10 Essential Questions To Move You Forward When You're Stuck

Part of Kathy Caprino's series "Braving Up To Build Your Best Life"

Hundreds of times a year, my clients and course members share that, while they know exactly what they don’t want in their lives and work, they just can’t pinpoint what they do want. They know they’re fed up with toxic bosses, crushingly demanding schedules, meaningless and empty work, and using skills they hate to employ, but they still struggle with how to change what they hate.

95% of the professionals I meet who desire something better can’t figure out what to do, so they do nothing. 

They often remain totally stuck for years or until a huge crisis and breakdown moment hits that paves the way for breakthrough.

I was in this exact same position in 2001 – in a corporate role I disliked intensely, with colleagues who were constantly at each other’s throats, in a toxic environment that was damaging for almost everyone. The problem was – at age 41 – I asked myself every day “What can I do that is substantially different and better without losing my income and benefits, and without starting over completely?” I couldn’t figure it out (despite my efforts to get outside help about it) so I did nothing, and kept getting more sick, depressed and demoralized.

The answer to that question came not after a thorough exploration of possible career directions, but in one fateful conversation with a powerful therapist I was seeing at the time. After my brutal corporate layoff in the days following 9/11, I was in his office crying about my situation, and he said this:

“Kathy, I know from where you sit, this is the worst crisis you’ve ever faced. But from where I sit, it’s the first moment you can actually choose who you want to be in your life. Now…who do you want to be?

From that one powerful, probing question, everything changed forever for me. I realized in that one pivotal moment that I deeply longed (and in fact, had always wanted) to help people thrive and grow. I longed to be a positive force in the world, not hurt people and be hurt every day as I had been in my corporate life.

It became crystal clear then that I was ready for a completely new direction that would allow me to learn how to facilitate my own development and that of others, and use that new knowledge every day in a new career. So I did it. I got moving. Finally, the motivation to make this change was unstoppable, and I was ready to do anything and everything that was required. I earned a master’s degree in marriage and family therapy, trained as a coach, and launched a business providing both those services. And I’ve never looked back.

If you don’t have a great therapist or coach to assist you in determining a satisfying new direction, try asking yourself the following 10 critical questions, and then do something brave about it. Don't waste one minute more. Take a step forward to get you moving towards a new direction that will be not only thrilling and rewarding, but also lucrative and satisfying financially as well. Don't buy into that myth that you can't do meaningful work and make great money. It's a lie that our society has bought into, and it's a damaging one. 

But realize that bold and committed action is required on your part if you want a better life and career.

First ask yourself:

1. What is inside of me today (skills, passions, expertise, longings) that I want to leverage but haven’t found a way yet? What would my life look like if I could leverage these longings and passions? What would be different?

2. What do I want to stand for in the world? What legacy do I want to leave behind after I die? What will I give up everything for?

3. Without changing my career completely, what three small, doable steps can I take this month and next month that will help me physical and behaviorally “try on” (without risking everything) and explore three new directions that would be thrilling to me?

4. What am I running away from (emotional pain, poor boundaries, lack of communication skill, etc.) that I need to address and heal before I can be happier and stronger?

5. What dysfunction from my childhood and early family life is playing out in my work-life and workplace today that I need to address? Was there emotional manipulation or narcissism that affected me negatively?

6. Whose expectations am I trying to live up to that keep me stuck, unhappy and afraid to be my true self?

7. If I could do anything and know I wouldn’t fail, what would I try? What one small step can I take to pursue this new direction?

8. To build a beautiful life and livelihood, we need a wonderful support community. How robust is my network and “tribe” and what can I do today to start expanding my support network?

9. What assumptions, myths and misguided beliefs (about myself, work, people, careers, money, etc.) am I still holding onto that are keeping me paralyzed?

10. Finally, do I feel truly worthy of making a big change that will bring tremendous happiness, success and reward? Or do I feel deep down that I don’t deserve a beautiful life?

Once you answer these questions as honestly and deeply as you can, you’ll start to see things more clearly. 

Start talking to people about the changes you want, and speak compellingly and fearlessly about your talents, gifts and longings. The world needs your talents, but first, you need to recognize what you’re made of and why that matters.

For more from Kathy Caprino, download her new e-book "A Surefire Plan To Figure Out Exactly What You Want" and take her Amazing Career challenge.