The Art of Doing Hard Things - The Art of Living

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The Art of Doing Hard Things

Life challenges test our resolve and resilience. Inspired by "We Can Do Hard Things," this article explores 20 questions we face during difficulties. From identity to meaning, from strength to self-worth, we learn that embracing discomfort with courage leads to growth and transformation.
A long railway track showing a long tough path.

Life is filled with challenges that test our resolve, resilience, and strength. Some of these challenges are external, while others are deeply personal, rooted in our identity, self-worth, or fears. Doing hard things requires us to confront these challenges head-on, embracing uncertainty and discomfort. Drawing inspiration from We Can Do Hard Things by Glennon Doyle, Abby Wambach, and Amanda Doyle, this blog explores the questions we ask ourselves when faced with difficulty and provides insights to help us move forward with courage and clarity.

Who Am I? The Questions about Identity

One of the most profound challenges we face is understanding who we are at our core. When life gets hard, we often ask ourselves:

  • Who am I when nobody is watching? Stripped of external validation and societal roles, this question forces us to confront our true selves. It’s an invitation to explore our values, passions, and inner desires. Glennon Doyle writes about the importance of tuning out the noise of the world and reconnecting with our authentic selves.
  • Why am I like this? Self-reflection can be a daunting process, especially when we’re trying to make sense of our behaviors and patterns. Instead of judging ourselves, we can approach this question with curiosity and compassion, understanding that our experiences, upbringing, and circumstances shape who we are.
  • Why can’t I just be happy? Happiness feels elusive when we’re in the middle of a struggle. But as Doyle emphasizes, happiness isn’t a constant state—it’s something we create moment by moment, often by embracing the messiness of life and choosing to show up anyway.

Why Is This Happening? Questions about Meaning

When confronted with hardship, it’s natural to search for meaning. We wrestle with questions like:

  • Why is this happening to me? This question often arises from a place of pain and frustration. While there may not always be a clear answer, Doyle reminds us that meaning is something we create. By reframing challenges as opportunities for growth, we can transform adversity into a source of strength.
  • How am I supposed to make sense of this? Making sense of hardship involves accepting that life is unpredictable. Instead of focusing on finding immediate answers, we can learn to sit with uncertainty and trust that clarity will come with time.
  • Is there a reason for everything? This age-old question has no definitive answer, but Doyle encourages us to find our own meaning. Sometimes, the reason isn’t in the event itself but in how we choose to respond to it.

The Hidden Strength of Questions

One of the most remarkable lessons from We Can Do Hard Things is the idea that we are stronger than we realize. Even when the path ahead feels unclear, we can find the courage to keep moving forward. Consider these questions:

  • How do I move forward when I have no idea what comes next? Doyle suggests taking one small step at a time. Progress doesn’t have to be perfect—it just has to be intentional. By focusing on the present moment, we can build momentum and create a path forward.
  • How do I start when everything feels overwhelming? Starting is often the hardest part. Doyle advises breaking tasks into smaller, manageable pieces and celebrating each small victory along the way.
  • How do I do this when I feel so afraid? Fear is a natural response to the unknown, but it doesn’t have to paralyze us. Doyle highlights the importance of acknowledging our fear while choosing to act anyway. Courage isn’t the absence of fear—it’s moving forward despite it.

Questions of Worth

Our sense of self-worth often comes into question when we’re facing difficulty. We may find ourselves asking:

  • Am I enough? In a world that constantly bombards us with messages of inadequacy, this question can feel overwhelming. Doyle reminds us that we are inherently worthy, not because of what we achieve but simply because we exist.
  • Why do I need so much validation? Seeking validation is a natural human tendency, but it can become a trap if we rely on external approval for our sense of worth. Doyle encourages us to cultivate self-compassion and learn to validate ourselves from within.

What If…? Questions of Fear & Possibility

The “what if” questions are perhaps the most paralyzing of all, as they force us to confront both our fears and our potential. These include:

  • What if I am making a huge mistake? Taking risks can feel terrifying, especially when the outcome is uncertain. Doyle emphasizes the importance of trusting ourselves and remembering that even mistakes are opportunities for learning and growth.
  • What if I am not ready? Feeling unprepared is natural, but waiting for the perfect moment can lead to stagnation. Doyle’s advice is to start anyway—the act of doing is what prepares us.
  • What if I succeed? Success can be just as intimidating as failure, as it often requires us to step into a new version of ourselves. Doyle encourages us to embrace the possibilities that come with success and to trust that we are capable of handling it.

Practical Use Cases and Applications

These questions are not just for reflection—they can be powerful tools for personal growth and clarity. Here are some practical use cases and quick steps to put these questions into action:

Use Case 1: Journaling for Self-Awareness

  • Step 1: Set aside 10–15 minutes each day or week for reflective journaling.
  • Step 2: Choose one question (e.g., “Who am I when nobody is watching?”) and write freely about your thoughts and feelings.
  • Step 3: Review your entries after a week to notice patterns and insights about yourself.

Use Case 2: Decision-Making During Hard Times

  • Step 1: When facing a tough decision, ask yourself questions like “What if I am making a huge mistake?” or “How do I move forward when I have no idea what comes next?”
  • Step 2: Write down your answers and any fears or hopes associated with each option.
  • Step 3: Use your responses to clarify your values and priorities, helping you make choices with more confidence.

Use Case 3: Building Resilience in Daily Life

  • Step 1: When feeling overwhelmed, pick a question such as “How do I start when everything feels overwhelming?”
  • Step 2: Break your challenge into small, manageable steps and take action on just the first one.
  • Step 3: Celebrate each small win to build momentum and increase your resilience over time.

Quick Tips for Action

  • Write your chosen questions on sticky notes and place them where you’ll see them daily.
  • Discuss these questions with a friend or mentor to gain new perspectives.
  • Revisit your answers regularly and update them as you grow and change.

Using these questions intentionally can help you navigate difficult moments, build self-understanding, and take meaningful steps forward—even when life feels hard.


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