“Fortune Favors The Bold”

Audio Blog, 14:51

“Fortune Favors The Bold”.  Virgil

Bold action is defined as “not hesitating or fearful in the face of actual or possible danger or rebuff; courageous and daring”.

Fourteen days after America suffered the devastating Japanese air attack on the Pearl Harbor naval base, President Franklin D. Roosevelt met with his Joint Chiefs Of Staff in the White House.  The President had declared war on Imperial Japan, but the nation was still reeling with shock and humiliation over the deadly surprise attack that took the lives of 2,403 Americans and dealt a psychological blow to the nation.

The President expressed, to the Generals and Admirals, his desire to strike back as soon as possible.  The military leaders acknowledged his directive, but they understood the strategic, tactical and logistical challenges that attacking the distant pacific empire would entail.   From the Emperor down to the average citizen, the Japanese population felt invulnerable because of the natural obstacles of distance and water, their control of the Asia-Pacific region, and a very powerful Air Force and Navy.

America needed a bold plan of action.

So on April 18th, 1942, sixteen B-25B Mitchell medium bombers were lined up on the flight deck of the U.S. Navy’s aircraft carrier USS Hornet, steaming towards Japan. The aircrews were selected from a group of volunteers with significant flight experience, courage and commitment.

All 80 crew members knew the mission was extremely dangerous, and the likelihood of safe return was very low. However, they were motivated by a simple fact:  If they succeeded, the mission would strike a retaliatory blow into the heart of Imperial Japan, and cast doubt on the empire’s invincibility.

The flight plan called for the bombers to fly a great distance over water to hit military targets in Tokyo Japan, and then continue westward to land in China.  After careful planning, it was determined that returning back to the aircraft carrier was impossible due to fuel and landing limitations. Lieutenant Colonel Jimmy Doolittle was chosen to lead the daring mission, known as “Doolittle’s Raid”.

Doolittle’s plan was to move the aircraft within 480 miles of Tokyo loaded on an aircraft carrier before launching the bombers.  Unfortunately, a Japanese scout ship spotted the task force 650 miles from Tokyo, and triggered a premature exchange of fire. The engagement sunk the Japanese ship, but Doolittle was concerned that the Japanese sailors were able to transmit a warning signal back to Imperial Japan, which would forfeit the raiders’ element of surprise.

Demonstrating extraordinary leadership, Doolittle gathered the crews on the flight deck, and told them of his decision to launch immediately, a full 170 miles and 10 hours before they had planned.  This greater distance would eliminate the fuel reserve calculated by the planners, and increase the odds that crews could be killed in action or fall into the hands of the brutal enemy.  Complicating the situation was poor weather and rough seas, introducing the risk that the heavily loaded bombers may not even be able to safely launch off the carrier.

Doolittle told the group that he was not forcing anyone to follow him, and he only wanted brave volunteers to step forward.  He informed them that he would be the first to launch into the increasingly dangerous environment, and they would follow him.  All crew members immediately confirmed that they were “all in”.

With all 80 crew members ready to go, Doolittle launched the 16 aircraft without fighter escort, each with a crew of five men. They flew extremely low, wave-top level, to avoid detection.  Six hours later, flying in groups of 2 to 4 aircraft, they climbed up to 1,500 feet over Tokyo and successfully bombed ten military targets.  The aircraft took anti-aircraft fire and had to shoot down a few enemy fighter aircraft, but all 16 were able to exit Tokyo airspace. Fifteen aircraft headed to the planned landing zones in China, but 1 bomber broke off and headed for the Soviet Union, due to low fuel.

The aircraft, now flying at night in bad weather and low fuel, somehow made it to the Chinese designated landing zones.  Of the 80 crew members that launched from the USS Hornet that day, 69 evaded capture or death, 3 were killed in action off the coast of China, and 8 were captured and became prisoners of war.   Of the 8 captured, 4 were eventually repatriated, 3 were executed and 1 died in captivity from a starvation diet.

Doolittle was awarded The Medal Of Honor, and eventually promoted to 3-Star General.   He went on to command the Twelfth Air Force in North Africa, the Fifteenth Air Force in the Mediterranean, and the Eighth Air Force in England during the next three years.  All 80 Doolittle Raiders were awarded the Distinguished Flying Cross, and those who were killed or wounded during the raid were awarded the Purple Heart.  The mission was an audacious stroke of genius, and considered a significant morale booster for the nation.

Whether the objectives deal with military missions, personal relationships, career ambition, financial objectives or athletic pursuits, for example, the gap between the status quo and the ideal outcome, can be bridged with bold action.

What are a few practical examples when bold action is most useful?

When a situation is stagnant or desperate.  If things are going well, most people don’t want to upset the apple cart.  However, if a relationship has fallen into a rut that is counter-productive, uninspiring and destructive.  Yet both parties desire to make it work.  Bold action, in the form  of professional counseling, change in social routine, or planned separation may create a new fertile environment for positive change.

When the path to ambitious goals seems unachievable via the traditional path. It is always frustrating for a young ambitious person to join a well-established business with a team of experienced professionals who don’t seem to be going anywhere soon. They have established a functional operating procedure that generates sufficient results, and maintains the current hierarchy.

The young employee, anxious to assume more responsibility and earn larger rewards, will have to take bold and unconventional steps using a fresh perspective to create non-traditional solutions and improvements to the status quo.

An example?   Young people are highly competent with technology.  When entering into a mature business, there is much to be gained by improving the outdated methods of communication, cyber security and electronic commerce.  A seasoned employee, comfortable with the way things work, will likely not recognize, propose or execute a bold initiative to seize future opportunities.

What lessons of the bold Doolittle Raid can we apply to our lives?

Combined with motivation, planning, self-confidence, and acceptance of risk, bold action is an important ingredient to achieving your most ambitious goals.


Bold action entails risk, uncertainty and volatility in outcomes. You are shaking up the system, and that naturally means the change will not be smooth and linear.  There will be ups and downs.

To handle this, you need to be highly motivated to endure through the trials and tribulations in order to achieve your bold objective. This is why Doolittle only wanted motivated volunteers.  He knew that this mission would be harrowing, and he wanted to know that his crew members were “all in”.

“Manufactured” motivation cannot be sustained to support bold action.  It has to be genuine, based on a thoughtful purpose, and consistent with your core values and internal desire.   Other sources of motivation include self-esteem, power, autonomy, security, achievement, affiliation and competition.  The key is to identify the source of your motivation, and to embrace it.


Identify necessary tools:

Before setting off on a bold course of action, you must ensure that you have access to the necessary tools, such as relevant skills, education, information, and capital.  The important point is that you don’t have to already have these tools, but your plan must have a reasonable expectation of acquiring them along the way.

For example, When the Doolittle Raid was conceived, the nation didn’t have the ideal aircraft for the mission. The U.S. Navy didn’t have a bomber with the necessary range or payload, and the U.S. Army Air Force didn’t have an established airbase within range of Imperial Japan.

However, modified B-25 Medium Range Army bombers could carry the 2,000 pound payload, had stable flight characteristics at heavy weights, and could take off within the 500 feet of usable carrier deck runway.

Identify the necessary human talent: Ambitious goal cannot be achieved on your own. We all need enablers, mentors and teammates to make it happen.  Once again, to begin bold action you don’t need to have these people in place, but your plan needs to identify the type of talent, and the approach you will use to find them.  Use your current network of friends, clubs, school alumni offices, etc.  If you can enthusiastically articulate your plan, the right people will eventually emerge.

Once LTC Doolittle identified the B-25 as the best aircraft for the mission, he approached the most experienced B-25 bomber unit, the 17th Bomb Group out of Pendleton Oregon, and selected the most competent volunteers.

Embark on training:  Along with identifying the necessary tools, you must also become proficient in the practical application.  It does not advance your bold plan if you are unable to effectively utilize the tools and talent. This is the difference between formal education and applied knowledge.

Doolittle’s Raiders, after being selected by leadership and provided the modified aircraft, spent significant training time learning how to take off within the maximum allowed distance of 500 ft.


“No plan survives contact with the enemy”, German Field Marshall Helmuth von Moltke. In other words, you must be prepared to improvise and adapt to the changing scenarios once the action is commenced, keeping your ultimate objective in focus.

Bold action implies a reasonable amount of surprise and uncertainty in your environment.   That is what makes it bold, but also likely to present multiple, decision-making crossroads. It is helpful to establish your guidelines for handling a variety of potential scenarios, which provides a framework to surmount unexpected obstacles.

Prior to embarking on the mission, Doolittle created a framework for contingencies. He decided that if the naval task force was discovered within range of Tokyo, they would launch early even if they knew the fuel was not sufficient to reach the Chinese landing zone.   If they were discovered out of flight range from Tokyo, but within the range to the island of Midway, they would fly there for temporary refuge.  If discovered so early that they were out of range of both islands, they would literally push the bombers into the sea to make room for the fighter planes to launch and protect the battle group.


Initiating bold action requires self-confidence.  If you are not self-confident, you will struggle to act boldly. Why?  Embarking on a bold and ambitious endeavor requires you to believe in your ability to reach a successful outcome.

How does a person gain self-confidence?  It occurs naturally when aligning your strengths and pursuing interests. In other words, act boldly only when it harmonizes with your core strengths and natural interests.

Jimmy Doolittle exuded the type of self-confidence that others gravitated towards naturally.  This was developed from years of hard work, preparation and honing of his aviator and leadership skills.  His men shared a level of self-confidence that came from their selection on this elite team after years of success building the pilot skills and knowledge necessary to succeed in combat.

Acceptance of the Outcome

After all of the planning, network building and training, one primary question needs to be reconciled:

If this bold action fails, can I accept the outcome?

Doolittle and his Raiders knew that the outcome could be very bad (loss of life), but their purpose and motivation was more important to them than the potential consequences of failure.  When you identify a bold endeavor where the successful outcome outweighs the potential failure, you will be ready to initiate bold action.


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