Questions I Asked Myself During a Career Transition

Everyone approaches a job search differently. Several years ago when I lost my job as a marketing professional, I looked at my career transition as a marketing opportunity.

I had watched others in similar circumstances as they obsessed on finding the right answers. I took the opposite approach. Rather than seeking answers, I began by asking myself a series of questions, recalling the wise words of James Thurber who once said, “It is better to know some of the questions than all of the answers.”

Only after developing what I felt were the right questions did I begin wrestling with the answers. The questions were incredibly easy to ask but excruciatingly difficult to answer. To my amazement, however, this turned into a most insightful and even invigorating process. I’ll share with you the questions, but first let me explain my process.

For a couple hours each day, I went to a local coffee shop and found a secluded table where I could engage myself in a private conversation. I left my laptop at home because I wanted to drill deeper. I used an old-fashioned method of communicating—handwriting on blank sheets of paper. I purchased a leather-bound book containing only blank pages and on the first page I wrote the title:  Journal for the Journey—A personal assessment, a scrapbook of ideas, and a map for navigating an important career transition.

Something magical happened when I held my fountain pen and allowed it to begin writing things I needed to know. My writing was primal and I was amazed to see how my original, unedited writing helped me uncover ideas I didn’t know were buried beneath the debris. My hand grew tired and the pages were often messy, yet the words that appeared on the paper helped me to rearrange the random ideas in my mind so they made sense. My writing helped me cut through the clutter.

Within my journal I wrestled with several core questions. Like bright stars against a black sky, the following questions formed the stellar constellation by which I navigated my journey:

  1. Who am I? Knowing that others would inevitable try to pigeonhole me, I decided to lead them so they would not make wrong assumptions about who I was. I proactively guided them to place me in the right career categories.
  2. How am I different? Lots of people had resumes that looked a lot like mine—same job titles, similar track record, same degrees, and even the exact same cliches that were in my professional profile. How could I stand out from the rest of the pack? What was my unique niche? What differentiated me?
  3. Where am I going? This seemed like an easy question to answer until I realized that the paved road in my rearview mirror was in much sharper focus than the pathway ahead that emerged into a dense fog.
  4. What have I done? It was easy to describe my responsibilities or the processes I used, but that didn’t address the issue of the real impact I’d had. What had I really achieved that made a difference? Had I produced measurable results?
  5. What can I do? What “campaign promises” could I make during the job search that I could later deliver on once I was hired? A job search is a time to promote oneself, not with arrogance but with a humble confidence. This is done by assuring the potential employer that you will produce the desired results.
  6. So what? How could I show all the stuff on my resume in a way that a potential employer could see value and relevance? Good sales people know the difference between features and benefits. I needed to lead with the benefits and then follow up with the features.
  7. Why would someone hire me? What memorable “sound bite” might best summarize who I am, how I’m different, where I’m going and the impact I could make?

My journal pages were not as neatly organized as this list now appears. After all, I was navigating an uncharted journey towards an undisclosed location. Therefore, my thinking was seldom linear. On the blank pages I gave myself permission to take detours or to stop at interesting points along the way. In addition to answering the foregoing questions, I also used my journal to:

  • Capture inspiring quotes to keep me motivated.
  • Write out talking points for possible interview questions.
  • List the priority people in my network who could be of most help.
  • Jot down miscellaneous notes to help me stay focused.
  • Brainstorm ideas on how to build and maintain momentum.

My journey began by asking myself penetrating questions. To drill deeper, I often answered my questions with questions. Only then did answers begin to manifest themselves, illuminating my pathway enough to take several more steps forward.

I’d be interested in hearing from someone who has developed a game plan for his or her unique transition. What advice would you give to others who might be on a similar journey?

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