How to Predictably Fail Forward

How to Predictably Fail Forward

In life, the question is not if you will have problems, but how you are going to deal with your problems

John C. Maxwell

Learning to fail forward is key to your success and momentum. By consistently challenging the status quo and your current level of comfort, you will experience both success and failure.

Your ability to be resilient, even in the midst of adversity and seemingly failure, is a skill set that can be learned, improved and mastered.

What makes the difference? How do we all embrace resiliency?


Success is not final. failure is not fatal: It is the courage to continue that counts.

Winston Churchill

Successful leaders don’t want failure or obstacles, but they know it is part of the process.

Running a successful business isn’t easy or simple, and is full of hard work, calculated decision making, mental toughness, and complexity.

Developing your idea and taking it to the marketplace will be full of actions that often don’t result in successful outcomes. Others may reject your ideas or be unable to catch your vision.

Often decisions are not clear cut, but decisions need to be made. Choices are not always simple or apparent, but leaders choose.


Inevitably, business is like a science experiment, testing theory after theory to come up with the formula for success.

Testing takes place with sales, and with marketing, and with operations. When something works, you keep it; when something doesn’t work, you tweak it and try again or discard it and move on.


Obstacles are the raw material of success. Once you know failure is part of the game, you begin to view obstacles differently. As Thomas Edison said, “I have not failed. I’ve just found 10,000 ways that won’t work.”

Our brains naturally make lists of obstacles, whenever our vision exceeds our current comfort zone. For those unaware of this natural brain process, the list of obstacles will become a dead end.

For example, if an organization were to set a goal of increasing leads by 25% this year, immediately obstacles come to the surface. The brain automatically starts to figure out all the reasons why this wouldn’t work or why it would be difficult.

These obstacles could be: “We’ve never done that before?”, or “We don’t have the budget!”, or “We don’t have enough bandwidth on our marketing team.”

If you want to lose twenty-five pounds, you may talk yourself out of it, even before you begin, by saying things like, “I don’t know what to eat.” or “I’m too busy.”

Instead of obstacles being dead ends, successful individuals and organizations see them as steps to success.

Each obstacle can then be individually diagnosed and treated. Undiagnosed and untreated obstacles will often stifle progress.


Successful individuals and leaders know how to recognize and push through resistance. Becoming comfortable with resistance is paramount to failing forward.

When failure happens, it is painful. It can be disheartening, frustrating, and heart-wrenching.

Learning how to work through and push through pain is essential to success. If you avoid the pain and don’t push through obstacles, you’ll lose momentum and vision.

Courage and persistence are skill-sets. They can be acquired and mastered.

If you want to consistently fail forward, be prepared to face internal battles such as facing your demons, negative self-talk, and lack of confidence. If you consistently fail forward, at times you’ll face rejection and isolation.

But…if you stick with it, success is often on the other side of resistance.


Progress is impossible without change, and those who cannot change their minds cannot change anything.

George Bernard Shaw

The innovator’s mindset is a term I use to embody three different core questions. Together, they transform outcomes, good or bad, into learning and action.

When these questions become a daily part of business routine, confidence will thrive, even in difficult circumstances.When used personally, they transform the way you deal with setbacks.

In essence, progress is made when we continue to leverage what is working, discard what isn’t working, and intentionally make plans to improve our results.

While this may seem easy, when life and business gets complex and difficult, it’s easy to become distracted and make decisions that aren’t calculated or correct.


These three questions can be used regularly and applied to almost any event or period of time.

For example, they could be used at the end of a year or quarter to evaluate the past results and make plans going forward.

They could be used when an employee is making a self-evaluation. I’ve used these questions with members of a sales team with great success.

They could be used as a debrief tool, after a customer event was just held. It will help celebrate and isolate important “wins” but also will create an environment where the team can contribute to future innovation and change.

When used with a team, I’ve consistently been surprised by the group genius that comes out of this process.

Individually, the innovator’s mindset can also be a powerful self-evaluation exercise.


What worked? By asking this question we start by focusing on the positive results and actions. By isolating the key ingredients to your past success, you’ll make sure to include these in further iterations.

It’s a common occurrence in business development that teams can easily become distracted and excited about new opportunities but accidentally fail to continue doing what has brought them results to this point.

Individually, we can have good days or bad days. But the real question is why was it good? Did you go for a walk, talk to a friend, meditate, or pray?

It’s like baking the perfect cake. Each time you make it you want to isolate the ingredients that made that cake work.

As you intentionally isolate and repeat the good, your personal and professional momentum can increase. In addition, as you focus on what’s working, you’re feeding your confidence so it can grow.

What didn’t work? When you’re willing to look at results honestly, a process I call “confronting reality,” a realistic and complete picture is much more likely to be seen.

Often, individuals don’t want to confront failure, as it can pierce the ego, but this skill is essential to maximizing the learning from our negative experiences.

With teams, confronting reality can open the flow for dialogue and communication.

Some may not like this question because it can be seen as negative. To avoid a complaint session or pity party, I suggest this “what didn’t work?” discussion always be used with the other two questions of innovation.

Those individuals, entrepreneurs and business leaders who can ask the question, “What didn’t work?”, openly and honestly, will innovate faster and with greater accuracy than those who hide from reality.

What will I do differently next time? This last question forces you to integrate the positive from, “What worked?”, with the lessons learned from, “What didn’t work?”

It guides you to formulate a concrete plan going forward that intentionally “rinses and repeats” and builds upon the success from the past, while proactively discarding the bad ingredients.

It leads you to always calculate next steps that are thoughtful and purposeful, getting you into motion and action.


Fortitude is an old word that isn’t used much anymore. It means courage in great pain or adversity.

Those who experience repeated success and momentum have learned to bounce back over and over again. They have learned to push through the difficult times.

They maintain the charted course, despite how they feel in the moment.


  1. Don’t make big decisions in low moods. When our moods are low we can make decisions and say things we really don’t mean. When our moods are low, we don’t see possibility, we see dead ends.
  2. Have perspective – this too shall pass. When things get dismal and dark, try to keep perspective that tough times are like storms and clouds; they come and they go. The rough stuff is part of the journey.
  3. Don’t isolate yourself. Talk to someone you can trust that will listen. Often, people isolate themselves when they feel down, when what they really need is support.
  4. Surround yourself with greatness. Immerse yourself with positive influences and encouragement that supports your vision. One way to do this is read or listen to great books, podcasts, and articles. Consider reaching out to a mentor who has walked this path. I find great support through spiritual practices as well.
  5. Put yourself in a peak state. When you’re going through a tough stretch, intentionally put yourself into a peak state. This can be hard but can be done through a variety of methods such as gratitude, focusing on how far you’ve come, meditation, prayer, journaling, etc. This allows you to make decisions in your best frame of mind.

As a side note, I’d encourage number four and five from above every day, not just during tough times.

In summary, fortitude, courage, and resiliency can become skill sets. They can become habits, a part of who your are.

Rarely will the life you desire become reality without being stretched, adapting to change, and being resilient.

Go and fail forward. As you move forward and take action, give yourself permission to fail. Be kind to yourself.

Along your path you’ll experience resistance and failure. Expect these, push through them. What you want is on the other side of resistance.

And don’t forget to enjoy the journey!

Change Your Brain

“…since the 1990s brain researchers have come to realize that the brain— even the adult brain— is far more adaptable than anyone ever imagined, and this gives us a tremendous amount of control over what our brains are able to do. In particular, the brain responds to the right sorts of triggers by rewiring itself in various ways. New connections are made between neurons, while existing connections can be strengthened or weakened, and in some parts of the brain it is even possible for new neurons to grow.”

Peak: Secrets from the New Science of Expertise by Anders Ericsson

You Can’t Grow Without Sacrifice

Every time you see a person, family, or organization grow and develop, sacrifice has always been working behind the scenes to make that happen. It may take the form of time, focus, or money but it is always necessary.

To make our families better, we must let go of selfishness. To make our health better, we may have to sacrifice our cravings. To make our businesses more successful, we may have to sacrifice the old for the new.

Our country and communities are greater because of sacrifice.

Today, we celebrate the many veterans who have sacrificed through their service. Many have given their lives.

May we use that freedom to choose to make ourselves, our families, communities, and our country better and stronger.

Are You a Leader?

Leaders see a vision and make it their north start.
Leaders persuade others to follow that vision.
Leaders put in the work…the hard work.
Leaders lift and serve.
Leaders inspire action.
Leaders inspire greatness.
Leaders fight the inner battles to get the external results.
Leaders play bold and big.
Leaders create deadlines and are accountable.
Leaders listen and learn.

Are you a leader? How can you be a better leader?

Races Don’t Have Ties

At the end of the day, a winner is always selected.

Whether it be a presidential candidate, a sport, or even a job opening at the office, there will never be a tie.

When ten or twenty teams play for a championship only one team wins. When dozens of job applicants are interviewed for one job position only one candidate is selected.

Sometimes you win, many times you lose. In fact, most of the time you lose.

Even if you lose, you can still win, if you choose to win.

You can see pain at a catalyst for growth. You can see setback as perspective. You can see obstacles as the raw materials for growth.

When you play to win, you grow, even when you lose.

When you set a goal to lose twenty pounds and you lose only seventeen you still win. When you start a business you may not succeed but you’ll learn, be stretched, and become stronger.

When you run a marathon, you’ll most likely not take first but you’ll still win.

Challenge yourself, think big and bold, and take risks. That’s how you’ll succeed.