worst day as an entrepreneur


A day in the life of an entrepreneur is different than most professionals working for a company. A normal day for us starts early and ends late. When Nathan and Connor launched their first product, they knew it wasn’t going to be a walk in the park. And they had experienced bad days. 

But when FreeeUp co-founder Nathan had no idea how bad it could get until his worst day as an entrepreneur came. His experiences will help you understand what matters when your worst day as an entrepreneur comes — how you conquer it and turn every bad day into a positive every time.

Nathan’s Worst Day as an Entrepreneur

FreeeUp CEO, Nathan Hirsch, has been sharing his success story to everyone online and across the country through podcasts and networking events. Starting as an e-commerce entrepreneur back in college, his worst day as an entrepreneur did not discourage him from rising up to where he is now.

Nathan shares with us this turning point in his e-commerce career — his worst day as an entrepreneur.

At 20 years old, he was making millions of dollars from selling baby products on Amazon. When his business was booming, he thought that he could do everything on his own. There had been a lot of long nights and hardly any breaks on weekends. But he powered through the tough startup period.

“Before the gurus, courses, and software, I had successfully done two big things,” says Nathan. 

This college kid had built a strong relationship with a big supplier and hired an all-around manager for his growing Amazon business. With the assurance that these two big things had been successfully set up, he decided to take his first vacation.

worst day as an entrepreneur

Vacation Celebration — or Not

On his first day off of work, he gets 3 phone calls.

  1. His only supplier backed out.
  2. His trusted manager quit.
  3. His identity got stolen and used to file a fake income tax return for $40,000.

Before this worst day as an entrepreneur, Nathan’s accountant had already suggested hiring additional people. However, for Nathan, business had always been great without help. He was willing to do everything every day to earn and keep more money for himself. He thought, “Why get someone else who you have to pay?”

Everything he built from the ground up was crumbling that day. He went from an all-time high celebrating his early success to an all-time low — was this the end of everything?

You know, when you’ve reached the bottom, they say the only way is up. And how you come back from failures is what defines your core as an entrepreneur.

So Nathan decided to move on and build everything back up once again from scratch. It was double the hard work, but being smarter about it this time around, it was definitely worth it.

worst day as an entrepreneur

The Challenges of Entrepreneurship

Did you know that 98% of people are not capable of handling the highs and lows, stress, and pressure of running a business? This is why most opt for a steady paycheck working for somebody else than spearheading a startup.

Entrepreneurs face a lot of problems as early as the pre-launch of their first big product or service. Worst hiring experiences, bad days, and long nights are pretty common for us. Apart from Nathan’s experiences, here are some of the worst problems you can encounter as an entrepreneur.

  • It’s shopping season and there’s a glitch on your website.
  • Your new product was a flop.
  • You start missing orders and get complaints.
  • One of your biggest clients cancelled their contract.
  • Your hard drive crashed and you don’t have a backup.
  • Your financial expenses are not adding up.
  • You’re burned out and don’t have help

A normal day can easily turn into a bad one. There’s a lot that can happen when you’re running a business of your own. The responsibility resides on you as the owner. You can either run from it or turn it around to your advantage.

worst day as an entrepreneur

How To Turn A Bad Day Around

Have you just had your worst day as an entrepreneur?

As they say, “When life gives you lemons, make lemonade.”

Take stock of that experience and what it means. Focus on what you can improve to make yourself and your business stronger.

If it’s a lack of help that’s got you down, for example, partner with a hiring expert to get introduced to the best fits for the tasks you need done.

Did your website just crash and you can’t afford to be offline? Hire a freelance web developer to quickly get it in proper working order without having to worry about paying a monthly salary for website maintenance.

There is always a silver lining to every dark cloud that comes your way. It is up to you to turn a negative experience into a positive one.

Here are a few tips from experts to help you get through your worst day as an entrepreneur:

worst day as an entrepreneur

1.  Pause and reflect.

The moment you receive a piece of bad news, you will tend to express anger and disappointment. It is normal to be in a bad mood, feel hurt, or even cry — but only for a minute.

You need to take a deep breath and reflect on what happened. Gather your thoughts and keep your feelings in check. Take this moment to find peace despite what’s happening around you.

You’ll be surprised to see that at this point, your bad day becomes a little better. It’s a small first step and it really counts.

2.  Refocus your mind.

The key to keeping yourself calm is accepting the truth. Facts will remain facts and it’s best to admit reality rather than focusing on the what ifs and should haves. With the right frame of mind, you can turn your failure into a motivation to create the next big success in your business.

Make every inch of effort to not feel sorry for yourself because of one mistake. It cannot be changed in the past, but with the right attitude now, it can be changed for the future. Be thankful it wasn’t worse. And prepare yourself to stand up and move forward.

worst day as an entrepreneur

3.  Pinpoint the problem.

Finding out the root cause of the problem allows you to think of a solution to prevent it from happening again. Explore the facts and determine what went wrong. 

Take measures to rectify the mistake but be realistic in doing so. Reset your expectations and take into account the current situation your company is in as you come up with steps to solve the problem.

4. Think everything through.

Rekindle your passion for starting this business. You know you will get through this because you believe in your product or service. Before taking action, remember the vision you had for your brand from the beginning.

Do not be afraid of change if it serves you and your business best. Remember that every course of action you take from here on out will make you and your business stronger and help to provide an amazing experience for your customers.

5. Take action.

The next big step in overcoming disappointments is taking action. Failures will remain failures if you don’t start doing something about them.

Whatever you’ve decided to do to turn your worst day as an entrepreneur around, get to work on it right away. It takes but a single concrete action to set the stage and get you started on a new and better path.

worst day as an entrepreneur

Preventive Measures

Maintaining the status quo is simply not enough for a hardworking, driven, and talented entrepreneur. The ultimate goal is to make your brand known, optimize your sales channels, and grow your company. Your worst day as an entrepreneur will come, but it doesn’t have to spell disaster.

There are always preventive measures you can take against recurring problems and issues. Take the following proven methods as examples of how you can thwart the worst and attract the best results.

Outsource to Freelancers

Time is the best gift you can give yourself as a business owner. If you are too busy handling everyday tasks like managing orders, sourcing products, and answering customer complaints, when are you going to develop your next big idea? When are you expanding your operations to cater to the international market? When are you opening your second store?

Let’s face it. We can’t run a business solo. There is too much going on daily at the storefront alone. Furthermore, there are tasks that are beyond our expertise. If you want an efficient way of doing things, leave them in the hands of experts. This prevents the repetitions, back-and-forths, and the waste of your precious time as the business owner.

The advancement of technology has opened up a multitude of resources for entrepreneurs to easily tap into. The growth of the freelance market globally has widened the talent pool that we can tap into. Your business can even be run completely by experts working from different parts of the world.

worst day as an entrepreneur

Tasks to Outsource

Have you experienced struggling with your product descriptions? Or your website crashing during the shopping season? As an entrepreneur, your talent is to find best sellers or create amazing products that solve consumer problems. As a content writer, my work is to create compelling content from product descriptions to blog articles and social media posts. Together, our goal is to attract buyers and increase sales.

You need freelancers to help you with the different aspects of your business. These could be everyday tasks or one-time projects, for instance:

E-Commerce Tasks

If you are an e-commerce entrepreneur, for example, your focus is on your operations. Here are the most common tasks e-store owners delegate to remote experts.

  • Website Design / Store Set Up
  • Product Sourcing
  • Inventory Management
  • Cutting Purchase Orders
  • Order Fulfillment
  • SEO
  • Social Media Management
  • Customer Service
  • General administrative tasks

worst day as an entrepreneur

Creative Business Tasks

For creative entrepreneurs, your selling point is your unique outstanding service. You need creative experts like yourself who will allow your firm to increase capacity to accept more projects. Growing your business means fortifying your client connections and expanding your services.

Check out some of the most common expertise that freelancers can offer for your creative business.

  • General administrative tasks
  • Research & Outreach
  • Website Design & Development
  • Graphic Design
  • Photography & Videography
  • Mobile App Design & Development
  • E-Book Writing
  • Marketing

worst day as an entrepreneur


Developing an organizational structure proves to be efficient for any business owner. As you expand your connections (e.g. clients, suppliers, target market), you also diversify your workforce. This allows continuity in your operations even if, let’s say, one of them turns out to be your worst hiring experience.

First, sort out the tasks that you need help with. Next, hire freelancers to do the work. Now each of the tasks belongs to a section of your business operations. Departmentalization offers clarity of purpose for everyone and helps bring everyone together working towards a common goal.

You will be hiring more than one expert to help you with each major area. Make sure that if you lose one, business operations can continue to move forward smoothly as you look for a replacement.


Entrepreneurs are a busy bunch. We wear all kinds of hats just to keep our business going. When stress catches up on us, or fatigue from long days and longer nights, we make careless mistakes. But that doesn’t mean that our bad decisions can’t be made better.

Let your worst day as an entrepreneur be a good lesson that helps you come out better and move forward with renewed passion and focus.

If hiring is the theme of your worst day as an entrepreneur, you can tap into online resources to solve the problem. Partnering with a hiring expert like FreeeUp is one of the best investments you can make in your business. Schedule a call with FreeeUp CEO Nathan today. He knows what its like and can help you explore how FreeeUp can bring your business to success. When you’re ready to make your first hire, join FreeeUp as one of our valued clients. We can’t wait to have you with us!

Leave a Reply

Your email address will not be published. Required fields are marked *

Name *