How To Make Hard Decisions - Solo
7 Dec 2025 · 11 min
A solo podcast episode in which Will Humphreys teaches a checklist-based approach to making difficult decisions for leaders and entrepreneurs. He emphasizes aligning choices with core values, leveraging unique strengths, prioritizing long-term/transformational impact ("more marshmallows later"), assessing financial sense, and considering opportunity cost ("what does saying yes require saying no to?"). The episode ends with illustrative stories (marshmallow experiment; Australian rowing team "does it make the boat go faster?") and a call-to-action to apply the filter and join the host's network.
Chapters
Rockstars. It's amazing to me how I work with some of the most powerful people who own businesses and they get so stuck on this idea that they have these difficult decisions that are usually one of two options. We act, all of us, as if we have this limited number of opportunities in life and we forget that as creators, we have endless potential. We can create opportunity out of nothing. And so I find as people start to get stuck in these ruts, that they don't understand how to make decisions, especially hard ones, like there's no criteria for them to define success or they don't know how to create guardrails in making their decision. And as a result, they get super stuck in one or two options and forget that they have endless opportunities. So in today's episode, we're going to talk about how to make difficult decisions. Now, for entrepreneurs, they kind of have the opposite problem. They have so many options ahead of them and they see that, that they have this shiny object syndrome. And you know who you are. If you're that person who's working on one thing, gets it off the ground just an inch, and then sees something shiny and starts chasing it. This is also for you because even though you don't feel limited in your decision making process, you're finding yourself going a mile wide and never going a mile deep like you know you can. So how do we make decisions? We're going to use information from a book called the Gap in the Gain by Dan Sullivan to help express this one form of decision making criteria. All successful people I've ever worked with, rock stars, they have decision making criteria. One of my old coaches and now partner, Scott Fritz, he had a three filter decision. Is it fun? Does it bring me closer to God? And does it make money? Now, these are business decisions he's talking about. He may not be talking about decisions he makes at home. I know he has his own criteria for that. But just having something to filter decisions through allow us to feel more objective in these processes that oftentimes are so highly emotional. And that's why these decisions are so difficult, because there's so much emotion tied to them, especially when it's in the family or with ourselves. Right. So let's walk through this criteria together. What I'd like for you to do is take a decision that you have to make right now. It could be something that is at work or personal. It could be a relationship that you're struggling with. It could be an expense that you're deciding on. It could be any number of things that you're just making a decision on. And let's ask these questions. Number one, first and foremost, is this opportunity person expense, whatever it is, is it aligned with my values? So if it doesn't align with our values, it's an immediate no and we don't have to keep going. So here's the problem I see with that rockstars is that most people, they're not making big decisions that go against their values blatantly. It's usually small little deviations from their values that they can justify. That's where we get bit, is we decide, you know what, it's not that bad, it's not going to be that painful. Yeah, I don't know if it's totally above board. Those are the moments that we make the decisions we regret. Because at the end of the day, our values are black and white. They're very clear. It either produces the result or they don't. And if you don't know what your values are, don't feel bad. No one's born knowing how to create a value system. We have them, but we don't necessarily define them. Like I've said in previous episodes, purpose, vision and values, they exist like gravity. But if we don't know about it and know how to use it, oftentimes we feel lost. So listen to one of my previous episodes on how to create a value system and then come back to this and decide, is that person decision in alignment with my values or is it not? And make it a hard yes or a hard no? Second question. Will this opportunity person experience take advantage of my unique abilities and lengthen my stride? Remember, rockstars, most successful people don't waste time trying to improve their weaknesses. They are focused on bettering their strengths. They don't want to waste time making everything average. They'd rather be super powerful in a very specific way. So is that relationship or decision going to strengthen that or is it going to weaken it? And if it's a no, then probably it's a no. 3, how will this opportunity benefit mankind? Is there a greater purpose?
I think one of the things that we get in the mistake of deciding is what can benefit us now versus what's going to benefit us in the long run? There's a famous study that you've probably heard of where experimenters took children and they sat them down, they put a marshmallow in front of them and said, you can have that marshmallow right now, but if you wait two minutes, we'll give you two marshmallows and it was a very high number of children who just ate the marshmallow as soon as that researcher left. Right. But researchers stayed with those kids after the experiment and found a very direct correlation to the children who could wait for two marshmallows to be way more successful in life in every capacity. So when we think about the greater purpose, one marshmallow now or multiple marshmallows for lots of people later, it gives us the ability of knowing if this is just a simple decision that is more short term or if it's going to be more impactful for everyone in the long run. A very easy question to ask is, does it make sense financially? I don't have to go into this one even further other than to say, you know as well as I do, just like our values, when we make decisions against this one, it's never or usually isn't blatant. It's. It's usually just a little bit over budget. Rockstars, please remember, financial freedom is an essential tool of leaders that allow them to help other people. So let's not make the mistake of that one marshmallow now. Even if we can't afford it, that's going to limit us later. Number five, is this transactional or transformational? Oh, I love this one. Transactional decisions do not have a bigger impact. Transformational decisions are gateway opportunities to a whole new world for us. That's the difference between making a sale or one relationship that opens the door to a whole new industry of sales in the business sense. Number six, if I say yes to this, what do I have to say no to? We forget rock stars that our energy is limited. We have only so much time in the day. So if we're going to do something and agree to it, then we're going to say no to something else. Now here's what I've learned in terms of balance when it comes to decision making. Early on in something new, it's always yes until no. However, I always remember too that the most successful people, after they start getting traction, get in the habit of saying no way more than they say yes. So early on, it's yes until no. But once we start getting things defined or created, that could be a relationship, it could be a business, we have to start saying no so that we can go a mile deep in the impact that we want to make versus a mile wide. So if this thing that you've been thinking about isn't clear yet, I'd like to share a story to wrap up today's short episode. The story goes Back to Australia. In the 1970s, Australia had a row team that was literally the laughingstock of the world. They bombed at every Olympics. They were the worst. It was so bad that they were shamed at most of these events. And then somewhere in the 1990s, they found this coach who decided to simplify everything that they were doing down to one question. And the question was, does it make the boat go faster? So as they were making decisions as individuals or a team, did it make the boat go faster? Was brought up if someone was going to go party that night or go to bed early. Well, which of those two things would make the boat go faster? If they were investing in a certain training, would it make the boat go faster? Everything became hyper focused, just like sunlight with all of its power being dispersed across the universe versus being magnified through a glass to burn and catch fire. Their results started to catch. They ended up winning multiple gold medals, became leading in the world of row. And that came because of their decision making process. So my question to you rock stars. No matter what you're deciding today or down the future, is what makes your boat go faster? And what is that? What is your boat? What relationship is that? Is that a relationship with God? Is that a marriage? Children? Is that a result that you're striving to achieve? A a change in the world that you're hoping to create? Once you define what that one thing is, everything else will become easy. Everything else will become simple. It still is hard to say no. Just like it's hard to see more than two options when we're making decisions. But in the end, it's the effort that we put into this that matters. What I love one of my favorite leaders once said, is that effort matters. It really matters. So remember Rockstars, no matter what decision you're making, there's only two outcomes. You'll either win or you'll learn. That's it. Failure is just learning. You know this already. It's nice to be reminded when you're making a hard decision. And please listen to this episode any and every time you find yourself stuck in making decision. Hear my voice again. Let's walk through these questions together because I know if you'll put the energy into creating guardrails in this filter of decision making, you are always going to come out on top. No matter what. Rockstars, thank you so much for listening. Until next time, guys. Thank you for taking time to listen to today's episode. If you found today's information to be useful, could you take a minute and help me. I would love it if you could leave a podcast review in your app so that other people who are looking for this information information can find it. Plus, my dream is to have the largest network of medical entrepreneurs and leaders in the world so that together we can change healthcare to make it better for all. So in addition, if you can think of anyone that you could send this to, not only would that mean a lot to me personally, but it would build this network so that we can make healthcare the way that we want it.
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