3 Common Challenges New Business Owners Make & How to Overcome Them


If you had to ask business owners, collectively, to agree on what were the top 3 challenges faced when starting their self-employment journey, it would be next to impossible. It’s safe to say that each of our paths is as unique as a fingerprint or a snowflake. Who we are, where we came from, our educational background, on-the-job experience, financial stability, family support, and probably at least 1000 other factors all play a major role in determining where we excel and where we might have more weaknesses. Therefore, I can only speculate about what others see as their top 3 challenges compared to my own struggles.

My experience as owner and operator of a full-service marketing and web design firm for over ten years has taught me a great deal about customers, target markets, selling anything, and about my own personal strengths and weaknesses. I’ve worked with close to 200 business owners during this time and have learned a great deal about how other people run their business.

One of the biggest lessons I’ve learned thus far, for any business owner, is to embrace who you are and let that be the “torch that guides you” through your self-employment journey. In Romeo & Juliet, William Shakespeare wrote, “a rose by any other name would smell as sweet.” He’s saying that what matters most is who you are at your core, not your title, name, or job description. I know at my core, I was born to be self-employed. From an early age I was extremely independent and have always led instead of followed.

Instead of discussing my top three challenges it makes more sense that I focus on challenges I see most would-be business owners facing. And, often these are overlooked or not given the importance that they deserve. If you do not take the time to embrace each of these challenges your chances of success are most certainly slim to none. The good news is, there are measurable and actionable steps you can take to minimize their negative impact or avoid them entirely.

Challenge #1: No Point of Reference or Guidance

Growing up in a household where my mother and father were business owners, I think I got a real sense of what it took to truly become my own boss. My father opened his commercial printing company the year prior to my birth. I was born into self-employment and remained exposed to it ever since.

Anyone who has spent time around a successful business owner or even someone who just “freelances” or does contract work, more often than not it seems they have a much greater work ethic and drive to accomplish something than those who settle for working a typical 9-5 shift for the rest of their working lives. The greater number of business owners today are in fact small business owners or sole proprietors which is often why they seem inundated with work on a regular basis. Running a business and servicing customers at the same time is most definitely a juggling act.

While, my father did have employees, he certainly has kept his plate full with as much as possible so that he did not have to hire unnecessary help. By watching him and the ups and downs of the business, I had a clear understanding of what to expect in terms of effort, desire, and commitment to building something from nothing. Not many self-employed or aspiring business owners can say they’ve had such a powerful point of reference throughout their life.

Not having a guiding light or reference point for many aspiring business owners is a huge challenge. In today’s information age, however, I find that to be more of an excuse than a true challenge. Why? Well, because there are thousands…. I mean thousands of resources out there which can help you in any stage of your self-employment journey. From blogs to podcasts, to local groups and organizations, to social networks, life and business coaches and much more.

Most of these resources you can find for free or at minimal cost as well. No man is an island. Never forget we are all part of a larger society and aspiring business owners especially need to learn to not be afraid to ask for help! This is something I did not learn early on and it hurt me and the business several times over. Even growing up with business owners and having people in my life I could easily tap into for advice, I did not do this as often as I should have.

Business owners (especially entrepreneurial business groups and networks) are some of the most generous people you can meet and usually it’s because they were right where you were at one point so a little empathy goes a long way! Take the time to reach out locally as well as over the internet to as many groups and like-minded individuals as you can. I’ve embraced this more and more the older I get and nary a week goes by that I’m not tapping into several business groups with questions, concerns, or ideas to see if they are worthy.

Challenge #2: Blindly Creating Business Ideas, Products, or Services

One of the easiest things any aspiring business owner can do is research. The second easiest thing to do is plan.

How many business owners take the time to truly get to know about their target market or if their business idea is attractive to any sustainable market group(s)?

My best guess would be 9 out of 10 businesses never plan and certainly never do any research. Why am I so pessimistic? Well, first and foremost, statistics show that 8 out of 10 businesses do in fact fail within 18 months or less. And out of the businesses that make it past 18 months 50% fail within the first 3-4 years. So the correlation between planning and research to this fail rate is awfully close. I say “9 out of ten” never plan because there is probably one occasional business owner who is fortunate enough to fall into something with a built-in market ready to buy without having to research or plan for it. But blind luck or a built-in market will only get you so far. I also say 9 out of 10 because I’ve worked with probably close to 200 business owners in the past decade and the majority of them did no planning or research when starting their businesses.

I’ll be the first to admit I did not research or plan at all when I started my business. So is it hypocritical of me to advise others against this? Absolutely not! Hindsight being 20/20 I would have done a ton of research and made sure I had a rock solid plan in place. My logic at the time, led me to believe there was a market out there for marketing and design services because I was already working in the field and was well aware of what was out there and how to get my foot in the door quickly.

However, this assumption, while working out for me at the time, would not work in 2014 over ten years after I got my start. Times are different. There are a far greater number of vendors (albeit most are highly unprofessional) than there were ten years ago. For one, the global economy has flattened considerably. Customers are not afraid to shop for service providers overseas like they once were. While being a US based company used to be a point of pride, its no longer a “commodity” or “asset” like it once was. For most businesses and customers they will work with whomever, offers the best value for their money regardless of location.

So, research and planning should both be at the top of your list if you are thinking about starting a business. If you think something is a great idea it doesn’t mean it is, and more important, it doesn’t mean it will generate revenue. Take the time to create an actual business plan. There are a ton of resources out there that will help you do this for free and there is even software available to purchase that will guide you through this every step of the way. When creating Steps to Self-Employment, I wanted to do things right this time around. So I planned, I researched, I took the time to create a formal business plan and strategy. For me, that has brought an immense amount of clarity and focus to this new business venture that’s enabled me to take it from just an idea, to a viable online community, business, and resource tool in just over six months.

I made a point earlier about great ideas versus profitability. Take the time to understand what your goals are when starting your business. Do you want to solve a problem for people? Heal a pain and add value to lives? Or do you want to start your business because you are passionate about something and believe others will be passionate too? Sometimes the latter is poor judgment and the wrong reason to start a business. It’s the wrong assumption to make and could mean your idea is emotionally driven instead of thinking in terms of financial stability or gain. It’s also a poor assumption to make that your passions could produce a business idea, service or product that like-minded individuals would want to purchase. Finding a way to be profitable and work within the areas you are passionate about do not always coincide. My recommendation is to not focus on the “what” but the “why.” Why are you choosing this business idea, matters more than the idea itself. Personally I’ve found my greatest satisfaction comes from helping people and adding value to their lives. Building a lucrative business around helping others will help you find happiness long-term with your business. I’m at the point where what I do no longer matters but why I do it, is the reason I get out of bed in the morning.

One final point here. Helping others and adding value to their lives or to their business is more of a mental shift you need to make than a physical one. Some of you might hear “helping others” and think I’m talking about starting a charity or some other organization that gives back. But the reality is, many businesses are already doing this but are simply not embracing it fully. For example, with my marketing firm, I saw myself as a service provider for years, nothing more. And when I felt that way about my business I wasn’t happy. I kept thinking, “What’s the point… this is so self-serving.” It wasn’t until I realized I was a problem solver and I was the one enriching my customer’s lives by helping to grow their businesses, that this concept hit home for me. Ever since remodeling my own perspective and my business model around this concept, I have seen my business growth and profitability climb higher and higher every year.

Challenge #3: Building Endurance & Accepting Failure

Telling someone to “expect the worst and hope for the best” is probably the worst piece of advice you could give an aspiring entrepreneur. What type of message are people sending when they have such a negative outlook? Expect that things will be challenging but if you are expecting the worst, why do it at all? Instead I propose you think about and focus on these two concepts: Endurance and Accepting Failure.

Endurance: the power to withstand pain or hardships; the ability or strength to continue despite fatigue, stress, or other adverse conditions.

Could you even possibly find a more fitting word when describing what it takes to make a business idea a reality? While most successful businesses seemed to have sprung up out of the ground from nowhere, more often than not they spent years building their brand, honing their craft, and creating a network of vendors, partnerships, and connecting with customers who all rely on them to some degree and helped shape their importance within whatever space they operate. This takes time, it takes patience, and it takes the ability to accept and embrace failure.

Failure is a tricky word. I look at failure as a lesson… always teaching us something about what we could be doing better or things we should never do again. Embrace this because if you only make decisions where the likelihood of a positive outcome is extremely high, then you are playing it safe. While that sounds good overall it hinders growth. As a business owner you need to embrace this learning process and grow from it. It never stops and every day I learn something new. As time goes on, failure becomes much less and what once seemed like mountains are now only road bumps on a relatively smooth road.

Final Thoughts

Starting a business and even just making the transition from working for someone else to being your own boss is quite possibly one of the most difficult and challenging events you’ll ever encounter throughout your adult life. Make endurance your greatest ally. If you cannot muster up the strength to persevere than you should start thinking about pursuing another career or… go work for someone else.

Endure through challenges of planning and researching. It will get easier.

Endure through the struggles of getting others to believe what you believe is a viable business idea.

Endure through the building process before and even after you open your doors, launch your product, or advertise your services.

Endure through the bad advice, missed opportunities, blunders, and poor choices you make that will undoubtedly affect your business at some point.

And most important, endure through all that life will throw at you and know that if you are providing value to others and solving the problem of a sustainable market, you can and will be successful.

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