals and the trajectory you’ve set for yourself?


Your Trajectory

Every person’s life has a trajectory. This trajectory can deviate or even change completely, but every individual has one. By knowing where you want your course to go, with anything you do, you will have a better grasp on knowing when to hold and when to fold. This is by virtue of being able to predict what to do with the cards in your hand, no matter what kind of cards you’ve been dealt.  You’ll be able to better analyze whether the cards are actually helping your situation, helping to make you better, helping you to evolve, and helping you to stay on your intended course.

You’ll also be able to rationalize your own involvement and your level of accountability. As previously stated, ideation is easy, but the execution is hard. Are you really willing and able to do this? Are you capable of putting in the work to get yourself to where you want to be? If you stay, will you make it? If you leave, will you still be on the trajectory you’ve set for yourself? Are you still focusing on what’s in front of you, or are you succumbing to idealized fantasies of what it could be?

Remaining Objective & Rejecting Romanticization

It’s easy to romanticize a situation, to fill in the blanks with what you want, not what’s there. Romanticizing can lead you to over-investing in a poor idea, an immoral person, an impulsive plan, and so on. There’s a difference between seeing genuine potential and simply seeing what you want to see.

Be observant. Read that again. Cultivate your ability to look at things for how they are. Keep an eye on  your role, their role, the dynamic between you, and how all parties are committing.

You never want to get to where your breaking point is within reach. You never want to wake up with your back against the wall, all because you held onto cards that you talked yourself into keeping. Pay attention to the realities of your situation. The person you’re investing in may be a good person but are they good for you? How does that person’s relationship with others compare to their relationship with yours? What are their values, and do those values align with yours? 

When the world is trying to speak to you, listen.

But what about you? If you’ve determined the reality of a situation without finding any warning signs, then why are you folding? Are you projecting your own fears and weaknesses? Are the reasons actually there, or are you trying to convince yourself to fold due to your own insecurities? If you’ve decided that the situation has become unfavorable or unsalvageable, how did you come to that conclusion? Was it truly the other party, or were you the one who changed? Is it really a bad investment, or did you just stop investing?

By having a steady head, you can develop a steady hand.



You’re not always going to get it right. Sometimes you’ll fold when you should’ve held on, and sometimes you’ll hold when you should’ve let go. You can do everything to the best of your ability and still not get there, and that’s ok. Even at my age, with my learning experiences, I don’t always get it right, and that’s ok. You can never know the exact outcome of a situation. However, by making an effort to understand yourself and evaluate the reality of the cards you’re dealt, you’ll be able to figure out how to play the game.

“The secret to survivin’

Is knowin’ what to throw away

And knowin’ what to keep”

Like the songs you hear on King’s Passage? Then check out the KP Jukebox playlist on Spotify