The 10 Hardest Things About Running a Business

Ask any small business owner what the hardest aspects of running a company are, and you’ll likely get a wide range of answers. Some people aren’t good at money matters, for example, while others don’t know how to delegate. But just about every business owner has, at one time or another, experienced all of the challenges listed here.

What are the toughest things about running a business? Here are ten biggies.

  1. Managing the transition from entrepreneur to business owner — There’s a world of difference between starting a business from scratch and growing an existing operation. Small-business owners must switch gears as they take on marketing, branding, financial management, and other duties. A big challenge is realizing that your responsibilities now apply around the clock vs. 40 hours a week (back when you had a “normal” job).
  2. Being your own boss — In previous positions, you most likely answered to someone else. Now you’re the boss, with responsibility for handling everything related to the business. This means making a total commitment, sometimes at the expense of your personal life (family and friends).
  3. Focusing on the big picture — With so much to do when running a business, it’s easy to get “lost in the swamp” of small details and lose sight of the real goals of your company. The ability to develop a vision for the future is essential for long-term success, even when pressing daily tasks take your eye off the ball.
  4. Learning how to delegate — Not having time for strategic thinking is directly related to many business owners’ inability to delegate tasks they really don’t have time to do themselves. In the startup phase, most entrepreneurs handle everything on their own. Transitioning out of the “if you want something done right, do it yourself” mind-set can be difficult.
  5. Hiring and leading employees — Feeling comfortable enough to delegate requires hiring the right staff for your business. Smart, dedicated workers are what every business needs, but the time and expense involved in the hiring process can be daunting. Even when you recruit the right people, there’s still the challenge of effective leadership. As an employer, you must be able to motivate others, resolve conflicts, delegate efficiently, and stay on top of the messy details involved in working with others.
  6. Staying motivated. You work long hours, including evenings, weekends, and vacations. All of your time, energy, resources, and even your health seem to go into keeping the business alive and kicking. Chances are, there’s no one around to thank you for all this effort. It’s up to you to remain motivated for the challenges — and rewards — ahead.
  7. Making tough decisions. From the time you start the enterprise to the moment you sell it or move on, the decisions you make can involve thousands of dollars and affect the lives of other people. Some decisions will turn out badly; others will move your business to the next level. The experience will likely make you a better person and stronger leader.
  8. Facing risk. Every business venture involves risk. Not everyone has the stomach for this kind of thing — but you wouldn’t have built the business you have today without believing in yourself and your ability to confront and overcome risk.
  9. Balancing work and family. There’s an elusive work-life balance out there, though many small-business owners can’t seem to find it. You build a business in order to enjoy life, but the demands of the enterprise often keep you from doing so. Having the right people in place and knowing how to delegate is often the best answer. (See above.)
  10. Knowing how to handle money. Many business owners don’t have a steady income; with ups and downs in revenue come fluctuations in your personal financial picture. You need to be skilled in sustaining cash flow. Without a strong business plan, you won’t necessarily know where the next dollar is coming from. Bad debts and slow collection are constant issues. Knowing when to spend money for expansion or equipment upgrades also requires skill.

What’s the hardest thing about running your business? Share your thoughts and experiences in the Comments field below.

About Lee Polevoi

Lee Polevoi is an award-winning freelance copywriter and editor and a former Senior Writer for Vistage International, a global membership organization of chief executive officers. He writes frequently on issues and challenges faced by U.S. small businesses.
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Kyle M Brown
Kyle M Brown

Solid list. #3 and #4 are killers if you are not careful. There is a difference between running your business and it running you. These two items are often at the root of the latter.

Maria Marsala
Maria Marsala

There are many book keepers out of work.  While in good times, they charge $30-55 per hour, often you can get one for $20 per hour.  I've met good book keepers who are willing to work for minimum wage because they've been out of work. 


I'm sure you make more than they make an hour.


I have a business background and have run an accounting dept., but don't do all my own QB.  I have a book keeper do the work for me.  I do create invoices.    My book keeper prints reports for me each month.  I look at the reports and that's my picture into my business.  An accountant can go over the book keepers work or often accountants recommend book keepers they work with w ho are good.


Look up SCORE online and make an appointment with a local consultant.   Also get the book Emyth For Contractors. 


A few of my clients have been contractors.  Something doesn't add up that you can't afford an employee or contractor to keep your books, print reports, etc. with your years in business and experience.  Based on what you've written about QB Pros, I'm guessing that your prices are low, you have no niche, ideal clients, or business plan.   Those things will help you run your business better and you'll have money to pay for whomever you need to grow it.


QB Pros spend a lot of time learning their craft and then perfecting it.  They deserve to be paid what they ask.  The question is, are you getting paid what you deserve.  If not, then when you look to hire others, everyone will cost too much.



Make an appointment with that SCORE Rep.  Let them help you out.   I'm unable to provide any additional information for free.  


Best of success in your journey. 




Thank you, for your reply. I have a good amount of work. I have been running my self-owned-run business for 7 years so, it's not a new venture. I have been in my trade for over 25 years. I do not need the Quickbooks program. I have had Quickbooks for 7 years, been through 3 upgrades. I just have not been able to learn it well enough to not be frustrated with it each time I use it (amazing how time leaves you behind!).

As far as the QB "trainer/Advisor" that came to my house, it was obvious she was trying to see WHAT my income was. That really bothered me. Maybe, because she was local and wanted to know how much I was really making in my business, locally. Thats the past, though.

Anyway, how about the lessons I see online, such as on YouTube? I wish I could have a Quickbooks instructor teach me but, around here, they are way too expensive. I think they set their prices based on the belief that EVEYONE in this area is wealthy. 

I do appreciate your input, though. I will look into accounting classes. Thank you, for that. Can you tell me what a SCORE office is? I have not heard of that. YES! I should be doing my trade and not Quickbooks. However, again, I cannot afford, an accountant. 

Thank you, again, for your help. 


My toughest problem is accounting/bookkeeping. I need to learn how to effectively and efficiently use Quickbooks. I can't afford a class on Quickbooks. I tried a Quickbooks " Trainer/Adviser. That was a waste. What I caught her doing was staring at my financial income. I ended the session and, later emailed her my disappointment. She NEVER even responded. I NEED to learn it but, I am a sole proprietor in construction and can't afford it. Can anyone help?

Maria Marsala
Maria Marsala

Excellent List.

To it I'll add my thoughts...

#1.  The shift from JOB to entrepreneur is even more difficult for many. 

#2.  Being your own boss means cleaning up after yourself AND cooking 3 meals a day if you work from home, too.

#3.  A mistake is that either people create a 5 year vision or 1 one.  I recommend 12 months, 10 years and an exit vision.

#4 and 5 involve trusting --- yourself first, and others second.  It also involves giving up control.

#6.  When you love what you do, and you have a plan for growth that you're monitoring, being motivated is made much easier.

#10.  Ask a business owner to create a budget (personal or business)  -- even asking financial professionals, seems to raise the hair on their arms.  Yet, money is such a big part of running a business.




While these points are certainly part of responsibilties of a leader, most of these "struggles" are a result of self-limiting views. Not being able to motivate, delegate, focus etc. are all internal challenges -- internal meaning in the mind. These are all soft skills. Point number 10 seems to be the only tangible "biggie." For leaders and those aspiring to do so, that says a lot about what skills and mindsets need to be shaped.


 @Maria Marsala Thank you, Maria. I believe I have looked at this wrong. I was assuming I needed an accountant 8 hours a day. Maybe, someone to come in once a week may be the best approach.

Thank you, again.

Maria Marsala
Maria Marsala

Just because someone is good in their trade and has much experience doesn't mean they know how to run a business.  These things are two very different things; as many of us have learned.   

Maria Marsala
Maria Marsala


 You need more work.   Sorry to say this but often, especially in the beginning of a business, people need to have part time job -- of any sort -- of any $, , too.  


A good QB Pro will look at your income.  They set up your account based on your business, and every business is different.  They can make suggestions on your expenses, etc.   If you are paranoid because of your income, do something about that part.  


If you can't afford QuickBooks of any sort, you can also buy it on ebay,  look for sales at Costco or Sams, use an excel spreadsheet, etc.


Set up a meeting with your local SCORE office.  They provide free business coaching.  Not as well rounded and not as much support as a business coach, but you'll get some. 


But it sound like to me that you need some accounting classes and knowledge.   Go see what your local library offers as far as books, etc.   See what the local college offers regarding continuing education classes. 


You should not be doing your own QB.  You should be doing your trade and have someone knowledgeable in book keeping -- do that part.




And it sounds like, to me, that you need


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