The safest way to take big risks

How can you know if you’re making the right move in your life?

Short answer: you can’t. 

You can’t predict the future, and neither can I. But if you could, life would be boring. Some might even argue pointless.

So let’s take away our desire to want to know for sure if everything’s going to turn out ok. Ok?

We can all relate with this feeling – that as long as we knew the final result, taking the risk would be less scary. Should I quit my job to start my own venture? Should I start a family? Fly solo? Go to medical school? Move to another country? What if I don’t like living abroad, or I struggle with meeting new friends? I asked these questions (and many more) of myself when I weighed the idea of moving to South America in 2017. I was terrified at the thought, and that fear was ultimately based in the fear of the unknown. This fear caused me to back away from the idea. Then I started to ask, “If I don’t do this, how will I spend my time instead?”

That’s a big question.

The options of how we can spend our time are endless. Time is moving, and we never get to live the same moment twice. Whether or not a decision seems “risky,” (investing in real estate, moving overseas, etc) everything we do involves some level of risk. The risk is opportunity cost, which refers to the value that you could gain following one opportunity, that is foregone because you chose to do something else. 

And having multiple interests combined with innumerable possibilities in today’s world can make it daunting to choose. A friend of mine was deciding which to study between his two passions: language acquisition and computer science. He realized that he could not simply dabble in either of these fields and expect it to pay off in any lucrative way. So he chose computer science, and a little more than halfway through his studies, he realized that he wasn’t as interested in coding as he thought he was. So he switched his focus to language acquisition, but he felt that he was very far behind at that point.

He was frustrated. He asked his mentor, “Did I just waste two years of my life?”

His mentor told him: Absolutely not! You’ve just learned something extremely valuable – what you don’t want. This discovery is a pivotal part of our learning, and it will strengthen our decision-making process moving forward.

K, but I would rather just make good decisions.

Just because you make one “bad” decision doesn’t mean you will do the same thing next time. Likewise, making one decision that pays off well doesn’t necessarily mean you will always be able to replicate the same result. Since this question comes up in my life time and time again, I’ve developed the following formula to guide my decision-making process, as the safest way to take risks of all sizes:

  1. Choose to choose.
  2. Let your intuition be your compass.
  3. Do deep research.
  4. Calibrate.
  5. Do it! 

Bonus round:

Assess results, recalibrate, and repeat.

Choose to choose.

I’ll admit, I’ve gotten bogged down assessing opportunity costs before. So much so, that I’ve found myself choosing nothing at all. The fear of missing out on one opportunity, or the desire to do it all, can each seriously hinder you from going anywhere. If you try to chase two rabbits, you’ll catch neither. Similarly, if you sit around with analysis paralysis about which rabbit to chase, you’ll catch none.

So while research and analysis before making a decision about your life are generally valuable undertakings, it is absolutely vital to not let them lead you into indecision. With the scale of the internet, we have enough reading material at our fingertips that we could research for the rest of our lives without doing anything. While this may sound like a great way to become well-researched, action is eventually necessary if you want to achieve anything in your life. You must make the choice that you will choose something, even with risk present.

That’s great – I can choose to make a move. But how do I know if I’m making the right move in my life? Is it all based on analysis, or do I follow my intuition?

I would argue that both components are necessary in order to make the highest yield decision for yourself.

Isn’t intuition paradoxical to analysis though? Not entirely. In fact, together, they do a beautiful tango. 

Let your intuition be your compass.

What does intuition feel like? For me, it’s when I have a feeling inside of me that’s strong, yet indescribable. It’s pointing me in a certain direction, but I can’t say why. I don’t have much or any background knowledge or “reason” to follow it, but something in my being is pulling me. I can’t get it off my mind, but if I do, I find myself coming back to this idea repeatedly.

We all get this sensation at times. This “gut feeling” is worth exploring. It’s communicating with something bigger than your consciousness. I suggest not overlooking it when considering your options. 

But don’t follow it blindly, either. Let it point you in the direction. This is like your “why” – your purpose that’s calling you. Actually carrying out the action of the decision, however, is how you will navigate the terrain. 

Do deep research.

This is the point when your analyses should begin. Doing research will give you the foundation of knowledge that you’ll need in order to keep your head above water as a novice. And it will continue to serve you as you level your way up on this new endeavor. 

It is important to not let this step precede steps 1 and 2 in your decision-making process. If you start your research before you have made the decision that you will choose something, you can fall back into decision fatigue (feeling so overwhelmed by all the options that you go with the default) or analysis paralysis (not choosing at all). Likewise, if your research begins before your intuition has pointed you in the direction you think you’d like to go, your research will be both aimless and endless.

What if what you’re deciding on seems like a REALLY BIG risk? I felt this way when I was pondering my move to South America. This was something I couldn’t get out of my mind since I was 16. I’d experienced a taste of Latin America and I felt an unending desire to dive in deep ever since (intuition). When the opportunity presented itself a few years later, I had never been to the continent before, and my idea was to move alone. Naturally, my mom was not a fan of this plan, so I knew I had to back my intuitive pull with some rock-solid facts (deep research).

Plus, as previously mentioned, I was scared as hell! So I fulfilled two core components of research for this venture:

  1. Tim Ferriss’s fear setting – I clearly identified my fears, logical and illogical, about moving overseas (I’d run out of money, hate it, miss my family, get kidnapped, etc), along with a thought exercise on what I would actually do if each one transpired. Writing this all out was not only eye-opening, but it also provided me a plan of action in case any of those fears did materialize. Having this guide boosted my confidence because I knew that I had already thought of every possible thing that could go wrong, and that I would be ok if any of those things took place.
  2. Researching the hell out of my prospective new home. In order to decide where to move in the massive continent, I created a spreadsheet full of big cities in South America (my only two criteria). Column headers were categories of interest to me – quality of life, cost of living, crime rate, expat community, climate, proximity to hiking trails, etc. Through extensive research on various cities, I landed on Quito, Ecuador. Then I got myself involved in Expats in Quito Facebook groups, researched visa requirements, and looked for apartments to rent.

Calibrate.

Looking at my research, I checked back in with myself and reviewed the facts. I asked, 

  • “How am I feeling about this now?” (Intuition check)
  • “Do I notice any red flags?” (Research check)

I certainly still felt nervous, but not nearly as terrified as I had before my research. I knew that I would never be 100% ready for something I’d never done before. I had no “gut feeling” that this was a bad idea – my intuition still pulled me to go, and my research backed it up. I had no remaining questions, other than, “How will I feel when I’m there?” This final revision was my calibration between the intuition that guided me and the research I’d done, and it all checked out.

Do it!

To spoil the ending – this was one of the best decisions I ever made. Some of my fears did materialize, but none of them were unrecoverable. The upside, however, was and continues to bring unparalleled positives. The people I’ve befriended, the career opportunities I’ve been led to, the skills I’ve acquired, and the beautiful cultural lessons I’ve experienced were all entirely unprecedented. That decision to move to Ecuador led me to a social, emotional, and professional foundation that I stand on firmly today. If I never went, I could have spent that time in any number of different ways, and I will never know if my life would be better or worse if I had. It provokes the question – does it matter?

You have one life – live it well. Take big risks, do the scary thing. The alternative is living in a predictable way.

Bonus round: Assess results, recalibrate, and repeat.

Sometimes you will follow steps 1-5 and you will yield fantastic results. Other times, you may end up feeling shortchanged. Even if the worst happens, though, it should not be insurmountable. If absolutely nothing else, you will have earned some excellent experience, and you’ll have a great story to tell. 

Whatever your results are, assess them as you go. I recommend keeping a journal – even recording voice memos and videos – to track your thoughts and feelings. Later on, reflect on these records, and ask yourself: “What would I do differently, knowing everything I know now?” The answer will either be nothing or something, and either way, you will have just added some deep wisdom into your decision-making process. Nobody can take that from you!

To recap…

There is no sure-fire way to know if we are making the right decisions in life. We can only make our most educated guesses using a combination of intuition and information. If we try something out and then decide it’s not for us, it isn’t time wasted as long as we apply that knowledge to our next move. This knowledge becomes part of our information bank from which we pull to develop our decisions, which will consistently improve over time. 

Knowing what we do not want, allowing our intuition to point us towards what we might want, and following up with deep research and calibration, is the formula that I’ve found works best. You may feel like you hit some dead-ends along the way, but those are just opportunities to pivot and apply what you’ve learned in your next endeavor.

But most importantly, whatever you choose, choose something.