Six Questions to Help You Cultivate Authentic Grit

Posted on in Healthy Living by Caroline Adams Miller


One reason I’m compelled to work in the field of motivation, goals, happiness, and grit is because I had the formula for finding success all wrong in the earlier part of my life and suffered greatly as a result. Through failure and an early-adulthood reboot, however, I learned how to do what was necessary to find the right goals and summon up the perseverance to achieve them—and I developed grit in the process. My experience taught me that grit is not a quality reserved for the select few; it is available to anyone who wants something so badly that they won’t let anyone stop them until they’ve gone as far as they can, often achieving or coming close to that which they sought.

I’ve even come up with a term to describe the type of grit I think elicits the greatest results: “authentic grit.” I define it as “the passionate pursuit of hard goals that awes and inspires others to become better people, flourish emotionally, take positive risks, and live their best lives.”

road sign "Follow Your Dreams"

Here are six questions to ask yourself to help you cultivate authentic grit:

  1. What is the dream (or dreams) you want to pursue and will regret not pursuing if you don’t get started?

It all starts with a dream. People who come to me for help have a dream to go beyond their normal boundaries to do something that is significant and fulfilling, something they will regret not pursuing if they never make the attempt. These are sometimes people others would describe as successful and don’t necessarily have to change anything to live a comfortable existence, but who have a hunger to dig deeper and go further with a cherished goal—sometimes a hidden one.

My follow-up question to “What is the dream?” is “So what then?” What will change in the person’s life once they accomplish that goal? “So what then?” also helps to elucidate how important the goal is to them, as opposed to anyone else close to them. The word should, as in “I should go to medical school,” is a giveaway that the person might not have intrinsic goals. Goals that matter to you and that will keep you in the game when it’s challenging are goals that don’t matter to anyone but you. If your dream is to please someone else, including your family or your coach, then it’s not going to work out well.

2. What do you wake up for?

I like to ask people what they wake up for. In the process of discussing passion, one’s purpose often emerges, but if it’s not clear, I want to hear what pulls them forward. Purpose is never about doing something just for oneself. The happiest people feel like they do something that contributes to others, and that is what gives them passion.

3. Who wants you to succeed?

This might be the most important question I ask people when assessing their likelihood for success. I know from experience and research that you can have a passion and be hardworking, curious, and hopeful, but if you are surrounded by people who don’t want you to succeed or who are ambivalent about any changes you want to make, then we will need to include a clear-eyed assessment of what I call your “web of influence.” People who succeed at long-term goals never succeed alone. They build and nurture relationships around them that provide support, advice, and accountability. Without that supportive network, they’d never be able to regroup during difficult times and find the will to keep going. In a technologically driven society, when it’s easier to text someone than look them in the eyes, some people have let important relationships lapse or haven’t ever confessed their fears or goals to anyone who might be able to help them.

4. What are your top strengths?

Every client who enters my practice takes the Values in Action (VIA) Character Strengths Survey right away. (You can take the free, 15-minute survey at I find this survey to be affirming and accurate, and when I go through the results with clients, they see themselves in new and positive ways. The reason I start all engagements with the VIA is that it’s been found to boost well-being, and people who want to be persistent in goal pursuit will need to have a flourishing outlook on life if they are going to persist in hard times, handle stress with humor and resilience, and put their best foot forward whenever possible. Some of the top findings from researchers who study the results of the VIA among different cultures and age groups are that people who identify and use their top five strengths in positive ways throughout the day are happier and more successful in the pursuit of their goals. It has also been found that people who deliberately “own” their top strengths and interact with others through the prism of those strengths come across as more authentic to other people, making it easier to be around them.

5. When are you at your best, and how do your strengths emerge in those situations?

Building on the VIA, I ask all of my clients to write an essay called “Me at My Best.” In this essay, you write about a time when all of your top five strengths were used in a transformational moment or at a time in your life when you were at your best. This can be a personal experience, a professional experience, or both. The idea is to find a time or times when your strengths came out in the right way and at the right time to create a positive outcome. This might be a time when you made a difference in someone else’s life, when you achieved something important for yourself, or when you were going through a tough period that was made easier because you leaned on those strengths to survive and thrive. This essay is usually an aha! moment for people for several reasons. One is that many of us take our strengths for granted and don’t realize that how we see the world isn’t how everyone else sees it.

6. Who is your best possible future self?

An elegant and powerful writing exercise called “Best Possible Future Self” revs up the engine of happiness and fuels the energy for goal pursuit. It is deceptively simple: people write about their life 10 years from now as if everything has gone as well as possible and their dreams have become a reality. There are several reasons why this is an essential step to take on the road to cultivating grit. The first is that this exercise unlocks a vision of who you want to become, and it’s 10 years in the future, a wonderful time frame for contemplating the fruits of long-term labor. It also helps you prioritize your life, because many of us carry around different ambitions but don’t realize that pursuing one will make it impossible to accomplish another.

This writing exercise is also valuable because it puts you in touch with who you want to be. It also generates more hope and optimism for your future, which are essential mindsets for grit as well. Finally, by going into the future and returning to the present, you engage in “mental contrasting.” It’s been found that when we visualize our ideal future and then bring ourselves back to the present to contemplate whatever obstacles stand in our way, we are more zestful and committed to taking first steps than if we start with where we are and think about what has to happen to make our dreams a reality, which can feel overwhelming at first.

Although authentic grit isn’t a magic wand and won’t solve all problems, I do think making it a priority is the right move. Too many of us are languishing because we are not shooting for the stars. We are settling for less than what we really want because we don’t have the inner resources—and confidence in those resources—to sit through sadness or physical pain when we need to. It’s never too late to start down the path that will take you exactly as far as you want. Take the steps necessary to fill your life with authentic grit, and I promise you that you will not only never regret it, you’ll also have nothing but respect for yourself when you look back and ask yourself what you did to make a difference in your own life, and in the lives of others, while you could.

Caroline Adams Miller, MAPP, is a positive psychology expert, executive coach, guest lecturer, and best-selling author whose works include My Name Is Caroline, Creating Your Best Life, and her new book, Getting Grit: The Evidence-Based Approach to Cultivating Passion, Perseverance, and Purpose.

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