How to Make the Best Decisions for Yourself When Results are Not Guaranteed

How do you know you’re making the right decision when the future is uncertain and success is not guaranteed? This question comes up most when it comes to something you would like to have happen, not something you have to do regardless. For things you know you have to do (like get that degree, find a stable job, buy a house for your expanding family, etc.), you can be sure societal pressure will get you there. You’ll see it through just because that’s what you’re expected to do. But what about the things you want on the side that no one will hold you accountable for? That thing you really want but you’re not sure will actually work out, yet hope that it might if you try?

Sure, you’re going to have to keep going to your 9-5 (at least for now), but should you start that Etsy shop on the side? How about that pool cleaning business? Should you spend your extra hours learning how to day-trade when you could be relaxing or spending time with family? Should you even bother doing anything on the side if there’s no guarantee of success? I mean, you’re already strapped for time as it is. You know you’re going to have to take time away from either your family or your leisure time to do it. Will it be worth it in the end?

Plus, you’re comfortable where you are. Your job pays well, your family is happy. Will going after another job for new challenges and higher pay be a good idea? What if you leave and the new job ends up not being what it’s cracked up to be? How can you come back from that? Is it even something you can fix?

What about that thing you got going with someone? It’s not a relationship, you don’t know what it is. It’s not really anything, but you’re really into them. Should you continue with it when you know it won’t lead anywhere?

What if despite all your concerns, you take a look at all the paths before you and figure you want to start anyway? But then you wonder, out of all the things you want to achieve, which one should you be working on first? What if you realize half-way through that the one you chose was not what you really wanted and you should’ve started on a different goal instead? Now you’ve wasted all that time and energy on something you’re going to have to abandon. Or maybe you managed to see it through to the end, but failed to get what you want out of it. Will it be worth it?

How do you figure out which step to take when:

  1. you don’t know which road will get you to where you eventually want to go OR
  2. even if you choose the right one, there is no guarantee you’ll make it all the way to your destination?


Before you read on, feel free to grab a copy of the decision-making flow chart to help you follow along. First page is if you wanted a poster version, the 2nd and last are more printer-friendly. They’re all 8.5″ x 11″. Hope it helps you make your next decision! Let me know how it works out!

Do You Know Where You’re Headed?

If you’re like me, you work best when you have a goal pulling you forward rather than drifting aimlessly from one thing to another. If there’s no goal that directs your movements, it’s easier for you to feel confused and unmotivated. You tend to question every move you make, wondering if they’ll eventually prove to be fruitless and a waste of your time and energy. If you’re not certain of where you want to eventually end up, you’ll question every step you take and wonder if it’ll even be worth it in the end.

In that case, your first goal should be to figure out your life purpose. A tall order, but necessary and essential. As well, it’s important that you classify it as your first goal, so that anything you take on during this phase is considered an experiment. It would then not matter if it fails or succeeds because you’re doing it to figure out what you’re meant to do. You might not be able to achieve it right away and that’s ok. It could take anywhere from 1-3 years (or more) to figure out. It’s a long-term project that’s worthwhile for anyone to take on. And non-negotiable. Because trust me, once you’ve figured it out, the amount of energy you’ll have to put towards it will be astronomical. You’ll no longer be weighed down by self-doubt or “what-if” scenarios that would’ve otherwise continued to vy for your attention and drain your resolve. You’ll be able to focus your efforts without any worries and accomplish more than you would have if you had continued to scatter your energies because you were unclear about what you were meant to be doing.

Yes, there is a possibility that you might end up realizing you’re a renaissance person (i.e., someone with multiple interests and talents), but I’d like to posit that you would still need an underlying theme or a common string that runs through everything you do. I used to think of myself as a renaissance person (and with the likes of Leonardo Da Vinci, Michelangelo, and Oprah fitting that title, who wouldn’t want to be part of the cool kids?), but having multiple—and at first glance, unrelated—interests tended to make me question myself incessantly. I would take on multiple projects and see very little progress across any of them because all throughout, I would question if it was worth it. What did I even hope to accomplish with it? Where was it heading? Maybe somewhere south with sun, surf, and sand? Or straight off a cliff, sinking to oblivion? (Second option = no beuno.)

Not to mention the famous Steve Jobs ‘connecting the dots backwards’ speech , the gist of which is to follow your interests even if they don’t relate because you can only connect the dots looking back on your life. To a multi-passionate person like me, this seemed like a free pass to follow every shiny new idea that had the misfortune of crossing my line of vision just because I could. And hey, Steve Jobs hinted that you might want to consider it.

But when I took a step back, I realized a few insights I missed the first time around. For one, it was a small time investment (one course) and Jobs saw it through to the end. Then he purposely applied what he learned to another project he worked on later (i.e., the Mac computer). So in reality, the real lesson behind this is to choose one interest to explore and put in a small time investment. Test it out in a project and take what you learn, then purposely cross pollinate in new projects. You might not have an idea how the individual dots connect yet, but you’ll be able to figure out the connections faster if you consciously link them yourself. Even if the first links don’t end up panning out, you’re just experimenting in this phase right now. No big deal, you just keep trying new things.

And you keep going until you start seeing a common thread running between the projects you take on. That’s when you know you’re hitting the pavement on your life path. When you start to notice that you’re tending towards certain activities and you seem to have a natural talent for some tasks over others, you’ve hit your life purpose. This is where your potential lies, what you need to continue doing to make an impact. This is where you’ll be most effective in leaving a positive footprint on the world.

Things That Might Help You Find Your Direction

Aside from experimentation, one other way to find your life purpose is to immerse yourself in as much information as you can get. The following sources helped me find mine and I hope it might point you in the right direction for finding yours:

  1. Why You Can’t Find Your Passion [Youtube Original Video]
    Go deeper into the activity you like. For example, “while you might think you like superhero comic books, when you dig in you find out what you actually like is the empowering storytelling that allows people to see a strength in themselves that they didn’t see before”.
  2. Ikigai [Youtube Book Summary]
    While it didn’t really help me in finding my purpose, it did make me double down on the search & realize how important it is to maintain healthy habits (healthy habits = more energy = increased ability to do/accomplish more/go after your dreams). Main message from this book that might help you figure out your life purpose is to find the thing you do that satisfies all 4 of the following criteria at once: (1) what are you good at? (2) what do you love to do? (3) what can you do that the world needs? (4) what can you be paid to do?
  3. Four Thousand Weeks [Youtube Book Summary]
    Helped me see that you have limited time on this world and therefore have to prioritize in order to be effective and there’s nothing I love more than being effective & efficient (my dirty little secret in life is to become a cyborg).
  4. Start Finishing [Youtube Book Summary]
    Lesson Learned: you owe the world your best work, that’s how you serve others.
  5. Your One Word [Youtube Book Summary]
    You have a core value (i.e., ‘your one word’) that guides everything you do. It took about 3 years for me to figure out mine. Mind you, it wasn’t 3 years of sustained effort. I had listed out some possible words when I first read the book, then let it go. Came back to it recently, watched a few video summaries and realized what mine was. This video in particular sparked my word. I think it was the fact that the person summarizing the book in the video mentioned that—and I’m paraphrasing here—your one word is the core value you use to guide your decisions. It’s what makes you come alive and serves as a steady source of motivation. So think about the decisions you’ve made in the past that ultimately brought you happiness? What was the main reason you made that decision? What fuels the decisions you make that brings you joy? (If you’re wondering what my one word is, for absolutely no good reason I’m oddly superstitious about it. So unfortunately, I can’t share it at this time. But…) To help you figure out yours, here are some examples from some of the commenters on the video: “Mastery” & “Depth” and a couple from some of my friends: “Bold” & “Fight”.
  6. Morning Pages | 15 Tips to Get the MOST Out of this Exercise (TODAY) [Youtube]
    One of the best morning pages or stream-of-consciousness writing videos I’ve watched. The first video that got me interested though was Lavendaire’s run through of how she does her morning pages. Clark Kegley’s take on how to journal effectively grabbed my interest because as a girl, I found it surprising that a dude was journalling. (Later I learned that many dudes do it, go figure. Yes, aspiring cyborgs can be guilty of stereotyping too. It’s a bug in the system and it’s being worked on.) Journaling is one of the methods you can use to take what you learned and conduct thought experiments to help you decide whether or not you’d like to pursue an interest or opportunity.
  7. Succeed [Youtube Book Summary]
    Taught me the importance of having a ‘why’ statement (i.e., and what bigger ‘why’ statement exists than your life purpose?) to motivate you and how to use it.
  8. The Dip [Book Notes | Extended Book Notes]
    Taught me why it’s important to pursue the hard stuff (because no one else will be doing it and if you can get past it, you’d be better off. Also, if you know when to quit, you won’t be afraid to start.

Although the above is not a comprehensive list of the things that have helped me figure out what my life purpose is, I hope that it can serve as a good jumping point for you to start on your search. Once you’ve figured out your purpose, you’re ready for the next phase.

Will This Get You There?

As Henry Ford once said, “Whether you think you can or you can’t, you’re right.” Which to me means that you create your own reality. If you don’t believe you can get to where you want to, why try? What would be the point of putting time into a task or project or going down a path if it’s not going to get you where you want to go?

But there are some things in life that are a gamble. You want to achieve financial freedom so you start a candle business as a side hustle but you don’t know if you will actually find any success in it. Or maybe you experience some success but you didn’t achieve it as fast as you would have if you had just started a Youtube channel first.

How do you make a choice when you don’t know if what you’re choosing will pan out, even if it is in line with your life purpose? (Although, I would argue that if it is your life purpose, it will pan out. For the simple reason that you will make it pan out. No matter what it takes. Because you were meant to do this. But we’ll get into the how of it later.)

Here you need to do two things:

  1. Separate yourself from the results. Because you can’t guarantee them.
  2. Ask yourself not “will I achieve a success if I went down this path?” but rather, “does it have the potential to get me to where I want to go in the end?” If yes, take a step forward.

What does this do? This allows you to decide whether or not to go ahead with a project if there is a possibility of it getting you where you want to go. Why project? So you know to break things down and test things. It gives you a chance to try things out, then step back and reflect so you can learn and change course.

Are You Having Fun?

In the last question, you’re considering the long-term impact of your decision. But you can’t forget to consider your present. Because it’s in the present you make your future. It’s important that you’re enjoying it, because this will determine if you can continue with it when things get rough. Every path in life includes rough terrain and just wanting to get to the destination might not carry you forward if you don’t enjoy the step directly in front of you.

Lets go back to the relationship question from before and say that you’ve met someone, but they’re not interested in committed relationship. But because you’re crazy about them, you’ve entered into some kind of non-relationship ‘relationship’ with them that can’t be defined.

In the long-run, you’re not sure if it aligns with your ‘purpose’, but at the very least, they’re not hindering it. You’re getting a lot of freedom to pursue your goals because you don’t have the added responsibility of a relationship.

For the question of whether there is a possibility of it getting you what you want in the end, you could say yes. Because who knows, maybe things will work out.

For the question of whether you’re having fun right now, you’d most definitely say yes. After all, you probably enjoy their company otherwise you wouldn’t be doing this at all.

But here is where you’d need to ensure you’re getting everything you need in the moment. If the future is not guaranteed, you need to make the present worth it. So you have to consider, given the circumstances and all the variables you can’t control (i.e., the future, a whole other person, etc.), if things go south, what will you have gotten out of this?

For example, if this kind of arrangement is something you’ve never done before, then you’re probably learning about boundaries and how to juggle expectations (yours in particular). You’re hopefully picking up new relationship skills and becoming more self-aware of how you operate and think in contrast to your ‘partner’. You could also be picking up ways of how to manage conflict (because even non-relationships have those). In the end, this is expanding how you view the world and allowing you to perceive more of its complexities, while also making you stronger.

But of course, it’s not all fun and games. You might experience some discomfort while you explore your choice. In our example, it could be the fact that you were more used to a traditional way of doing things. But then you would need to consider if the discomfort is temporary. If you can answer yes because you can see the long-term benefits for yourself and see a point in the near future when things will be fun, then keep going. If the answer is no or maybe because you can’t see if you can ever get past your current beliefs about what relationships are supposed to be like or you just don’t want to regardless of what you might learn from your current situation, then this is something that is not worth pursuing for you.


The core cause of indecision is the fact that there is no guarantee of success. This isn’t an issue for goals you decide to pursue where societal expectations can see you through (i.e., you do what you’re expected to do in order to be a productive member of society and not get kicked out of the cool kids club). But what about all those goals you dream of achieving one day but aren’t sure if you should spend your time and energy on? What if they don’t pan out? What if you choose the wrong one?

The best way to make a decision for something you want to do, not have to do is to:

  1. Find your purpose to focus your energies.
  2. Consider if any of your options have the potential to get you what you want in the end.
  3. Ask yourself if it’s fun. No joke. Cyborgs don’t joke.

Bonus Tips:

  1. What doesn’t help you succeed, helps you learn.
  2. Some decisions are reversible, but really, there is no decision that you can’t eventually come back from given time.

So no matter what you decide, think of it like this: so long as you become better in the process, you’ve succeeded.

What are some decisions you are struggling with? How have you tried to figure it out so far? Do you have any tips that can help someone decide on what they can take on next?

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