Fail Better: Mental Models for Overcoming Failure

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Fail Better: Mental Models for Overcoming Failure

“Ever tried. Ever failed. No matter. Try Again. Fail again. Fail better” -Samuel Beckett

As humans, we are not particularly interested losing, in any context. Scientists who study human decision making have identified several our predisposition to value losses over gains—failing can be biologically hard to embrace. It’s in our evolutionary recipe to take loses harshly, and therefore, getting excited about failure has been a bittersweet lesson for me.

My accomplishments take a central role in creating the narrative that I embrace. Failure, in a way, is the deconstruction of those ideals. Any idea I have of myself can easily be second-guessed from a circumstance in my life that proves otherwise.

But that’s just it.

It isn’t the event that is harming me, it’s my mindset. So how can we reconstruct how we think? What does it take to reinvent failure? How can we fail better?

Enter Mental Models.

“The chief enemy of good decisions is a lack of sufficient perspectives on a problem.” - Alain de Botton

 "A mental model is an explanation for how something works."It is a system, principle, theory, aphorism, heuristic and much more. Call it what you want, its central tenet though is essentially something you carry around in your mind to help interpret the world—broadly I like to think of it as a mental representation of how to think about stuff.

Commonsensically, the particular way you perceive reality will yield a specific perceptual experience. That means when you’re, upset, angry, or feel like a failure part of the reason is the given subjective lens you consider part of the experience—your mental model.

When you train your brain to rethink failure, you win.

Over time I have gathered a toolbox of mental models to help better grip failure by reconfiguring my perception. Failure is not a loss, but an opportunity. These are specific methods to disarm yourself from defending against failure, let’s get right into the 3 mental models for overcoming failure.

Failing Faster

“It’s fine to celebrate success, but it is more important to heed the lessons of failure.” – Bill Gates

When Henry Ford released the Model A it was awful. Mechanics found problem after problem from customers complaining about the quality of the vehicle.

But he and his partners already knew that—Henry Ford wasn’t looking for perfection, he was looking for opportunities to lose.

Subsequently, Ford fixed every single problem. With the information gathered from releasing an imperfect model A, Ford was able to produce the Model T. Ford opted to fail first and succeed later. Without the data from the Model A failure, Ford would have never been able to create a car that is now considered a pivotal moment in automobile history.

Fast failing is a longtime praised in business as the most effective methods for reach maximum effectiveness or efficiency. As a mental model, failing fast can be used to test out any habits, behavior routines that we would like to incorporate into our lives. When we get failure out of the way we save resources that would normally accumulate over the long term, develop correlations for what works, and avoid what doesn’t.

The Obstacle is the Way

“The impediment to action advances action. What stands in the way becomes the way.” -Marcus Aurelius

Originating from Stoic philosophy and popularized by bestselling author Ryan Holiday, the obstacle is the way is a mental model to better embrace the realities our lives that are bringing discomfort by changing your perceptions, actions, and willpower.

What do you get from running away from obstacles? Not much. Any discomfort you experience can be addressed. So when you choose to respond to obstacles with a realistic perception of what they are—your method for breeding success—you see how much control you really have over every situation.

Transform adversity into advantage.

As a mental model, viewing any trial that is to come in your life as exciting, invigorating, and perhaps even something to be grateful for it will bring a new life to all experiences—intentional living starts here.


It’s been said many ways but the first time it really clicked was a few months ago when I heard Daniel Pink say this…

“If you want to know what an experience is going to be like, find someone similarly situated and ask for their experience. A very good way to avoid failure is to learn on someone else’s dime. Let them make the mistakes and then learn from those mistakes. I much prefer learning from other people’s mistakes than from my own.”

We don’t need to reinvent the wheel. When I fail at something. I look for people who have done the same. Now I potentially have a collection of people who have been through the same situation and the best part is, they survived.

So not only does this settle any anxiety about an outcome being the death of me, it gives me information about where to go after that seemingly tragic event occurs.

Take how others have failed to broaden the perspective of your own failures.

Surrogation as a mental model is the meta-mental model—it is a model that heeds advice about the benefit of collecting mental models. The models above are themselves all methods of surrogation. What top performing humans have used or monitored in their own experience are the best tools for addressing your own issues.

We are not too different from one another. So when you find yourself failing, look towards those who have ventured into the same valley as you, how did they survive?

Fail, in fact, fail a lot; you’ll learn far more.

Many of these mental models for interpreting the world are similar. In one way or another they all state when things don’t work, make a serious effort to understand why, and you are bound to be successful. Part of living an intentional life is bringing meaning to even the banalest. Don’t minimize your failures, become aware of each event, and use the mental models above to modify your perception. Soon you’ll see failure will no longer be an inhibitor, but the contributor to all of your achievements.

My Motto: Today is the best day of my life

I treat every day as the best day of my life because no matter the praise, disappointment, obstacles, or success I know that I am doing everything that is in my control to live to the standards of my greatest self.

How? It all starts with my 5 habits. Find out more here.


How Habits Fail: Common Mistakes in Habit Formation

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How Habits Fail: Common Mistakes in Habit Formation

I fail a lot.

  • I fast intermittently between 8 pm and noon; I’ve but I ate an entire tub of ice cream at midnight.
  • Forces of Habit was a supposed to launch at the beginning of 2017
  • I was fired from my first ‘real’ job

When it comes to habit formation. I have a laundry list of failures.

But I’m grateful.

Because without those failures, I would never have been able to build a method for living the best day every day. Intentional living begins with failure in mind, and common mistakes in habit formation are a dime a dozen on our journey to becoming our greatest selves.

Look at the numbers. By this point in the year, over 50% of New Year resolutions enter the ether. Take gym memberships for example.

Gym membership rates are down. People say it's “too hard to get back on-track” or “its hard to find time”.

Try as we may, why don’t good habits work out? How can we make change easier to change our lives for the better?

If you build good habits properly, results will come.

Let me tell you what I’ve learned from deliberating reforming my ability. Piece by piece I harbored mistake after mistake. I’ve learned from the best and built great habits. It’s my turn to share the common mistakes you’ll encounter on your journey toward habit formation.

Building too many habits at once.

Changing behavior is by far one the most challenging things a person can do, so why do it in several domains of your life at a time? Habits take a substantial amount of time and energy to change, so when we take on multiple habits at a time we lose out on giving our all to making a change.

When I first started building habits I was only running. Every day I would run a bit and feel like a champion; that was it. I didn’t need to read, eat healthy, or meditate. Those things came once I felt deeply rooted in my first habit.

You seek the outcome rather than relishing the process

Goals are great but, getting wrapped up in the idea of hitting your goals will level your drive when change doesn’t come—there will be times you won’t see any change.

New goals do not yield results just because you put in some work.

You need to put work into building your habits every day and leave the expectation of an outcome at the door. As we improve, the effects of our actions become blurred and fear of stagnation sets in; have faith. If you have a system, stick to it, long-term growth is inevitable as long as consistency is present.

All of our efforts are not linearly related to the outcomes. Nonlinearity resulting from a linear force exerted on an object isn’t uncommon. Said another way the efforts we put in may not result in the same improvements we saw right when we started.

So when you find yourself thinking too much about the goal or outcome, step back, ask yourself what is the habit that gets you to the outcome, and do the thing.

Further Reading: Fooled by Randomness

Your Habits are Private

Part of making an obligation to yourself is making sure you’re not the only one aware.

Last month I edited three photos every day and I kept myself motivated by sharing a public google doc that I shared on social media and the newsletter.


I did it.

Missing a day would not only let me down but my readers. I made it hard to quit and easy to stay motivated.

Completing a task that everyone knows you are aiming for can be invigorating—the change becomes you. Social proof backed habits put your reputation on the line, something so precious that humans are evolutionarily predisposed to be ruffled by the idea of being socially ostracized; take advantage of this.

Use social proof. When you hide your habits from people it is easy to quit.

Who can think poorly of you if no one even knew what your plans are? But the flip side, who can encourage you if no one knew what your plans are?


Find the link to the google doc in this month’s newsletter.

Not signed up? Here is the link to all 90 pictures

Further Reading: Influence

You’re Attempting Unreasonable Habits

“I wanna start reading; I’ll read for 8 hours a day”

“I think I will start exercising; I’ll do 100 pushups and 10k every day”

“Maybe it’s time to start a diet; oh, I’ll just start a 20-day water fast”

When you set too large of a commitment from the start, you set yourself up to fail. It isn’t about the quantity of the change initially, that will come as you gradually raise your standards.

At first, think small.

Instead of 100 push-ups, how about 1? Your mindset may be motivated now, but your brain needs time to strengthen the synaptic connections. Letting out brains grow accustomed to the routine keeps the habit going when you aren’t so motivated; the habit is already ingrained in you. You no longer need to be pumped to do the thing because there is less inhibiting you from considering anything that isn’t the habit in the first place.

Pick a habit and start small. Focus on the repetition, and once you have then down, up the intensity.

Further Reading: Read More, Small Actions and Meditation: The One Minute Sit

Not tracking the change.

“What gets measured gets managed" -Peter Drucker

A common mistake in habit formation is forgetting to track. An easy way to demotivate yourself is to lose track of the metrics you’re using to access the progress of a habit. Knowing how long it’s been is great reference information for when you are tweaking the habit for better results.

When it comes to tracking I am a maniac.Forces of habit Journal

I track all of my habits in my personal development journal as a method to encourage myself and others. It really is a physical representation of all the hard work I put into becoming my greatest self.

Try to remember every time you hit an achievements mark. How far have you come? What patterns do you notice? Where did you write down that game plan?

Building a habit is a lot easier when you formally record your progress, and the best method to breed your success is keeping it all in a single place, like a notebook or journal.

Writing something down has a memorizing feeling to it. Putting something to paper in a meaningful place it makes it real. It’s much harder to back out of a commitment you make with yourself especially if it is solidified in writing.

Further Reading: Journaling for growth

Attempting to Reinvent the Wheel

If you want to know what an experience is going to be like, find someone similarly situated and ask for their experience. A very good way to avoid failure is to learn on someone else’s dime. Let them make the mistakes and then learn from those mistakes. I much prefer learning from other people’s mistakes than from my own.

-Daniel Pink

Another common mistake in habit formation is starting from scratch. Billions of lives have been lived, so why fall for the same pitfalls that cause someone else to fail? The lesson has already been learned, so instead of making the same mistakes try taking using what they learned and build upon it to create a new and improved habit.

Someone’s gotta fail, but no one said it only has to be you. Your next choice can be backed by the lessons of the entire human race.

Keep failing

If I can offer one parting piece of advice it would be to keep failing. All of the common mistakes in habit formation listed above only exist because people like me and you took a chance and failed—it’s just part of life.

Habit change won’t be getting any easier anytime soon. But by avoiding these common mistakes in habit formation, I know you can start to live more intentionally.