
I have a confession to make:
I'm a pessimist.
A huge pessimist. The sky is falling. The end is near. Anything that can wrong, will go wrong, and at the worst possible moment. Yep, that's me.
I have a near-zero tolerance for financial risk. I've pretty much convinced myself that our economy will remain weak and unpredictable, and probably get worse, over the next few years and decades.
Thus the creation, and ongoing success, of Keeter Consulting is the very definition of the word "ironic."

Entrepreneurs are, of simple necessity, optimists. To be willing to risk one's time, money and sanity on a new business requires a person to believe in the possibility - no, make that probability, even inevitability - of success and of catching more than a few positive breaks as the business grows. It's not a lifestyle for the timid.
So why would I, the most pessimistic, risk-averse person alive today, choose to be self-employed? And not just self-employed, but working to help other people pursue self-employment? Why would I opt to earn my livelihood in an optimist's world?
Actually, that's a pretty good question.
First, a little background on how I got started:
- Risk factor #1, “Will I be able to obtain enough business to sustain my business?” was pretty well addressed from the get-go. Based on my prior work with the CMU IBIE (formerly the CMU LEC) when I was an MRS counselor, they stated their willingness to single-handedly provide me with enough work to keep Keeter Consulting afloat. They already had a decade-old working relationship with MRS to support their ability to do that.
- Risk factor #2: “How will I obtain start-up funds, and what will I do if the business fails?” was also a non-issue. Since CMU's program handled most of the marketing work, my start-up costs amounted to little more than a notebook PC, printer, file cabinet and some business cards. I had very little money tied up in launching the business. That meant that I didn’t need to worry about losing a bunch of money invested in the business, or about having a big loan to pay off.
- Risk factor #3: “Am I actually qualified to do this?” I’d already written several reasonably good business plans, and worked in a home-based, self-directed setting in the past, so there wasn’t much uncertainty in my mind on this point.
In short, it was perhaps the lowest-risk small business start-up in human history save for opening a beer store next to a fraternity house.
Next, there's no denying that I probably feel the anxiety that accompanies launching small businesses more acutely than my optimist colleagues.

However, there's also a lot of value and satisfaction that goes with being a sort of "outsider" working in a world of optimists.
As a pessimist, I'm probably predisposed to overestimate the chances of potential problems occurring, and also of overestimating the severity of those problems should they actually happen.
But I'm also more attuned to identifying potential problems than my optimistic counterparts. I think that lets me help my customers approach their business ventures with a more complete picture of the risks and rewards that they entail. It also helps them to recognize an plan for "show-stopper" events, and to make sure they at least something in place to mitigate the range of less likely or severe developments.
Here's how I "harness the power of pessimism" in a way that reduces the risks of self-employment without scaring myself or my customers so badly that we scrap the whole thing and just curl up in a ball in a corner somewhere:
- Don't risk what you can't afford to lose. Even the most promising business idea, just like the most promising employment opportunity, can fail. Jack Parr, Johny Carson and Jay Leno had each hosted The Tonight Show for literally decades when it was turned over to Conan O'Brien. Who would have imagined that despite managing good ratings, he'd be fired from the show after only a few months? Well, it happened. While Conan's income was never at risk (he was already a multimillionaire), his professional career was, as were the livelihoods of many of his staff who left New York to follow him to L.A..
Pessimist Question #1:
If your business tanks, can you and your family withstand the financial, personal and professional hit you'll take?
Because even when it's highly unlikely, failures can happen. If you know you can survive this, you'll have fewer sleepless nights.

- Of all of the things that could go wrong during your first year of operation, SOME of them will.
Gas prices could go up. Taxes could go up. New competitors could enter the market. Customer needs and preferences could change. Natural disasters, terrorist attacks, trade disputes or labor strikes could disrupt your supply of products or raw materials. You could experience a personal or family health problem or other emergency that disrupts your ability to work. Laws governing how your product or service is made, delivered, or to/from whom it can be sold or provided can change. Technological innovations could make your product/service obsolete (iTunes and iPods killing off CDs and record stores; web services like Orbitz and PriceLine killing off travel agencies).
Will you face a perfect storm where all, or even most, of these catastrophes occur? Of course not. But it's a virtual certainty that one or two of them will happen to some degree during the early stages of your business's existence.
Pessimist Question #2:
In a realistic "worst case scenario," would your business still be able to stay solvent and generate enough income to meet your family's basic needs?
Failing that, would you be able to walk away from you business in a (personally/professionally/financially) tolerable manner? Do you have an exit strategy?
- "Born under a bad sign / If it wasn't for bad luck, I wouldn't have any luck at all."
Pessimist Question #3:
Does your business plan count on a lucky break somewhere during the process?
Because that's just stupid.
If your plan relies of a some law being passed or revoked in a specific time frame, or a bank loaning you a given amount of money when that's a far-from-certain outcome, you've got a recipe for disaster.
"Victorious warriors win first and then go to war, while defeated warriors go to war first and then seek to win." - Tsung Tsu (from The Art of War)
The point here is the notion of "We'll cross that bridge when we come to it" or "I'm sure some opportunity will present itself" is the Achilles Heel of the optimist's mindset. By all means, hope for the best, but always plan for the worst.
In the end, let your optimism open your mind to the possibilities that surround you. There's tremendous creative energy you can tap into with your can-do attitude.
Let your pessimism help you to spot, and plan for, potential pitfalls.
But don't stop there. Finally and most importantly, let your pessimism and optimism serve as checks and balances on one another to make sure that you're progressing "eyes open" with full awareness of the risks as well of the rewards.
You wouldn't be an entrepreneur if you weren't already leveraging your optimism. Now harness the power of pessimism. It will increase your chances of success, improve your profitability, and most ironically of all, it will help you to sleep better at night.
Bottom Line:
It can't be done.
Now go out and do it!
Other impossible things:
