Career Roadblocks: Break Down the Barricades with Help from 12 Entrepreneurs

career roadblocksWe all have them: career roadblocks that stand between us and our career goals. At the time, they can seem insurmountable. But as many of us have learned, there’s always away around even the biggest barriers to success.

Take it from the members of the Young Entrepreneur Council, who took the time to answer this question:

What has been your biggest career roadblock and how did you overcome it?

Take a look at their savvy answers. Then take the time to understand how their wisdom can best help your career.


1. Confusing ‘Working’ With ‘Doing’

I’m a doer. I like executing. In the early stages of a bootstrapped company, this is a fantastic characteristic for a founder. As your company grows beyond a few employees, the day-to-day role of the CEO simple can’t be to execute every plan. Eventually, I realized that I was making a FAR greater impact in my company when I was planning, encouraging and developing our team’s character traits.

Brad Weimert, Easy Pay Direct


2. Dedicating Time to the Startup

I kept my day-job when we first started our startup. Problem was: positive reinforcement at work met with constant rejection during the funding round, causing me to throw myself into the day-job instead of improving our pitch and business plan. When an investor finally pointed out that our part-time status hurt us, I scaled down my life so I could afford full-time entrepreneurship.

Manpreet Singh, TalkLocal


3. Handling the Board’s Reaction to Motherhood

Early on in my career as a chief executive, I was told by my board that they would never hire another woman CEO because I was the second to get pregnant in three years. I was planning on returning full-time, so their (illegal) response was most disheartening. Recognizing the strengths I bring to the table as mother and founder/president allowed me to quickly overcome any objections to my dual roles.

Jennifer Mellon, Trustify


4. Improving Communications and Transparency

I used to imagine the rest of the team didn’t want to know what was going on with “my side of the business,” so I kept much of my decisions and processes separate from them. No only does that breed distrust, but after growing to certain size, the team needs more and more information to make the right decisions. Being completely transparent with the team has unlocked growth and improvement.

Brennan White, Cortex


5. Being Overly Competitive

As an athlete, being competitive has been ingrained in me since childhood. While a competitive nature is essential in starting a business, it can become a deterrent when you are too busy comparing yourself to others to focus on yourself. Learning to look inward for gauges of success is a sign of business maturity. Tracking your competition will always be important, but never let it be all consuming.

Kim Kaupe, ZinePak


6. Taking the Wrong Role for the Wrong Reasons

There are a number of reasons we end up in the wrong role: ego, money, lack of self-awareness, people, responsibilities and fear are just a few. No matter the reason, when we’re in the wrong role, we struggle and most likely fail. By learning to ignore my worst motivations and outside opinions, and instead listen to my gut and live my top values, I’ve found both success and daily fulfillment.

Jonathan Gass, Nomad Financial


7. Accepting a Gentleman’s Agreement

A gentleman’s agreement is an informal, legally non-binding agreement between two or more parties, female or male, with the term “honor” as the basis for its fulfillment. These deals are often made orally, bound by handshakes versus autographs on an enforceable document. I learned the hard way this is a career killer. Ensuring the honor of all, I shake hands after the ink has dried on a contract.

Derek Hunter, Wanderlust


8. Overcoming Failure

I was fired from a job early in my career, and initially I was incredibly emotionally distraught about it. Looking back, I realize that it was this event that motivated me to found my own company. I credit that “failure” as one of the most critical events in my career, and leveraging it as a learning experience proved the best way to overcome it.

Josh Payne, StackCommerce



9. Raising Capital

Capital has always been a roadblock. I’ve overcome this by always getting capital from customers, versus raising money. It’s creating something of value, going out and testing the market, selling it, taking that profit and then going to the next step. I’ve raised money before, but in business entrepreneurial ventures, it’s all about capital. So create something of value and go sell it.

Hank Ostholthoff, Mabbly


10. Battling Contentment

One of the greatest challenges for entrepreneurs is continuing to stay driven even after your goals have been achieved. Contentment can hold individuals back from achieving even greater successes, so figuring out a way to continue to update goals based on evolving situations that are experienced in startup environments can continue to push individuals towards greater successes.

Robert Lee, Circa Interactive Inc


11. Trying to Do It All

My biggest stumbling block has been trying to do everything myself. Early on there are a lot of things you can and must hustle out on your own, but you can’t do that forever. I was hesitant to bring on other people and give up control, but it’s ended up being the best thing to happen in my business. Hiring taught me a lot, helped grow my business, and allowed me to focus on my strengths.

Kyle Goguen, Pawstruck LLC


12. Letting Go of Ego

The first decade of my career my ego helped me gain new client relationships and grow my company, however my company reached a point where my ego was holding us back. I had to learn to put my ego in the backseat and focus on building the team, including working to empower others instead of always “showing” them.

Brandon Dempsey, goBRANDgo!




show gratitudeYoung Entrepreneur Council (YEC) is an invite-only organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, YEC recently launched Business Collective. This free virtual mentorship program helps millions of entrepreneurs start and grow businesses.



This entry was posted in Career Advice and tagged , , . Bookmark the permalink.