5 Solitary Challenges No Entrepreneur Likes to Admit

Jayson DeMers
4 min readOct 1, 2020

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Photo by Fabrizio Verrecchia on Unsplash

It’s easy to glamorize the life of an entrepreneur. As the progenitor of a business, you have creative control, which means you get credit for the idea and you get to usher in a tangible enterprise that is, in most cases, entirely yours. You get to call the shots, direct your own efforts, and eventually (if things go well) reap the profits of your hard work.

But entrepreneurship is also very challenging, in solitary and personal ways. Unless you’re in a mutual partnership, you’ll be going the course alone, and you’ll have to face some major psychological and emotional obstacles throughout your tenure. These aren’t fun to admit, and some entrepreneurs flat-out deny their existence, but they’re very real, and they could have a serious impact on your performance as an entrepreneur (not to mention your mental health):

1. Making decisions. In some ways, getting to make all the decisions for a company is exciting. There’s no one to tell you no, no one to force you into an action you don’t want to take, and as a result, unlimited possibilities lay before you. You’ll be planning strategies, hiring new people, and guiding the company’s development, and for the most part, you’ll be alone in doing so. You may seek advice from others, but at the end of the day, you’re the one making the call. This can lead to a real psychological phenomenon known as decision fatigue, where making too many decisions in short order can decrease your ability to make decisions and focus on your work.

2. Taking accountability. You’ll also be the center point of accountability for your business. If your startup takes off and you make a major deal or end up selling the company, you’ll get the credit for getting the business to that position. But in the meantime, you’ll be taking the blame for every misstep and decision that didn’t pan out the way you thought it would — and there will be a lot of those. Knowing you’re solely responsible for something failing or deviating from the plan can be devastating to your psyche, especially during periods of demotivation.

3. Dealing with the fear of failure. The exact numbers of the statistic seem to change depending on who’s reporting it, but there’s always the constant, haunting reminder that the vast majority of new businesses fail within the first few years of operation. The fear of that failure is going to enter your mind, repeatedly, as you guide your business through multiple stages of development and encounter brutal obstacles in your path along the way. But the hardest part is you can’t express that fear; as the leader of your operation, you need to remain resolute and unfazed by the little things. Showing signs of fear or worry could disrupt your team’s morale or worse, compromise their faith in you as a leader.

4. Having no higher-up. It’s a fun idea to be the boss, but realistically, for many people there’s a comfort in knowing there’s someone above you. In that situation, you have someone to talk to about your challenges, ask advice when you aren’t sure what to do, and someone to check your work to make sure it’s up to snuff. When you’re the leader of your own enterprise, there is no higher up — the only exception being if you’re dealing with investors or mentors with a vested interest in your enterprise.

5. Feeling isolated. Isolation occurs in a number of different contexts for entrepreneurs, and both loneliness and depression are common among business owners because of it. For starters, you’ll be working on your business constantly, putting in long hours that take you away from your friends and family members. You’ll likely be physically isolated, working in an office or somewhere away from other people, and being the boss, you’ll also feel somewhat disconnected from your team members — even if you hand-picked them to join.

I’m not presenting these challenges to scare you away from becoming an entrepreneur, nor am I claiming that every entrepreneur experiences these challenges in the same way or to the same degree. However, if you know what to expect from them, you can better prepare for them, and improve your disposition and response when you begin encountering them for the first time.

Also, because these are solitary challenges, one of the biggest keys to getting past them is to understand that you don’t have to go through this alone. Work with mentors and talk to your peers — even reading articles like this should give you some sense of sympathy and support to help you through. You’re alone in some respects, but in a full, welcoming community in others. Recognize these challenges, and keep moving forward.

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

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Jayson DeMers
Jayson DeMers

Written by Jayson DeMers

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

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