Entrepreneurship is Hard

So let’s keep it real right now, and I’ll start with this disclaimer.


My goal in writing this article isn’t a rally for you to go into entrepreneurship. I’m writing this to tell you the pitfalls and demanding lifestyle of being a glorified risk-taker. If you’re looking how to be an entrepreneur, this may or may not be for you.

And no, I’m not trying to be overdramatic. I want you to know this is a lifestyle, not a hobby.

In 2020, I put out a five-minute podcast, Tip 199: Entrepreneurship Ain’t for Everyone. Click here for the iTunes version. The Stitcher version is at the bottom. 

Being an Entrepreneur

I’ve been an entrepreneur for over 15 years, starting back in 2004. In the jobs I’ve had since starting my own company, it was super hard to always “fall in line” and play the game. For me, entrepreneurship is hard because you’re always going against the norm, and not everyone understands.

Those who love a guaranteed paycheck, which I very much do too, choose another path. A regular salary doesn’t exist in this lifestyle. Kiss any of those essential benefits and perks you have or had at your current employer goodbye. Those are now extra expenses.

Seriously, they’re a luxury item for a startup without any financial capital.

I used to take that stuff for granted because one of my first jobs was in the military. Military benefits are a standard-issue, so you don’t think much of it. One of the best gifts was the freedom my job gave me.

Being Disciplined

My Marine Corps career has had something—really a lot—to do with my inability to maintain and hold onto a corporate America career because I do hate to be micromanaged. And yeah, I’ve been fired several times. On the flip side, I advanced extremely fast for my successes in Corps. They gave me complete autonomy in my niche, and it was something that I always craved from all my future employers but never received.

The journey of any entrepreneur comes because they’re a self-starter. You might be an entrepreneur in the making if you answer yes to the following questions. 

– Do you like solve problems?
– Are you good with overcoming obstacles?
– Does your vision conflict with your employment?
– Tired of working for someone else’s way of life?
– Wanna retire with multiple streams of income?
– Not able to keep a job?

In my journey, I’ve learned we tend to be looking for problems to solve and stand out because we’re not looking to fit in the crowd. If you’re looking to go this route to get rich, I heavily caution against it and how that is a wrong decision.

Running a business requires you to make lots of sacrifices beyond what you could ever imagine. There are plenty of sleepless nights, and where are you some days. There’s no guaranteed source of income unless you create it. Therefore, you need to be extremely disciplined to stay focused.


The focus needs to be on your vision because you’ll be reminded of how you’re not succeeding by others. To only ‘put salt in the wound’ your business needs its customers to pay the bills, not your other income. Those who don’t have this experience (e.g., multilevel marketing schemes, trust fund babies, franchise models, etc.) won’t understand taking something from nothing. 

Not having any startup funds make the struggle that much more difficult, but not impossible. No matter what, the rejection of hearing ‘yes’ will dwindle when you get outside your comfort zone. Rejection and entrepreneurship go hand-in-hand.

Therefore, you have to sell. Selling a product or service to friends and family members is one thing, but selling to strangers is another level of confidence and growth. I call this failing forward.

– You have to sell every day.
– Selling requires you to develop a pitch.
– Your message and pitch are non-stop.
– The rejection of each ‘no’ will make your sales plan better.

In the movies, we see many people laughing and having a good time, but that’s not real life. That’s entertainment. Entrepreneurship is boring with a lot of failures. There’s more pain than pleasure. However, the pleasure is seeing the progress with the small wins that lead to the bigger victories.

As a new kid on the block, you’re entering a ring of fierce competitors, and they see you about to eat their lunch. Hence, why is it called free-market competition. Just as personal bills are due regularly, monthly business bills are due simultaneously and they tend to be less lenient without any grace. I had a late fee of a couple hundred dollars and there was negotiation.

Self Promotion

There’s one thing that’s undeniable about entrepreneurship is that it involves sales to the highest degree. To ensure your business goes beyond the startup realm, you have to sell beyond your family and friends. It does not matter what type of product or service you have or how great you think it is. Your business isn’t going to go to be a viral sensation that blows up overnight.

Overnight success never happens. You may think you can defy all the odds, but making it overnight success won’t be one of them.

To get sales, you’re going to have to promote yourself and your business, and promoting your business calls for you to have a marketing strategy. You don’t have to get all fancy and create a marketing plan that’s 10 to 20 pages long but at least have something that covers the four Ps of marketing

Your main goal should be focused on earning customers to cover the major financial aspects of your business. The first ‘P’ is ‘price‘ of the four Ps, and a major mistake young entrepreneurs make exclude operations and salary. They fail to include a marketing component due to its complexity.

The marketing world is intimidating at first, but it’s not incomprehensible. Get familiar with the terms as fast as you can, and hire an expert when you’re ready to grow. Every great successful company has a strong marketing team.

A well-branded product will make everyone’s life easier in the company, so don’t try to do it all on your own. Ask Phil Knight how far he would’ve gone without the “Just Do It” campaign. To be iconic, you must start with the basics of building a solid infrastructure.

A Solid Foundation 

The best advice I ever received was starting a business was the easy part. It’s sustaining the company is the hard part. That information has served me well throughout the years. Even to this day, you can find thousands upon thousands of books and resources on how to start a business, but not so much on how to scale and evolve a business. Throughout the years, I’ve learned the key to a successful business has a lot to do with the foundation and leadership.

The foundation starts with the actual reason why someone becomes an entrepreneur, which is to solve a problem. In the business world, we call this a value proposition. The leader solves this problem with a strategy of using resources and people. In short, he or she has started a business and continued to provide the value proposition to the world.

In other words, you have a solution to a problem.

COVID-19 has shown the world a new crop of businesses taking advantage of us being home, so with stuck using technology. Unfortunately, not all companies wanted to use technology and they’re paying the price.

Have a great idea started with an unsolved problem.

If you believe you have the next best idea to solve a problem, this journey is for you.

You’re ready to be an entrepreneur.

I write this because my business is personal because this service is for the advancement of all humanity. My failures and successes are for your gain. No strings attached.

Nathan A. Webster, MBA
 Marketing Consultant & Marketing Professor
 Consulting | Marketing | Websites


Author: nathanwebster
From a US Marine to nonprofit executive director, I've been fortunate to do a lot of stuff. My quick history is I’m a brand marketer with a background in social good. In the process of running a small educational nonprofit, I learned the value of storytelling and digital branding. That’s how I got involve in marketing, websites, consulting via my podcast as well, and being an adjunct business professor at the local community college.