6 Traits of the Successful Self-Employed

I've been a successful entrepreneur for 36 years and have been working entirely at home for 27. What to join me? Here's what it takes.

6 Traits of the Successful Self-Employed Photo by Michael C. Gray / Shutterstock.com

When I left my $18,000 a year job as a government auditor in 1981 to work as a stockbroker for a $12,000 starting salary, my friends thought I was nuts. Not only was I taking a giant pay cut, but after a few months of training, the $12,000 salary sank to no salary at all: 100 percent commission.

Five years later, I was making more than $100,000. After 10 years, more than $200,000.

That was my first stint at working for myself. Since then I’ve tried several other business ideas, some disastrous (restaurant/bar), some awesome (this website). But I’ve worked from home for 27 years and haven’t received a salary for 36.

While I’m not Bill Gates, I’m successful and have been for a long time. Would you like to join me? Here are the traits you’ll need.

1. Be more afraid of not trying than trying and losing

Over the years, when I’ve told people I’m self-employed, I’ve heard responses like, “Gee, I wish I could risk going into my own business. I would, if only _____.”

Thoughts that follow “if only” include, but are not limited to: being too old, being too young, having kids, having a scared spouse, not having enough money, having too much debt, not having enough experience, not having the proper education and not having a flexible enough schedule.

While any of these reasons could be true, here’s the difference between the successful entrepreneur and everyone else: They’re more afraid of regret than they are of failure.

Only an idiot isn’t afraid of working their butt off only to lose everything. Failing sucks. I’ve done it multiple times and in spectacular ways. But there’s no chance I’m going to be lying on my death bed wondering what might have happened if only I’d followed through on a compelling idea.

2. Be willing to show up

Every successful business I’ve owned has taken exactly five years to become rewarding. No exceptions.

Five years isn’t a very long time, but you’d think it was an eternity based on what passes for perseverance in most people. They’ll try something for a few weeks — sometimes just a few days — then decide they’re never going to make it, and walk away.

If you try something that turns out to be dumb or you uncover insurmountable problems you didn’t foresee, by all means, cut your losses and move on. But I’ve encountered far too many people who think that the only kind of success is the overnight kind. They think if the world doesn’t instantly beat a path to their door, they must have the wrong mousetrap.

We’ve all seen the news stories about the gal who invents an app and becomes an instant billionaire or the guy who sings on “America’s Got Talent” and goes viral at 17. But here’s reality: Instant success is so rare it’s practically nonexistent. That’s why these exceptions are on the news.

Maybe you’re smarter than me — the bar isn’t high — but working long, hard and consistently is the only way I’ve ever made a dime.

3. Be a salesman

The three businesses I’ve been most successful at over the past 36 years: Wall Street financial adviser, television news personality and online publisher. While these endeavors may sound completely different, they’re all identical in one key respect: They required picking up a phone, calling strangers incessantly and being rejected multiple times every day for years at a time.

When I was a stock broker, I cold-called the entire phone book of a nearby retirement community: more than 10,000 names. (I still cringe when I think of how many dinners I interrupted.)

When I started my own TV news service, I called every news director in the United States multiple times, mailed hundreds of letters and tapes and attended countless news conventions.

From the time I started this website until today, I’ve been calling, visiting, emailing and otherwise reaching out to every influential site I can think of, attempting to persuade them to feature our content so people learn about us.

Here’s an expression I coined years ago that every budding entrepreneur needs to hear: It’s much better to have a super salesman with a mediocre product than the other way around.

No matter how great the idea, it’s not going to sell itself. If you’re not willing or able to sell, find someone who is. Plan on paying them a lot.

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