How to Overcome Difficulties Your Business May Face

Everyone runs into obstacles, but the way you deal with them will determine whether you trip and fall, or overcome them unscathed.

Nick Bergman
Savanna Post Magazine
9 min readFeb 8, 2023

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overcoming business difficulties

Encountering obstacles is one thing we all have in common. The thing that sets us apart, however, is how we deal with obstacles. Some people allow obstacles to derail them; others have learned to jump the hurdles while running.

The majority of obstacles can be avoided. They are the result of unmanaged emotions, ingrained habits and habitual mistakes we make with other people. Unattended, these obstacles become emotional thieves that we allow into our lives. They steal our focus, sap our mental energy and, sometimes, thwart our most important initiatives. What can we do to close the door on these obstacles so we can capitalize on our opportunities to succeed? You assess, reason and solve them.

Here are 13 problems you’re almost certain to face and how to handle each of them.

1. Leaving Your Current Career

In the early stages of starting a business, it makes sense to operate alongside your current career. This method is a safe bet to avoid losing your stable income, while exploring your entrepreneurial side. But, if you are serious about running your own business there will come a point when it needs to be your top priority. Unfortunately no one is going to tell you when it’s the right time to quit your day job.

Instead, you need to decide when your business venture is promising enough to provide the level of financial support you require. For many business owners this can feel like a risky move. The good news is that leaving jobs is becoming more and more common, and stepping away from your office job will not create a gaping hole on your resume. Instead, if you ever decide to reenter your previous profession, you can simply explain that you started your own business. If you find success in your business venture, you will not think twice about your decision.

2. Listen To Your Gut When It Comes To People

We all have a built-in radar that tells us when we are about to make a mistake involving people. But we often choose not to heed that signal. Research shows that one in four startups fail. One of the major causes is managerial incompetence.

Choosing the right people, especially the right co-founder, is crucial. Some entrepreneurs end up picking a co-founder based on friendship, on having been like-minded buddies working together in the past. In the excitement of starting a new venture, you may ignore the feeling in your gut that tells you the person you are about to pick does not have the managerial competence for this next step. They may lack execution skills, or they may be weak on strategic thinking. Instead of bolstering your weaknesses, they compound them. Don’t let this be an obstacle to your success.

3. Feel Overwhelmed After Making A Mistake

It may sound cliche, but everyone makes mistakes. If you missed out on a business opportunity, skipped a big networking event, or even lost money on a deal: it is okay. The best thing to do is to view each obstacle as a learning opportunity. There is no point in dwelling on negative thoughts that could get in the way of new business opportunities. Instead, refresh your perspective and look for ways to improve in the future.

According to the founder and CEO of Bounce, “fear is not necessarily a detriment as it tempers our decisions, forces us to be more analytical in our decision making, and reinforces how important our business is to us. By viewing fear as a tool and part of the process of conducting business properly, we can not only overcome it but use it to our advantage”.

Today’s most successful entrepreneurs have one thing in common: they are constantly looking for ways to improve. If you are stuck in a rut after a mistake — branch out and look for a way to learn something new. I recommend starting with this list of resources for entrepreneurs, and going from there. Remember, every mistake you make in business can become a learning opportunity.

4. Managing Time

While it may seem like money is constantly in short supply, time is the only thing that will always be limited. Entrepreneurs must make sure their time is spent on the most important tasks, and they must avoid spending time on tasks team members can do. By freeing up this time, they can focus on the bigger-picture issues, such as how to take the company in a direction for growth.

How to overcome it: Be organized and delegate — Identify tasks that can be delegated and then delegate them. Resist the urge to do them yourself because you know you could do it perfectly. Trust your team members — they will surprise you with how much they can get done and how well they can do it. Focus on your own strengths and let others handle everything else.

5. Know The Perils Of Emotional Pricing.

One of the challenges small-business owners often face is having the right pricing strategies for their products and services. Sometimes, our emotions dictate the price we charge. For example, we may fear we will lose the sale and start charging too little, thereby continually lowering our profit margin. This can create insurmountable obstacles down the road.

Emotional pricing can also result from a feeling of pride — what one consultant called “the joy of the hunt”: getting the contract at all costs and feeling good that you beat the competition. On closer analysis, this is a hollow win. Price with your head, not your heart. Know what your costs are, keep your ear to the ground regarding your competition and periodically reevaluate your prices.

If you regularly fail to get a positive answer to your proposals, ask customers for their feedback on your pricing. Many are happy to help, and this can yield some useful information for you on your niche market. All of this will lead you away from emotional pricing into more rational pricing. (If you need help on how to price your products or services, check out the primer on pricing strategies from Oxford Learning Lab.)

6. Know The “Panama Canal” In Your Business.

This idea comes from Julia Pimsleur, who asked 800 entrepreneurs from 30 different countries what is the “Panama Canal” in their business — meaning if you could eliminate one big obstacle in your business that would allow you to grow exponentially, what would it be? (Completion of the Panama Canal saved ships months of travel around Cape Horn and generated billions of trade dollars.)

The number-one answer was “finding and training the right people to grow the business,” and number two was “easier access to capital.” What would your answer be? What is the Panama Canal in your business? Gaining clarity is the first step toward taking some action steps now to prevent the obstacle from obstructing your road to success later.

7. Be Willing To Abandon What Doesn’t Work.

Some products or services you include in the business might not work. We tend to fall in love with our own products and services and find it hard to let something go. It’s almost as if we develop blinders that prevent us from seeing what is very clear to outsiders, but not to us. If you’re going to play the game, you need to know when to fold the cards. As Gary Hamel put it in What Matters Now: How to Win in a World of Relentless Change, Ferocious Competition, and Unstoppable Innovation, “There’s a simple, but oft-neglected lesson. To sustain success, you have to be willing to abandon things that are no longer successful.”

Evaluate what doesn’t work and have the courage to walk away from it before it becomes a major obstacle. The energy you will have released from letting it go will increase your concentration on what works — it will allow you to apply the intensity of a laser focus on the right target.

8. Getting Overworked and Understaffed

Many new business owners struggle with taking on too much responsibility. After all, it can be difficult to assign tasks when you are used to doing everything yourself. It is crucial to learn how to delegate certain work to avoid burnout. Remember: you can’t do everything yourself even if you want to. That being said, building a trustworthy real estate team takes time. Start by researching virtual assistants and look for small tasks you can outsource. At the same time, begin networking in your area to build connections with other real estate professionals. In time, you will be able to build a solid team to work with.

9. Delegating Authority

It’s not good enough to hire a bunch of people — you must properly delegate work and responsibility to them. As an entrepreneur, the temptation is to try to do everything yourself, but this is not productive and will limit your company’s growth. Strike a balance between monitoring the business and trusting others to accomplish objectives.

How to overcome it: Learn to trust — Give your employees clear roles and responsibilities, as well as rewards for meeting certain benchmarks. Make them stakeholders in your company’s success. Avoid micromanaging people and processes. Give people the space to use their talents and only step in for minor course corrections. Be patient with others — and with yourself.

10. Finding capital

Before they even get to worry about cash flow issues, an entrepreneur needs capital to get off the ground. This is one of the most significant problems faced by entrepreneurs, particularly those striking out on their own who aren’t well-connected to angel investors with deep pockets.

Without enough financial resources to start your business, it will be doomed to fail. You will need capital for space, equipment, or to develop and produce your product.

How to overcome it: Be resourceful and aggressive — Just like you must be a good salesman to get customers to buy your product, you must also market yourself and your company to potential investors. Consult with banks and investors in your area, or look to public platforms like Kickstarter. Consider approaching family, friends, and associates seeking investment or for connections to someone who might be willing to invest.

A word of caution on taking money from friends and family, however: That money will affect your relationship if things go south, so be very careful before taking this route.

11. Starting To Forget Your Brand Identity

Building a strong brand identity will take time, and you will need to make improvements when necessary. The most important thing to keep in mind is to stay true to your business’s mission statement. From there — try to be consistent across any platforms or communications that you utilize. Remember, how you do anything is how you do everything. Creating (and maintaining) a strong brand for your business is critical to your future success.

12. Guarding Cash Flow

Cash is always running for entrepreneurs, so you must guard it carefully. It’s a challenge to ensure revenue is consistent and can always cover costs and payroll. The last thing you want to do is start paying employees late because you didn’t plan cash flow properly, which can have ripple effects on the morale of your staff and their trust in your company and leadership.

How to overcome it: Budget and plan — Entrepreneurs need an effective billing system in place and good record-keeping, which is where accounting software can save the day. This software can account for all costs and help entrepreneurs promptly invoice for service and products. Consider working with an accounting professional if you need extra help in this area — it’s that important.

13. Stick To The Knitting.

Simplify and stay focused on what you know, and what you do best. In other words, stick to the knitting. Tom Peters and Robert Waterman coined this phrase in their book, In Search Of Excellence: Lessons From America’s Best Run Companies. As the authors put it long ago, be wary of business diversity. Three decades later, we hear the same message from Scott Heiferman, CEO of Meetup, who says that “startups die of indigestion not starvation.” Don’t layer more onto your business, and stay focused on your core product. If you believe in your product, and you know that it adds value, don’t go looking for the next exciting thing. Take Heiferman’s example as an inspiration: Boring pays.

Have you had to overcome challenges when growing your business? What kind? How did you overcome them and what did you learn? I’d love to learn more. Comment below!

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Nick Bergman
Savanna Post Magazine

Nick Bergman is a writer and business owner who lives in Seattle, WA. He's married to his wife, Rachel, and loves to spend time with his family.