Corporate Leader or Entrepreneur: Which Road Should You Travel?

The LeaderpreneurIf you are investing the time to read this lengthy article, you are serious about your future and determined to be successful.

And perhaps you are asking questions.  Important ones.

Looking back over my own journey — first as a small business owner, followed by years as a corporate officer for a large company and concluding with 20 years as an online entrepreneur — I am taking a few moments to pause and reflect.

Which road would I travel if I had it all to do over again?

I have been asked this question many times before.  Today I will attempt to answer it.

I hope you find a few insights from my business life that will help you with yours.

Assuming you are an energetic, disciplined, yet socially conscious young man or woman in today’s world, should you strive for corporate leadership or entrepreneurship?  Which road should YOU travel?

This is not a trivial question.  The choice you make will influence your quality of life, security, income and self-esteem.  It will shape your world-view and affect your ability to help others.  It will determine how you measure your success, and how others will.

In short, it will establish who you are — not just what you do.

I would like to begin by sharing my favorite poem by Robert Frost entitled The Road Not Taken.  It has lightened my burdens many times, and has made it possible for me to choose the right road when decisions were tough. 

The Road Not Taken
The Road Not Taken

Two roads diverged in a yellow wood,
And sorry I could not travel both
And be one traveler, long I stood
And looked down one as far as I could
To where it bent in the undergrowth;

Then took the other, as just as fair,
And having perhaps the better claim,
Because it was grassy and wanted wear;
Though as for that the passing there
Had worn them really about the same,

And both that morning equally lay
In leaves no step had trodden black.
Oh, I kept the first for another day!
Yet knowing how way leads on to way,
I doubted if I should ever come back.

I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.


Any worthwhile discussion of this subject must have a fundamental starting point.  Not everyone is suited for — or inclined toward — either corporate leadership or entrepreneurship.  It takes a certain type of person to aspire to either career objective.  So ask yourself this question before we continue:  Do you care about either of these end-results enough to sacrifice sixteen hours from every twenty-four?  Or do you care more about friends, family, and relatively risk-free surroundings?”

Most would agree that either choice requires sacrifices — the kinds of sacrifices that some are unwilling to make — and rightly so.

If you consider yourself a candidate for either road, however, I can safely make a few assumptions to start:

  1. You are driven to excel.  Deep within you there is a small, yet persistent voice spurring you on at all times.
  2. You are accomplishment-oriented.  Basic to your makeup, you have a driving force to do, not merely to be.
  3. You are a leader.  In all situations you gravitate to the top.
  4. You care about others. You are inherently good.  You are neither selfish nor selfless, but you always notice how you affect others and care about their welfare.

Now that we have agreed upon the above assumptions, let’s consider the pro’s and con’s of each road to your future.

Quality of Life, Security and Income

Divergent Results of Success

Both corporate executive status and entrepreneurship, if accomplished successfully, will add to your quality of life as measured by traditional yardsticks.  Both can provide financial success and security.  Both can provide a level of self-worth and recognition; intellectual stimulation and life-long learning; opportunities for leadership and opportunities to assist others, in the professional arena and in charitable activities.

When seen through the prism of success, both roads are similar.

Where the roads diverge, is when the results are less than successful.  As a corporate executive, especially for a larger company, you are insulated to a degree from the vagaries of business, economics and changes in customer behaviors.  Your job will be there longer and more predictably, as will your paycheck.  As an entrepreneur you are much more vulnerable to all changes.  You are living on the edge.

The roads diverge again, this time widely in favor of the entrepreneur, when success is long term.  Consider this:  If you are a corporate officer or a ranking executive, and you have made a materiel contribution to your company’s bottom line, you may receive promotions and higher pay — but often you are less secure.  The division or department you head is now functioning well, profits are predictable but you are no longer indispensable.  Some companies will believe that they now can replace you with a lower compensated person, save money and still maintain profits.  Sadly, corporations (at least some of them) are heartless when it comes to bottom-line profits.  And since you don’t own the enterprise, you are at the mercy of the almighty dollar and the corporate management that make day-to-day decisions.

As an entrepreneur, on the other hand, you are more often in command of your destiny, and no one can tell you that you are no longer needed.

Company Politics

Another security issue is company politics.  As an entrepreneur, politics and internecine feuding are seldom an issue.  If you succeed you win.  In a corporate environment things may be decidedly different.  If you succeed, sometimes instead of winning you become the target of attacks, often vicious ones, from those below you in the organization who want your job.

Niccolò Machiavelli was an Italian philosopher, humanist, and writer based in Florence during the Renaissance.  His advice was widely sought.  He was also one of the main founders of modern political science.  He was one of the first disciples of what we now call organizational politics.  Because of the long popularity of his writing, he is credited with teaching the modern business world how to maneuver politically.  When a business person is called Machiavellian it is seldom a compliment.

Machiavelli once advised, “Before all else, be armed.”  He also said, “Hatred is gained as much by good works as by evil.”  So, if you choose the corporate route to success, be prepared.  Those shooting at you may not be the recognized enemy — the bullets may be coming from behind you.

Decision-Making and Adaptation

During my years as a corporate officer, I made the rounds of many top companies around the U.S.A and the World.  I stumbled upon many interesting facts — the kind you don’t learn in business school.  Here are three that are relevant to this discussion:

  1. The tops of most companies, like the tops of most mountains, are remarkably similar.  The tops of most mountains are snow-capped, and sometimes majestic — the tops of most companies are luxurious, but sometimes undeservedly so.  Not every mountain is an Everest, K2 or McKinley — and not every CEO is a Warren Buffet, Steve Jobs, or Bill Gates.
  2. Top executives can be opinionated and set like concrete in their ways of doing business, often to their peril.
  3. And as a result, sometimes the decisions made in top floor offices are no better than the decisions made in first floor cubicles.

A significant difference between being a corporate executive and an entrepreneur is this:

  • A corporate executive is at the mercy of poor decision-making above him — should it happen — with little control or recourse.
  • The entrepreneur is always the decision-maker, and is the one who suffers most immediately from poor decisions — if he makes them — with complete control and no one to blame but himself.

This reality has been true in business since time immemorial.  It is still true today, but the implications of poor decision-making in a business climate that can change overnight can be staggering.   Consider the plight of large booksellers, and publishing companies, that refused to adapt to changing conditions when mountains of information became available at no cost on the web.  Some poor decisions were made when change required adaptation and the result was predictable and unfortunate.

Machiavelli also said, “The one who adapts his policy to the times prospers, and likewise that the one whose policy clashes with the demands of the times does not.”

Self-Esteem and the Ability to Help Others

Psychic remuneration is often as important as financial remuneration.  If your accomplishments result in increased self-esteem, that is a valuable result.  So is the ability to help others.  Neither of these appear on the bottom-line, but they are very important nonetheless.

At some point in your business life, when you pause to reflect, these two factors alone may be your most prized rewards for a career well-spent.  They also represent a primary difference between corporate leadership and entrepreneurship.


Self-esteem may be achieved whether you are a corporate executive or an entrepreneur, it all depends upon how comfortable you are within your own skin.  But your accomplishments within a corporate setting commonly inure to the benefit of the company in the public mind, not to you personally.  As an entrepreneur you are the company, and you can take justifiable pride in your results, both as an individual and as a business.

Ability to Help Others

As a successful corporate executive you will have very little voice in how the company shares its profit with those in need.  As a successful entrepreneur you have the ultimate responsibility for your company’s generosity and community spirit, and you have complete control over your company’s munificence.

Perhaps more than any other benefit of entrepreneurship, the ability to reach out to others as a personal expression of your own priorities and purpose, is the most rewarding.  If you are more concerned with who you are than what you do, this is the most satisfying part of being an entrepreneur.


At some point near the end of your career you too will be asked, “If you had it all to do over again, what would your decision be?  Would you strive to be a corporate leader or an entrepreneur?”  Which road would you travel?

What will be your answer, I wonder?  And how will you advise those young men and women who come after you?

If I had it all to do over again, I would prefer to be a leaderpreneur.  I didn’t coin the phrase, but I like it.

Now, while you still have the chance and before circumstances dictate the road you must travel, why not make the decision to combine the best attributes of both career choices?  Why not exercise powerful leadership in addition to performing your daily duties as an entrepreneur?  Why not design your success so that the results will be the same either way?  Why not wear the mantle of a sensible decision maker while you are dealing with the struggles of making a living as an entrepreneur?  Why not adapt to changing conditions with knowledge and speed, instead of being throttled by corporate inertia?  Why settle for one road or the other, when you can travel both?

Remember as you decide, that despite Robert Frost’s insistence to the contrary, in today’s unique world perhaps you can “travel both and be one traveler.”

Getting in touch with me is very easy

Have a question? Or just want to chat about your business? Simply call the number below. During normal business hours (8 AM – 5 PM Scottsdale, Arizona time) it is my direct line. Otherwise, just leave a message. If you would prefer to exchange email I would love to here from you. Just email or click the email badge below. I promise I will get back to you within 24 hours.

Michael R.H. Stewart, President, Jericho Technology, Inc.

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About Michael R.H. Stewart
"Give me faith, freedom, resources, and a little time ... and I will make things happen that matter." Michael R.H. Stewart is a respected Internet executive with broad experience in all aspects of online business, with an emphasis given to social networking development, and company management. He has over 131,000 engaged Twitter followers. He enjoys 22 years of direct experience with corporate, entrepreneurial, governmental and non-profit clients, having advised them on all aspects of their online initiatives. Prior to his Internet career, he served as a Senior Vice President of AIG Marketing, doing business in 135 foreign countries as well as the United States. Stewart is an experienced public speaker and communicator, with worldwide experience; an expert on corporate branding; an accomplished writer, a creative thinker and problem solver.


6 Responses to “Corporate Leader or Entrepreneur: Which Road Should You Travel?”
  1. Vijay says:

    Michael, Very well written and very thoughtful. It shows a lot if insights and directions for questions I had – now I have some clarity. Thanks for the tweet and note ! Cheers. Vijay

  2. Vijay, Thank you for the compliment. I try very hard to be useful. Clarity is something we all need more often than we realize. Give me a call some time, I would love to chat. Or drop me an email. Your input is vital to me! Cheers to you too! Michael

  3. Vena Jensen says:

    Thank you a million, zillion, trillion times for this post. It spoke to me at exactly the moment I needed it. Thank you for your insight and for sharing your experience. But most of all, thank you for reminding me of, and articulating so well, my greater purpose. I can’t live well without honoring my true state of being, my values and my deepest nature. I have never doubted that my intention to respect authenticity and the integrity of community, humanity, nature and my own soul is my driving force. Thank you for reminding me to accept my discontent as a gift of remembering to take time to evaluate and make changes as needed. It is time for me to remember my commitments to listen, take time to feel, give generously of my time, work persistently, and seek balance and fulfillment. I suspect you are already there. Kind regards, Vena

  4. Vena,

    If any of my thoughts and reflections resonate with you, nudge you toward your dreams or give you a tiny amount of encouragement when you most need it — then my purpose in writing this blog is completely validated.

    During our brief acquaintance, it has become crystal clear that you are a woman of substance. Whatever road you choose to travel in business and in life, your fellow travelers will be blessed by your company.

    I know you will make the right choice. And I will consider it an honor and a privilege to walk beside you.

  5. Nita B says:

    I really liked the way this was laid out. The info is on target. Thank you.

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