On Risk Taking

“I wish they would lay me off so I can take time off”, “I would love to live abroad but it’s just too much of a change”,  “I thought of that idea first, I wish I had done it myself” and “That seems too hard” are some of the things I’ve heard friends and myself say so many times. Changing is hard, I know it, but why do we live “hoping” and “going with the flow” rather than doing? What are we afraid of? I don’t claim to know the answer but this blog post has some of my thoughts on how I try to approach taking risks.

The first thing is that each of us live in a comfort zone. It’s easier to deal with the known than with the unknown. It is easier to just go with the flow and let chance and others take decisions for us. This begs the question, why do we let this happen though?

We are afraid of failure. Failing is hard, and when you fail, you KNOW you fail. In Silicon Valley, failure is part of life and it’s encouraged. Only by failing we get better. People always talk about trying things and failing. However, there is still a big stigma in failing. In particular this is very strong in cultures like mine (I’m Mexican) where failure is synonym for loser.

I remember when I interviewed once and was asked what was my biggest failure and I couldn’t answer. I had an aha moment that I had not taken enough risks in my career and I needed to do something about it. Fear of failure stops us from taking risks so we first need to acknowledge that failing is OK. If you don’t fail it’s because you don’t take risks. Not taking risks leads to stagnation. I rather think like this: it’s better to fail trying than to regret not trying.

We don’t know what we want. Taking risks for the sake of taking risks is foolish. Jumping out of a plane because you want to take a risk is stupid. However, if you do decide to jump out of a plane is because you have a goal, such as wanting to know and feel the thrill of falling and living to tell it. However, it’s amazing how frequent we don’t know what we want. I’ve struggled with finding what I want through periods of time and it’s not easy, but it is critical to find it.

Let’s take for example a simplified converstation that I’ve heard several times: “I wish I would get laid off”. If you remember from my previous post we should ask “Why” to get to the root issue. So a conversation might go like this:

  • me: So why do you want to get laid off
  • friend: I want to get paid so I can travel
  • me: can’t you travel now?
  • friend: yes, but I don’t have the vacations and I want the money
  • me: don’t you have savings?
  • friend: yes, but I want the extra money
  • me: wouldn’t it be better to just quit and do the travel you want?
  • friend: well, I don’t want to quit. I make a good living now.

The challenge here is that my friend wants to travel but he truly wants to have a good comfy living. Knowing what your true goal or purpose is very important. Who cares what others think, it’s your life and you should do what you want with it. You can travel or not but it’s important to not let a third party decide how to live your life; you should make the decision.

Now, let’s talk about the journey of getting what you want. Today you are in point A in time, and you want to get to point B at a certain time. Might be travel, having a baby, retire, changing jobs, volunteer, build a product, make your own business, or anything you want. Ideally we want to get there in a direct line. However, life is not like that. You have to aim to get to B but as you go through the journey, you might find a way to get a step closer (At1), then you find another thing you can do that takes you even closer (At2). And then hopefully you reach B, but I can almost assure you it won’t be B, it will Bf. The key is that every day you will make decisions to get you closer to your ideal place, but you need to be flexible and adapt through out the journey to get to B. Identify the things that you can control and what you cannot. Stop worrying about the things you cannot and put your energy on the ones you can do something about.


One last tidbit, remember: when you look back, it is the journey that will count more than arriving to B! Also here is a wise quote from Viktor E. Frankl’s “Man’s Search for Meaning” that I found thought provoking:

“Don’t aim at success—the more you aim at it and make it a target, the more you are going to miss it. For success, like happiness, cannot be pursued; it must ensue, and it only does so as the unintended side-effect of one’s dedication to a cause greater than oneself or as the by-product of one’s surrender to a person other than oneself. Happiness must happen, and the same holds for success: you have to let it happen by not caring about it. I want you to listen to what your conscience commands you to do and go on to carry it out to the best of your knowledge. Then you will live to see that in the long run—in the long run, I say!—success will follow you precisely because you had forgotten to think of it.”



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