Lessons on Risk-Taking From a Harvard Law Grad Turned NFL Coach

Daron K. Roberts’s Courtroom

Many people go through life following a path that they think they should follow, rather than what they want to follow.

And to be honest, it’s easy to fall into this line of thinking.

We all experience fear, whether it is fear of failure, fear of success, fear of looking unintelligent, or something else.

The list goes on and on.

Multiply those fears by the expectations of others—friends, family, mentors—and it becomes increasingly difficult to try something new, whether that’s start a startup or make a drastic career change.

Inertia can be a dream killer. Along with this, we may even recognize that inertia is holding us back, yet still struggle to break out of the cycle of disappointment and regret.

So how can we break out of this cycle? How can we make a transition from a career that’s simply fine into something that we’re more passionate about?

For the twenty-eighth episode of The Power Of Bold, I spoke with Daron K. Roberts, a graduate of Harvard Law School who decided to take control of his career. Instead of following his classmates to jobs at some of the largest commercial law firms across the country, Daron decided to pursue his dream of becoming an NFL coach.

Ultimately, Daron’s dream became a reality. He coached for teams like the Kansas City Chiefs, Detroit Lions, Cleveland Browns, and West Virginia University. Daron speaks about his journey in his book titled Call an Audible: Let My Pivot from Harvard Law to NFL Coach Inspire Your Transition.

You can find the full episode on iTunes, Spotify or Stitcher.

As a law school graduate myself, it’s safe to say that Daron’s transition is extremely unusual. So unusual, in fact, that upon hearing his story, I had to immediately pick up his book.

I wasn’t disappointed.

Even though most—if not all of us—will not become NFL coaches, Daron’s story provides some excellent advice on taking a risk and making a substantial career change.

Here are some of the top insights from my interview with Daron on The Power Of Bold.

When Listening to Others, Consider Tactics Over Forecasts

After applying to Harvard Law School several times, Daron eventually received his acceptance letter. He was excited to be taking on the opportunity to study law with some of the most intelligent legal minds in the country.

Daron was also excited about his career prospects. His goal was to work at a large corporate law firm for several years and then pursue a career in politics.

Everything was going according to plan: Daron had clerked at several large law firms and all of them had extended offers for full employment after graduation. Having said this, Daron, on a whim, decided to work at a football camp for part of one summer while he was a law student.

Working at that camp changed the entire vision for his career.

Instead of reviewing documents late into the night or working on a merger between two large corporations, Daron wanted to be on the sidelines for an NFL team, coaching young men and dedicating his life to the game that he loved.

However, there were several problems with Daron’s vision. Very few (if any) law students simply walked into an NFL organization and found a job. Daron didn’t have much football experience. He didn’t have many contacts in the NFL world.

Beyond all of this, Daron had to deal with others analyzing and critiquing his career plans.

While his parents were supportive, other friends and family weren’t as excited. His law school classmates were bewildered while his law school professors were more helpful, providing great advice and emotional support.

Like Daron, there are some times where we want to take a risk or make a major career change. At the same time, there may be others—particularly those closest to us—who will provide their own commentary on our dreams. Sometimes that commentary can encourage or discourage us from going forward.

Often, what’ll happen is that there will be people in your life that try to tell you how to operate, yet have little (often no) experience in the opportunity that you are trying to pursue.

Because of this, Daron recommends that we listen to advice relating to tactics and not forecasts. In other words, ignore the advice along the lines of “Oh that’s crazy. It will never work,” and instead pay more attention to your friend’s advice on how your pitch is flawed and how it can be improved.

Listening to blanket forecasts requires you to provide a vote of confidence into somebody’s ability to predict the future. It’s hard enough for you to do it, so why should you place your faith in someone’s else ability to predict?

So remember: tactics over forecasts.

Listening and Humility Are Your Friends

Deciding to work in the NFL is one thing.

Actually getting into the building is another.

In his book, Daron speaks about how he wrote to every single NFL team looking for a job. He treated it almost like an election campaign, which was useful for him since he was previously student body president at the University of Texas.

Eventually, Daron received a call from Herm Edwards, the legendary NFL coach who, at the time, was leading the Kansas City Chiefs. He offered Daron a three-week training camp internship with the Chiefs, which Daron quickly accepted.

Not only was sheer persistence required for Daron to walk through the door, but he had to take drastic action to ensure that he stayed inside the organization. Even though he had a degree from Harvard Law School, Daron thought that the Chiefs staff would likely view it as a non-factor, or even a disadvantage.

Because of this, Daron walked into Arrowhead Stadium planning to listen and stay humble. He was going to learn as much as he could and embrace the grunt role, doing whatever task was necessary to make life easier for the coaches and players.

Sitting in meetings, Daron paid attention, took notes, and drank up as much as he could from some of the best football minds in the game.

He was in student mode the entire time.

Along with this, Daron took on some of the menial tasks that others didn’t want to do.

For some Harvard Law grads, it could be a massive ego hit if, for instance, they were asked to stock the kitchen. Yet Daron enthusiastically took on those type of tasks, never complaining and completing all tasks to the best of his ability.

Whether it’s building a startup or making a drastic career change, you may have to take on tasks that you don’t necessarily want to take on. You may want to focus on product, for example, when you have a pile of customer support tickets to answer.

It may be difficult, but listening and humility are the keys to your kingdom, regardless of whether you are running a startup or are transitioning from the legal world to the NFL.

The Power of Visualization

While most of us have goals for the immediate future, we all have sky-high goals of where we ultimately want to be.

Perhaps that is CEO of a billion-dollar startup. Or maybe a certain position within your current organization.

In Daron’s case, that was NFL head coach.

In his time with the Chiefs, Daron was doing the grunt work, but he was also taking vigorous notes on everything that he witnessed, from how Chiefs staffers cut certain players to the mementos and “collateral” on the walls of Coach Edwards’s office.

By writing everything down, Daron created a comprehensive “how to be an NFL coach” playbook from one of the best minds in the game.

Daron didn’t stop there, though. He internalized that data and would spend time visualizing how he would act if he were Coach Edwards.

Daron took this exercise seriously: he envisioned where he would sit on the team plane when traveling to an away game, how he would improve team meetings, and how he would select his team for an upcoming game.

These exercises were beneficial, not only because they helped him internalize why coaches were making certain decisions, but they gave him continual hope that he would, one day, be making decisions at the head coach level.

You may be skeptical of the power of visualization, even if athletes, entrepreneurs, and chess players swear by it. Nonetheless, visualization can be a great practice. By spending some in the future, you can work backward and determine what you need to do to get into the position that you desire.

That, in and of itself, is extremely valuable.

Best of all: it requires nothing except for your time.

What’s there to lose?

Ask Yourself: “But Did I Die?”

While all of us have career goals, the brutal reality is that few of us will achieve them.

Luckily, however, most of the barriers out there are self-imposed.

Most of them are based on our fears—whatever they may be. There’s a good amount of research that shows that we give too much credence to the worst case scenario. We envision investors laughing us out of the room or employees questioning our intelligence or leadership skills.

It’s easy for our minds to focus on the negative—especially if we are extremely ambitious.

If you find yourself focusing on the worst attributes of an upcoming decision, Daron says that you should consider two things.

First, acknowledge the simple fact that you are able to look back over the course of your life. That means that you didn’t die. Even if the worst case scenario happened with an earlier decision, you are still here. You will still be here after you make this upcoming decision.

Second, understand that you only have one shot at life. Time is finite and it moves without acknowledging our desire to slow it down. If you’re thinking of putting off starting a startup or making a major career decision, just recognize that it becomes even more difficult to make that change as you get older.

The more responsibility you gain, the harder it is to make a drastic pivot.

So even if your mind goes to the darkest places about your goal, understand that (1) that scenario, in all likelihood, won’t occur, and (2) now is the best time to take action—bold action if necessary.

You will thank yourself later.

Welcome to the Show

Daron fought through inertia and the “safe choice” of becoming a corporate lawyer to follow his dreams of NFL glory.

While some of his colleagues may have dreamed of making a similar switch, Daron made it happen. He took bold action and his decision paid off in spades.

You can do the same.

Whether you’re thinking of making the leap to become an entrepreneur or considering a decision to leave something “safe” to pursue a dream, rest assured that it can be done.

Sure, the road will be tough. But you will be more satisfied. You’ll be following your real dream instead of a dream that isn’t necessarily yours.

And that makes all the difference.


Thanks for reading! Once again, you can access Daron’s interview on The Power Of Bold by visiting our page on iTunes, Google Play, Spotify, or Stitcher. If you’d like to read a full transcript of the episode, you can access the episode’s show notes here.

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