Should Safe-To-Fail be part of the corporate culture?

Adil Addiya
13 min readApr 26, 2021


In the fast-moving and highly competitive world we live in, we need people in our organizations who are willing to take on risks. We need them to try doing new things, succeed, and if they fail they don’t get discouraged, so they can try again next time.

To achieve this, companies have to spend a lot of time and money establishing a culture of psychological safety among their employees. A culture in which failing is not frowned upon, it is just something that might happen to anyone.

This is summed up in phrases like “safe-to-fail”.

But should safe-to-fail be presented as part of the corporate culture

In my opinion, no. Failure is inherited to tasks, to the thing you are working on, not to individuals who do the work. Anything we do that is worth it, comes with its own set of risks. And when someone dared to take on this risk, struggle through tough times trying to get the work done but did not manage to achieve success, this does not mean that person had failed. Because the truth is, this person could have avoided all this by just not embarking on this journey.

When we present failure this way, you can see that in today’s business world, safe-to-fail should not be a part of any corporate initiative targeting individuals. The good news it is not.

Yes, people spend days strategizing about how to get their teams to innovate more by taking on more risks, but all this work end-up by targeting the wrong moment in the innovation process. The after the fact reporting of failure.

So when we talk about the culture of psychological safety, we are talking more about safety in reporting failure than safe-to-fail.

This is most visible in the tactics we use to achieve what we think is safe to fail. We often start by reminding the person that everyone had failed in something in their life, even famous people like Steve Jobs, Oprah Winfrey, Walt Disney, and others. And that talking about this failure will not diminish their value in the eyes of others. Or how this occasion can be the opportunity for a great learning experience.

We believe that creating a climate where our people are not being penalized or shamed for failing, will encourage them to take on more risks next time. And all that will foster innovation. but as anyone who ever built or fixed any complex system will tell you, this is not the most efficient way to do it.

Fixing a process by targeting the last step will require a lot of work and will not work all the time. We need to be working on solving the problem at the beginning of the process, that way we don’t have to count on people remembering what they learned in the last experience, each time they start a new one, and we can see the benefits of our work getting compounded the longer the process is running.

But how to do that?

Let’s start by saying that I recognize that getting to this point in itself is a big win.

We have made a lot of progress lately. We moved away from looking at failing as something that should be avoided like the plague. But the sad truth is that we didn’t move far enough, since we seem to have stopped at presenting failure as a necessary evil that some of us might have to go through to achieve success.

The problem comes from the way we envision success, not failure.

While not reporting failure is caused by the fear of the shame that comes with it or the fear of being penalized, not daring to fail in the first place comes from the misunderstanding of how we achieve success.

To illustrate this, let’s run these two thought experiences.

Experience #1

Let’s say you are hiring a new member of your team if you are a manager or you are expecting to get a new colleague if you are not one. Someone from HR, or the person in charge of hiring, comes to you and tells you, “I have your candidate”. A single candidate, and they show you a profile like this.

Yes, that’s all you get.

Name: X.

Picture, hidden.

Resume, redacted.

And you can’t talk to this person or ask any question about them.

What are the odds of this person having what it takes to do the job?

Experience #2

I give you a coin and ask you to flip it.

What are the odds of this coin landing face down?

Most people when faced with these two situations, give a different answer for each one.

For the second question, the answer is clear, 50/50. They don’t go into details analyzing the coin’s metal, the weather condition that day, which way the coin was facing when they toss it, or other variables that might affect the result. No, the experience is clear, you flip a coin, it is a 50/50.

But for the first experience, we do the opposite.

We try to list all that we know about this situation, from simple things like the fact that the HR person is a professional that will not bring the candidate to you unless they can do the job, to complex variables, like the number of potentially qualified candidates that might be interested in the job you are offering in your city.

And soon the situation devolves into a deep analysis, forgetting completely that there is a lot of unknowns and our best bet is the simple law of average.

Here you might say, “but I know things”, well actually, you don’t. You have assumptions and these assumptions can be true or false. Some of these assumptions depend on others, and as you go validating the ones you have, new ones are added along the way.

Your colleagues in HR are good at their job, yes, but for them to do something so out of process and out of character like this, who says they are not running this same experience on you, or simply missing with your brain to see how you react. And if this is the case, your second hypothesis about how big is your pool of candidates does not even come to play anymore.

We do all this mental gymnastics because, naturally, we want to succeed and when we planned for this success, we envisioned it as a simple journey from A to B. Here is where we are. Here is where we want to go. And here is the road we need to take.

We list all we have control of, and we try to account for some of the hurdles we will be facing along the way, and we stay open to the fact that we might have to learn and adapt. But we believe that the simple truth is, with enough hard work we will continue going forward until we get to our destination.

It is like going to your favorite restaurant for a meal. You have a vision about how to get from your place to the restaurant. You don’t have to create a detailed plan of each turn you will take but you know that you have to drive your car, and you know the road you have to take. You might even consider some of the roadblocks you will be facing along the way, like that construction project on X street, and how you will deviate to Y avenue until you passed the hurdle and continue on your way.

Is success a ladder?

This is most obvious in the analogy we use for success. Climbing a ladder.

We start on the floor, and we move step by step. We might be faced with a situation where we need to stop, pick our breath, or deal with something that popups, but if we continue climbing, we will get to the ceiling. It is a forward-moving process that will end up with you getting to your destination. And being back to square one before you achieved your goal, in our case eating that delicious meal, is a failure, and you have to start all over again.

This way of envisioning something before starting the work is crucial in achieving any success. Actually, it is more than that: to arrive at anything of value, we have to envision it first.

Yes, we might learn and adapt along the way, but this learning is then appended to the original vision, creating a new up to date version.

The problem is, while the vision evolves all the time, the set of rules governing it, does not. And when we are faced with something that does not conform to these rules, the system breaks.

If we think that success is a forward-moving process, we expect to be moving forward, or at worst not moving. And when we face something that sends us backward, we will not have any idea about what to do.

I would like to tell you that it is possible to break these rules when needed, but it is not. Without well-defined rules that you use to gauge what is going on, your plan does not work. It is not even a plan or a vision, it is just a dream.

The only thing we can do is envision success using proper rules, based on how success works in real life.

The ladder is not perfect

From all my years working for big companies and small startups, and from reading about and watching other people’s successes and failures, I can conclude that nobody who works their way through a success journey ever stopped somewhere in the middle. And this is not affected by the outcome of their work. You might succeed or fail in the end, but when you are still in the race you don’t stop, you either move forward or backward, you either climb up or down the ladder.

This might be hard to imagine at first. After all, at any giving moment we are either actively working or not, so it stands to reason that we can be either succeeding or not succeeding. And when something occurs that sends us back to where we started from, we have failed.

That is not true. Our effort is not the only thing that affects our success. In any given moment, we are under a lot of external force from climate to regulation, to technological advancement, and internal force, from our mood to our evolving skillset to our immediate entourage.

And all these changes are compounded with time.

To illustrate this, remember the last time you were working on some idea or project, then a new idea or project came out so you had to shift to it. After you finish working on this new project, if you go back to your original idea, you are never in the same place. You either find yourself now closer or further from your goal than when you left.

This is why some startup founders often revisit old ideas from time to time, to see if any change in context has made those old ideas worth pursuing now.

This constant movement closer and further from your goal, represents a continued stream of small failures and successes, that might not register with you when you are trying to solve your problems and get to your next big milestone. But you should not let it slide, you should at least acknowledge that they happened, even if you managed to overcome them quickly and without anyone knowing about it.

Recognizing that this is happening in every moment of our journey is important. This dynamic represents a microcosm of all the work we will be taking on in our personal and professional life.

And noticing these micro step-backs and developing some form of resiliency or even antifragility to it will train our failure handling muscles so we have no problem going through the big failures.

You don’t start on the floor

But if we are failing from the start, how can we make any progress. After all, when we start, we haven’t achieved any progress yet. We are still on the floor: where do we fall to from here?

Well, this is also another misconception with the ladder analogy: we think that we start at the bottom. The truth is, we start somewhere in the middle.

Remember in our first thought experience above: when we are dealing with lots of unknowns, our best bet is the average. At the start of any new venture, there is a lot of unknowns. Actually, at the moment of the birth of an idea, you often have only unknowns.

This means that, the moment you are just thinking about working on something new, you are already 50% there. And giving up on that idea at that moment means sacrificing 50% of your progress.

The weird thing is, we unconsciously understand that. People that are afraid of failure are not afraid of going back to the same place they started from, they are afraid of falling lower. This fear clouds our judgement and we start thinking that as long as we are standing still, we will not fail. We forget the simple reality: we are never standing still, we are always actively falling downward, and the only way to avoid that, is to actively move upward.

Here, the culture of psychological safety is not helping much, since it almost always puts forward this paradigm in which risks are associated with actions, when we all know that with the way things move in our world, the biggest risk is inaction.

From 50 to 100%

Getting from 50 to 100% of success might sound easier than getting from 0 to 100%. After all, you are halfway there. While this may be true, remember, you are not standing still. If you don’t make the effort to move upward, you are most likely to move downward.

So after you start from a moment of pure uncertainty, you begin by making some assumptions. Then you validate them, which might lead you up or down.

You design experience and you run them, you do the research and you extract value from the result. You can do a lot of stuff that can move you in either way on the success spectrum, the only constant is as long as you are doing something and making sure that what you are doing is the right thing, your odds of moving forward are more than your odds of moving back. And the opposite is true, if you are doing nothing, or just doing something to stay busy, you have more chance of moving back than moving forward.

You can enhance your chances of moving upward in the future, even if you are not making any effort. But this will require you to make an extra effort now. This might be building a program that will automate a part of your work or cultivating a great relationship with your colleagues so they can give you a hand when you need it, or so many other systems that you can build, to ensure upward mobility with minimum effort in the future.

Success is not a ladder, it is a mountain.

This careful dance of balancing effort and external factors (positive and negative), while moving back and forth in the spectrum of success, is what eventually going to lead us to achieve our goals.

But when we try to make all these variables fit in the way we envision success, it does not work. Because while the oversimplification of the rules for achieving success might be great in passing along the message quickly, it strips away a lot of details, which are critical in having a proper image of what it takes to achieve our goals.

It is like trying to compress an image so you can send it a someone over the Internet using a 56k modem. The more you compress it, the fastest it will go, but there are just so many details you can remove from the image before it becomes unrecognizable, or worst looks like something else. Fortunately, we don’t have to deal with this problem anymore, our understanding of technology allowed us to build better connection speed, which made the need for this kind of compression obsolete.

So isn’t it time also that our understanding of success allows us to build a better way of envisioning how we can achieve it? A way that accounts for all the variables that contribute to this process in real life. This will make our ladder analogy inaccurate since it is too precise and clinical to be a good representation of success in the chaotic real world.

Considering all we discussed, a more appropriate analogy will be, climbing a mountain starting from the middle with boulders dropping down over you, and each time you are hit, you do not get hurt, you are sent back some distance but you also get stronger.

While it might be silly to think that a new analogy for success will help more people take on risks, I believe the first step of conquering any fear is understanding it, and the easiest way to do that, is to present it in the simplest form possible without losing any detail.


I am amazed about how many people spend so much of their life avoiding risk. While not all risks are created equal, there are some unnecessary risks that we should avoid. I truly believe that some people could achieve so many great things if only they could manage to get beyond their fears and stop wasting their potential.

I believe that a shift in the way we envision success will lead us to a better understanding of where the failure lies and provide us with the courage to overcome our fears. And this starts by moving the success discussion from a cultural context to a job doing context. It is not, “you are safe to fail here, it is, “this project comes with risks and if you take them on, failure is an option, but if you do not, failure is a guarantee.



Adil Addiya

Using my over 10 years of experience with multiple startups and big companies to help people succeed.