Reflections of a Hypocritical Business Planner

Irony: I’m a business planner, and I have been for 30 years now; but the biggest decisions of my real life have been remarkably unplanned.

Rewriting history backwards

I could rewrite my own history backwards to make it all seem like it had been planned, but it wasn’t. Going from hippy to business planner to entrepreneur, I tripped over the most important right decisions, accidentally. It was a lot like a shiny metal ball bouncing around in a pinball machine, hitting obstacles and changing directions. Sometimes I made the wrong decisions and got the right results. Go figure.

For example, in college I studied what interested me: Literature. I wasn’t making a career choice, I was taking the path of least resistance. It was an easy step from Literature to Journalism, and — after 10 years with UPI and McGraw-Hill and others — from there to the MBA. And in 30-some years of business I keep meeting people whose careers seem to reconfirm the basic wisdom of studying what interests you. These are people who followed that path of interest and found, later, that it led to the right place.

Bad advice?

All of which could end up as dangerously bad advice, I suppose: if taking the downhill path leads only downhill. Sometimes you have to buckle down and work; but at least, if you’re doing something that interests you, the work feels better. That was certainly my case. I got my first job in journalism in Mexico City, by mail plus a plane trip from Oregon, because I was happy to work cheap and they guessed that since my wife is Mexican I probably spoke Spanish (which wasn’t true until a few months later). There was no planning there; it was a job, in 1971, when jobs were scarce (as they are now). It seemed to prove the wisdom of taking that pinball-like change of direction.

When I sold out

The next time I changed direction it was for the money. I switched to business writing from regular wire-service news journalism after three years of it because my wife and I had two kids by then and with kids, money became an issue. Before that, neither one of us cared that much. Journalism had enjoyed an aura of save the world for a while, but that gets old. That change doubled my income (from very little to a little bit more). I waded slowly and fearfully into business writing with about as much enthusiasm as an ophidiophobe (fear of snakes) wading into a jungle swamp. At first, it was just a sellout; but then it got interesting. I took business classes at night school. I really wanted to know what was going on underneath the press releases, in the numbers, where the truth hides.

So it took me 10 years to get from undergrad studies to business school, but that wasn’t a bad thing. By the time I got there I was — notice the theme here — once again interested in what I was supposed to be studying. I’d had enough of business journalism to want to actually know what I had been writing about (novel idea) and that made business school fascinating. And my years as journalist helped me get through business school while working full-time in consulting. I could write fast, and that’s a good thing in school.

Sometimes bad decisions have good outcomes

I made some very bad decisions that created very good outcomes. In some circles, we call that luck. Later I quit a good job to go on my own writing computer books, but with the help of my wife and my favorite former client, that became business plan consulting. And that — again with the help of my wife and some clients — became business plan software. It seemed like a natural progression. Just as it was critical to write for readers in Journalism, it was even more critical to write for users in software. And all of this changing directions meant that it wasn’t until 1994, 20 years after switching to business writing, 11 years after leaving that good job, that Business Plan Pro was first released.

And, while we’re on the general subject of unanalyzed decisions with good outcomes, doing what you want, in 1969 I asked a girl to marry me after knowing her about two weeks. As of 2023 we’ve been married 53 years. (And we both agree we were lucky. Don’t try this at home. Wait longer.) And at every key moment from literature to journalism to business to entrepreneurship, it was always two of us, never just me. When things were really dicey — like when we realized we had three mortgages and $65K credit card debt in developing Palo Alto Software — it was never “you idiot, what have you done,” but rather “we’ll take the risk together, and if we fail, we’ll fail together.” Knowing that you’re not going to lose a marriage over it makes it a lot easier to change directions.

1987: The Heat, the Kitchen, and Credit Cards

(This is reposted from my blog at

I was furious. This guy had stolen from us, blatantly, by ordering a software product, returning it, getting his money back from us, and then getting his money back from the credit card company.

This was back in the “old days,” the beginnings of Palo Alto Software, when I was the only full-time employee. I knew the guy’s history. He had done the same thing with the previous version, and then he did it again with this version.

So I was furious when I called the credit card merchant services line to get my money back. This guy was stealing from us and the credit card people were empowering him.

I got about five minutes into the call when I finally had to take a breath, which gave the very smart and presumably very well trained woman on the other end of the call a moment edgewise.

“Mr. Berry, can I interrupt you, break your train of thought for just a moment?”

“Okay,” I said, but begrudgingly.

“If your company is going to do business with customers who have credit cards, this is going to happen to you from time to time,” she said, calmly, with a reassuring tone.

“What’s happening is that our biggest problem is credit card fraud, merchants who take customers’ money and skip out. We live and die on our customers trusting us that credit card purchases are safe.”

I was listening. She continued.

“So you have to just think of it as a cost of doing business. We are always going to side with the customer, at the drop of a hat. It comes with the territory.”

And by then, I was getting it. Like the old saying, “if you can’t stand the heat, stay out of the kitchen.”

“So basically,” I asked, “anybody who is prepared to lie to you can take my goods and get them free?”

She hesitated only a few seconds, just the right amount.

“Well, please don’t quote me on that,” she said, “but think about it. Is it worth it to you to take credit cards?”

I thanked her, gave up the issue, and went on to do something else more useful.