Why Entrepreneurs Don't Feel Successful

Take a moment out of your busy day and celebrate the small things.

learn more about Jess Ekstrom

By Jess Ekstrom


Opinions expressed by Entrepreneur contributors are their own.

I'm on a plane, at the moment, en route to a speaking engagement, writing this post while answering interview questions on my laptop for Teen Vogue. Maybe it's the altitude affecting my brain . . . but for some reason I just paused and asked myself, how did I get here?

Related: The 9 Principles That People Who Feel Successful Say They Live By (Infographic)

I started my company as a college student around four years ago. Getting to a point where people wanted to pay me to speak, or magazines wanted to hear what I had to say, was something I always dreamed about in those early days. But I never took the time to realize that I had gotten there, because I was always -- and still am -- focused on the next steps.

One of the most common questions I get is, "When did you know you'd made it?" And my honest answer is, "I've never felt like I have."

There are times when I think that a certain tangible goal like a television placement or a certain number of sales will translate into that feeling of success, but it never does. Then, one day I wake up and realize that I'm sitting on a plane living all of my greatest dreams. But in my head, I'm already checking in for my next flight.

I've realized that one of the reasons we don't recognize our milestones is that once we hit one, we've opened the door to a new tier of entrepreneurs to compare ourselves to. Imagine the similar scenario of a a high school football star making it to a college team and then realizing he's not as good at football as he'd thought.

The higher you go, the better the players. This means it's harder to give yourself a pat on the back or recognize your accomplishments when your measure of success depends on the playing field you're playing on.

On one hand, you can argue that the "never satisfied" mentality of entrepreneurs is what makes us so driven and accomplished. But on the other hand, you can also argue that this mentality is the leading cause of burnout and craziness. So, where's the happy medium?

Related: 7 Things That Can Make You Look Like a Successful Entrepreneur

Like many entrepreneurs, I've tried to find it. I've used this "never satisfied" mentality to aim high and play with the "big dogs." But at the same time, my inability to feel satisfied has led to many forced meditation sessions in the middle of my day to prevent me from flipping out.

What needs to change here is an entrepreneur's capacity to recognize and celebrate growth and milestones without that recognition hindering our momentum toward our next goals. We can do this by creating a culture of celebration within our companies.

Citrix Systems exemplifies this practice so much that it's even in that software company's sales-team values: "We celebrate every accomplishment as a team." Citix recognizes that no one accomplishment is too small; each one represents forward progress. And just one person alone doesn't make growth happen, the summation of growth is everyone.

Rewards systems aren't just for your employees; you can set them up to structure celebration around your accomplishments. For example, if I'm in the running for a keynote spot at a conference, and I get it, I'm going to treat myself to a massage the day after I speak.

Related: 5 Ways You Can Develop a Positive Addiction to Success

Your personal rewards don't have to be a massage or any particular expense, just anything that equals "a pat on the back." As entrepreneurs, we work so hard for each milestone. So, why not celebrate them?

Jess Ekstrom

CEO and Founder of HeadbandsOfHope.com, Speaker and Author.

Jessica Ekstrom founded Headbands of Hope when she was a senior in college in 2012. She created the company to bring joy back to kids who have lost their hair and help fund childhood cancer research. Headbands of Hope has given tens of thousands of dollars to childhood cancer research and has donated headbands to every children's hospital in the United States.

Related Topics

Editor's Pick

This 61-Year-Old Grandma Who Made $35,000 in the Medical Field Now Earns 7 Figures in Retirement
A 'Quiet Promotion' Will Cost You a Lot — Use This Expert's 4-Step Strategy to Avoid It
3 Red Flags on Your LinkedIn Profile That Scare Clients Away
'Everyone Is Freaking Out.' What's Going On With Silicon Valley Bank? Federal Government Takes Control.

How to Detect a Liar in Seconds Using Nonverbal Communication

There are many ways to understand if someone is not honest with you. The following signs do not even require words and are all nonverbal queues.

Science & Technology

How ChatGPT and Generative AI Can Transform the Way You Run Your Business

Let's take a high-level overview of how generative AI might transform your fledgling business. The benefits of this technology innovation remain crucial for any entrepreneur to grasp.


Streaming Free: The Habits of Happy People

Now streaming on EntrepreneurTV, 'Habits and Hustle,' which shares the stories, habits, and rituals of people on their journey to living fulfilled lives.

Business News

Carnival Cruise Wants Passengers to Have Fun in the Sun — But Do This, and You'll Get Burned With a New $500 Fee

The cruise line's updated contract follows a spate of unruly guest behavior across the tourism industry.


Bringing the Neighborhood Back to Business: Lessons From Mr. Rogers

What potential could a business unlock if the message it gave to every employee was, "You don't ever have to do anything sensational to belong here?"

Business News

Amtrak Introduces 'Night Owl' Prices With Some Routes As Low As $5

The new discounts apply to some rides between Washington D.C. and New York City.