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The Top 10 Challenges You’ll Face as a New Entrepreneur

So you are ready to take the plunge into the Entrepreneurial world? You’ve finally seen the light…no more bosses for you…NOPE! So now what? As a new Entrepreneur you will experience obstacles, failures, mistakes, loss of friends, sacrifices....but you will also experience freedom, happiness, purpose, excitement and complete peace. Sounds like a roller coaster aye? Don't worry the universe just wants to see how tough you are.

SN: The weak never survive.

I am saying all this not to scare you but to prepare you.

You have to step out of your comfort zone, get use to feeling very uncomfortable. Be broke for a while. Lose some friends. Have some sleepless nights...Most people either don’t get it or the fall short of their blessing by giving up when the worst happens.

I don’t want that to happen to you so I compiled this list of 10 Challenges you may face as a new Entrepreneur and how to conquer each of them.

1. Choosing the right business

Most businesses fail due to lack of research and preparation. For me as a multi-passionate individual. I had to literally sit myself down and figure out exactly WHO I wanted to help, what SOLUTION I wanted to provide and how I wanted to deliver the information. You must narrow down your niche and write out a specific business plan which includes target audience, social media platforms, products/services, etc. Getting specific with your goal will help you to believe in your business. When you do people will believe in it too, your customers aren’t buying a product, they are buying you.

To help I create 14 Essentials to Building a Brand That Begs to Be Noticed!


This stops so many people from starting. You either choose a side hustle that doesn't require start up costs or use one of the options below to finance your small business.

Here are my top choices:

Fundraise- Host a car wash or community event to get people excited about your brand/organization/mission

Minimize- De-clutter and sell the things you aren’t using

Crowdfunding - Create a manifesto, ask others to support you

Assets - Take a look at the assets you already have and see where you can invest.

Save - Ole Faithful…Plan out how much you will need and refraining from dipping into it.

Notice: I left off Borrow and Loan for a reasons. These may be the easiest ways to obtain money but it is also the easiest way to become buried in debt. Use ONLY as last resort! ( My financial coach would be proud! :))

3.Getting in front of your target audience

I'm sure you've heard of the saying, "If you build it, they will come." Well the saying isn't true in regards to your business. You have outline your target audience and created a product or service that solves one of their problems, but you have to find them where they are, no need to spend hundreds or thousands on advertising, just get out there and connect with people.

Draw people to you. Social Media is an amazing tool for this. Comment meaningful, funny, unique things on your friends pages and leaders who are in a similar niche…usually when you do they’ll want to peek at the things you have going on. Get into forums and connect with people in your niche. Post meaningful and related content on your designated platforms. Get your friends and family on board, they'll be super proud of you wanting to spread the news…can you say FREE marketing.

Keep in mind you have a target audience for a reason. You will not be everyone's cup of tea and that's ok. You shouldn't have to convince someone to work with you and you shouldn't have to go all 'pushy used car salesman' on anyone. This is where Quality over Quantity prevails yet again.

Pushy salesman = buyer's remorse = refund requests = fewer profits = bad reputation = failed business.

4. Quitting your 9 to 5

This is crucial…you need money to survive so to quit your 9 to 5 you must have 1 of 2 things:

a) Have at least 3 - 6 months of expense saved up (recommended; some do more some do less) and a real business plan or

b) if you are already making an income from your entrepreneurial gig and you know you are able to afford to pay bills next month.

I DID NOT take this route I had 2.5 months saved up and was stressing the entire journey. Yah..I was over zealous and truly believed in what I planned to create...But trust me you want to try to have the most stability possible, without it will get you focused on making money rather than having an impact.

5. Stress due to not having a steady paycheck

It can be extremely stressful when you don't know when you will be paid next or if you will even get paid again.

Coming from a stable 9 to 5 where your Direct Deposit hits automatically and you have scheduled bill pay is the direst opposite from the life of an Entrepreneur. The income of a new entrepreneur may literally look like a roller coaster….. You will rubbing two pennies together then solidify a large deal worth 10 grand. I like to call it 'The Test of Flexible Income Adjustment'. Trust...you will be tested.

This is where #4 comes in...make sure you set yourself up for success. Save your pennies and be frugal. You won't be able to sustain a lavish lifestyle and be an entrepreneur at the same time. Sorry ladies….learn how to do your own pedicure and manicure at home.

Also, try to find a side hustle that provides some stability but doesn't take up all you time. Here's an article about 6 Side Businesses You Can Start Without Going Broke.

6. Money Management, legal protection, and taxes

Unfortunately money management wasn't taught in school so this is the one subject that scares a lot of people when becoming an entrepreneur.

Managing your money can be a real burden if you don’t know what you’re doing and if you don’t know when your next paycheck is coming through.

I manage my money in a very simple way – I rarely buy anything. I pay my bills, I buy my food, I pay my gym dues and the rest is for business or for the bank account.

When you’re building your business I recommend you live like a Spartan and don’t haphazardly spend your money. You may very well have some lean times ahead of you and you’ll want some money in the bank to help get you through.

On the other hand, nothing lights a fire like having no money and needing money....


Taxes are a real pain. When you have a 9-5 job they steal, I mean take, taxes from your pay before you even see your paycheck. When you’re an entrepreneur your money comes to you first.

So there are two very important things that you need to do:

  1. Write off everything you can for your business. This will save you a ton of money in taxes.

  2. Pay your taxes. It’s one thing to receive a de-taxed paycheck, it’s another thing to get out your checkbook and write a check to Uncle Sam. But you’ve got to do it, just make sure you’ve written off everything you can and taken every deduction you can.

You’ll keep a lot more of your money by preparing your own taxes rather than letting the tax-man loot you. That’s the easiest, #1 step to making more money. The guy that makes 30k as an entrepreneur takes home a lot more money than the guy who makes 30k as an employee.

The tax-man rips you off, he takes every cent he can. When you’re self-employed you’re in control of your taxes and you use write-offs to keep more of your hard-earned money.

Legal protection

You’ll need to set up your business as a business, not a hobby and not as a sole proprietorship.

I wouldn’t open a business until a) you are making money or b) are absolutely certain of your business.

For American small business owners the best structure is an LLC taxed as an S-Corporation.

*An LLC is a “pass through” tax entity. That means that the LLC itself does not pay tax, you pay tax on the profits you receive. The trick to reducing your tax liability is two-fold: start an LLC but tax it as an S-Corp. Pay yourself a small but reasonable monthly salary and once per quarter you can take out a chunk of the profits as a distribution. You will pay standard tax on your monthly salary but the quarterly S-Corp distribution is not looked at as employee wages so you will not have to pay social security or medicare tax on this distribution amount.

7. Dealing with negative people and self-doubt

You will lose friends….let me repeat that. YOU WILL LOSE FRIENDS!! Being an entrepreneur is tough! You will get criticism from 9to5 lovers and even your friends and family. Unfortunately some people receive pleasure from watching others fail. If you have toxic people in your life always being negative and never supporting you, they are a mental burden on you and stealing the energy you need to build your legacy. Be aware of their tactics and give them the boot. #positivevibesonly.

With money and success comes choice, that means you get to pick and choose who you spend your time with. You are the average of the 5 people you hang out with ..you have no time for those who aren't on your same wavelength. And you don’t have to spend time with go-nowhere nudniks. Make sure you build a strong team that will help you achieve your goals.


Self-doubt is simply a fear of success. It’s hard as hell to be on top of the totem pole but it’s easy to be average. Ladies, let's not be easy…All of us feel self-doubt at one point or another.

When starting my website was discouraged on the number on views my website was getting and BAM! …self-doubt was there to accompany me. They didn't like what I put out…I look stupid in my videos… No one wants to hear about motivation or what is growing from my potatoes…etc. Blah blah blah..Self Doubt.

To overcome your self doubt…Write down a list of your accomplishments…look how far you've came. You have surpassed all the people still dreaming about their goals you are actually in execution phase… and trust me that's a big deal. So many dreams die because people don't execute their goals.

The richest place on Earth is the graveyard.


8. Finding trustworthy business partners, building a reputation

Be careful who you do business with.

It should go without saying, but I’ll say it anyway. Never go into business with scumbags or people who lack integrity. Going into business with a scumbag will not only give you a bad reputation but eventually your whole business will fall apart. Your reputation will waver because of the company you kept.

It can be hard to tell in the beginning if someone is a scumbag, but you will always find out eventually. When you do find out you must instantly dissolve the relationship.

Very valuable lesson: Cut scumbags out of your life forever. No 3 strike policy. One strike, then kick them to the curb. It's not a moral issue, it’s not an ethical issue, it’s an issue of having a clean soul vs having a dirty soul.

If you help people you help yourself. If you hurt people you hurt yourself. You don’t have to be a tooty-fruity save-the-world liberal. Just have integrity and do good to others, especially in business.

9. Dealing with competition

I like to believe there is no competition. We are all created in a unique manner, we all have different talents and abilities not like anyone else in the world. No one can out do YOU, because there is literally NO ONE EXACTLY like you. If you start to compare your success or efforts to someone else... STOP IT. Your journeys are not the same, think of ways you can make your uniqueness shine.

Hundreds of people have tries to be a copycat of someone else work but they never succeeded because they weren't meant to. Stay in your lane, find out who you truly are and how you want to express YOU to the world.

Copying is the path to mediocrity. Pioneering is the path to success

10. Hiring employees

You aren't truly an entrepreneur until you are delegating some the tasks you need to do to run your business. Usually this is one of the last things you do in your business when your workload is too much to handle yourself and you have the revenue to pay your employee(s).

As a business owner you will have the opportunity to create a great company that people want to work for. Your job as an employer is threefold: teacher, motivator, check writer.You aren’t a babysitter or a personal therapist and you should never act like one but there is one easy way you get your employees to be happy, feel like part of the team, and come up with new ideas….

You give them a voice. You listen to them. They are helping to build your company, they want to be a part of something, and they will often have ideas that you would never think of.

As a small business you would be wise to hire freelancers, contractors and virtual assistants rather than hiring traditional employees. Let them take care of their own taxes (they’ll make more money) and it’s less paperwork hassle for you.

It's not easy being a new entrepreneur but make sure you understand what you are getting in to. In the end it will all be worth it!!

If you know any other challenges New Entrepreneurs face, fell free to add to the list by commenting below! Would love to hear from you!

Ask Me Anything - Zipporah Monique

Being on your own out there can feel like a unfocused, failure filled, jumble mess. Been there done that and I wish I had someone to reach out to when I felt like entrepreneurship was kicking my ass.

Well I want to be that person for others. I have tons of experience with finding the right niche that utilizes your passion and purpose, marketing to the CORRECT target audience, building a LEGACY from the bottom up and using psychology to build a begs-to-be-followed brand.

If you have a question or are needing any guidance to reach the next level of such reach out to me for a FREE strategy call.

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