10 Biggest Career Mistakes Made by Today’s Successful Entrepreneurs

mistakeThere is no such thing as a career sure bet. Failures will happen. Pivots will become necessary. In fact, even some of today’s most successful entrepreneurs made some mistakes along the way.

To help shorten your career learning curve, and to help you avoid some regretful mistakes yourself, we asked members of the Young Entrepreneur Council (YEC) this question:

When you first started your career, what mistake did you make that regret most today?

Here are their thought-provoking, and helpful, answers:

1. Living Someone Else’s Life

Fan YECWhen I first started my career, I worked in finance. Many of my peers were going to Wall Street; it’s a profession that pays well and comes with status. After a few years, I burned out and felt frustrated that I wasn’t happy in this golden career path. But in reality, it was only golden to others, not to me. Spend time doing what you’re passionate about. The rest will take care of itself.

Fan Bi, Blank Label


2. Acting as a CPA

Kim KaupeWhen we started ZinePak, we tried to do everything ourselves from web design to legal documents. While DIY works for some aspects of the business, the more important areas, like accounting, should not be on your “I got this!” list. In our first year, we tried to learn Quickbooks and tax code but the only thing we managed to do was upset the IRS. It’s best to leave accounting to the professionals!

Kim Kaupe, ZinePak


3. Not Pushing Back

Jt-AllenIn my early efforts to get people to believe in my company vision, I would try to incorporate and accommodate every new idea from potential investors. But in reality, some of their ideas were pretty bad! Somewhere along the way, I realized I knew the market and the dynamics far better than they did, and I began to politely push back. That’s when I earned a whole new level of respect.

– JT Allen, myFootpath LLC


4. Not Putting Myself In My Client’s Shoes

andre-ChandraLet’s face it, everyone’s got motives. There are plenty of theories out there trying to prove that no one is purely altruistic, but I digress. My point is, you’ll do better at selling when you know what the other side really wants. A lot of times it’s hidden. Once you uncover that, you’ll find what needs to be done to align your interests with theirs, and that’s 90 percent of the battle.

– Andre Chandra, I Print N Mail


5. Not Saying No Sooner

Mathew-SititlaWhen you’re growing an agency, you want to take on every client. You want to please everyone; you want to grow and expand as much as you can, no matter what time it takes away from you. I wish I could go back and tell my younger self it’s OK to say no. Once I learned to balance my business and personal time and keep them separate, my life became so much less stressful.

Mathew Siltala, Avalaunch Media


6. Not Advocating for Myself

Jennifer-MellonMy biggest career mistake was not being my own best advocate. After the birth of my first child, my board wanted me to do immediate international travel. Their unrealistic expectations made me feel like resignation was my only option. I wish that I advocated for myself in having a work-life balance as an executive and new mother. I urge other new moms in that position to lobby for themselves.

Jennifer Mellon, Trustify


7. Losing Focus

james-YECEntrepreneurs tend to constantly think up new ideas for businesses. It’s exhilarating to come up with an idea and begin executing it. However, following this pattern is a huge mistake that will generally never get you to your goals. To have the greatest chance at success, you need to laser focus on the one thing you believe in the most and throw everything you’ve got at it.

James Simpson, GoldFire Studios


8. Biting Off More Than I Could Chew

David-EhrenbergWhen I was looking to expand my company out of the Bay Area, I had grand visions of being a leading player in each of the major U.S. markets. Rather than taking a “divide and conquer” approach, we went after each of these markets simultaneously, putting an enormous strain on our operations. Go with more measured tactics when it comes to sweeping projects like this.

David Ehrenberg, Early Growth Financial Services


9. Relying on My Resume

Tracey WeidemeyerWhen I went on to find a job after attending a small liberal arts college, I had this perception that what was on your resume mattered more than your hard work: things like the college you attended or the people you know matter, but not to the extent that hard work and hustle do. Being willing to do the things that others won’t is what really matters. Knowing this would have saved me from making lots of bad decisions.

Tracey Wiedmeyer, InContext Solutions


10. Letting Fear Get in the Way

Jarrett-McCrawI challenge young professionals to try something new — something that may or may not work. It’s better to look back and say you tried something than to wonder what could have been. You have your entire life to build a career, and it only gets more difficult to experiment as you get older and build a family. Fail early and fail often in your younger years.

Jarrett McCraw, Mighty


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



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