Are You Ready for This? 5 Challenges New Entrepreneurs Must Overcome – And Tips to Help

Unfortunately, we can’t give you all the answers, but we do hope that after reading this article, you’ll understand that it’s okay not to know everything. You just need to start.

If you’re about to or have recently launched a business, you’ve probably asked yourself some of these questions.

  • Am I ready for this?
  • Am I doing it right?
  • Who do I ask for help?
  • Why does everyone else seem to know what they’re doing?
  • Will my business make money?
  • What if I fail?


Fear not, friend, these types of questions are a completely normal part of the entrepreneurship journey. There’s no secret club that keeps all the answers hidden in a private vault. (Not that we know of, anyway… But if you hear about it, we’d love an invitation.)

To help guide you as your build your business, we’ve put together a free Business Launch Checklist that includes 25 things to do before launching. You can get it here.

The list covers some practical steps, but it doesn’t cover all the challenges you’ll face along the way. In this article, we list 5 common challenges all entrepreneurs face and offer some guidance to help you work through them.

Unfortunately, we can’t give you all the answers, but we do hope that after reading this article, you’ll understand that it’s okay not to know everything. You just need to start.


Get Comfortable Being Uncomfortable

We live in a world where answers are at our fingertips. You need something? Google it. Add to cart. Done. You or your kids want to watch or listen to something? Log into your favourite streaming service. We’ve learned to expect results immediately.

When you’re thinking of becoming an entrepreneur, you can’t expect success immediately. Comparing where you are today with where someone is ten years into their journey can stop you in your tracks. And that’s not fair. Every successful entrepreneur started where you are now.

It’s normal to feel uncomfortable when you’re stepping outside your comfort zone. Being uncomfortable is part of the entrepreneurial experience. We’re all learning as we go.

Sarah Blakely, founder of Spanx, famously shares her story of how her dad used to ask her and her brother at the dinner table what they had failed at that week. A week wasn’t fully successful without a failure.



Sarah says, “So many people don’t take risks for fear of failure. Once you redefine that, and realize that the failure is just not trying, then life will open up for you in so many ways.”


If your entrepreneurship journey doesn’t involve any sort of failures, odds are, you’re playing it too safe. When you expect a few “oops” moments here and there, they won’t hold as much power over you. Learn from them – and grow.

You’re more ready for this than you think.


Here are 5 common challenges entrepreneurs face – and some ways to make them a little less stressful.


Challenge 1: Financial Pressure

Financial stress can be heavy. Keeping that in mind, you can reduce some of this stress if you have your personal finances in order before launching your business. You can use our Business Viability Kit to see how much you’ll need to launch your business, then develop a savings or financing plan.

While it’s a romantic idea to quit your job and dive fully into your new business, you may be setting yourself up for added stress. Financial worry can take a lot of joy out of what can be a joyful experience.  Deborah at Izere Coffee worked another job to save up for her first order of coffee beans. Even though it was a lot of work at the time, having a second job empowered her to do what she loves today. You can read her story here.

Make sure you’re taking home enough income to cover your needs and live a life you enjoy before fully relying on the success of your new business. If you’re not sure you’ll be able to pay rent next month, you’ll be making business decisions based on fear, not purpose or vision.

A solid financial foundation will remove the pressure for your business to be profitable on day one. This doesn’t mean you can never quit your other job. As your business grows, revenue becomes more predictable, or your business secures external financing that you can afford to take on, then you can revisit this.

When the time’s right, you can do a jig right into your boss’s office and hand in your resignation letter with confidence.


Challenge 2: Risk Aversion

How risk-averse are you? Do you have financial investments? Where do you fall on those investment quizzes that assess your investment style? Low risk? Moderate? High?

Bottom line – the less risk-averse you are (today), the less likely you will succeed as an entrepreneur (today). And that’s fine!

You can come back to your wild idea during another season of your life. Circumstances change and you change. The level of risk you’re willing to take on is not set in stone for the rest of your life.


“If it scares you, it might be a good thing to try.” – Seth Godin


That said, feeling scared shouldn’t be enough to stop you. If you’re truly excited about your business idea and believe it will bring real value to the world, look yourself in the mirror and tell yourself “I have what it takes!”  Revisit stressor #1 – you don’t need to quit your job today. You can start small and build momentum one day at a time. Even small acts done consistently lead to growth.


Challenge 3: Number Crunching

Number crunching. Few people love it. Every entrepreneur needs to do it. Understanding your business numbers and how they relate to your personal finances is particularly important.

If you’re not a personal budgeter and hate looking at your personal bank account balances, you’ll need to flex that muscle before starting your business.

Invoicing clients, paying the CRA, paying yourself, understanding profitability, and many other financial functions are vital to the survival of your business.

If money and numbers are anxiety-inducing for you, start small by checking your account balances weekly and work yourself up to budgeting your personal finances.

You can use an app like Mint for this. Once you’re feeling more confident, move on to preparing your business financial projections as part of your business plan.

And there’s good news. You don’t have to do all of this on your own. You can hire a bookkeeper or virtual assistant to help with a lot of it. There are a lot of great tools and resources to help you.


Challenge 4: Writing a Business Plan

I know what my business is. Do I really need to write a business plan? No, you don’t need to. But will it help. Abso-darn-lutely.

Creating a lean or comprehensive business plan helps prepare you for entrepreneurship.

Gain a solid understanding of how your potential industry works, who your competitors are, and what the potential pitfalls and opportunities are. You may uncover some exciting ideas during the process!

Even if you’ve started your business, it’s not too late to create a business plan. It can be that roadmap to help you stick to your vision, mission, and goals.


Challenge 5: Facing the Unknowns

There will always be unknowns in business. While we can’t see the future, we can do some forecasting.

Here are a few things you can do before launching to help make uncertainty slightly more palatable.

  • Validate your business idea
  • Market-test your business idea with a focus group or surveys
  • Consider launching with an MVP (minimal viable product)
  • Attend virtual or in-person networking events and practice your pitch
  • Talk to trusted friends and family about your potential venture (avoid asking opinions from negative Nellys or know-it-all Norms)

These ideas can help you address areas you haven’t thought about and get a more accurate answer to the question “am I ready for this?”

Because of the unknowns, many budding entrepreneurs choose to invest in a business coach, an online entrepreneurship course or chase another more profitable income instead of the business idea they’re passionate about.

While each of these approaches can be useful, a word from those who have been there before – be wary of the cycle of bouncing from one coach to another course, and back again. Paralysis by analysis is real. Quit second-guessing yourself. The only way to know if you’re ready is to start.


Final Thoughts

As we finish up, let’s jump back to Sarah Blakely’s advice:  the only failure is not trying.

If you’re passionate about your business idea, are confident that it has the potential to become a viable business, and are willing to fail as you grow, then friend, you’re ready.

We hope this article helps you build your resolve, increase your swagger, and confidently step into entrepreneurship.

Remember to download our free Business Launch Checklist to feel even more confident about your first steps.


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Sarah Gencarelli

Sarah’s an awarded brand strategist, copywriter, instructor, and entrepreneur. Sarah works closely with founders and marketing teams to clarify and amplify brand stories.

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