Starting a Small Business? 8 Honest Questions To Ask Yourself First

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Last Updated on February 13, 2023 by Treana Wunsch

If you think starting a small business is easy, you’re right. Anyone can start a business. 7-year-old kids start businesses…but do you have what it takes to build a successful business? With a plan, failure is likely. Without a plan, failure is imminent.

If you fail to plan, you're planning to fail.

I was fortunate enough to be involved in an entrepreneurial course which lasted 9 months. They taught us the ins and outs of starting and building a business. Everything, from coming up with the initial idea right down to how to do the bookkeeping. They even supported us through the beginning stages of our startups and the program was supplemented financially. Even with this education and support, it…is…hard.

It is impossible to predict how each individual is going to handle the emotional aspects of running a business. For instance, rejection is an ego killer and you haven’t experienced rejection like you will when you own a business. Also, no matter how much of an introvert you are, if you’re working from home, the isolation will wear on you.

Desire alone will not make you successful. Approximately 150,000 new businesses startup in Canada each year. Almost half fail before their 5th year. This is due to various reasons including financial issues, lack of planning, and poor management decisions just to name a few. 

To increase the odds of your small business becoming successful, you should ask yourself these 8 questions:

Do you know your strengths and weaknesses?

four people sitting around a table with coffee and tablets
Photo by Brooke Cagle on Unsplash

In business, it is often said that you should know your strengths and weaknesses. But what does that actually mean? It means that in order to succeed in a small business, you need to be honest with yourself about what you can and cannot do. You also need to have a clear idea of what you’re good at and what you’re not so good at.

Knowing what you don't know is more useful than being brilliant.

Once you know your strengths and weaknesses, you can start to develop a plan to overcome them. For example, if your weakness is marketing, you might need to hire a marketing specialist to help you out. Or if your weakness is bookkeeping, you might need to find a bookkeeper who can help you keep track of your income and expenses.

Knowing your strengths and weaknesses is critical for small business owners, as it will help them focus their efforts on the things they are good at and delegate the tasks they are not so good at to someone else.

Being self-aware is an incredible trait to have but it’s not so common. In order to run a successful small business, you need to take responsibility for your shortcomings and get support where you need it. Knowing what you don’t know is one of the best attributes to have as a small business owner.

Are you emotionally resilient?

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Photo by Taylor Grote on Unsplash

Small business owners have to wear many hats. They are responsible for the financial stability of their company, as well as its day-to-day operations. This can be a daunting task, especially when times are tough.

Resiliency is knowing that you are the only one that has the power and responsibility to pick yourself up.

That’s why it’s important for small business owners to have emotional resilience. This means being able to cope with stress and setbacks in a healthy way. It’s also important to have a strong support system, both personal and professional.

Friends and family can help provide a shoulder to cry on during tough times, while colleagues can offer advice and support. By developing emotional resilience, small business owners can better handle difficult situations and stay focused on their goals.

Being emotionally resilient means your stress tolerance is higher. Your ‘stress bucket’ isn’t going to overflow at every slight setback. You’ll have the capacity to stay focused on finding solutions rather than spinning out. 

Are you prepared to work more hours?

Did you know, the average employee in Canada works about 37 hours per week? Many small business owners work over 60 hours per week. Business owners take less vacation time, as well. We can see how a small business owner’s schedule would become very high and tight, in order to make the money they need to survive.

As a small business owner, you’re probably juggling a lot of responsibilities. And while it’s important to keep your eye on the bottom line, you also need to make sure that your business is running smoothly. Sometimes that means putting in some extra hours.

You need to be there for your customers. When things are slow, it’s tempting to take a break or head home early. But as the boss, you need to be there for your customers. They may have questions or need help completing a purchase. If you’re not available, they may go somewhere else.

You need to stay on top of things. As the saying goes, time is money. And when you’re working fewer hours, you’re not making as much money as you could be.

Do you love your small business idea?

man sitting at desk with macbook talking on the phone and smiling
Photo by bruce mars on Unsplash

When it comes to starting a small business, you need to have a lot of passion for what you’re doing. If you don’t love your idea, it will be difficult to put in the hard work necessary to make your business successful. When you’re excited about your business, it’s easier to stay motivated and dedicated during the tough times.

Most experts will ask if there is a market for your small business idea. This is important but if you don’t love the idea first, you won’t be able to sell it to anyone and you’ll lack the drive to create a business out of it. If you don’t believe in your business idea, it’s unlikely that anyone else will.

You also need to be passionate about your customers and what you can do for them. Your enthusiasm will show through in your products and services, and customers will appreciate the dedication you have to make them happy.

Finally, be passionate about your team. Your team is one of your most valuable assets, and they will respond better to a leader who is excited about their work and their future.

What is your risk tolerance?

man walking on a wire over a cavern
Photo by Loic Leray on Unsplash

There is always a chance that clients won’t pay or that you’ll become sick or injured and won’t be able to work. Not to mention, almost half of small businesses fail within 5 years is a risk in itself. If you prefer the comfort of job security and not having full responsibility, you may want to consider staying an employee.

Small business owners work hard to make their businesses successful and create jobs. However, in order to be a successful small business owner, you need to have a high-risk tolerance. You need to be able to take risks and make mistakes without fear of failure.

You also need to be able to withstand the ups and downs of running your own business. Small businesses are often feast or famine, so you need to be prepared for both good and bad times. If you don’t have a high-risk tolerance, then you may want to consider staying away from small business ownership.

If that’s not an option for you, you’ll have to work on changing your mindset. There is always going to be a certain level of risk when you’re running your own small business. Having a plan to mitigate those risks is going to go a long way to help you succeed. 

Risk comes from not knowing what you are doing.

What drives you as a small business owner?

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Photo by Blake Wisz on Unsplash

Small businesses are vital to the growth and success of our economy, and they are driven by a number of factors – including passion, creativity, and dedication. However, one factor that should not be driving these businesses is money. Money should not be the sole motivator for starting or running a small business.

Money is an important factor in any business, but it should not be the sole motivator. Small businesses should be driven by a desire to create something new, make a difference, and help their community. Money is important for covering costs and generating profits, but it should not be the focus of a small business.

Focus on the solution, not the problem.

If all you can picture are dollar signs, you’re in for a rude awakening. If you don’t provide value for your customers, they won’t come back and the word will get out that you’re just in it for the money. Focus on the process and how you can help your customers and you’ll be further ahead.

Do you focus on problems or solutions?

It can be easy to get bogged down in the problems you face. Every day, it seems like there are more things to worry about and less time to solve them all. However, if you focus on the problem, you’ll never find a solution. In order to find a way to fix things, you have to turn your focus from the problem itself to how to solve it.

Focus on the solution, not the problem.

This means looking for potential solutions and considering different ways of approaching the issue. It also means being creative and flexible in your thinking so that you can come up with a plan that works for you. When you focus on the problem, all you see is frustration and dead ends. But when you focus on how to solve it, everything becomes an opportunity.

If you are always stuck on problems your small business will never succeed. As a small business owner, you need to find solutions quickly. If you can’t do that, you may want to reconsider starting a small business. 

Are you able to let go?

There will come a time in the life of every small business owner when it becomes necessary to let go. Whether it’s because you’ve outgrown your current space, you’ve hired too many employees and can no longer afford to manage everything yourself, or you’ve simply reached a point where continuing to own and operate your business is no longer feasible or desirable, letting go is an important step.

It can be difficult to take that step, especially if your business is your baby – but it’s crucial to remember that there comes a time for all things to end. Giving yourself permission to let go and move on to the next level can be liberating, and may even lead you to new opportunities.

In order to build a successful small business, you’ll need to delegate tasks at a certain point. Wearing all the hats within your business isn’t sustainable and your business will become stagnate. Not only will it become stagnate, but it will also be impossible to scale.

In order to be successful, you need to delegate tasks to people who are more capable of handling the task. If you wear all of the hats, you will quickly become overwhelmed and stressed. Delegating tasks will free up your time so that you can focus on the bigger picture.  


If these questions have helped you decide you are cut out to be an entrepreneur I couldn’t be happier. There are many, many benefits to starting a small business. I’ll save them for another post.

You also don’t have to do it alone. Surround yourself with experts and a support network and you’ll increase your chances of success. Know when you need help and ask for it. Even if you have a bunch of money saved up to start, write a business plan or have someone help write it for you. Refer to it regularly and update it as needed. It’s a living document and your business will need to be able to adapt to change.

So tell me, do you think you’re cut out to start a business? I’d love to know why you think you are or aren’t and I’ll try to answer any questions you have about starting a small business. Please comment below!


P.S. If you’ve decided to start a small business, download the FREE Starting a Small Business Checklist

FREE Starting a Business


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