What is the most difficult part of running your own business?

If you have the opportunity to go into business for yourself, I would recommend you do it. It's an experience marked by creativity, ingenuity, and extreme growth. It is one of the most challenging, exciting, rewarding, creative, and scary things you can do in life. At least that was my experience.

If you've never started your own company, your perspective might be colored by some of the romantic notions people have about what it's like. They latch onto the benefits like:

  • You can call the shots as to when and where you work.
  • You won't have to work for The Man.
  • You can pursue your passion.

If you have done it, your perspective might be, shall we say, more precise. For example, I used to describe the freedom over your hours by saying…

“Being in business for yourself means you get to choose which 20 of the 24 hours in a day you want to work.”

Others describe their new boss as quite a demanding taskmaster (to be polite).

Let's just say it's not all fun and games. At best, it can be as exhilarating as I described above; at worst, it can end in complete and utter financial ruin. And even though I would encourage people to venture out, it's certainly not for everybody — and it shouldn't be undertaken without careful planning and consideration.

Investigating the Downside

One of the best ways to make such a decision is to investigate the downside. The more specific you can be about all that is required, the better. If you can tolerate the worst of the worst, it could be a direction worth pursuing.

There are so many challenges in business. But I took to most of the challenges like a duck to water. I loved taking the reins, dealing with customers and employees. But two issues proved particularly difficult for me — marketing and cash flow.

Eventually, I found a way to market my court reporting agency, but cash flow remained a vexing problem until I closed the business after almost 25 years.

Just as it is in personal finance, inadequate cash flow is crippling to a business. In terms of income, you can truly make significant sums if you work hard. The sky is the limit — except there are no safety nets.

At one point, a large, new client put my business into expansion mode. And I learned the hard way how difficult it can be to collect accounts receivables and make payroll at the same time. My savings account was depleted quickly, and it was very difficult to recover from that hit because the cash flow in my business was so erratic.

Share Your Experience

Increasing your income is one of the basic tenets of Get Rich Slowly, but I bet there are a lot of people who have questions about what it's like to be in business for yourself. So I thought it would be neat if the readers would share their experience and advice in the comments about the pitfalls and difficulties of working for yourself.

Are you thinking about starting a new business? What questions do you have about venturing out on your own? What do you think it will be like? If you have been in business for yourself, what advice can you offer?

[We're reaching out to talk to readers about their experiences as a business owner for future articles. Have you had extraordinary success in business or could your experiences help someone else make better choices? We'd love to talk to you. Contact Linda Vergon at [email protected]]

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MeneerEnMevrouw.com
MeneerEnMevrouw.com
4 years ago

Absolutely! It’s one of the best ways to learn, building experiences and to expand your horizon. Still looking for the great idea. Probably something will pop up at the moment we don’t expect it..;)

JSR
JSR
4 years ago

Several months ago, I started a real estate investment business (flipping houses and holding rental property.) I can’t honestly say that I really considered the worst case scenario beforehand. My life was already in “bad case scenario” mode. I was a stay-at-home mother with two kids in school when my husband died unexpectedly. We had savings and were debt-free so I was able to stay at home until my younger child went to college, (very thankful for that!) but I knew then that it was time to earn a living. Without a college degree and with so many years out… Read more »

Bryan@Just One More Year
[email protected] One More Year
4 years ago

I think you touched upon the issues with cash flow and attempting to run a business undercapitalized. Some other things to consider: -Do not expect to be an expert in all areas of your business. Employ or contract for your weaknesses. Examples could include a CPA, your taxes, an attorney, electrician, a plumber, HR, etc. -I may take some time to make a living in your new business. Make sure you have other income to support yourself until the business is viable. -Do not go all in buying all the stuff you think you need for multiple years. Grow organically… Read more »

Hulu
Hulu
4 years ago

For real estate beginners I’d suggest AffordAnything as a good resource. She went from zero property to good cash flow.

If I were starting from scratch I’d flip until I had enough funds to but all that I needed. They are two very different skills. I’ve only bought properties and would advise to pick the states with the best long term prospects. Selling is expensive so start with the end in mind. I wish I never invested in MA vs. states with better laws. It’s costly.

Donna Freedman
Donna Freedman
4 years ago

Time: Never enough of it. Work-life balance: It’s harder to leave the job behind and focus on family/your own needs because work is right there with you. Cash flow: Yep. Record-keeping: Recently a company for which I had been writing contacted me asking why I hadn’t cashed a check for more than $1,200. Um, because the check apparently got lost in the mail — and because somehow I’d spaced the fact that I hadn’t been paid. Now I’ve changed the way I keep track of what’s gone out and what’s come in. Isolation. If you work for yourself at home,… Read more »

Jerome
Jerome
4 years ago

My wife runs a business and it is running well. Most of what is described above rings a bell with us. But in addition there is one thing which drives us nuts: the complex tax-rules once you work for companies outside your own country. From all admin work this is by far the most time-consuming and complex. It is in fact so complex that even the Revenue people have no clue and seem to give random answers if you ask them something. Finding a specialist for help is complex as well as these usually work for large companies and have… Read more »

Laura
Laura
4 years ago
Reply to  Jerome

Well, not to advertise, but Helfer & Co CPAs in Duluth, Georgia (helfercpa.com) have a lot of experience with businesses that do business with companies outside the US, both large businesses as well as small.

Kaye
Kaye
4 years ago

The hardest part for me has been the anxiety. I started a side business because there was something specific I wanted to do, and there was just no other way I was going to be able to do it. I never exactly wanted to be an entreprenuer, and learning things like bookkeeping was tough for me. I spent a lot of time being afraid I was making mistakes. Also, I live in a place where the legalities of starting a business are complicated, as there are state, city and county regulations (and taxes, and licenses) to contend with. I got… Read more »

MoneyFed
MoneyFed
4 years ago

I think managing the espenses wisely is very much required while running a business. That too from day one. How much to invest, how much in infrastructure, what should be running stock, calculating profit margin isn’t a kids play. It becomes more difficult and confusing when you are the sole owner.

Marleigh
Marleigh
4 years ago

For me it has been trying to stay organized. I am not into too many software programs and prefer still using checkbook ledgers and spreadsheets and Microsoft Money ledger to track the business’ expenses and income. I know it’s antiquated but that’s more comfortable for me than anything else. My receipts are awful though. I need to get back to organizing them in envelopes and storing them somewhere and keeping everything together either per quarter or per year. It just gets overwhelming sometimes. Also for me just learning how to embrace new ideas for the business or a different way… Read more »

Jordan
Jordan
4 years ago

Some great points here! Running a business can be very rewarding – but that doesn’t mean it’s going to be easy. Thanks for sharing your thoughts.

Mike Gauthier
Mike Gauthier
4 years ago

I’ve been wanting to start my own business for several years now. I know it will to be difficult. I have no problem with the hours and the pain and suffering that comes with getting a business off the ground. I look forward to the many things I’ll have to figure out, learn on the fly, and worry over. I’m even happy with failure because I will at least have tried. I haven’t yet because I don’t know if I can put my family through it or if they could deal with it. Reading posts like this really get the… Read more »

Reed
Reed
4 years ago

Time is a challenge. Seem like you are always working. Unpredictable revenue can also be a worry.

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