The remote CEO who left his company to see the world

remote control for TV

A remote control. Photo: espensorvik / Flickr

Most career break literature out there is focused on the employee who requests a leave of absence from his boss.  Rarely is it about the boss who takes a sabbatical from his own business.  Inc. magazine had this story: Inside the mind of a runaway CEO.

While most office satire is about the workers being stuck in their jobs, this article illuminates that entrepreneurs can feel trapped by their companies as well. They may have started their business to escape the grind of working for someone else, only to realize they just created their own grind instead.

The social dynamics of a boss taking a sabbatical were interesting too.  Entrepreneurs often fancy themselves as being leaders who are essential to the company’s survival. It can jarring to discover your employees are much happier when you’re away.  Of course, it can be more humbling if the business actually does better when you’re not there.

One thing the article focused on is the complications of the CEO’s relationship with his No. 2 manager while he was gone. Initially, the deputy manager felt abandoned and afraid of not knowing what to do. As time passed, he became more comfortable with having that authority.  By the time the CEO returned, it had come full circle: now he was afraid the boss would take away his newfound sense of leadership.

The employees are also greatly affected.  Initially, they enjoyed the freedom of the boss being out of the office.  However, what does it do for their morale, to read a steady flow of Facebook and Twitter updates of all the fun the CEO is having while the staff are still busy with work?

Have you had a business you left behind to travel?  Or the opposite, you had a boss who did that?  Please share your experiences in the comments.

Posted by | Comments (2)  | November 25, 2011
Category: Expat Life, Lifestyle Design, Notes from the collective travel mind

2 Responses to “The remote CEO who left his company to see the world”

  1. Jeff Says:

    Although I’m in the non-profit arena, I was gone for four months… the staff seemed to have survived. Last week I was talking to a CPA who was trying to sell me on her firm’s auditing abilities, and was surprised when she told me that she was going on Sabbatical for five weeks (I think it was) as required by the company and she’d have no company email or cell phone connection during that time.

    Annie Dillard in her book “An American Childhood” tells about her father, the president of American Standard, who left his job and the family business to boat down the Ohio and Mississippi River…

  2. Konrad Says:

    I’m preparing to do that now! I am the co-founder of a consulting firm and am leaving in early 2012 to travel the world. I plan on working remotely and volunteering my entrepreneurial/finance/strategy expertise along the way in most of the countries I visit. If you know of any organizations that I should work with abroad or if you have any advice on running a non-virtual business virtually, please let me know!

    (konrad at, twitter: WorldVentureP,