6 Stressful Things New Entrepreneurs Never See Coming

Jayson DeMers
4 min readAug 4, 2020
Photo by Ryoji Iwata on Unsplash

By the time you get to starting your business, you’re already prepared for how hard entrepreneurship is. You’ve been told by classmates, friends, family members, peers, investors, and partners that you’ll need to put in long hours, work through nights and weekends, and solve ridiculously hard challenges to eventually be successful.

But the dangers of entrepreneurship aren’t usually found in the conventional sources of stress. These are difficult, but predictable, and most dedicated entrepreneurs are well-equipped to handle them. Instead, you’re more likely to be stressed and challenged by the things you never see coming.

These are six of the most common surprises you’ll face:

1. Cash flow hiccups. There are many potential businesses that you can start with almost no money — but once you get going, cash flow becomes super important. Cash flow is what keeps your business’s doors open. It pays your employees, keeps your shelves stocked, and enables you to reinvest in the business. Even a profitable business on paper can suffer from cash flow problems (from customers not paying on time, sudden emergency expenses, or other surprises), and when you do, it’s a mad scramble to cover all your financial bases. Be as proactive as possible here, and detail every cent going in or coming out of your business.

2. Partner departures. When you start your business, you may have a partner, a mentor, or at least an employee or two who are there to help you round out your ideas and tackle the early hurdles of building a business. It’s easy to imagine these people sticking around forever because they’ve been there from the start, but sooner or later, one of them is likely to leave. Unless it’s a gradual build, it’s likely to take you by surprise, and you’ll be forced to make a drastic change to your approach. Psychologically, this can be very difficult to face.

3. Loneliness. Some entrepreneurs are natural introverts, who thrive on working in solitude. Others are extroverts, who prefer constant engagement with the team. Either way, eventually, you’ll start to feel the loneliness associated with entrepreneurship. You’ll be forced to be the “face” of the company, hiding any concerns or reservations you have about the business, and you won’t have anyone to talk to within your business about the stresses of your own role. On top of that, you’ll be working long hours away from your loved ones, so you’ll start to feel even more isolated. It’s a rarely-discussed downside of being an entrepreneur, and it’s hard to prevent.

4. Major client departures. It’s never a good idea to put all your eggs in one basket, but oftentimes, businesses grow dependent on “anchor” clients, who either provide a majority of incoming revenue or seem like they’ll be around forever. When an anchor client leaves, it can be a shock to your system. It may cause you to doubt your approach, and will certainly force you to rebalance your outgoing sales and client retention efforts.

5. Imitation. It doesn’t matter how long you’ve been building your company’s reputation. When a competitor arrives who replicates your business model almost completely, your entire company will be put in jeopardy. If they’re able to differentiate themselves or do what you do a little bit better, it can seem like an insurmountable threat. Instead of panicking, take the time to analyze their approach, and find a way to outcompete them — it may include cutting prices, offering more to your customers, or just targeting a different audience.

6. Burnout. No matter how enthusiastic and energetic you are at the beginning of your venture, you’ll face the possibility of burning out. It may take several years, or it may take only a few months, but when it sets in, it will become nearly impossible to reverse. The real danger here is that burnout develops gradually; you’ll keep working hard, barely noticing that you’ve started to grow resentful of the business and tired of the work. Then one day, you’ll hate the idea of getting out of bed in the morning, and you’ll realize your passion project has become a chore. The best way to address burnout is to prevent it before it grows; take time for yourself, and don’t work too hard.

Even knowing some of these potential sources of stress are on the horizon, they’re still likely to catch you off guard. You might not be prepared for the specifics, or ready for their intensity when they do arrive. Instead of trying to predict everything that could happen to you and your business, focus on developing yourself as much as possible.

Remain adaptable, focused, patient, and most importantly, build a network of support that you can rely on in your darkest moments. This will give you the resilience and foundation you need to handle just about anything — even the surprises.

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



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!