By Cliff Ennico

“I was laid off from a corporate job a couple of years ago.

I tried finding another job but there was nothing out there for someone over the age of 50.

A few months ago I learned about a local retail business that was for sale. With the help of a business broker, I made an offer and the seller accepted it. We hired lawyers, prepared documentation, and I got a license from the state for one of the product lines the store was carrying.

We were scheduled to close last week, but I found I just couldn’t go through with it. Nothing seemed wrong with this business, and everyone – including my spouse – told me it was a good thing to do.

But I just froze at the last minute. After years of working in corporations I just couldn’t see myself as a shopkeeper. The risks involved just scared the Hell out of me.

Needless to say, there are a few people mad at me right now. I will forfeit my deposit (10% of the purchase price) and will probably have to pay the broker’s fee. I’m also not sure what the next step of my life will be right now.

What do you think? Am I just being a baby about this? It’s easy to tell someone to ‘man up’ when you don’t have to face the consequences.”

I don’t think this reader is being a “baby,” although I would have counseled him to give in to his fears before putting a significant amount of money at risk as he appears to have done.

At the end of the day, any entrepreneurial venture involves a certain amount of risk. No matter how much research and due diligence you do, no matter how much “tire kicking” you do, no matter how many experts you consult (including me), you never have 100% perfect information before you have to make a “go/no go” decision. If I had to pick the biggest difference between working for yourself and working for an employer, this is it.

I myself know what this reader went through. About 30 years ago I left a large Wall Street law firm and struck out on my own in a solo practice in the wilds of Connecticut. For almost a decade I was accustomed to wearing thousand-dollar suits, riding a train to work each day, having investment bankers return my phone calls, and seeing deals I was working on featured prominently in the Wall Street Journal every day.

I was burned out of working for a large firm, but I was terrified – absolutely terrified – of going off on my own. Would the clients be there? How would I get the word out? How long would it take before I could pay overhead expenses?

More importantly, how would my spouse, parents and other family members look at me? How would they adjust to the fact that Cliff was now a small town attorney working out of the house in his bathrobe, no longer a “master of the universe”?

As it happened, almost all of my fears were unfounded, and I have enjoyed being on my own these past 25 years more than I ever did working on Wall Street.

I think this reader needs a little help from someone in his age group – perhaps a SCORE counselor ( or career coach. The likelihood of someone in his situation finding a corporate job is close to zero, and it doesn’t sound like he’s willing or able to retire. Simply put, he has to find some way to earn a living.

This reader needs to find something to do he is so passionate about that he won’t even feel the fear. In my case my desire to work with entrepreneurs and small business owners, giving them the same level of service I gave the Wall Street investment banks at an affordable price and being part of their success, was what got me over my fear of failure. Being a shopkeeper clearly wasn’t enough for this reader.

A useful trick – if you can psyche yourself into it — is to turn fear from an obstacle into a strength. There have been times in my career when I intentionally took on a project I wasn’t sure I could do, “burning my bridges behind me” so that the only way out was forward. When you commit yourself 100% to something you usually do see solutions to problems that seemed insurmountable when you were contemplating them from a safe distance. But without total immersion in the project you can’t see them.

Find a mountain worth climbing, then start putting one hand over the other until you are too far up to turn back safely. Trust me, the handholds will be there when you need them.

And if you don’t see them right away, the prospect of a 1,000 foot drop will sure as Hell motivate you to find them.

Cliff Ennico ( is a syndicated columnist, author and host of the PBS television series ‘Money Hunt’. This column is no substitute for legal, tax or financial advice, which can be furnished only by a qualified professional licensed in your state. To find out more about Cliff Ennico and other Creators Syndicate writers and cartoonists, visit our Web page at COPYRIGHT 2017 CLIFFORD R. ENNICO. DISTRIBUTED BY CREATORS SYNDICATE, INC.