There’s a sense of liberation we get every January. We mentally hit the reset button and replenish the ambition tank after another challenging year. Most people set forth on their Climb to conquer new-found goals or revive some from the prior year that have gathered dust.

I had a conversation with a Leader I mentor in early January 2020. He had an exciting, challenging year previously and eagerly shared the exciting things he’s pursuing in 2020 (though I’m sure those goals have pivoted).

As I listened, I could sense there may be an opportunity to help him better focus on why those goals were so important to his journey.

So I asked him, “Tell me what questions you asked yourself before you decided on these tweaks to your Climb?”

He was silent.

I remembered having similar plans and excitement earlier in my leadership journey. But I also remembered how daunting and overwhelming picking the right goals could be. I shared with him that I could feel his energy and it was contagious, but I wanted to understand how intensely he’d looked in the mirror prior to resetting his course. I explained that whenever I reset my Climb, the first thing I do is ask myself some key questions to assess whether or not I’m making the right changes.

Bobby Herrera speaking in Las Vegas, pictured with his family in the background.

The right questions open doors that otherwise remain closed. They keep you humble, honest, and curious; and they require you to dig deeper into understanding why you’ve chosen your goals.

Here are the 5 questions I ask myself every year (and you should too!):

1) What gives me energy?

This question is about purpose, identity, and meaning. There’s an invisible force driving all of us. Are you pursuing that thing that’s deep inside someway, somehow? Are you making progress towards it? For me, what gives me energy is bringing The Bus Story to life by helping kids born on the wrong side of the opportunity divide and mentoring veterans. Everyone has their own force. Go after it. You get one chance at this game called life.


2) Where will I invest my time with Team One?

Team One is what I call my family. I refuse to compromise this part of my calendar, so I block all the important dates with them first. If someone looks at your calendar, they should quickly be able to tell what’s most important to you. What story does your calendar tell them?


3) What boxes need to be checked for me to say “Yes?”

Too many Leaders struggle with ‘no’ because they don’t know what their ‘yes’ boxes are. Said differently, if someone asks you to do something, what criteria must it meet for you to say “yes?”

Here’s my ‘Yes’ Box:

  1. Does this help me raise joyful, kind, independent kids?
  2. Does this impact Roslyn (my wife) being involved with her purpose?
  3. Does this help me transform how the world views struggle?
  4. Does this help me bring The Bus Story to life?
  5. Does this help me narrate the Populus Group story?

I revisit this list every year. Most of these boxes must be checked. Otherwise it’s a simple and polite, “no thank you.”


4) Who am I choosing to learn from and why?

There’s a Buddhist proverb that states, “When the student is ready, the teacher will appear.” There’s always one thing that will help you more than any other thing (note I did NOT say the only thing; there’s a difference).

Have you identified that one thing? Once you do, you get to choose who you’ll learn that one thing from. Is it storytelling? How to better give recognition to people? How to pitch your company? Sales? Whatever it is, identify people who are the best at that one thing you need and study them fiercely (re-read Chapter 7 in The Gift of Struggle for additional encouragement).


5) What is scaring me right now and who can help me?

We’re all afraid of something. If you say you’re not, you’re Pinocchio. Name your fear, say it out loud, and demonstrate one of the strongest signs of leadership: ask for help.

As Leaders, we’re often afraid to expose those cracks. But if you don’t reveal the cracks, how else will the light get in?

Once you know what’s scaring you, share that with someone you trust. Bringing them into your story will help you better understand how to change the narrative.


We All Struggle

You want to get to that place you imagine in your Leadership transformation. We all do. To carve that path, I encourage you to do more reflecting. Look at the person in the mirror and ask better questions so you understand why before you set out on what you need to do.

Many of you intuitively do this! What are some of your best questions others can learn from?

Here’s to a better 2021, where we can come together and build a better team, a better organization, and a better world.

Hail the Underdogs!


  1. Joanne Rupprecht

    What a timely and lovely message and reminder ~ thank you Bobby for always being a source of light and positive direction.

    • Bobby Herrera

      Thank you Joanne! I hope you’re doing well!

  2. Christopher Minnick

    Hi Bobby, Great read and reminder. Happy New Year to you and your family – Team One and Populus Group!

    • Bobby Herrera

      Happy New Year, Chris! To you and all of yours!

  3. Skip Lineberg

    Bobby –
    This is excellent guidance. I’m going to dig into it and see how I can adapt it to my climb. Thank you for sharing these powerful insights.

    • Bobby Herrera

      Happy to share, Skip! Keep Climbing with Style!


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