Subscribe to Entrepreneur for $5

4 Challenges That Make First-Time Success Hard to Repeat

Opinions expressed by Entrepreneur contributors are their own.

Every first-  works hard to see their dream become a reality, to fulfill their vision, achieve big goals -- in a word, succeed.

However, there are four pitfalls to the first time around that entrepreneurs don't typically consider when in hot pursuit their initial dream, vision and success.

Related: 10 Tips for the First-Time Business Owner

1. What's next?

It's not uncommon for entrepreneurs whose singular focus on achieving success for the first time, experience a sense of disappointment or even once a lifelong dream is realized. 

This concept is embodied in the famous misquote from Plutarch's Tranquility of the Mind.

"Alexander (the Great) saw the breadth of his domain and wept for there were no more worlds to conquer." 

While the misquote above partially makes the point, it's helpful to read the actual quote below:

"...when Alexander heard from Anaxarchus of the infinite number of worlds, he wept, and when his friends asked him what was the matter, he replied, 'Is it not a matter for tears that, when the number of worlds is infinite, I have not conquered one?'"

The fact that Alexander had not conquered every world made him weep, but first-time entrepreneurs can find inspiration if they give a little forethought to the infinite possibilities of the next "world" they might aspire to conquer following their first campaign of success.

2. Expectation anxiety.

This is a common question among Olympic-winning athletes, -winning performers, astronauts who've gone into space and successful entrepreneurs. There are no obvious honors that are higher than those mentioned, so what's the next achievement that will deliver the same challenge and euphoric pursuit for the driven individual? 

Former Baltimore Ravens head coach, Brian Billick, often shares the story of the panic attack he experienced in the shower the night his team won their first in 2000. As a second-year head coach he said the expectations seemed overwhelming at the time.

To combat such expectation anxiety that can follow first-time success, many entrepreneurs come to the realization that the most rewarding pursuit after they achieve success is philanthropy. There's a reason why and gave billions to a charitable foundation.

Related: The 7 Most Fascinating Things Bill Gates Said in His Reddit Chat

3. Complacency.

I experienced this firsthand when I first started running full marathons. I trained hard and ate properly leading up to my first two - setting personal-best times in each race. I thought I had "cracked the code" to running 26.2 miles without stopping. Because of that confidence, I took a relaxed approach to my subsequent training and eating regimens.

Needless to say, my third marathon was a rude awakening where my race weight was 10 pounds heavier than my previous races and it took me three extra hours to finish it.  

I've since rebounded, completing three full marathons in my previous form - but that doesn't change the fact that I let my initial success devolve into avoidable complacency.

4. Inability to handle success.

This is one of those pitfalls most people dream of experiencing, that is until it actually happens to them. While this pitfall is most commonly associated with , actors and professional athletes - think Kurt Cobain, Lindsay Lohan and Johnny Manziel - successful entrepreneurs are not immune. 

One of the best ways that first-time entrepreneurs can avoid this pitfall is by surrounding themselves with a team of advisors or enlisting an experienced mentor to help guide them through the trappings that can accompany success.

The pursuit of entrepreneurial success can be all consuming within the mind of a driven individual, so it's helpful to give a bit of preventative forethought to these possible pitfalls.

Related: Richard Branson on the Secret to Success: Failure.


Entrepreneur Editors' Picks