On Making Successful Career Transitions

Each January, so many of us go into sprint planning mode to set our plan in place for what we want to accomplish in the coming year.  These New Year's resolutions often occupy our thoughts temporarily, only to be washed away and replaced by another thing to do.

Career change considerations rank high on New Year's resolution lists.  What are the best approaches to incrementally advance career transition and career change considerations and undertakings beyond the New Year's resolution window?  Transformative results, be they rebuilding natural disaster shaken societies or reshaping careers, take sustained efforts over time. 

Career change is not a January concern; rather, it is an ongoing concern.  Over the past year, several Capture Your Flag interviewees have touched upon change, specifically why they made career transitions and how this reshaped their future.  Some shifts were minor and some massive, but all mattered. 

Watch Capture Your Flag interviewees share Career Transition experiences

How do career changes develop and what happens throughout the process considering and acting upon them?  In reviewing interviewee stories, I see three common themes through the processs.  They are as follows:

- Why Leave?

- What Comes Next?

- What is Possible?

There is a lot of fear trapped in these steps.  Fear of leaving behind the known, fear facing the unknown, and, most importantly, fear of failure.  But there is also a hope.  Loads of hope.  When we think through the steps making a transition and communicate them to others clearly and passionately, something magical happens.  We find unexpected support in surprising places and expected support in larger, unanticipated quantities.  With the intent and the support we find ourselves in the Capture Your Flag sweet spot.  Cultivate those passions.  Shape that purpose.  Guide those dreams.  That is why we do what we do.  Now, let's see how our interviewees are inspiring us across the three stages: 


After performing in bands and playing guitar for nearly a decade, stand-up comedian Matt Ruby decided to not only relocate from Chicago to New York, but also to put the guitar down and give stand-up comedy a try.  Four years into performing five nights a week on the New York City circuit, Ruby looks back on leaving a stagnant place in music - one that should be more fun or more lucrative - to take a crack at making others laugh. 

Whereas Ruby left music, Teach for America educator Andy Epstein found it.  After several successful years teaching, Epstein entered the music business from the bottom, literally, to get his foot in the door.  With a college rival from Michigan State presented Epstein a temp job answering phones and making copies at Island Def Jam Records, he lept into the abyss and took a chance.  It may look like a long road when making that leap, but with support, effort, and, most importantly, time, amazing things can happen.  Epstein's temp job was indeed temporary.  His several year progression up the Island Def Jam ranks was anything but. 

The Goldman Sachs trading floor provided Phil McKenzie an unmatched finance experience after attending business school at Duke University.  Learning how to successfully operate in chaotic, unpredictable, time-sensitive environments, McKenzie fortified skills that could never be taken away.  Over time, McKenzie concluded Wall Street finance was less a long-term career than a temporary stop on his journey. Shifting his focus to philanthrophy and non-profit with Parks Hall, McKenzie proceeded to opened doors to the next life chapter.  There, McKenzie applied his Goldman Sachs' skills and relationships to accelerate his efforts shaping the FREE media mission to celebrate socially conscious tastemaking audiences across arts and culture.


The pessimist says there is a long road ahead full of uncertainty.  The optimist says there is a long road ahead ripe with opportunity.  Either way, the change has occured and now it is time to test one's mettle and, simply put, go for it.  Setting aside the past to construct the future helps identify the unknowns, challenges that over time must be addressed.  Departing Digg to co-found SimpleGeo, Joe Stump left behind the comfort of a previous team leadership role to become a business owner and learn new ways to lead.

Career transitions all involve a point A and a point B, however the timeline getting from A to B varies.  For Joe Stump, leaving Digg and founding SimpleGeo was the product of months experimenting with side projects, gathering information and advice, and committing to the entrepreneur route.  New York Magazine editor and writer Mark Graham entered media and publishing in a similar way.  While working in digital media marketing within General Motors' OnStar group, Graham began his blog and cultivated his talent writing about popular culture.  Over time he attracted interest in media professionals, including Fred Graver, who engaged Graham in development conversations.  All the while, Graham continued honing his craft, shaping his voice, and building his audience.  Planning what comes next was difficult, given blogging was stil in its infancy.  Yet, Graham continued the conversations and, over time, shaped those exchanges into viable opportunities, ultimately opening doors for his transition to VH1

Similar to both Stump and Graham, entrepreneur and MyFootpath founder J.T. Allen shaped his vision of what comes next collecting experiences as an Ernst & Young management consultant.  Upon deciding to leave the firm, Allen exposed himself to newfound opportunities unavailable in his client services role.  In short, he could own and implement the decisions he was recommending and assume responsibility for making them happen.   

After years planting trees and working in forestry across Alaska, Washington, and Oregon, Patty Green was ready for a change.  Similar to how Andy Epstein left one profession for entry-level at another, Green's foray into winemaking began with the basics, specifically picking grapes at Hillcrest.  This did not last long, as Green began applying her operations and mechanical aptitude to incremental responsibilities in the winery, cumulating in her move to winemaker.  Reflecting on the initial transition, Green, proprietor of Patricia Green Cellars, showcases how identifying what comes next opens doors to possibility. 


Career transitions and career changes are not complete upon making the move to what comes next.  Rather, the reset redefines possibility, more often than not in ways not considered previously. 

As Shaheen Wirk puts it "You probably never realized you liked Thai food until someone took you to a Thai restaurant."  Wirk's own "Thai food" moment came upon being exposed to the intersection of medicine, technology, and finance as while studying medicine at Duke University.  Role models facilitated this learning experience and Wirk, realizing career paths were anything but linear in medicine, changed his course and applied his education toward making investments and financial decisions in biotechnology, medical devices, and pharmaceuticals. 

Mike Germano has always known his career would be about building better communities.  As an elected official operating within Connecticut politics, Germano came to realize how risk profiles differ between public and private sector opportunities.  Germano decided to leave politics for an entrepreneurial career at Carrot Creative and risk financial failure in return for the much higher financial reward possibilities business provides. 

There are many approaches to transitioning and changing careers.  The constant across all - Why Leave?  What Comes Next?  What Is Possible? - is that it is a continuous process.  There is no standard finish line in career and there is no measure of success that is applicable to everyone.  You have a right to define your own goals and pursue them in ways most relevant to you.  Capture Your Flag aspires to continue sharing stories on how individuals shape their own sense of fulfillment, in this case through considering career change and transition.  Start now by writing down what you want in life and what questions remain unanswered.  Do not force yourself to answer everything in context of a New Year's Resolution.  Name your goals, put a commitment in place (day, milestone, etc) and begin your mission.  Think of it this way: There is no final draft paper to be submitted, only steadily improving drafts that get you excited about what comes next and what you need to do to get there.  Onward.  Upward. 

*** For a complete list of all "Career Transition" chapters, click HERE ***

- Erik