How to Win an Opportunity of a Lifetime and What to Do Next

Thursday Oct 11, 2012 by Dennis Keohane - Contributor, VentureFizz

Reid Hoffman thought he wanted to be a career intellectual; he figured that fulfillment could be found by publishing an article in The Atlantic every now and again and maybe even teaching a philosophy course or two at a liberal arts college.  Deciding he wanted to impact more lives than the fifty or so niche readers of some esoteric literary journal, Reid changed his career plans and tried his hand in the tech industry.  Landing a job at Apple in the mid-1990s, he realized that he had found a calling.  Eventually, he would found a little start-up called LinkedIn.

Ben Casnocha knew from an early age that he wanted to be an entrepreneur, and he achieved his aspirations by founding multiple successful companies.  Yet he too had recognized an urge to create and an unfulfilled intellectual curiosity.  He used his entrepreneurial experiences to fuel a very prodigious blogging career and he wrote a book, My Start-Up Life, which combined his passion for entrepreneurship with his love of writing.

In 2009, Reid’s and Ben’s paths crossed, and they immediately recognized kindred spirits in each other.  During one meeting in Palo Alto, they discussed their ideas on how to use their experiences to help others.  Separately, they had both been generating philosophies that individuals could better themselves by mimicking the lessons learned from successful start-ups.  Together, they refined their ideas to create what would eventually become a New York Times bestseller, The Startup of You.

In the summer of 2012, their paths crossed with my own.  Reid and Ben joined forces with Tim Ferriss on a Four-Hour Work Week blog post, “How to Take Intelligent Career Risk (and Win Mentoring from Reid Hoffman, Chairman of LinkedIn)”.

Because I was thinking of making a move out of education, I added my own story to the almost six hundred others from people looking to make career pivots.  To my surprise, I received an email from Ben’s assistant, Ian, informing me that I was selected as a finalist for the contest. 

Over most of August, I hustled to get votes so that I could beat out the other two worthy finalists: Cheryl, a multi-million dollar business owner who was going to pass on her company to her sons to write and promote a book on financial fraud; and Samuel, a former Army officer and West Point professor looking to give up his military pension to start a fitness company.  Honestly, I didn’t think a teacher trying to raise a family stood a chance against these two, but I leveraged my social media contacts as much as I could and something shocking happened. 

I took a lead and eventually won the mentoring opportunity from Reid and Ben.  I probably annoyed a ton of people on Twitter, Facebook, LinkedIn, and Google+ in the process, but I learned first hand the power of social media marketing. 

So far, the experience with Reid and Ben has been awesome, and they have shared some insightful advice on how to actually make a risky career change. 

Some of the best advice thus far:

  • As far as narrowing down a career path, they have talked a lot about finding a career that not only stokes my passions and fulfills my ambitions, but also allows for my work experiences to be transferrable to other industries and viewed as assets. (For teaching, they would be writing and editing, speaking in front of groups, and marketing and selling Shakespeare to literature-averse teenage boys, etc.)
  • In the book, one idea that is hit on repeatedly is the idea of being in a state of “permanent beta”.  This idea is behind a lot of the advice I have received from Ben and Reid, as permanent beta is the readiness to be able to change preconceived career plans to match the unstable business climate.  By being able to adapt to sudden industry changes and having a contingency plan for all your contingency plans, you will be better prepared to take advantage of surprise opportunities that may turn up.
  • Lastly, some of the best advice I received from Ben and Reid has focused on my biggest weakness: my lack of experience or perceived lack of experience.  

One of the difficulties in my career pivot is that any change I make has the added risk of having a major impact on my young family.  Giving up a steady job while being responsible for a mortgage and childcare is a pressure-filled endeavor; it makes taking any experience-building entry-level job almost impossible.  And yet, I don’t have close to enough “real” experience most employers want for non-entry positions. 

Ben and Reid have been very helpful and full of suggestions in trying to help me navigate this murky water.  They have suggested finding creative ways to gain experience: writing, guest blogging, connecting with the influencers, etc.  They have also pointed out ways to find companies who are young and whose values align with my own.  By connecting with and writing to key players at these ideal companies, someone may recognize in me a kindred spirit.

Dennis Keohane is a teacher, journalist and contributor to VentureFizz.  You can follow Dennis on Twitter (@DBKeohane) by clicking here.

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