I walked into my office recently and gave my two weeks notice. My bosses assumed I was leaving for another company. When I told them I was leaving to start my own business, they appeared pretty shocked.

Sure, I make some decent side-money from my freelance writing business, but can that and my new “full-time” business be enough to stay afloat?

In surprisingly little time since quitting my job, my mind has shifted from a feeling of liberation to a now semi-constant fear of failure.

Entrepreneurship and the Fear of Failure

It’s no secret that starting a business is risky.  For this reason, gallows humor about entrepreneurial failure is not uncommon. But no matter how big your sense of humor may be, the pitfalls of a start-up business soon become readily apparent.

Here are just some of the issues I have had to contend with, even though my business is a professional office, and currently employs no staff:

Money/Capital – In the early days of a start-up, there’s a lot of money going out the door; and, at least in my case thus far, no money coming in.  Worrying about money when starting a new business is self-explanatory.  After all, I’ve traded in my steady weekly paycheck for an uncertain future.

Timing – When I say timing, I mean how difficult it is to get a business started.  You want to send out announcements, but you can’t do that until you have all your contact information finalized.   You finally decide on Verizon only to learn that they can’t service your telephone line until their strike ends.  And then, when you finally get all that set-up, you realize you still need to officially register as a business, obtain the proper insurance, and start pushing for clients, all the while wondering if you could currently handle any business even if it did come through the door.  (After all, it’s not like the office space is likely even furnished yet)!

Self-Doubt – I can over-think things to the point of absolute self-doubt.  When an entire business is on your shoulders, there is nobody to blame for its failure other than yourself.  I worry sometimes whether I have enough experience in my field to be successful.  I worry if I will be taken seriously because of my age.  I even worry that maybe I’m not all that great at my job–or at least I do in my darkest moments–while laying restless in bed wondering if I just committed career suicide.

It’s All On You – Now that I have my own business–but no staff–it’s up to me to do everything.  I’m the IT, the marketing department, the book-keeper, and the CEO.  This is difficult not just because of the time involved, but also because it requires a multitude of different skills.

In just the past week, I’ve been forced to try my hand at an accounting software, and to make decisions that I would rather not have to think about–like which brand of external hard-drive to buy for the company.

Reinvesting in the Business – Even when money is made, I know I’ll just want to use it to upgrade a part of my business.  Now that I have a “draw” (hopefully), rather than a steady paycheck, hopefully I’ll be able to properly allocate any monies made.  It will also be tough to know when to expand the business.  At what point should I bring on a full-time secretary (or at least a secretary)?  How much money should I reinvest into the business?  These are all difficult questions in need of answers, particularly because every business is different, and thus research will never be perfect.

No Clients (Ever) – Perhaps my biggest fear is that I’ll fail to attract clients.  Perhaps I won’t have even one client.  It’s certainly not unheard of, although I hope to assume that at some point I would get some sort of pity client.

Allocating Time – My final fear of failure is the inability to properly allocate time.  For instance, I might think that blogging about my business is a good use of my time, but it’s also possible that it’s a complete and abject waste of my time.  In some instances, it can take months–if not years–to be absolutely sure of whether a certain business-related activity is a waste of time or not.

I’m always worried that I’m spreading myself too thin, or spending my time on activities that are not as beneficial as others for my business.


I know that fear of failure is something every entrepreneur feels at one point or another.  Provided that the fear isn’t of the paralyzing variety, a healthy dose of fear (at heart, a survival mechanism) might be a good thing.

For better or worse, entrepreneurship and the fear of failure go together like paper plates and barbeque’s.  Any tips on how to control that fear, or use it for good rather than evil, would be really appreciated.



Chris Thomas, owner of the online freelance writing and web-copy company, FreelancePF. Chris’s interest in personal finance stems from leaving grad school with six figures in student loan debt.