It’s Friday, the end of another tediously-long work week, working for a person or a company you don’t particularly believe in, doing work that doesn’t inspire you. You find yourself, once again, day dreaming about the possibility of becoming an entrepreneur, working for yourself, making way more money than you could at a 9 to 5 job, and having the freedom and flexibility you’ve always wanted. You’ve got a great idea, or perhaps several great ideas, and you’re incredibly close to walking into your boss’ office to quit your job and embrace the life of the solo-preneur.

Excellent idea! Nothing beats the entrepreneurial lifestyle. Before you make the leap though, consider these ten challenges of being an entrepreneur.

1. You will be your business.

Every single aspect of your business is a direct reflection of you.

You will have to confront your own demons. If you don’t believe in your dream, if you aren’t highly motivated, if you have a tendency to self-sabotage, or if your business idea is completely misaligned to who you are as a person, then all of that will be reflected in your business. You won’t succeed. You are the creator of your own destiny. How you function will be how your business functions.

On the flip side, you will be your business when it’s successful! All aspects of your business will be a direct reflection of your success. And you are fantastic, sans demons.

2. You will have to know yourself to know your business.

Why? Because (see above) every aspect of your business is a direct reflection of you. If you don’t know who you are, what motivates you, crushes you, inspires you, and what your strengths and weaknesses are then you aren’t really serving yourself in your own life, and you certainly aren’t being of service to your own business.

If you hate direct sales and love bookkeeping, then know that about yourself, and get the support you need so that sales will still get done in your business and you won’t hide behind the auspices of bookkeeping. If you know you only function on deadline, start creating daily deadlines for yourself. Know how you work, how you don’t work, and figure out how to maximize your potential and either learn how to do what you can’t do, or hire out what you can’t or won’t do.

3. You will not be your own boss.

You being the Founder, CEO and President of your own company means nothing, because you will also hold every other title. You generate the trash and you take out the trash. Your real boss is your customer (and your technology). They call the shots, and you must figure out how to respond to their wants and needs…all the time.

Once you have customers, it can be liberating to respond to their needs rather than just build the infrastructure of your business. They will be your customers, investing in you and your products!

4. You will miss having a steady paycheck.

And you will not initially be the highest paid person in your business. Most likely your tech support will be. Unless you choose to be your own tech support to “save money,” which will actually cost you money because you will spend hours every single day working on your website, auto responder, social media, SEO, and other tech savvy ways of reaching out to customers. Entrepreneurs spend the majority of their business day building and managing the infrastructure of their businesses.

You will not be the first paid: your infrastructure will.

These hours will accrue on top of all of the hours you will spend developing content for your business, marketing, networking, bookkeeping. In other words, the work-life balance which you managed to have in your day job with the steady paycheck will no longer exist.

But all of the hours and all of the money your business earns will be yours to do with as you please. There is no upper management taking a cut of profits because you are now upper management.

5. You will be frustrated by everything.

Everything will take twice as long…if it even happens. What seems easy on paper (launch a new website) can take weeks or even months if it’s at all complicated, or if it includes a shopping cart of available products. Writing marketing copy takes twice as long and you will find yourself frustrated by blank pages, customers who need any explanation or sales pitch, as well as the whole marketing industry.

But the end result is that you will become an expert in technology, website design, marketing and sales, bookkeeping, product development, copywriting, networking, and business acumen. You will become an expert in these areas when you push past your frustration and stick with it.

6. You will be frustrated by everyone.

Your friends and family won’t get what you are doing and might not even won’t support you. Your customers (if any) will frustrate you. Your virtual assistant, web guy, bank manager, and any and all sales representatives will piss you off. Nothing will move at the pace you will like it to, and everyone in your life who is not an entrepreneur will annoy you, irritate you, and cause you to stop answering your phone.

Plus, the majority of people you interact with will not believe in your vision, and will nitpick it apart until you start doubting your own abilities and ideas.

But when your dream actually happens, when that first customer pays for your service or product, you will have proved everyone else wrong. And, more importantly, you will have believed in the most important person in your life–you.

7. Self doubt will become your new best friend.

…and your bed will be your constant companion.

Seriously, if you are in bed reading this article, the most practical advice I can give you is to get out of bed. Find a different dedicated space to work from.

Self doubt is normal and natural in entrepreneurs, sometimes as familiar to us as breathing air. That does not mean that self doubt gets to be the master. Figure out what you need to move through self doubt–a team of trusted advisors, a mantra you say to yourself when you start doubting, therapy, a time out. The more frequently you are able to move through self doubt the less hold it has on you.

8. Your first iteration of your business will be wrong.

Sorry folks, I didn’t believe that either. That was until I reworked my business just two months in, and then four months after that. Defining your business is like a dance between yourself, your belief in yourself, and your customers. The more you understand yourself and your customers the more your business will be reshaped to reflect the best of who you are and the deepest needs of your clients.

The more you allow the dance to happen, as a natural course of events, the better your business will be.

9. You will not be all things to all people.

You have to buckle down and create a niche. The more watered down your business, the less successful you will be.

Trying to be all things to all people doesn’t work and comes off as a flaky business strategy. This can annoy you and your customers, as neither of you will really understand what the business is about. Being all things doesn’t serve you or your customers. If you don’t know what you’re selling and who you’re selling to, how will the customers know they need to buy it?

Stop trying to be everything. Your success lies in specificity.

10. You will become an expert on all aspects of your business, whether you like it or not.

This point deserves repeating. One of the most rewarding parts of being an entrepreneur is in how fast you become an expert in all aspects of running a business. It can be a painful process: like learning to ride a bike, drive a car, and do multiplication tables all while having your teeth extracted (I’m not exaggerating). But then, on the other side, you are a wealth of knowledge and information about small business! It is an empowering feeling to understand your own business inside and out.

Still think you want to be an entrepreneur, even after reading this? Excellent–you may have what it takes! Believe in yourself, take a calculated leap, and fly. I believe in you.

Featured photo credit: Macbook Pro Keyboard Detail/Viktor Hanacek via

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