15 Big Hurdles You’ll Face as an Entrepreneur — and How to Beat Them

Members of the Young Entrepreneur Council explain how to overcome some common obstacles business owners face during their careers.
Young Entrepreneur Council
Expert Contributor
November 2, 2020
Updated: November 5, 2020
Young Entrepreneur Council
Expert Contributor
November 2, 2020
Updated: November 5, 2020
Headshots of contributing YEC Members
Top row, from left: James Behmke, Erik Severinghaus, Jason Khoo, Andrew Schrage, Nanxi Liu. Middle row, from left: Kalin Kassabov, Solomon Thimothy, Blair Williams, Matthew Capala, Thomas Griffin. Bottom row, from left: John Turner, Kristin Kimberly Marquet, Joey Bertschler, Amine Rahal, Stephanie Wells.

Throughout your career as an entrepreneur, you’re going to face obstacles. Roadblocks and setbacks like self-doubt, dropped clients and burnout come with the territory of owning a business, but they don’t have to get in the way of your success.

We spoke with 15 members of the Young Entrepreneur Council about the biggest hurdles most entrepreneurs face during their careers. Here’s how you can work to overcome them.

1. Figuring Our Your Why

One of the biggest hurdles is simply the why. The who, what,” “when,” “where and how will all sort themselves out so long as you truly understand your answer to each why. Why is this important? Why would anyone pay for this? Why am I still the best one to make it happen? Why am I spending this much time on this? If you can’t pass any why" hurdle with a satisfactory answer, why are you still going? —James Behmke, Behmke Ventures LLC

2. Tempering Optimism With Reality

Entrepreneurs are an optimistic breed — otherwise, we wouldn’t start companies in the first place. One big hurdle is tempering that optimism so that you can see the world for what it really is. For example, statistics show that it takes years for a typical company to achieve financial success, but entrepreneurs often don’t consider that broad of a time horizon when making decisions. —Erik Severinghaus, Hyde Park Angels

3. Falling in Love With Your Narrative

Get rid of the narrative. Entrepreneurship involves believing in your dreams and taking a leap, but it’s also easy to start writing the story of how your life will go and how entrepreneurship played a role in this beautiful story. Falling in love with a narrative sets you up for some irrational decision making and clouds judgment. It also creates a lot of unnecessary pain when things don’t play out like you’d envisioned. —Jason Khoo, Zupo

4. Fearing Your Financial Future

To help overcome fear around your financial future, launch your business while still working a traditional career. Also, don’t celebrate too much after a great month because, especially in the beginning, there will likely be a softer one in the future that you’ll have to get through. —Andrew Schrage, Money Crashers Personal Finance

5. Not Getting Enough Sleep

Entrepreneurs have a tendency to make sleep a lower priority than getting work done. Even though we know that we will be more productive with adequate rest, we still don’t take enough breaks in practice. Like measuring sales in our business, consistently measuring our sleep helps us work on our bad habits. I use a sleep tracker to help me track whether I’m hitting my sleep goals. —Nanxi Liu, Enplug

6. Letting Go of Unprofitable Ideas You Love

From examining my own experience, talking to others and studying the careers of well-known entrepreneurs, one of the biggest challenges we face is letting go of an idea that you love but that’s just not profitable. Your timing may be wrong, or it may just not be a viable idea. You need to keep reminding yourself that a business is for the customers and not you, so if they’re not interested, you can’t succeed. —Kalin Kassabov, ProTexting

7. Hitting the Growth Challenge

I think that one of the biggest problems most entrepreneurs face sooner or later is what I call the “growth challenge.” They usually manage to establish their business processes, but can’t scale due to the lack of resources, a team, expert knowledge and so on. Find out what your weak point is, and address it. Only then will it be possible to overcome this obstacle. —Solomon Thimothy, OneIMS

8. Changing Your Original Ideas to Fit the Market

Learning that your original ideas and concepts need to change to fit the market can be quite hard, especially when it’s your passion and drive that led to your initial success. Remember that no growth comes without discomfort. By being aware that you’re feeling resistance, you’ll be in a better frame of mind to make a radical product, culture or other change to your business. —Blair Williams, MemberPress

9. Building Self-Confidence

I came to the United States and worked my way up. I went from being a window washer to a Madison Avenue Agency search marketer to a professor at New York University as an expert in my field. My biggest hurdle was confidence in my abilities, especially as a non-native English speaker, but I had a laser-sharp focus on websites and search marketing that never wavered. Have confidence in your pursuits and abilities. —Matthew Capala, Alphametic

10. Working Through Financial Uncertainty

One hurdle that almost every entrepreneur faces during their career is financial uncertainty. If you want to overcome it without much stress, set aside an emergency fund for difficult times. It’s also advisable to consider having a back-up plan in any situation in case things don’t get off the ground. —Thomas Griffin, OptinMonster

11. Missing Resources

All new entrepreneurs will get to the point where they are missing the resources they need for maximum productivity. Instead of letting this stress you out, start thinking about the programs and applications you need the most. After prioritizing what you need, purchase the necessities and get the rest of the applications out to your team when funds become available. —John Turner, SeedProd LLC

12. Delegating Tasks

One of the biggest hurdles that entrepreneurs encounter is delegating tasks to team members because they are afraid that the job won’t be done correctly or in a timely manner. I struggled with this in the early days of launching my first business, but once I started training team members, delegating became much easier. —Kristin Kimberly Marquet, Marquet Media, LLC

13. Finding the Right Hires

Finding the right people to work with can often feel like it happens almost entirely by chance. This is true to some extent. We can, however, drastically increase our odds by working on our hiring processes, networking, personal brands, leads, content, relevance and humility. —Joey Bertschler, uniworld.io

14. Scaling at the Right Time

I think one big hurdle entrepreneurs face is knowing when to scale up their business. Scaling up means spending more money and giving up some control over things you probably used to do yourself. It can be nerve-wracking, for example, to let go of your marketing and branding or spend money on something without knowing if it’s going to work or not. —Amine Rahal, IronMonk Solutions

15. Just Getting Started

Most entrepreneurs face the hurdle of simply starting their business and putting their money where their mouth is! If you can’t see yourself officially starting your business processes, then perhaps being an entrepreneur isn’t for you. It takes a lot of time, money and resources to sustain a business, so those not willing to do the work at the beginning aren’t likely to succeed. —Stephanie Wells, Formidable Forms

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