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Field Report: How to Make the Hardest Decision of Your Life

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Tyler’s Note: This is a Riskologist Field Report by Therese Schwenkler from The Unlost. Field Reports are written by readers just like you, so be nice, enjoy the story, and take action on the lesson.

I was hanging out with my friend Julie the other day when she asked me a question I hear quite often.

“Therese,” she asked, “How did you find the courage to make such a tough decision?”

She was referring to the big leap I’d taken this past spring: despite having a steady job in corporate accounting, owning a home, and appearing to “have it all together,” I’d decided to leave it all behind in order to embark on an indefinite road trip around the country and to focus on building The Unlost community.

I thought about it for a second before responding with an honest reply.

“It wasn’t really about courage,” I told her. ”In fact, I think that sometimes relying on courage alone can lead you astray.”

She cocked her head to the side, and I could tell that my words had really piqued her interest.

“See, despite the monstrosity of the decision, this was in fact one of the easiest choices I’d ever made. While I couldn’t be sure of the outcome (when is this ever possible?), I could be 100% confident that the risk was worth taking.”

I proceeded to tell her about the two game changing questions I’d asked myself before taking the leap. Once I’d answered these two questions, my decision became crystal clear—instead of freaking out like, “OMG, am I making the right choice?” I was more like, “Duh! What else would I do?”

If you can answer yes to at least one (and ideally both) of these questions, I told her, then you can rest assured that the risk at hand is worth taking.

Today I’ll tell you what these two questions are and how to apply them to your own decision-making processes. Best of all, I’ll do so in a cool and unexpected way: through my own official internet version of Choose Your Own Adventure. (Am I the only one who used to read the Choose Your Own Adventure books when I was, like, 8? You know, where you got to choose what the main character did next? Aside from Goosebumps and The Babysitters Club, those were my fave.)

Anyhow, I digress. Let’s get learning!

The First Question: Have You Fired a Sufficient Number of Pre-Cannon Bullets?

Imagine for a moment that you’re out at sea when you spy a hostile pirate ship bearing down on you. You’ve got a limited stash of gunpowder at your side.


Quick! What do you decide to do next?

By now you’ve probably clicked through all the options (CHEATER!), and you’ve realized that shooting a puny bullet is the one decision that does not result in imminent death by pirate sword.

This only makes sense when you think about it: if you shoot a small bullet and miss, you’ve got plenty of chances to readjust before running out of gunpowder. But if you shoot a big cannonball and miss, you’re crap outta luck!

The lesson? Before using all your gunpowder to make the hardest decision of your life, ask whether you’ve shot a sufficient number of pre-cannon bullets to gauge the probable outcome. In doing so, you’ll minimize the risk of being plundered by filthy pirates.

How I Shot Bullets

When making the decision to quit my corporate job, here’s what I did not do: upon dreaming up my idea for The Unlost, I did not immediately quit my job and announce that this was it!

Instead, I continued going to work every day but began shooting lots of little bullets on the side. For an entire year, I experimented with building my blog and tested the waters to see if I, in fact, could grow a readership or create engagement with a community. I carefully evaluated the outcome, adjusted accordingly, then shot again.

When I finally decided to leave my job, the choice was rooted in a deep understanding of what I could likely accomplish given the right amount of time, focus, and effort rather than on mere delusion or wishful thinking about an untested pursuit.

In order to apply this to your own situation, try asking yourself, “How can I chunk this big decision down into smaller risks?” or “How can I experiment without going all out?”

  • If you aren’t sure whether you should start a business, can you start one on the side using limited resources rather than quitting your job/using your entire life savings to fund an untested pursuit? Can you take micro steps like Tyler teaches in his Bootstrapper Guild?
  • If you aren’t sure what to do with your life, can you start by volunteering after work or getting involved in interesting side projects rather than spending $67K and years of your life for a degree in a field you’ve never actually worked in?
  • If you aren’t sure whether you should marry your fiancé, can you start by… oh wait, nevermind.

Once you’ve shot lots of small bullets and adjusted accordingly, you’ll be able to shoot a cannonball from a place of confidence rather than from bravado or ignorance.

The Second Question: Would You Do This No Matter What?

Regardless of how many bullets you shoot, you can never know for certain what the outcome will be. Other times you can’t or won’t want to shoot bullets, and that’s okay too—as long as you can answer yes to the second question: Would you do this no matter what?

I was willing to quit my job and leave my life and my hometown behind regardless of the outcome. If the worst happened and I ended up barefoot and penniless on a California beach (or on the Las Vegas strip), I was okay with that. Once I realized that taking the leap would be worthwhile even if I “failed” or was “unsuccessful,” it no longer felt like a risk—instead, it simply felt like something that had to be done.

It was. So I did.

In order to apply this to your own situation, simply ask yourself, “What’s the worst that could happen if I made this choice?” Then ask “If the worst happened, would I still feel that making this decision was worthwhile?”

Yes, it can be that simple.

Have you shot a sufficient number of pre-cannon bullets? Would you do this no matter what?

Now that you know the two important questions for decision making success, go forth and make the hardest and best decision of your life. May you never be plundered by pirates.

What should you do with your life? The Unlost exists to help you answer questions like this. Contrary to popular belief, you DON’T have to have it all figured out to end up somewhere great—click herrre to learn more.

Image by: Stephen Poff

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What smart people are saying about this...

  1. Sarah says:

    Great post! I loved the Choose Your Own Adventure book too, but I used to obsessively have to go through and try all the options…. Anyway… I think the questions are awesome. I recently followed a similar path (leaving the day job for a whole lot of uncertainty) and knowing that I would do it no matter what and that I couldn’t not do it and still live with myself at the end of the day was what made the decision easy. It always looks like bravery from the outside, but it’s not…

    • Therese says:

      Yep, exactly… sometimes staying where you’re at becaomes a bigger risk than leaving. THAT’s really when your decision turns into a logical next step. It’s not so much bravery as it is, “Duh!”

      • cj renzi says:

        First off, I love pirates. My wife and I totally wanted to have a pirate themed party at our place, but could not find enough cool people to bring it off. Ok, digression now out of the way. What an exceedingly entertaining and inspiring post! This is exactly what I did when transitioning from teaching music in public school to owning my own guitar studio. I began teaching lessons in the evening after school and only needed to do that for 3 months before I had enough students to pay the bills. That was in 2005. Life is, well, let’s just say that rather thinking about how fat and tired I am, I am trying to plan pirate parties. Nuff said.

  2. I agree with both Therese and Sarah – What seems like courage/bravery to others is simply the next logical step to the one taking the step/leap.

    I took the leap the first time about 15 years ago and never felt fear. My biggest fear was spending the rest of my life doing what I was doing at the time. Basically, the pain of staying where I was was bigger than the pain of changing.

    I love the idea of shooting bullets. It makes the final decision easier and more likely to succeed since you’ve taken the time to poke around and explore the “what if’s” that tend to paralyze us. It’s like making an educated guess/decision.

    In line with your second question, mine was, “Why not? What have you got to lose?” I usually feel that I have more to lose for the rest of my life by not trying something new. If it doesn’t work, at least I tried. And when it works (as it usually does), I have more fun and excitement in my life and know that I’ve pushed the boundaries of my comfort zone a few more notches.

    Keep rockin’ with all your greatness Therese! You’re AWESOME!!!

    • Therese says:

      Thanks, Paige! Agreed, agreed, agreed. We seem to have quite a bit in common– thanks again for sharing your story with me. Can’t wait to get it out there! I

  3. Kim says:

    I never had a big cushy job (or any “real” career for that matter), so I’m not sure if I’d think differently had that been my situation, but I never really had that fear of “shooting” so to speak.

    To me, the fear of living life with a job I despised was WAY scarier than jumping into the unknown. And while I’d like to say that I chose to leave it all behind to pursue my dreams, the reality is that life chose for me in the form of a car accident. And as bad as it was, I still look back at it as the best thing that ever happened to me.

    • Therese says:

      Hey Kim,

      I love the way you frame this: “the fear of living life with a job I despised was WAY scarier than jumping into the unknown.”

      And yes, sometimes life does seem to “choose” for us…

  4. wahyu says:

    I Did! both of them and, of course the answer were both BIG YES.
    I did shoot small bullets before the pirates (or pink bunnies or evil clowns , whatever)appears, and YES i think “this” is the thing i will definitely gonna regret if i dont do it. Scared? another yes, haha!! but who’s not, after 14 years of cushioned corporate life and national-wide-responsibility position i had. But as we’re all here feels: there’s something out there that really means something for us to do, and it worth the adventure of a lifetime.
    Good posting Therese, enjoy to see it from your point of view, and a very interesting site you have.hope a big success for you.

  5. Kyle says:

    I was trudging along alright in my job but then realized one day that “nope” this is just not what i’m meant to do. I don’t want to. I don’t think i am selfish or lazy or anything like that. I’ve started busting my butt on the site to start my own blog on the side because i want to be location independent, want to work for myself, and ultimately be free from bosses who can treat you like they own you. So yes, I am still working the 9-5 that isn’t that great to me but i’ve starting taking my shots and perhaps in a year i will unload the cannon. All i know is that the barrage has begun and this battle will be won in due time. That’s how i’m approaching it.

  6. Christine says:

    Awesome post, Therese! I used to love the Choose Your Own Adventure books too (though like Sarah I checked out all the options… I like options).

    For many years I had this feeling that something was missing. But since everything in my life was good – job, family, friends, etc. – I felt guilty for not being satisfied with the status quo. I went back and forth between denying anything was wrong to trying different jobs to discover the “one thing” that would be “it.”

    Now I no longer deny my need to live “on purpose,” and the fantastic thing is, I have no desire to go back to the way I was, suppressing my authentic self. So I’m starting to fire the small bullets, and look forward to unleashing the cannon! (that sounds kinda wrong ;)

  7. Denny Robert says:

    Love it! I did a bit of an in-betweeny. My wife and I quit our jobs, flew to China, and took English teaching jobs. It cut our work hours to about 20, lets us have fun and live adventurously, as well as frees up a ton of time to get something off the ground.

  8. [...] want something to read, check out my friend Therese’s guest post on Riskology.co about how to make the hardest decision of your life. She [...]

  9. valentina adami says:

    I really appreciated this post, I’ve learned 2 things:
    - “Choose Your Own Adventure” must be an intriguing book to read (I’ll go googling with that!)
    -I am following the right strategy, that is I am ‘shooting little bullets’ to get back to my own track.
    This is reassuring, sometimes I am doubtful about the result but in the end I am sure that all this time spent in research -of my myself- and doing stuff that I haven’t done before will lead me somewhere. Don’t know exactly where, but that’s ok at the moment. Thanks Therese & Tyler for sharing your experience!

    • Therese says:

      Hahaha, thanks Valentina!

      Your current thinking is right on point– keep testing, experimenting, and trying new things and keep letting the wisdom of your truest self guide you, and I have no doubt you’ll be led somewhere great. (In fact, you’re already well on your way ;-)

  10. Jill says:

    I love the fact you didn’t write that you just up and left your job, boom, and that you did some planning and experimenting to make you feel comfortable doing it. I’m a planner and a tester myself, and I’m taking your route. Great read. Thanks!

  11. [...] >> How to Make The Hardest Decision of Your Life << [...]

  12. Thari says:

    Hi Therese, great post :) I like that you don’t suggest making the big leap based on a little courage and a lot of faith; that always seemed a little implausible for the practical side of me. The puny bullet on the other hand, it solid advice :) Experimenting as I am with that, was a helpful read.

  13. Sarah says:

    You know, my inclination was to fire the one bullet but I thought, “I’m going to get killed,” so I was too nervous to choose any answer and so I didn’t! Bad sign?

    Honestly, though – I think I’m implementing the testing bullets strategy in my own life, hard as it is, and glad to hear some of you are in my current position as well. Perhaps the next question is is there a way we can provide support for each other in these endeavors? Internet correspondence is a great start, but how do we build on that?

  14. James Holder says:

    Another Choose Your Own Adventure fan here, Therese. For one of my own cannon shots, I even experimented with a game engine designed with such stories in mind. I see a lot of other parallels between our stories, too, so thanks for the positive example!

  15. Izzy says:

    Bringing the Power Therese :).

    You bring up interesting questions. I like both of them. I think the question that I have grown to enjoy asking is “What if I actually succeed?” For me, this is inspiring and motivating. But I think I had to sit with your other questions first (for many months). Then I took action based upon my answers.

    Now, I no longer ask those questions. In fact, I don’t think too much about the future – probably because it’s already in a spreadsheet and I’ll be looking at it on Monday morning (LOL!). But I love these questions and think they are darn powerful.

    Here is the thing I now often ponder. So you asked those questions and then you took action. But so many people can stare at those questions give the appropriate answer and then never actually take action.

    I feel like there is a chasm between taking action and answering those questions. What is this chasm filled with Ms. Therese? It boggles the mind… But maybe if you can answer it for me then it will stop boggling my mind :).

  16. soubhik says:

    How did you get the courage to take up such a huge decision ? :)

  17. Like Kim, “life” made my choice for me. I started my freelancing business 4 years ago because I’d been laid off twice in a 7-month period. I love this: “While I couldn’t be sure of the outcome (when is this ever possible?), I could be 100% confident that the risk was worth taking.” I think this is a great perspective.

    This was brought home to me yesterday. The marketing director for one of my favorite clients resigned, and the client wanted to interview me about taking her job. After reviewing the job description, I knew the job wasn’t for me. Aside from that, the salary was a bit low. I loved being able to say to him: “No, I’d need twice that much to be able to accept this position.”

    I have found so much joy and peace working from home, in spite of the income roller coaster. Yes, becoming a freelancer and running my own business definitely WAS a risk worth taking!

  18. John says:

    “courage alone can lead you astray.”

    I love it!!! In my life I’ve found that courage or fearlessness requires some wisdom behind it. Any fool can have courage.

    I think you got a great story and glad you’re sharing it. Many got caught up on the conveyor belt of what society says they must do. This is not living life but giving into fear.

  19. [...] Go big!  Take on what you previously thought [...]

  20. Kayla Cruz says:

    In order to apply this to your own situation, simply ask yourself, “What’s the worst that could happen if I made this choice?” Then ask “If the worst happened, would I still feel that making this decision was worthwhile?”

    You are a genius.

    Thank you.

  21. Iris says:

    Okay, I totally got lost at Unlost (haha…) after reading this post. YOU’RE AWESOME. That’s it.

  22. Jeff Bronson says:

    Yep. So many people are paralyzed by fear, “agonizing” over what is the best next step to take. This leads to just doing nothing quite often, it’s easier that way.

    It’s usually the people who take RISKS, that come out ahead. Either they succeed, or fall flat on their face, get up, brush off the dust and learn from their mistake.

  23. [...] career capital. THIS is where so many of us get in trouble (check out my Riskology.co post, How to Make the Hardest Decision of Your Life, for more on this [...]

  24. Hope you’re having fun!

    The one thing I encourage everyone to do is NEVER QUIT, but get laid off instead. I managed to engineer my layoff and got 6 years of living expenses as part of my package.

    There is big money to be made quitting your job. You just have to realize your rights as an employee and develop the right relationships.



  25. Andre Blais says:

    Great advise, I appreciate you taking the time to share this.

  26. Varun says:

    That was a wonderful piece of advice. I really felt great after reading it. I was stuck with a very important decision of my life and this article of yours will definitely help me in taking the right decision.

  27. [...] I read an article on the Riskology.co blog that talked about making hard decisions. That week’s guest blogger, writing about making the [...]

  28. Clay says:

    Great tips on one of the toughest issues in life, thank you for sharing!

  29. Amber says:

    I think those 3 books were the ONLY books I read when I was growing up… maybe a few Box Car Children thrown in, too??
    I really enjoyed reading this – thanks for writing!

  30. Marek says:

    Thanks! Nice post. I found it while writing The art of making right decisions. I think the key is to make all decisions while you calm, without emotions, otherwise you might regret them.

  31. [...] that even when you don’t decide, you are taking a decision: you are deciding to be inactive. Learn to take the decisions that make you move toward your [...]

  32. [...] eliminate the immediate risk that comes with such a big decision, but it also allows them plenty of testing ground to see if their business ideas are actually [...]

  33. […] you have trouble making important and difficult decisions? Field Report: How to Make the Hardest Decision of Your Life may just […]

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