The Top 10 Biggest Challenges You’ll Face As An Entrepreneur

“Being an entrepreneur is fucking difficult.”

You want to be an entrepreneur?

You want the watches,  girls and laptop on the beach lifestyle? Sorry to break it to you but it doesn’t exist for 99% of people.

Although many BULLSHIT artists, sell their “lifestyle” to you. The reality is they only become rich after you buy their product/

I’m thinking of no one in particular.

… Cough… Tai Lopez.

I used to think being an entrepreneur was all about:

  • $10,000 watches,
  • Swedish girls on yachts
  • Super cars
  • And expensive houses

Which is something more and more people believe because of the BULLSHIT pictures on Instagram. With their username usually involving the word “millionaire.”

The reality is if you want the glamorous lifestyle you have to work.

Because entrepreneurship is not as SEXY as it’s made out to be.

So before you dive right in, make sure you fully understand that this lifestyle requires: hard work, creativity, determination and the self-belief of Mohammad Ali.

That being said I fully encourage you to give it a go.

Just so you’re ready for them here’s 10 struggles you’ll face as an entrepreneur.

1. You need to have a good idea for a business

This is one of the biggest mistakes first time entrepreneurs make.

Your business needs to solve a problem.

This means you have to come up with a solution your solution could be in the form of a product or service.

You can’t just create a business because it sounds cool, or it’s something you would like to do.

If you can’t create a business people are willing to pay for – your business dies.

2. You have to have money to make money.

Many people believe you have you need to somehow finance your big “idea” before you can begin.

But remember ideas are worth fuck all.

To take that idea from your imagination to the real world isn’t entirely free but it certainly isn’t expensive.

If your business is online you’ll need money for web hosting, domain names or initial stock. You’ll also need money to pay your rent, feed your family and not become homeless.

But none of this requires financing or huge loans.

There are two approaches you can take:

You can borrow money or you can bootstrap your business.

If you’re a new entrepreneur – you should AVOID borrowing money at all costs. Borrowing money for first time businesses is how you end up getting your house repossessed.

Instead you should always be bootstrapping your business at least in the beginning, but ideally for as long as possible.

Bootstrapping is simply starting a business with a small amount of money and finding ways to get shit done.

It requires creativity, it can be struggle but ultimately you’ll be infinitely better off.

Because borrowing money before you have a working prototype or your first sale is a recipe for disaster.

Remember you don’t need to have everything perfect straight away, think about Twitter, YouTube, Instagram they all looked terrible when they launched – it’s just more important to actually take action and get the ball rolling.


(Twitter when it first launched – with the much cooler name Twitta.)

Don’t use the bullshit excuse you have to have money to make money, just find a way.

In this day and age, I always recommend an Internet business because of the much lower costs and risks. All you need is a web host, a domain and a way to process payments and bing bada boom you can make some money.

Even using Ebay will let you get a feel for entrepreneurship before you ever have to get a “loan”.

3. Getting people to buy is tough.

People often underestimate this, they think just because they have a website. Just because they have a product. Just because they have a service

People will BUY from them.

This is not true, getting customers is really tough.

You need marketing, referrals, advertising and a KILLER PRODUCT or service.

Don’t expect a free ride.

In the beginning you can rely on friends and family but remember the majority of first time businesses fail.

Understand you need to sell and you’re desperate for cash.

But don’t be pushy, if someone doesn’t want your product move on, don’t hard sell.

It’s much easier to sell to people that have already expressed an interest in your product or service. By all means, make them aware. But don’t beg or try to force them – you’ll just look sleazy.


Focus on the benefits to the customer, have an excellent product or service and find people that want to buy and you’ll be fine.

4. Deciding when to go full time entrepreneur

There’s two mistakes you can make here.

You can commit to being a full time entrepreneur too early

Or you can lose time, energy and money working two jobs.

The people that commit to being a fulltime entrepreneur to early will fail for one big reason. They won’t make enough money to support their lifestyle. Not only will the not make enough money, they probably won’t make any money for at least the first few months.

Especially if you’re going down the CONTENT CREATORS path, don’t be expecting to live off AdSense payments for quite some time.

The only time you should quit your day job and become an entrepreneur is when your business is actually making money.

If you’re leaving because you’re afraid “you’ll miss the opportunity” – be very careful. Are you sure you’re actually going to miss the opportunity? What happens three weeks from now when you have car insurance to pay, will the opportunity still be there?

Your best option is usually to work a day job or at least a part time job, until your business starts to gets some cash flow.

A good rule I live by is it will probably take 10x longer than you think to get the money you need.

Which I didn’t come up it’s from Grant Cardones book 10x rule, basically it’s going to take 10x the amount of time you assume.

So don’t underestimate how hard it is to make it by yourself.

But definitely don’t be put off.

You need to minimize your risk, especially if you have a family to support, but remember you can always live more frugally. Instead of having to save more to support your current lifestyle, you can simply learn to live on a lot less.

  1. The customer is always right

The customer is not always right.

Sometimes the customer is just an idiot.


If you’ve been working in a job for a considerable amount of time, or you run your own business – it’s very likely you’re somewhat of an expert in your business. But some customers seem to forget that.

They’ll harshly demand to see your manager, which is you if you’re an entrepreneur. Or they’ll abuse one of your employees because employees in their eyes are lesser human beings.

These people are ASSHOLES.

“The customer is always right” has some truth behind it, because the customer is the one keeping your business alive.

But I recommend a rather different approach. First off before you follow this advice make sure the customer is WRONG. If the customer is right and you argue you’re an idiot who let their emotions get in the way.

One of the many things working in McDonald’s and Subway taught me is that sometimes people are just looking to argue, and if you take it personally – you’ll become severely negative and hostile.

Regardless if they are right or wrong never take it as a personal attack. The majority of the time these people are just trying to abuse the power they think they have because they’ve been fed the CUSTOMER is always right bullshit all their lives.

If one of your customers does have a problem you should go above and beyond to fix it, this builds trust and loyal customers.

But their is another type of customer that doesn’t have a genuine problem.

In McDonald’s it would be the customers who would eat ¾ of their burger and say it was cold.

In Web Design it’s the clients who do you everything for and then they either change something at the last minute or scream and shout if you don’t add a new feature they’ve never mentioned for free at the end.

These customers are the customers that try to abuse the “customer is always right mantra.”

Sometimes it’s ok to just give into their demands if it’s small.

Other times you need to take action and ensure you NEVER work with this customer again.

If someone is rude or disrespectful to one of your employees or yourself for no reason, don’t give into the terrorist’s demands.

Instead think of the following things.

Is the person in the process of buying or have they bought items in the past? If they’re a regular customer and you can’t afford to lose them, just let them vent. Then apologize to the member of staff that had to deal with them – focus on the lifetime value of these clients.

But remember  20% of your customers account for 80% of your sales – so if a customer is being troublesome for the sake of trying to abuse your nice nature, simply  say – “Thank you anyway, but we don’t think we’re a suitable business to meet your needs, have a nice day” and don’t sell them their product or service.

A big realisation for me was that you don’t have to deal with these types of people, it’s YOUR business. You can choose your customers. Obviously you can’t reject everyone that doesn’t smile, but if someone’s genuinely horrible to work with ask them politely to go elsewhere.

You don’t want to destroy your brand image by humiliating or being cheeky back, just politely decline their business. They probably weren’t going to buy from you anyway.

Just to be clear though this should only be used rarely for the really troublesome customers who you know are a just nightmare, you’ll find your business, employees and you will become a lot happier.

6. Taxes

Taxes are a struggle when you’re an entrepreneur. I just use an accountant so I’m not going to say anything on this matter other than keep your receipts, and deduct every business expense you can.

Take all you can give nothing back. 

7. Dealing with negative people


This has really been getting me down recently, I’ve just noticed that the majority of people I’ve been hanging about are negative.

Which has made a massive shift to my outlook.

A few months ago I was super motivated to work because I was surrounded my motivated people, now I struggle to write a blog post without being anxious or feeling the pressure.

I just want to lie in bed all day –  which is something I never would have said a couple of months ago.

Largely because of the people I’m surrounding myself with.

Having negative people in your life is one of the hardest things to deal with, these people might be your friends, families, or colleagues. But over time they can destroy your ambition, make you feel like shit or even worse make you feel embarrassed to chase your dreams.

They might not do this consciously, often it’s subconsciously.

Remember you’re the average of the 5 people you hang about with so be sure you’re choosing the right people. Otherwise you’ll slowly warp into a negative person yourself.

This is currently my main focus to find people with similar interests and goals to get me out of this slump.

If you want to be successful, you may have to make some tough decisions and cut some people out of your life – that’s the harsh reality.

8. Dealing with self-doubt

Self-doubt is a KILLER.

It usually creeps in when you face a set-back, or a few bad days in the road.

Your confidence takes a hit and you begin to wonder, “Am I really cut out for this?”


You have two options.

You can push it to the side and hope it goes away or you can address it.

I’m currently in a period of self-doubt over a daily vlog I’ve been trying to do, in an attempt to build my personal brand and connect with my audience, I’ve ran into so many setbacks; technical problems, people talking behind my back because it’s different and not being comfortable in front of a camera. My self belief is not strong at the moment.

This started to affect all my work without me noticing because it happens slowly then BOOM. You don’t want to do anything.

The idea of a 9-5 job looks so damn appealing.

To be honest this is something I struggle with from time to time, because being an Entrepreneur is fucking difficult. Don’t let anyone tell you otherwise.

Recognise that there will be ups – which you should celebrate and that there will be downs which you should recognise as quickly as possible.

When you start to feel that self-doubt creeping in you really need to get to work.

  • You need to focus on your goals to remind yourself why your choosing this uncomfortable lifestyle.
  • Think about what will happen if you stop chasing your dreams.
  • You need to figure out what reason or task is causing your self-doubt. You need to pinpoint it and overcome it.

If a truck is driving towards you and you’re heading for a head on collision, you might experience some self-doubt that you might not survive. You have two options – give in and accept the collision or take the steering wheel and avoid a collision.

Remember self-doubt is usually a fear of something, you’re usually focusing on the worst possible outcome, try to change your perception and focus on the best possible outcome.

It won’t be easy but you can do it.

9. Dealing with loneliness.

Being an entrepreneur can be lonely.

You want success, a better life and freedom. These things are natural desires to you. You hate the thought of doing what everyone else is doing and the idea of working for someone else makes you feel ill.

These are all common symptoms of being an entrepreneur.

Other people think your nuts, you’re a modern day leper to the masses.

Why cant you just get an ordinary job? 

Whats wrong working in a job you hate until you die? 

All questions people will ask when you tell them you’re an entrepreneur, self employed or a business owner.

If other people don’t understand you at least you have staff, the people who you trust with your business.

You hire people to help you, but these people are your employees so you might feel a bit of a disconnect between them. If you’re not careful, you’ll just be the “boss” to them.

You’re the decision maker so you have to separate yourself from the group.

Unless you’ve carefully crafted a network of mentors and other entrepreneurs you can turn too, who else can you talk to about work?

Dave’s an accountant.

Marks a fireman.

Jen works in fast food.

They all work for the boss so their work lives are completely different.

They don’t like how you have to reply to emails late at night, how you have to come into your office at the weekend or how your free time is usually focused on your family.

So you slowly start to drift apart.

Your friends don’t get you, you don’t get along with your co-workers but at least you have your family.

If you’re young and single without a wife or girlfriend maybe you’re family don’t get you or on the opposite side of the coin, your 24/7 hustle could have destroyed your relationship with your wife. So that support network isn’t there. You’re lonely.

This isn’t really spoken about. Because the celebrity entrepreneurs seen to be hanging about with other super successful entrepreneurs. But for the majority of us it’s a lonely solo grind to the top. Until we can get access to a mentor or someone else.


Humans are social animals, so over a few weeks, months or years of this feeling of loneliness can slowly chip away at your happiness – it might even cause depression.

The solution is simple on paper, difficult in real life.

You need more friends and people that are going through similar situations, you need a group of people – that gets you.

The importance of having a support network of mentors and like minded people has been talked about for centuries.

You need to develop your own, and the only way to do that is to reach out to people.

It’s tough but you need to be the one to reach out.

I got into the horrible habit of complaining that I didn’t have people who get me, do you know who’s fault that is.


It was entirely my fault. It’s your job and yours alone to actively seek out people who can prevent loneliness, you need to work hard to build up a network.

This is scary and it requires you talking first.

You have Facebook groups, LinkedIn, blogs all these ways to find people with similar interests to you. So you just need to find them and reach out.

Utilize co-working space so you can be around other entrepreneurs who are running a company.

If it comes to it, get professional help. Don’t think of talking to a professional as weakness, or not feeling like you deserve it because your underselling your problem. Depression is a killer in entrepreneurship and you don’t want to suffer. So get help if  loneliness has got you down.

Loneliness is a lifelong battle it takes time to tackle but it’s far better than the lonely path we’ve all been told entrepreneurship is.

10. Hiring Employees.

You’ll start to find the workload is too much.

So you decide to take the leap and hire an employee.You have some extra cash flow and you know you need extra help, so you decide to take the leap.

  • You might go onto a freelancing website and look for a personal assistant.
  • Someone cheap straight out of college just to give you a helping hand.
  • Or someone to do something you literally have no idea about.

The best thing is the choice is yours you can choose exactly who you want to work with.

You’re the employer, the decision maker, the motivator and the wage payer.

It can be kind of daunting. Who do you know who’s best? Who’s trustworthy? Who actually has the qualifications they say they have? When’s the right time to hire?

So many questions…

Hiring employees will always be a challenge.

This could be an entire blog post in itself so instead I’ll make some recommendations,

It’s 2016 if you’re a small business you should be hiring location independent freelancers, they’ll handle their own tax, theirs more flexibility and less paperwork.

Obviously, there is downsides to this, but you’ll be able to find a higher quality worker, that only gets paid to work and if you find a good one (more difficult than it sounds) they could really help your business.

You’ll have to deal with employee complaints – mostly about pay. No employee ever thinks they get paid enough. Your job is to make sure they get paid what you told them they would be paid. There’s a lot of pressure that comes with the idea of having to support someones livelihood, but use that as a motivation and something to be proud off.

That’s the ten biggest challenges I could think off, there are countless more but that’s part of the fun, the struggle and ultimately the bumpy road to success – overcoming the many challenges you will face.

If you’re already an entrepreneur or your planning to be one you’ve earned my utmost respect. You’re in for one hell of a ride.

What do you think is the biggest challenge an entrepreneur faces? Let me know in the comments.

If you prefer you can subscribe to my YouTube channels and watch the YouTube videos, if you’re getting a bit fed up with this whole reading thing.

If you haven’t taken the leap to becoming an entrepreneur because you can’t think of a profitable idea, take my free 5 day course and I’ll show you how you can start your own profitable side business.

Rich Young Adult Reece Kidd


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