30 Situations That Entrepreneurs Secretly Love

Jayson DeMers
5 min readOct 6, 2020

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Photo by Humphrey Muleba on Unsplash

In the business world, there are plenty of conventionally negative situations. When a new competitor emerges to threaten your business, for instance, your entire livelihood is put in jeopardy. But not all these situations are necessarily worrisome — entrepreneurial personalities are able to see the bright side of these moments, and many entrepreneurs can learn to love and appreciate them.

These 30 situations are ones that entrepreneurs secretly love, despite their possible negative consequences and connotations:

1. A direct competitor emerges. Competitors are typically major threats, and direct ones copy your business model and target audience note for note, making them the most intimidating. Yet the thrill of competition forces you to step up your game in new ways.

2. A new consumer trend disrupts your market research. You predicted your users to behave one way, but a new trend is changing that — for entrepreneurs, that just means a new opportunity to take advantage of.

3. A new technology forces your consumers to change. New technology can disrupt your plans by changing consumer habits, but the savviest entrepreneurs can spin this to their advantage.

4. Your product doesn’t work the way it’s supposed to. When a product fails, it’s never fun, but for entrepreneurs, it’s a problem solving opportunity; you now have a chance to make this product better, before it gets any bigger than it already is.

5. You’re cutting it close to the launch date. Ideally, you’d be prepared for launch weeks or even months in advance. Creeping up on the deadline may not be fun, per say, but the added pressure adds a thrill to the process.

6. Your marketing plan isn’t working. The original marketing plan you laid out isn’t cutting it — that means you need to go bigger or riskier — both of which are exciting notions to most entrepreneurs.

7. A new technology gives your competitor an edge. A competitor is now armed with better technology than yours. What do you do? Learn from it, and one-up them with even better technology.

8. A business in a separate industry starts competing with you. When a distant company starts encroaching on your territory, it’s inefficient to worry about the new competition. This could represent a whole new market and industry for your business to expand into.

9. Your projected numbers aren’t accurate. The numbers you projected — for better or for worse — are wrong. But most entrepreneurs thrive in unpredictable situations. If you wanted stability and predictability, you never would have started your own business.

10. Your star team member doesn’t know what to do. Hearing your star player say “I don’t know” is alarming, but that also means you’re venturing into completely new ground.

11. You don’t know what to do. Similarly, when you find yourself unsure what to do, it’s a sign you’re in uncharted territory.

12. You’re all out of ideas. Your back’s against the wall, and you have no idea what to do next. That means it’s time to listen to others’ ideas, and entrepreneurs love brainstorming.

13. Your latest idea is rejected. Your latest idea has been rejected by your investors, employees, or another group — that means you can nurture a new idea from the ground up.

14. Your plans and thoughts are challenged by your employees. Your employees should support you, but being challenged means they’re thinking independently.

15. Your investors disagree with you. Disagreements are normal, but any situation is a possible win — for example, if you side with your investors despite the disagreement and they turn out right, you still benefit from the concession. If they turn out wrong, you get the “I told you so” moment.

16. There’s no data to support your instinct. No data simply means it’s never been explored.

17. Your mentors offer dissenting advice. For reasons similar to number 15, when your mentors disagree with you, it’s an opportunity to prove yourself.

18. One of your team members leaves. Team members leaving is never easy, but if their heart wasn’t in it, they’re better off gone — and now you have a chance to hire someone new.

19. You lose a potential client. Missing out on a deal hurts, but it also gives you insights you can use in the future.

20. You lose a current client. Learn from what went wrong, and you have the chance to do better with your other relationships.

21. There’s a PR disaster on social media. The blowup might not be flattering, but even negative attention can be a blessing in disguise for a small business.

22. Your operations fail at some point. Another opportunity for improvement.

23. You’re seen as vulnerable by your staff. Some entrepreneurs try to be seen as legends, but most are more down-to-earth and want to be seen as such.

24. You’re overloaded with work. It’s stressful, but feeling overloaded with work is also rewarding as a thrilling challenge.

25. You’re taking on more than you can handle. Similarly, when your business is overloaded, that’s a positive sign that things are working.

26. Your friends think you’re crazy. If everyone thinks you’re crazy, you have the perfect chance to prove them wrong.

27. You put more of your personal money in the business. Going “all in” with your business is risky, but it shows your volition.

28. An employee changes or shapes your idea. Your idea is like your child, and like a child, you can’t always guarantee how it will grow. Seeing that idea grow and change is rewarding in its own way.

29. Your idea is a gamble. You know this isn’t a sure thing, but that just makes everything that more exciting.

30. You’re growing too quickly. The thrill of expanding beyond your capacity is part of the reason you wanted to be an entrepreneur to begin with.

Do you find yourself loving or at least appreciating these 30 situations? Perhaps you were born to be an entrepreneur. You find the promise of challenge and improvement in almost anything, and that makes you virtually unstoppable.

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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