The 5 Biggest Psychological Hurdles of Entrepreneurship

Jayson DeMers
4 min readJul 27, 2020
Photo by Interactive Sports on Unsplash

There are plenty of logistical hurdles you’ll face as an entrepreneur. Quitting your job, getting funding, finding a location, and making hires are just a few of the many challenging obstacles you’ll have to overcome. The good news is that most of them are procedural, and even though they may pose difficulties, they can be overcome by following a logical process and committing yourself to seeing a final solution through.

The more difficult obstacles, and the ones more capable of impacting your livelihood, are the psychological ones. These are internal struggles, sometimes spurred by events and sometimes brought up spontaneously, that interfere with your ability to make decisions, your confidence in your actions, your enjoyment of the work, and ultimately your capacity to continue as a figurehead of your organization.

These psychological hurdles are ones that every entrepreneur must someday face, probably in the earliest stages of your startup’s development:

1. Uncertainty. Uncertainty is around every corner, especially when you’re first developing your business. You don’t know if your market research is accurate. You don’t know what competitors might emerge in the coming months. You don’t know if your profitability model will work in real life as efficiently as it seems on paper. The uncertainty can get the better of you if you let it, but remember this: uncertainty exists for everyone, and successful entrepreneurs are the ones willing to embrace it, under the mentality that without risk, there can be no reward. If this isn’t enough to motivate you, understand that the worst-case scenario is never as bad as you imagine — even if your first business fails, you’ll always have a chance to build something new.

2. Instability. Beyond the uncertainty of your startup’s infancy, be prepared for some inherent instability in your first several months. You’ll have sudden surges of consumer interest followed by long droughts. You’ll have random necessary expenses crop up, major team members leave the company, and windfalls that make them seem insignificant. To abuse a cliché, it’s a roller coaster ride, but even if you enjoy the variety, the constant instability can get to you. People crave routines, foundations, and reliable structures. Without those, you’ll experience much higher levels of stress, which in turn can make you impatient, overly emotional, and miserable in general.

3. Responsibility. Being an entrepreneur means investing yourself in a venture in ways you’ve never experienced. Every decision you make, from naming the company to closing your first client contract, will affect your business’s bottom line. As your business grows, this responsibility grows — eventually it’s not just you on the hook, but your partners, your employees, and your investors as well. There’s no easy way to overcome this other than by reducing decision fatigue in your daily life and understanding that bad decisions can be recovered from.

4. Balance. It’s easy to get sucked into your startup, especially when you’re passionate about the industry. It’s your idea — your baby — and it’s natural to want to invest as much time as you can into it. Unfortunately, that sometimes leads to 100-hour weeks, long weekends, and sleepless nights, leaving you little room for anything else in life. What’s most dangerous is that this imbalance often sets in without entrepreneurs ever realizing it. Prioritize your health, and don’t be afraid to take breaks.

5. Loneliness. Loneliness is a bigger problem in the entrepreneurial world than most people realize. Entrepreneurs are often depicted as naturally isolated geniuses, who function contentedly as introverts when working on a project and turn into extroverts when it comes time to talk to clients or the press. In reality, every entrepreneur is pulling off a delicate balancing act, bottling up all their stresses, worries, and fears whenever in the presence of someone else. Telling clients or the press about how scared you are could ruin you. Showing your anxieties to your team could unsettle them and destabilize your company. The only time you get to be your true self is when you’re alone. This is a manageable lifestyle for a few weeks, but after a few months it starts to interfere with your wellness. Seek support — your friends, family, mentors, peers, and even counselors are there to help you through this.

Overcoming these hurdles isn’t about ignoring them, pretending they don’t matter, or avoiding their manifestation. They’ll stick with you, whether you like it or not — what really makes the difference is how you respond to these hurdles. You can overcome them by accepting them, yet not allowing them to interfere with your plans or your goals. You can ask for help from those around you, and make meaningful changes in your life to compensate for them. Your strongest asset against psychological turmoil is awareness, so remain cognizant of these potential mental pitfalls, and keep moving forward.

For more content like this, be sure to check out my podcast, The Entrepreneur Cast!



Jayson DeMers

CEO of EmailAnalytics (, a productivity tool that visualizes team email activity, and measures email response time. Check out the free trial!