The Career Changer


  • “I know what I really want to do but I’m not sure how to determine if it makes sense for my life first.”
  • “Am I stuck in the industry I’ve built my career in?”
  • “Am I too old?”
  • “Do I have the energy to start over?”
  • “Can I afford to make this change?”
  • “What will my colleagues think?”
  • “Will my spouse support me if I do make this change?”





How do I transition into the work I’ve always wanted to do? I’ve been an account manager for my whole career, but I’ve really always wanted to be a math teacher.



Established professional looking to shake things up in the career department.

CURRENT JOB:         

Account Manager at an events company for 15 years.


  • Chuck had been harboring this career change fantasy for so many years and wasn’t 100% sure when we started our 3-month program together if he was actually going to take the plunge.  Part of our Discovery phase of working together was to ascertain what he really wanted, free of any outside influences/perceptions.  Our discovery also entailed a lot of deliberate assessments– assessing what he was and wan’t getting out of being an Accounts Manager, assessing how he’d benefit from teaching algebra, assessing the impact the career change might have on his life.
  • The discovery goal of coaching Chuck was to enable him to see all options and perspectives possible to make his own decisions… especially the views he wasn’t inclined to see.  Chuck was so wonderfully analytical (no surprise on that love of math), so it wasn’t easy for him to suspend the idea that there might be a way to make his dream work.  We put the How on hold while we looked at the Why and then came back to a purely analytical approach that he was comfortable with.  (To loosen up Chuck’s tendency to get stuck on the How part of making a career change, he completed an exercise of coming up with a list of 50 “What If…” statements, which surprisingly helped him to schedule a South African vacation that he and his wife had been prolonging for years.)
  • Our Design phase included an action plan for Chuck to research what the path to teaching might look like, inclusive of education (schools, start dates, length of program, costs), financial impact (education, possible gap in income), future opportunities (likelihood of being hired, school locations), social implications (gaining his wife’s support, perceptions of his colleagues), and creative alternatives (evenings and weekends for education to maintain job, possible part-time transition out of events company, starting over by moving to west coast to teach and be near family, etc.).
  • Chuck was also tasked with initiating informational meetings with education professionals in and out of his network to learn more about preferred education routes, role opportunities in the area, and additional insight into the experience of teaching.  We also connected Chuck to another education professional in our Happy Spectacular network.  He fortuitously met with a local principal who suggested he volunteer for an after-school program to continue with his experience-building mission.
  • Early in his Happy Spectacular program, Chuck completed an exercise that revealed the significance of his fears about making a change.  He realized he had been putting off the simple task of researching education options for years because of a reluctance to approach his wife on the topic, and a fear of failure to a certain extent.  We role-played ways for him to broach the subject with his wife, and given that he was ready, he was challenged to have the conversation with her in advance of our next meeting.  He was prepared for her questions and concerns, and was able to empathize with her as she voiced her own fears about income and job security.  After having this conversation a switch seemed to turn on in Chuck, and he became increasingly confident with his plan.
  • Chuck’s lessons learned during our time together allowed him to come to an informed decision to officially make the career move.  We redesigned his plan to reflect action items such as applying to his school of choice, giving notice to his employer, making investment adjustments to allow for a more relaxed monthly cash flow during his transition time, and a consistent communication plan with his wife, whom was still anxious yet increasingly supportive.  Chuck’s Happy Spectacular Work + Life Plan contained his true motivators, his values, his 2, 5 and 10-year plans, and some of his most inspiring What If statements (one of which was “What if I didn’t do this? How would I feel on my deathbed: regretful or proud?”).  That question, authored by Chuck, was single-handedly responsible for his impetus to act.


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