The 6 Most Common Obstacles You’ll Meet as an Entrepreneur

Be well prepared for what to expect instead of hoping for positive experiences only

Ivan Popov
Entrepreneurship Handbook

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a man in front of his laptop panicking
Photo by Sebastian Herrmann on Unsplash

Don’t get me wrong — I love the magic in the entrepreneurial world.

But just like any other exceptional adventure, entrepreneurship comes with pros and cons, and there are plenty of obstacles and difficulties that need to be taken into account, especially when just starting. (I remember looking pretty much like the guy from the featured photo back in the day.)

It’s inspiring to listen to the best entrepreneurial minds of our generation speak about the path to success and how elegantly they managed to overcome the initial difficulties. However, I assume there is a high chance that aspiring entrepreneurs can get so caught up in the magic behind the words that they could be caught off guard when things become tough.

And, by all means, they will.

Today’s article’s goal is not to discourage you. It’s on the contrary. I strongly believe in proper preparation before executing a plan or emerging into deep business waters. If you’re familiar with the most common obstacles and difficulties you’ll face during your first entrepreneurial steps, there is a high chance you’ll overcome them far more easily when they hit.

Being an entrepreneur is a dazzling and inspiring life role. It allows you to chase your dreams, turn your side hustle into a full-blown business (more on this you can find here), meet like-minded individuals, broaden your communicative horizons, acquire an outstanding new set of skills, etc.

But one should not have tunnel vision when starting. By knowing what could go wrong, you can easily predict and prevent the crash way before it happens. Being prepared for all the negative aspects of entrepreneurship can help you instantly become a better business person.

The 6 entrepreneurial most common obstacles to have in mind when starting your new business endeavor are;

  1. Executing your initial idea in practice
  2. Finding the perfect team
  3. The money issue
  4. Battling stage fright and establishing a name for yourself
  5. Balancing between work life and personal life
  6. Knowing how to handle discouragement

1. Executing your initial idea in practice

I’ve always believed that the best entrepreneurial approach is to offer your audience a product or a service they already need.

This way, you won’t have to persuade anyone on why they essentially would need your services.

I got quite lucky because my all-time favorite hobby (I refer to coding) turned out to be a sought-after skill nowadays. Back in the days, I started programming and developing websites just out of pure love for the process — years later, I was happy to discover how enormous this business niche turned out to be. My target audience has already needed my services. Phew!

But of course, there are some fellow aspiring entrepreneurs out there who have this innovative and unique idea they strongly believe in. Should you leave it to rest and give up turning it into a full-blown business? Hell, no. What’s important here is to think in advance about how you will present it to the public in an attention-grabbing manner. It’s crucial for your initial business plan to be well-built and to follow certain steps when offering your new idea to the public.

2. Finding the perfect team

I’ve talked previously about why I highly value team spirit. Entrepreneurship is more of a team play instead of you going solo. Once you’ve managed to get a crystal clear idea of what your business will be all about, it’s essential to start looking for the perfect additions to the company.

Building a successful team can be quite a challenging endeavor. Sure, many people will apply for your job position, but how many of them will be an excellent fit for your business? My advice is not to wait long before searching for the ideal fit for your exceptional future team.

I value hiring the perfect team members to the point when I search for ideal candidates and approach them first. Once I stumble upon a perfect fit for the team, I reach out like: “Hey, it’s me, your boss-to-be!” Don’t overdo it; no CEO wants to enroll in the “creepers and weirdos” blacklist.

3. The money issue

It’s a no-brainer — when we discuss business, we also need to discuss money.

The vast majority of entrepreneurs need an initial investment. Your best approach would be to consider the money question in advance. Try to sum up how much money you’ll need for the initial start; how much money will you need in the first few months of the company’s existence? Of course, keep in mind the additional costs that may emerge. Having a clear mind about money will give you comfort and certainty right from the start.

And one more thing — prepare to live through some hard times. No one can guarantee you that your business will skyrocket during its first month of existence. At the very beginning of my company’s development, I found it hard to pay the bills and have delicious gourmet meals at the same time. You get the idea — buckle up and go grocery shopping for a while if money is an issue.

4. Battling stage fright and establishing a name for yourself

You are familiar with the “mom’s spaghetti” line from that Eminem song, right? I remember during one of my first-ever public speaking events, I was pretty close to cosplaying him (8-mile-toilet-vomit-scene-reference-here)!

The truth is, entrepreneurship would be quite a difficult task for people who don’t feel comfortable being in public communicating with loads of people on a daily basis.

If you suffer from stage fright, I believe now it’s the time for you to try and overcome it. Your role as an entrepreneur will most likely lead you to events, seminars, and public speaking events where people will love to hear from you about the company and your products and services. It’s important for you to get comfortable talking in front of a crowd and to learn how to present your company’s essence in a thought-provoking and interesting way.

Here I share some useful tactics for battling stage fright that I’ve implemented personally and did wonder for me.

Remember that you’ll soon turn into your company’s face, and people will begin connecting the dots between your public persona and your business.

Building a name for yourself will greatly boost people’s trust in what you do.

5. Balancing between work life and personal life

The thing with entrepreneurship is that it could take a lot of your time, especially initially, without you realizing it.

It’s common for aspiring entrepreneurs to lose track of time and work even during evening hours. For example, I still find it hard to battle the temptation to open my laptop on a Saturday evening with the hope of getting rid of that Friday issue. So leave it be — maintain your relaxed state of mind and avoid clashes between you and your significant other.

Sure, hard work is a great skill that will guarantee you a spot on the successful businesses scene, but it’s also important to balance work and rest. Don’t let business overtake your entire conscious, making you forget about sleeping, eating healthy, proper exercise, and meeting with friends and family. With entrepreneurship, burnout is always peeking behind the corner so beware not to unleash the Kraken.

6. Knowing how to handle discouragement

If anyone tells you that entrepreneurship will always go smoothly, they are downright lying to you. Like any other endeavor, entrepreneurship is also presented with many downfalls and disappointments.

You need to withstand discouragement and not let disappointment hit you hard and knock you over. When your plan fails, try viewing it as a business lesson and learn from your mistakes. It’s one of the best business approaches I’ve implemented in my entrepreneurial career. There were times in the beginning when things went so wrong that the only thing that helped me keep a clear head was going out for a run. Heck, I boosted my marathon scores and durability thanks to the business going downhill.

Eventually, all turn out better but only if you have the courage to overcome discouragement in a healthy way.

The bottom line

Do yourself a favor, and don’t expect entrepreneurship to be smooth sailing all the time. Prepare for some obstacles and difficulties along the way and create a plan that will help you overcome mishaps more easily.

I’m pretty sure with the proper preparation and execution of smart business steps, anyone can shine in the role of an entrepreneur.

Hi, guys, I’m Ivan and I’m here to share with all of you my passion for words, great content, entrepreneurship, personal development, management, hobbies, and everything in between.

I serve as the CEO of my WordPress Development Agency @ Vipe Studio where I have the pleasure to lead a diverse, wonderful and energetic team of experts. Feel free to contact me anytime — I would love to exchange new ideas and inspire each other!

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i was once an athlete. then a journalist. now i am a ceo of vipe studio. still running marathons though.