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Masters of Third Half: Kerry Dawson

The unknown. Not knowing which path to take or what lies ahead. Sound familiar? For many potential Third Halfers, this ambiguity is the scariest part of transitioning. Our next Master of the Third Half, Kerry Dawson, is a prime example of a Third Halfer who was perplexed by thoughts of transitioning. Meet Kerry and learn about her transition from a successful career in finance to working with a start up and how she leaned into her Clifton Strengths, to plan her path forward.


When thinking about transitioning out of her career, Kerry's big dilemma was... was her financial career still truly fulfilling to her – or was it time for a change? Her contemplation around this central question was peppered by self-doubt, uncertainty, and more questions than answers.

The Third Half Transition


The decision to leave behind a hard-fought career as a successful financial service executive was enormous. While the itch to change was becoming stronger and stronger, Kerry didn’t know what else she would or even could do, outside of the work she was currently doing at a company she had worked at successfully for decades.


For Kerry, finding satisfaction at work has always been a vital source of happiness. Her top ten CliftonStrengths include Significance and Belief, two strengths that make it essential that an individual feel empowered by the work they are doing. In Kerry’s case, this has always meant investing her time in projects that allow her to have real impact and hold true to her value system.


Historically, her jobs in the financial sector had lined up with these strengths and brought her lots of energy. But now, she was finding this to be the case less and less. As her energy and passion waned, she became distracted. Kerry explained, “When you’re not as happy, you start focusing on different things.” As this restlessness reached a crescendo, Kerry used this feeling as an impetus to answer her nagging question “Is it time for a change?” with a “Yes!”


An Internal Struggle


Kerry’s next challenge became facing herself; Did she have the confidence and emotional wherewithal to transition? After sticking with one company for most of her career, always ascending its ladder rather than going to a competitor, she lacked the “confidence that my skills were transferable.”


Aside from personal insecurities, Kerry faced another issue familiar to many in transition who might take a much-needed pause to reflect on what to do next. The comfort of a predictable paycheck from a job done so confidently cannot be underestimated. Kerry felt trapped “by the income. It’s all you know, and you’ve been successful at it, reputationally and such, and all of a sudden it went from something you thought you were hugely successful with, and rewarded for, to holy smokes! I don’t think I have the confidence to do anything else.”


In her day-to-day life, Kerry intrinsically knows she has what it takes to succeed. Describing herself, she said “Believe it or not, I’ve been successful at most of the things I’ve tried.” This makes sense; another one of Kerry’s top 10 CliftonStrengths is Self-Assurance. Yet in facing her transition, she lacked her usual poise.


Having the Courage to Start Over


Transitioning can often feel like starting over. And starting from scratch is rarely an attractive attribute for loyal and dedicated professionals. It can rattle even the most confident executives. Moreover, it takes time. Sometimes a lot of time. For Kerry, and for many others, transitioning is “a step backwards… anytime you step into a new role, there’s a learning curve.” As we age into the Third Half, this can be particularly daunting.

Fortunately as she contemplated next steps, Kerry was lucky that she had strong support from those around her and talked to lots of people. In reflecting back, Kerry “came to realize, it would have been easier to go to a competitor, but it would have made me postpone the inevitable.” Namely, that “I really wanted to do something different.”


One colleague in particular, who had made such a pivot, had advice that stood out. “My friend [also a senior financial service executive] had made the choice to walk away and choose something different,” Kerry says. “And we are the same age.” Kerry valued her advice as their circumstances were so similar. When Kerry’s transition questions intensified, the same colleague introduced her to Third Half Advisors. She explained to Kerry how she’d benefitted from this unique learning community - learning to recognize her strengths and weaknesses gave her the necessary confidence to transition.


The Third Half Advisors Experience


Going through the Third Half Virtual program helped Kerry sort out her non-negotiables. “Knowing why you enjoy and are more successful at doing some things versus others, is a powerful motivational tool,” said Kerry. She realized in Third Half discussions that there were certain things she would never be good at; but she doesn’t have to do those things anymore.


“Give yourself permission to step off the treadmill,” Kerry says. “It might open your eyes to something else, that you will find just as valuable. That was actually something that [Third Half Coach] Polly Chandler was very good at. She was constantly focusing the group…on something that brings you joy.” When asked how she’s currently balancing the activities she now enjoys doing versus the things she knows she has to get done, Kerry laughed wryly. “I’m being very bad, I’m getting other people to do the shoulds,” that she either is not good at or doesn’t want to do anymore. “It’s okay,” Kerry says, “because on the balance, I do a lot of things really well.” It’s good to see that self-assurance kicking back in.


To those questioning whether or not to transition, Kerry offers this advice. You don’t have to have all the answers, “But don’t be directionless forever. And be open to other people’s ideas.”



Ironically, Kerry is now all about the business of transition and change. A senior executive in the start-up “WayForth,” Kerry helps aging adults downsize. Prior to starting with this new company, she took a hard look at her strengths and negotiated an ideal position which now takes advantage of her strategic and mentoring strengths. Kerry is newly energized knowing that her values are in alignment with her work and she is having a big impact on people’s lives. We are so proud that Third Half Advisors was able to help her get there.


Learn more about the WayForth and connect with Kerry on LinkedIn. Make sure to check out our other Third Half Masters stories to learn more about others who are transitioning from their corporate career to “what’s next”.