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Unlocking Your Dream Job

How Asking Two Simple Questions Can Transform Your Career


June 20, 2023


I consider myself incredibly fortunate to wake up every day and pursue my passion. However, it hasn't always been this way. I've taken on various jobs in the past that lacked fulfillment and glamor, such as spending two years providing bed baths to spine surgery patients for long 12-hour shifts. About seven years ago, I was fortunate enough to find an exceptional mentor who helped me discover the professional path that would bring the most fulfillment and align with my passion and purpose: leadership coaching. From that moment of clarity, I dedicated myself to gradually transitioning my work to be more closely connected to coaching. Just last year, I finally took the leap and fully embraced my identity as a coach. The transformation has been incredible. I'm genuinely thrilled to engage in my work, and I feel a strong sense of creativity and authenticity when working with my clients.


Feeling stuck in life and unsure about the direction we're heading is a common experience. We might believe that our ideal life is out of reach or struggle to redirect ourselves. I want to encourage you to dream big and realize that it is entirely possible to live the life you've always desired. To assist you in making decisions that align with your goals and dreams, I'd like to share a quick process that I personally went through. While this article focuses on asking for what you want in the workplace, the process can be applied just as effectively to relationships or other personal goals beyond work.


In fact, the inspiration for this article comes from a recent coaching session with a client who was dissatisfied with their job. This client holds a high-level leadership position in the tech industry and earns a substantial salary. However, the increased salary came at a cost. They are now overworked and pulled in directions that exceed the scope of their role. Consequently, their teammates often blame them for impeding progress toward important deadlines and business objectives. Feeling exhausted and unfulfilled, they question whether this role, despite the generous paycheck, is truly worth it.


During our coaching session, I assisted the client in creating a list of requests to present to their boss, the CEO, in order to make their work more impactful and aligned with their preferences. However, while we formulated this list, I encouraged them to pause and reflect on whether they genuinely desired this role in any form, even if all of their requests were granted by the CEO. The client is currently in the process of clarifying their answer to this crucial question, but I couldn't wait to emphasize the significance of this pause.


I absolutely love it when people have the courage and vulnerability to ask for what they truly want, what they really, really want. Through my coaching practice, I've discovered that when you ask for what you want but aren't willing to demonstrate your commitment to making it happen, you undermine the likelihood of successfully aligning yourself with your aspirations.


Therefore, it's essential to take a moment and ask a clarifying question before making terms-altering requests to your boss, partner, or anyone else. I invite you to follow a quick two-question process that will help clarify whether you're on the right path and ready to claim a life that aligns best with your goals and preferences:


Question 1: Can I envision a version of this role that completely aligns with the ideal role I aspire to?

→ If it's a resounding "hell yes!" then proceed to Question 2.

→ If it's not a resounding "hell yes!" then it's likely a "hell no." In that case, determine why you're staying in this role and establish a timeframe for how long you're willing to endure it before reassessing. Commit to not questioning your decision during this predetermined period, and then revisit Question 1 when the time comes. Consider setting a reminder in your calendar to prompt you to reevaluate the alignment of your role.


Question 2: Am I prepared to dedicate myself to the work required to reach that point?

→ If it's a resounding "hell yes!" then excellent! Get to work, and rest assured that this role has the potential to become your dream job.

→ If it's not a resounding "yes" then figure out what you are willing to do to transform your work into something you genuinely desire. This may involve creating a new role for yourself or even exploring new job opportunities that align better with your aspirations.


A few years ago, I underwent this two-step questioning process when I had a clear vision of becoming a personal development coach. At the time, I held the position of local director at a large non-profit organization. I was earning the highest salary I had ever received, and my job felt meaningful and generally fulfilling. However, I sensed that my role at work wasn't fully aligned with my unique strengths and preferences. The most significant misalignment was my strong desire to travel, embark on adventures, and have autonomy over my schedule. The organization expected a traditional 9-to-5 commitment, placing importance on physical presence in the office and being available for early morning emergency calls from staff members. It felt as though I was trying to fit a large, round peg into a small square hole.


When contemplating my future in that role, I saw two primary options:


Choice #1: Maintain the Status Quo. It would have been easy to simply endure my circumstances and suppress my preferences until I eventually accepted the role as it was. This choice would have provided financial security, and I likely would have received a promotion with increased responsibilities within 2-3 years.


Choice #2: Make the Ask. Alternatively, I could have asked for what I wanted and committed to working hard to mold the role to suit my preferences. This would have involved setting boundaries regarding emergency communications with my team, strategically utilizing vacation time, and requesting extended leave to pursue my adventurous aspirations.


However, in the end, I chose neither. I opted for a third option. I paused and asked myself the same two questions:


Question 1: Can I envision a version of this role that completely aligns with my ideal, aspirational role?

Question 2: Am I prepared to dedicate myself to the work required to reach that point?


Asking myself these questions provided me with the clarity that this job would never fully align with my deepest preferences, and I wasn't willing to invest the effort or time necessary to try. I openly shared this realization with my manager without requesting any changes to the position. Instead, I approached her with honesty and clarity, communicating my aspirations for my work life. In response, she inquired if there was any way she could adapt the role to make me want to stay. Deep down, I knew that nothing could be done to achieve that; the differences in the role were beyond the scope of alteration. After conveying this to her and expressing my gratitude for our relationship, she began formulating an offer for me to consult with the organization on a contract basis. This new arrangement fully aligned with my preferences and leverage my unique talents. That marked the beginning of my coaching career, and now, four years later, the organization continues to contract my services to coach their operational leaders.


Transforming dreams into reality requires a great deal of energy and focus. You must find motivation in the desired outcome and allow the future realization of your goals to propel you forward. I frequently pause and ask myself these questions, and this moment of reflection has proven invaluable in clarifying my desires before taking action. It has also yielded positive results for my clients. Since beginning writing this article, the client I mentioned earlier has discovered that their current role isn't the right fit for them. While they have requested changes to improve their work environment, they are actively searching for a new role that aligns with their aspirational life.


If you've been feeling stuck or dissatisfied at work, or if your current role fails to fulfill you, I encourage you to ask yourself these two quick questions to gain clarity and guide your next steps. Sometimes, a pause is exactly what we need before making a significant leap.


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