7 Failures Every Entrepreneur Must Face

Jayson DeMers
4 min readNov 9, 2020


Photo by Christian Erfurt on Unsplash

Failure is a part of life, especially for entrepreneurs. Most new businesses fail within the first few years, and even if your business is one that survives that harsh initial trial, you’ll experience plenty of smaller failures along the way.

Seasoned entrepreneurs know that no single failure could ever be enough to compromise the success of a dedicated mind. Instead, failures are merely temporary obstacles in a long journey. They are experiences to be learned from, and mistakes that improve our abilities.

As you develop yourself as a business owner and work to achieve your goals, you’ll inevitably experience these seven failures:

1. Neglecting a portion of your research. Research is going to form the foundation of your expectations, plans, and goals. Market research, competitive research, and pricing research are just some of the in-depth forms of research you’ll perform — and they all have vulnerabilities. Whether you misestimate the strength of a potential market sector or completely neglect a factor in your initial research, that failure is going to affect your business negatively. Fortunately, even the most egregious research mistakes can be corrected through reevaluation and subsequent adjustment.

2. Missing an important deadline. Many deadlines are arbitrary, but there are some that can’t be missed. For example, if your investors are expecting your technology to launch by a certain date, or if your clients depend on you hitting a certain production volume, a missed deadline could mean the collapse of an entire segment of your business. When you miss a deadline, and inevitably, you will, don’t dwell on the failure. Determine what went wrong, make up for what you can, and correct your procedures to prevent it from happening again.

3. Losing an opportunity. Whether it’s a major client leaving due to unmet expectations or a major PR opportunity that slipped past you, at some point you’re going to lose a major opportunity, and it’s going to feel terrible. Depending on how you’ve structured your business, the loss could be relatively minor or devastating. If you’re going to recover in the short term, you’ll need to look for a replacement to serve as a bandage for the wound. If you’re going to recover in the long term, you’ll need to diversify your opportunity pool with more clients or a wider outlook, to hedge your bets against such a loss.

4. Hiring the wrong person. Finding good help is difficult, and eventually you’re going to hire someone who isn’t a good fit for your organization. A lack of productivity, motivation, or the presence of a negative attitude could ruin what would otherwise be an outstanding working relationship. Don’t let negative employees compromise your workforce; acknowledge your failure in hiring them, and either correct the problem or move on.

5. Forgetting or overlooking a key disruption. It might be an old competitor who has a greater reputation than you expected, or a new technology that’s making waves in ways you hadn’t anticipated. When disruptors in your industry start to make their moves, it’s easy to lose ground quickly. No matter how prepared you are or how much you try to anticipate the patterns of the future, there will always be something to confound your expectations and interrupt your business flow. All you can do is mitigate the immediate consequences and implement new strategies to accommodate your new challenges.

6. Mismanaging your operations. There are hundreds of ways that your operating process can go wrong. You could have a flawed sales flow, an inefficient production schedule, an unsupervised segment of operations, or just a bad model, and you might not realize it until it’s too late. At some point throughout your entrepreneurship, you’ll look back and realize how much ground you’ve lost because of a critical failure in your plan for operations. Take heart that there is always time to turn things around — look for opportunities to make positive changes, and make those changes a priority.

7. Missing your financial projections. There are two big reasons for missing your financial projections; overestimating the amount of sales and revenue your company was going to bring in, or underperforming compared to your goals. Either one can leave you with a sense of dread and a fear for the future of the business. Keep in mind that projections are only projections, and as long as you’re stable enough to keep moving forward, you’ll have more chances to adjust your expectations, and improve your company’s performance.

Don’t ever let failure hold you back. Some of the most successful companies in the world, including Microsoft, Apple, and Virgin Group, were founded and guided by entrepreneurs who encountered a crushing failure and kept working hard to achieve their dreams. Learn from your mistakes, lead without regrets, and keep moving forward toward your ultimate goals.



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!