4 Ways You’re Sabotaging Your Entrepreneurial Success (and How to Stop)

by / ⠀Entrepreneurship / January 6, 2014


You are a young entrepreneur who eats, sleeps, and breathes your business – yet, all too often you feel stuck and frustrated.

As a business owner, you’ve chosen to carve your own path and be the one responsible for your success. But do you ever wish that sometimes you could just get out of your own way?

What you might not realize is that specific, unconscious behaviors may be stalling you and holding you back.

Here are 4 bad habits to ditch to stop sabotaging your entrepreneurial success and tips for demolishing inertia:

1.    Saying “I can’t”

When you say “I can’t”, are you saying you don’t have the skill to do something? Or are you really saying you don’t want to do something? Nine times out of ten we fling around the phrase “I can’t” when we fear failure or lack the will to step up to the plate. Your words shape your reality, and every time you say “I can’t” you’re limiting yourself and allowing fear to win.

But if you begin changing your language, your behavior will follow. Try looking at “I can’t” as the signal for an opportunity to learn and improve a skill. For example: “I can’t understand why this campaign is performing poorly, so I’m going to survey our customers.” Also, start subbing in “I won’t” or “I’m not going to…” when you want to more assertively and confidently communicate when you’ve made a decision: “I’m not going to that meeting tonight.”

2.    Constantly judging yourself

If you compare how your finances or accomplishments stack up to friends’ or other companies’, you’re unnecessarily incubating toxic thoughts and distracting yourself from the goals at hand. Though you may feel insecure when others publicize a big success, letting that insecurity breed will erode your confidence.

When you catch yourself in a tyranny of the “should’s” (I should be doing this. I should be at this point.”), take a deep breath. You are not behind. Remember there is no linear path or handbook to success. 

3.    Having blinders on when it comes to change

Are people afraid to present you new ideas because they’re scared you’ll tear them apart?  If so, you’re “danger surfing”, a self-sabotaging reaction where you instinctively think of all the ways it something could fail. As a business owner, it’s very easy to slip into the ego trap of thinking you are the only person in the world who knows what’s best for your company. And while, yes, you may certainly hold the decision-making power, that attitude could be closing you off to creative ideas that could take your business in exciting directions.

When someone brings you a new idea, look for ways you can add to it instead of firing it down. Replace saying “but” with a more encouraging, collaborative stance of, “Yes and…”. This creates a collaborative interaction rather than an adversarial one. If you’re leading a team, resist the urge to micro-manage. You’ll find your employees are a lot more productive and creative if you give them freedom and your confidence.

4.    Burning the midnight oil

When was the last time you took a weekend off?

As an entrepreneur, it can be hard to “turn off”. To move past your workaholism towards better work-life integration, start setting up systems to draw boundaries and give yourself a break.  You can try creating a hard stop at night when you stop working to make time for relaxation.

It’s impossible to stay on top of your game without making time for fun, so schedule it! The barriers between work and personal life can become blurred for many busy young professionals and entrepreneurs, and it really is true that all work and no play can get you down. Schedule time for fun just as you would professional tasks –whether it’s a happy hour with friends or even 15 minutes reading a fiction book. Socializing, laughing, and relaxing are good medicine.

Melody Wilding, LMSW, is a therapist for female entrepreneurs who specializes in personal and professional development for successful women in their 20s and 30s. Melody has helped women running some of today’s top startups along with published authors and media personalities and has been featured on Glamour.com, The Huffington Post, The Daily Muse, and other major media outlets. Schedule your free 15-minute session at www.melodywilding.com and follow her on Twitter at @MelodyWilding.

About The Author


Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on Under30CEO.com, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.

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