Feeling comfortable with being uncomfortable

Man running in a wide snow mountain
Photo by Markus Henze on Unsplash

here’s something in me that whenever a new challenge arises and I’m passionate about it, I’m just all in even without being 100% sure of how to do it. I’m by no means reckless — those are calculated risks that I’m willing to take in favor of achieving something great. But I’ve found that more often than not, people don’t agree with me on taking risks.

I didn’t expect to hear “I don’t think I’m ready yet” so many times in the last few years. To me, it’s worth the calculated risk in favor of a big reward, like any trade-off in life. But I didn’t understand at first until I tried to find the why. To help me with this, I asked my friend Mary Ngo to co-author this article in which we explore the why behind avoiding risks, the effects it produces and how to overcome them.

Why don’t we ever feel ready?

Do you know that feeling of stability when you have everything under control? You know where to find everything, how to do things, and who to ask when you need something. It feels great. Until you realize that it has been months or even years without reaching the goals you thought you would by now.

There are times when this stability is not only good but actually necessary. When life throws something unexpected at you, the last thing you want to add to the mix is not having everything else under control. But once that passes and your energy is back again, you must feel ready to take on a new challenge, right? until the opportunity knocks at your door and you feel unprepared to take it.

Let’s take a look at this from another angle and let me ask you a few questions:

  1. Are professional sports athletes born ready for the Olympics?
  2. Would you ask a drummer that started playing just a week ago to record a single, even if I tell you that in ten years he’ll be the best in the world?
  3. What did the first-ever surgery of a renowned neurosurgeon look like twenty years ago?

None of those scenarios look promising, do they?

They all seem to have potential once I tell you that all three became successful decades later, but when they were just getting started they were just like us, with an unknown future in front of them and a lot to learn to reach their goals. There’s no guarantee of the outcome, and this unsureness is paralyzing compared to the safety of many other things you’re already comfortable with.

Uncertainty is uncomfortable and we wish we have a time machine to know for sure if it was worth the risk. We’re all humans after all.

The effects of it

What happens when you sit around and wait for that “perfect moment” to take the first step towards your goals? Here are a couple of things that would likely happen:

1. Nothing happens.

Literally, nothing happens because you continue to wait, ponder, and make never-ending plans on how to go forth. But you don’t actually use the time to make the jump.

You might feel stuck and paralyzed. You’d think to yourself, “Oh, maybe next time I’ll be ready for it”. Next time rolls around, but you just end up using the same excuse. Or maybe you decide to move on to a new challenge and ditch this current one. But the question is, will you stall yourself and abandon ship once again?

It’s a cycle where you’ll be perpetually breaking promises to the side of you that wants to grow out of your comfort zone.

2. You feel unfulfilled.

The growth that you yearn for but aren’t getting might leave you in a state of being unfulfilled.

You’re comfortable where you are right now, but it’s not where you want to stay, and that’s why you want to seek a new challenge or opportunity. However, you’re in that “Nothing Happens” cycle (see above), and now every day feels drab. You might even start to fantasize what it would be like if you just went for it without feeling like you’ll ever be ready.

But you can never be 100% ready.

How to overcome it

In her book “Thinking in bets”, Annie Duke proposes a very uncommon approach when it comes to decision-making, especially the tough situations: Think about them as bets, just like a poker player. Contrary to popular belief, life resembles poker more than it does to chess, because there are an incredible amount of things outside of our control (defined as luck in the book), and regardless of them we still have to decide. Turns out that doing nothing is also a decision.

Learning how to deal with uncertainty starts by evaluating the probabilities of an unknown future, making a bet, and ultimately learning from it. You can go on with your life making decisions to be right or to win. Results may or may not be what you expected them to be, but if you do a change of mindset and look at it as a learning opportunity, I bet that next time you’ll be better prepared to make a decision.

To improve the quality of our decisions, there are a few things that can help us to make those decisions and feel confident about them:

1. Stop thinking that you’re 100% sure or that you should’ve known.

The future is never certain because luck can interfere and change the outcome even if we thought we had it all planned out. Even if the chances of things not working out represents only 1% of the probabilities, it may still happen.

Good decisions can turn into bad results, and bad decisions can evolve into good results, just like the kid who didn’t do his homework but the next day the teacher forgot to ask for it. So if we can’t predict the future we should stop thinking that we’re fully responsible for it. It’s ok not knowing how things will turn out, we need to accept and live with it.

2. Dive into it, headfirst.

Here is the mantra that needs no introduction: Just Do It.

Acknowledge the ambiguity, then go for it.

Every outcome is a result, even if it doesn’t turn out the way we prefer. If we’re able to count desired and undesired outcomes as gained experiences, we don’t end up thinking we “lost” or “wasted time”. Any type of outcome could be a winning situation if we go into it with the mindset of getting results.

Oftentimes, we’re able to learn from results (e.g. What might we do differently next time? How can we prevent this from happening in the future?). But if we don’t go ahead and take action before that, how would we learn and grow?

Action taken + result: Reaching out to a hiring team about a job. Getting turned down after going through the full interview process, but taking notes where you think you can improve for a future interview.

No action: Being doubtful of your own skills, so you don’t apply or reach out to the hiring team. Maybe you’ll try again later, when you feel “ready”….Whenever that may be.

3. Explore the future with decision trees.

We often fall into the trap of thinking that things can only turn out “right” or “wrong”, that’s just plain unrealistic. To consider a more objective future, Annie proposes examining our beliefs and exploring the possibilities that may happen based on our decisions and how luck may play a role in it. This process is called scenario mapping.

A belief leads to a bet, from which one of many possible scenarios may unfold
Scenario planning, from “Thinking in bets”

Analyze what you know about the past in similar scenarios and the probability of each possible future happening, especially those that may seem unfavorable, to be prepared in case it happens. Act proactively about your future, instead of being reactive to outcomes that catch you by surprise.

4. Use a decision journal.

Once we’re ready to make a decision, we can make a record to revisit it later and analyze our decision with the actual events once things have already happened.

If we’re only making decisions on a whim, they can easily get distorted when looking back to fit our expectation that we’re the heroes of our story. We should take into account our future selves and document things objectively to refine the quality of our decisions over time.

Take this guide created by Farnam Street as a template, inspired by psychologist Daniel Kahneman’s own suggestions. Ultimately, it should include what makes the most sense to you because you’re the one making these decisions.

We hope you take a chance on yourself and start making calculated bets. As time passes, you’ll improve your decisions by broadening your perspective of past experiences, regardless of how things turn out and how you feel in the moment that you’re going through them.

The key to all of this is to keep on learning because life is rarely black and white. Even though we can’t control the future, we most definitely can improve the quality of our decisions. By doing this, we’ll feel more comfortable navigating the uncertainty of an unknown future.

Identifying a negative outcome doesn’t have the same personal sting if you turn it into a positive by finding things to learn from it. You don’t have to be on the defensive side of every negative outcome because you can recognize, in addition to things you can improve, things you did well and things outside your control. You realize that not knowing is okay.

— Annie Duke, Thinking in bets

If you found this valuable, please share it with a friend or a colleague to whom it would be helpful.

You can find Laura and Mary on Twitter, talking mostly about design, but often times deviating into music, delicious food, or the MCU.



Leading Design @ Ravn

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