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Use the Daily Dig to Improve Your Habits

Do you struggle to make progress on an important goal? Try the Daily Dig for 5 minutes a day for 30 days, and I’ll change how you develop habits forever.

When my clients first come to me, they usually have janky reflection routines to help them grow healthier, wealthier, happier, etc. We all have goals, but most don’t have a daily system that helps them reach those goals.

It’s why most of us give up on our New Year’s resolutions so quickly.

I had a friend whose New Year’s resolution was to exercise every day. That resolution lasted two days. 

It’s hard to make changes in our lives. We are so used to doing things the way we’ve always done them. 

Understanding our beliefs is the best way to improve our careers or any aspect of our lives. We have to believe that we are meant to exercise daily. If we believe that exercising every morning will make us happier and healthier then we’ll do it. The problem is that most of the time we don’t really believe the new routine will make us happier and healthier. 

Well…we logically know it, but we don’t believe it. We lack conviction. We don’t feel like it’s worth the effort to make a change. So we wake up on that third day and we ask ourselves, “Do I feel like exercising today?” 

The answer is, “Nope,” which means we hit the snooze alarm and we miss our chance to continue our streak and build the habit. 

The dialogue goes something like this:

“Do I feel like exercising today?”

“Nope. I’m tired. I have a big day today. If I exercise, then my energy will fade this afternoon. I should probably get more sleep.”

These bad questions are often the culprit of us not making lasting changes in our lives. We end up putting our focus on the immediate desire for more rest instead of helping our future selves become happier and healthier.

Listen to the complimentary podcast that helps you improve your decision-making habits:


I’ve developed a consistent writing habit, meditation, exercise, etc., through one simple technique that I like to call the Daily Dig. When you take the time to slow down and dig into your beliefs, you start to see what is really holding you back.

Let me share a story about the importance of great questions. When my youngest son was two, he punched me in the crotch. I saw stars and fell to the floor, and my son stood over me while he laughed. 

I remember it like it was yesterday. He was lying on top of the dog while holding onto her fur while hitting her with a red ball. I didn’t want the dogs to nip at him, so I told him to get off of her. He didn’t listen. I took a little red ball that he was holding in his other hand away from him. His face scrunched up, stood up, and punched me in the right spot to cause a grown man the most pain.

At first, I was pissed off, but then I started laughing. We laughed together. We talked later that morning about how to treat dogs. He never treated the dogs like that again.

I remember the moment that I started laughing. I asked myself, “What is amazing about this situation?”

As I reflected on the situation, it has become one of my favorite memories because I figured out how to be grateful for that moment. Even in all the pain. I would never have thought that was possible a few years prior. That’s the beauty of the practice of the “Daily Dig”. You can truly appreciate anything or improve anything because it helps you frame it into an opportunity. 

I was able to do this because of the questions I asked myself. This is how you put your spotlight on what matters. You improve your inner dialogue, which helps you be honest about your beliefs.

If I had asked myself, “How should I teach him a lesson?” then this would have been a terrible question because it would have magnified my anger. On the other hand, if I ask myself, “What can I learn from this situation?” then I can pull away from my emotional reaction and try to be wiser in handling the situation.

I’ve overcome a lot of pain, internal struggle, and health issues, and they all used to zap my energy until I learned how to process and learn from them. I’ve been through depression, being fired from jobs, being laid off, relationship issues, and cancer, and I’ve learned how to use these situations to help increase my energy. I’ve even found a way to see the bright side of my son punching me in the crotch. 

This took lots of practice. Let me explain the science behind the Daily Dig.


Optimistic salespeople outsell their pessimistic counterparts by 56%. This comes from their ability to bounce back. People with an optimistic mindset view adversity as just being temporary. They believe it will get better. People with a pessimistic mindset see negative events as more permanent. They tend to think, why try, it will just stay the same. Their beliefs dictate their actions. (1)

Your beliefs are dictating your actions. When you dig into your beliefs, you will find these internal gems that can change your life and help you rewrite your story so you become the person you want to be.

Your ego is there to protect you. It doesn’t want you to fail, so instead of exercising, it will rationalize an excuse to ensure that you don’t fail. Your ego protects you from emotional pain, but doesn’t always support your future health.

You begin mastering your thoughts and emotions when you recognize and acknowledge each feeling as it pushes you up or down like the wind on an airplane. You navigate the turbulence as you head to your destination. You glide along, aware but not carried away by the emotions. You are just fascinated by the opportunity to be in this experience.

I prefer to reward myself when I do something positive because I struggle with motivation when I’m a tyrant to myself. This has taken many years, but this mental switch has helped me reduce my procrastination and take more consistent action. 


There used to be some hesitation when I sent an outreach email to someone new to my network. I would worry about how people viewed my emails. I would picture them rolling their eyes at my emails or worse, laughing at me. I would think about what they said about my email after they read it. In my head, they often said, “Who was this dummy who thought I would respond to him?” I know it sounds awful. The bully in my head can be rough on me.

I had a bad habit of focusing on the potential negative outcome instead of the potential positive outcome. Now I have learned to ask myself questions like: 

  • “How will this email help people in my community?”
  • “Why should I not worry about what other people think?”

It’s hard not to answer these questions. That’s why they are so powerful.

Great questions often highlight the positive impact I can make instead of focusing on how others will perceive me.

I visualize how these emails can help my audience and how they will be relieved that someone cares enough to help them better understand themselves and their employees. Then I take some time to feel the moment. This is important. How does it feel in my head, heart, and gut. Maybe it’s encouraging or draining, but whatever occurs I try to be open to how I feel. This mini-celebration helps learn from the situation.

I took action to reach out and make a bigger impact. That deserves some positive reflection. 

Great Questions

I use the Daily Dig in all phases of my career. When a client tries to add work to the project, when a colleague ghosts me, or when I feel overwhelmed by all my work. 

I dig a little and ask myself a powerful question to understand the situation and turn it into an opportunity. 

I call this moment of reflection the Daily Dig. It’s all about asking questions that empower you to learn and grow.

Here are three questions that are very powerful. I will challenge you to log your answers every day for one week. Then watch the magic happen.

Ask yourself:

  1. What decision went well today?
  2. Why did it go well?
  3. How can I make more decisions like this one tomorrow?

When you review something, you often can change how you feel about it. By doing a Daily Dig, you can consciously choose how you want to remember a situation.

“Your memories are never fixed – they aren’t sitting in a vault, perfect, unchanged. Your memories are modified every time you remember them and pull them back.” Dr. Moran Cerf of Northwestern University

That means when you review a good decision, you deepen this memory and learn from it. You are building your confidence and ability to make good decisions for your future self.

Here are a few other questions that have worked well for my clients:

  1. Did I take some time for self-care?
  2. Was I refreshed and motivated to bring energy to my work?
  3. Did I make decisions to positively impact my personal relationships?
  4. Did I contact someone I haven’t talked to in a while just to chat?

These questions can help you determine what is working and what needs improvement. If you aren’t getting the answers you want, then you can course correct.

If you struggle with developing a healthier habit, try asking yourself questions that will help nudge you in the direction that will make your future self happier.

Here are two that have worked well for a client of mine:

What support can I give myself to find meaning in my work?


What will help me ask for help when I need it?


This is the beauty of practicing the Daily Dig. You ask yourself better questions to understand what is blocking you, so you can let it go and focus on what matters. This is how you take consistent action to grow your career and life.

What questions can you ask yourself to help you grow your career, relationships, etc.?

Once you identify your question, try asking yourself this question at the beginning of each day. By doing so, you’ll help plant the seed to take consistent action. This process helps you deepen your self-awareness so you can make better decisions. 

What lens are you using to make a decision? 

This is a powerful question that has helped me make better decisions. Instead of letting my emotions sway me in a certain direction, I’m able to step back and be more aware of how I want to handle the situation.

You want to understand how your beliefs can support you or hold you back. This self-awareness helps improve your decision-making.

Try the Decision-maker personality assessment to better understand how you make decisions, so you can create a clear flight plan that gets you to your goal quickly and without stress.


  1. Peterson, C., & Barrett, L. C. (1987). Explanatory style and academic performance among university freshman. Journal of Personality and Social Psychology, 51, 435-442. Seligman, M.E.P., & Schulman, P. (1986). Explanatory style as a predictor of productivity and quitting among life insurance sales agents. Journal of Personality and Social Psychology, 50, 832-838.

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