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Ash RoyNov 15, 2013 12:05:44 AM5 min read

On corporate prisons, freedom and meaningful enterprise

Have you ever felt trapped in your career?


Your life?


Perhaps you started out with all these idealistic plans.


You were going to change the world by leading your company to new frontiers.


But then you found that the corporate world wasn’t all that idealistic after all ...


Things didn’t work the way your young mind had once assumed they would ...


... And then, gradually, your idealism gave way to mediocrity.


A few years later you found yourself wondering "What happened to those dreams?"


You felt like a glorified paper pusher — working in a job that paid enough to keep you coming back, but not enough to set you free.


If any of this sounds familiar, read on. 


You might find my story interesting.


Escaping the corporate prison


It was 4:30 pm on the 2nd day of spring, and the sun was shining down brilliantly. I felt like a bird about to soar off the edge of a cliff — never having taken flight before.


There I was ... feeling an exhilarating mixture of fear and excitement. (Feelings often come in pairs.)


I was ready to plunge into the world of blogging and entrepreneurship.


Having finished my final consulting assignment, I stood at the bus stop outside the glass-covered office building that once constrained me.


The place to which I'd committed so many of my precious waking hours, gleamed in the sun.


And I felt thrilled to be on the outside of it.


The journey to this point had been painful and slow.


Striking out on my own was something I'd agonized over for years.


I'd finally decided to bite the bullet and leave the corporate world behind — a decision I didn't take lightly as it would inevitably impact others around me.


To think that just a few years earlier, I had strived to get into one of these very buildings.


That I'd dreamed of occupying the corner office with teams of professionals ready to do my bidding.


And now as I stood across the street shielding my eyes from the blinding sun that reflected off the building, it seemed to be mocking me,


Oh, the irony!


But it wasn't all bad. 


I felt free. Like I'd been let out of prison ... a corporate prison ... but a prison nevertheless.

Discovering freedom


The dream that my CPA and my MBA had ‘prepared' me for, and propelled me toward, now felt like a fool's errand.


The illusion of happiness that comes from a corner office and a house on the hill were well and truly shattered. 


I'd been climbing the wrong ladder, and the goals I was pursuing were now meaningless. 


I'd been kidding myself all along.


The unexamined definition of success that I'd embraced around becoming the CEO of a large profit-obsessed corporation now felt vapid.


Stupid even. 


I stood there in the sun questioning the profit-at-all-costs motto that had been drilled into me in my undergraduate years, during my MBA, and later in corporate boardrooms.


I remembered being one of the many sleep-deprived corporate climbers who wandered around corporate hallways, wearing the dark circles around their eyes like badges of honor.


There was a lot wrong with this picture.


What a scam!


Busting out of the corporate cocoon


And then it dawned on me.


Each minute of my journey was as important as the destination.


And each minute I'd spent hankering for ‘success ‘and ‘achievement’, at the expense of present moment happiness, was a minute I'd lost.


Suddenly it was all painfully clear.


I'd been deferring my fulfillment to a dim distant point in the future — the achievement of "a dream".


A point at which I would've realized (too late) that ‘dream’ wasn’t mine, to begin with!


I'd spent the last 15 years going from one insipid task to the next, but it wasn't too late to change things. 


I'd learned some useful skills over the last 15 years, and I could use them to my advantage. 


I boarded that bus, feeling hopeful and driven by my new purpose.


I was determined to succeed.

The pure joy of entrepreneurship


The first podcast I'd ever listened to was Seth Godin's startup school.


That was the hook.


From that day onward, I've been enchanted with the idea of being an entrepreneur.


I've learned from those who create inspired lives and livelihoods.


I've had the honor of having Seth Godin as a guest on my own podcast.


The entrepreneurial path has been far from easy — It's been downright grueling a lot of the time.


But if I had to do it all over again, I would do a few things differently.


Here are a few lessons I've learned over the years. Hopefully, you'll find them useful. 


Four (of the MANY) lessons learned from my journey:

  1. Before creating products or offers, I'd do the following things as suggested to me by Seth Godin in this conversation
    1. I'd ask myself:
      • What change do I want to make in the world?
      • Who do I want to deliver this transformation to?
    2. Then I'd find the smallest viable audience and then seek to deliver an outstanding user experience to them. Maybe they'll tell their friends, and their friends will tell their friends. 

  2. I'd work on my mindset earlier in my journey, and shoot for big goals because they can set you on a different trajectory as explained by John McGrath in this conversation. (Forward to the 2-minute in this conversation where John talks about how his school friend Russell Crowe (and John himself) used the power of setting big goals to drive better decisions.)

  3. I'd then harness the power of habit to develop a consistent and regular practice to move me toward those goals.
    • Specifically, I'd focus on optimizing my environment to set myself up for success.
    • I'd focus on better mental habits (making better choices around my thoughts in each present moment to the extent possible)
  4. I'd try to remember that in business cash flow, profit, and revenue matter in that order of importance, and that people matter most. 


What lessons have you learned over the years?


Comment below. I'd love to know.



Ash Roy

Ash Roy has spent over 15 years working in the corporate world as a financial and strategic analyst and advisor to large multinational banks and telecommunications companies. He suffered through a CPA in 1997 and completed it despite not liking it at all because he believed it was a valuable skill to have. He sacrificed his personality in the process. In 2004 he finished his MBA (Masters In Business Administration) from the Australian Graduate School of Management and loved it! He scored a distinction (average) and got his personality back too!