Top Challenges Entrepreneurs Face When Starting a Business and How to Overcome Them

March 5, 2021

It’s a huge leap of faith, this whole entrepreneur thing. The first step is abandoning another career. It can feel like saying goodbye to an old friend. Or maybe it was more like getting out of an abusive relationship. But the rollercoaster ride doesn’t stop there. Here are the top challenges entrepreneurs face when starting a business and how to overcome them.

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challenges entrepreneurs face when starting a business

It’s a huge leap of faith, this whole entrepreneur thing. The first step is abandoning another career. It can feel like saying goodbye to an old friend. Or maybe it was more like getting out of an abusive relationship. But the rollercoaster ride doesn’t stop there. Here are the top challenges entrepreneurs face when starting a business and how to overcome them. 

The first challenge entrepreneurs face when starting a business: Choosing what to sell

Hey, if we knew exactly what everyone wanted and would pay for, we’d be rolling in dough, amirite? This is a big challenge entrepreneurs face when starting a business. What’s gonna sell, and will you earn a living doing selling it.  

Let’s skip all the guessing games and go straight to the source — a freelance researcher. 

Identify the field or industry your business is in, and then get a freelance researcher to mine for gold. With their expertise, you can find out which niches to explore, their profit margins, and get a complete SWOT analysis: 

  • Strengths
  • Weaknesses
  • Opportunities
  • Threats

Figuring Out a Marketing Strategy and Finding Customers

There are so many ways to get your offerings in front of the right people. You’ve got inbound and outbound marketing, digital marketing, traditional print marketing, and so much more. But that’s not all. How do you fit them all together into a cohesive, effective strategy?

Here’s the key to creating an airtight marketing strategy and finding customers: 

Who is your audience? Where are they hanging out? How does your value proposition align with what they need and are looking for?

If you haven’t already, get my free guide to optimizing your social media profiles. This will make it much easier to market your offerings and get them in front of the people who want them. 

Waiting and Self-doubt

Results are typically tardy to the party, and they take some time to show up. This doesn’t mean your business is doomed to fail. When I first started my business, it took almost nine months to get the cash flowing. And it began with a trickle.  

When you’ve worked so hard at your business, and the take-off is slow going, the self-doubt starts creeping in. 

Did I quit my 9-5 too soon? Will I never make enough to replace my income? Will my kids hate me and my cat run away?

All right, first of all, the answers are no, no, and no. The self-doubt you’re feeling is something that practically all of us entrepreneurs face when we’re in the early stages of a business venture. It’s natural to feel like this, but it’s not helpful. 

When self-doubt strikes, let’s take a trip down memory lane. 

What first drove you to become an entrepreneur? What are you passionate about? Think about all the times you hated working for a boss. Remember the excitement you felt the first time you ever sold something? 

Concentrate on the good stuff, the stuff that drove you to start a business. 

I know it’s hard to be patient and positive when the bills are coming in, and your kids need new shoes. But trust in the process. If you keep working hard and working smart, you’ll start replacing your old income. This brings me to my next point. 

The trifecta of challenges entrepreneurs face when starting a business: Cash flow, inconsistent income, and late payments

Getting the cash flowing is one thing. Managing that cash flow is a whole other ball game. If you’re struggling to pay your business bills, you’re not alone. 

Many new entrepreneurs hit this roadblock and have a tough time paying the bills, let alone paying themselves while they wait for the invoices to clear. So, what to do?

You’ve got to keep your business expenses separate from your personal expenses. Not only will this protect your cash flow, but it will also make tax prep and filing a lot easier. 

Budgeting and planning are crucial, but I’ll be honest with you. The budget alone won’t cut it. 

Get tough. Require a downpayment or a retainer for your services. If you bill for weekly recurring work, make the invoice due upon receipt. Doesn’t get paid? Then no more work. But really, just ask for down payments. Saves a lot of trouble. 

What if you’re consistently dealing with late payments? Consider giving people a discount if they pay early. That way, they’ll have an incentive to do it. Late payments get charged a penalty. 

On the flip side, if you have a good relationship with your vendors, ask if they can invoice you every 45 or 60 days. This can help you stay on top of monthly bills and protect your cash flow. 

Time Management When You Wear Many Hats

This is a significant problem for entrepreneurs who wear many hats. If you had more time, you could accomplish it all! It’s kind of like if you had more money, all your problems would go away. 

But here’s the thing about time. Like money, it doesn’t grow on trees. You’ve got to watch your spending and manage it. Getting a handle on your time management will help you strike the work-life balance you need. 

So, do this:

  • Always ask yourself if what you’re doing is the best use of your precious time. 
  • Create a goal list. Start big with the yearly goals. Break them down monthly, then weekly. Finally, break those down into daily goals. 
  • Look at your daily goals. Do they absolutely positively have to be done by you? No? Great, let’s delegate. 

Delegating and Building Your Team

Delegating will free up so much of your time and make things more efficient. A more efficient business will equal greater cash flow in the long run. 

So, what if you’ve delegated in the past, and stuff always got messed up? Well, there are a couple of things you can do to overcome this entrepreneur challenge when starting a business. 

  • You get what you pay for. If you keep going for the cheapest solution or contract work, you’ll get shoddy work, guaranteed. Take the blue pill. Start spending a little more on quality, and you won’t have to redo someone else’s work. 
  • Be specific. Avoid assuming people know precisely what you want or know exactly how to do the things you need. It will take some time, but write down specific instructions. Instead of put the statistics in a spreadsheet and finish it Wednesday, instruct them to list the statistics alphabetically in an Excel spreadsheet and deliver by Wednesday 4 PM EST. 

Paying more for high-quality work and giving your team specific instructions will help them succeed. A consistently high-performing team is going to have better morale and more confidence. By being specific and investing in your team and business, you’re giving them the tools they need to win and deliver great results every time. 

Balancing Perfection, Progress, and Keeping that Ego in Check

Are you a perfectionist? I’m raising my hand right now. When everything has to be just so it gets in the way of progress. Trust me, I know. As a bonafide perfectionist, I’ve had to learn this lesson myself. 

Here’s the thing, friend. Perfect is the enemy of good. You don’t need something to be perfect. In fact, nothing is ever perfect. Ever, okay? Things just need to be good enough and get the job done. Trying to make everything perfect will waste your time. 

We, perfectionists, struggle with letting go so others, who are just as capable, can shine and deliver. Delegate, let go of perfectionism and watch your business thrive and your team morale skyrocket. 

The most painful challenge entrepreneurs face when starting a business: Combating loneliness

When I became an entrepreneur, this was a challenge that I had no idea I’d face. 

Most people are not entrepreneurs. They work a 9-5, and there’s nothing wrong with that. But it’s something that just isn’t for me, you know? I’m sure you can relate. When you’re the only entrepreneur in your peer group, it gets lonely. And quick. 

Most people don’t know what you’re going through. It’s hard to bounce ideas off of people who’ve never been in your shoes. Most can’t relate to your struggles with cash flow, delegation, coming up with a marketing plan, all that jazz. When you’re a visionary, you might struggle with feeling like an odd duck. 

Okay, so what to do? You’ve got to find your tribe. 

Join entrepreneur groups. Reach out to other business owners on social media. Prioritize your closest relationships and make more time for them. It’s in these types of relationships where we feel the most understood, helping combat loneliness. 

Experiencing Business Growth

Business growth sounds like a good thing. And it sure is! But it also presents specific challenges. Grow, and you’ll eventually reach the point where you can’t take on any more work at your current capacity. 

Here’s what you need to do.

Create new processes with a focus on task delegation. You love wearing different hats, I get it. But you’ll need to hang some up if you want to keep your business profitable and productive. If you do everything, you’ll hit the ceiling — a self-imposed one. 

So, be your own best friend and not your worst enemy — breakthrough that ceiling through delegation and take yourself out of the production end. Go into management and on to pure unadulterated and blissful ownership. 

Overcoming Common Challenges you’ll face as an Entrepreneur: Action Steps

Starting a business comes with many challenges. But know this — you’re not alone, and many have traveled this road before you. Me included. I’ve figured out how to overcome these obstacles, grow, and thrive, and I know these tips will help you do the same. 

You’re the builder, the designer, the chief architect of your business. You’re building this gorgeous castle and kingdom to rule over. So, how do you ensure that you’ve got a strong foundation from which to grow?

Marketing, growing, becoming profitable, and building a business you love really boils down to this: 


Get my Branding with Influence Guide. It’s a proven step-by-step process for creating cohesive brand messaging and visuals across multiple channels and platforms. 

Branding is the key, the secret sauce, if you will, to building an audience and marketing your products effectively. Let’s get you on the road to success. 

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