6 Traits of the Successful Self-Employed

Self-employed restaurant owner
Photo by Flamingo Images / 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% 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). I’ve worked from home since 1991, and for most of those years, I never paid myself a formal salary.

While I’m not Bill Gates, I’m successful and have been for a long time. Perhaps you’d like to join me — self-employment might seem more attractive during a recession, and working from home is certainly more attractive amid a pandemic. Following 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
  • 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: The success story is more afraid of regret than of failure.

Only an idiot isn’t afraid of working his or her 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 several decades: 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 stockbroker, 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 U.S. 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.

4. Pay attention to detail

You’ve got to become comfortable with both numbers and paperwork.

When I talk about embracing numbers, I’m not speaking of simply keeping track of day-to-day expenses. Although that’s important, what’s more important is understanding and studying your cash flow, then experimenting with various ideas to enhance revenue and/or reduce expenses. Often, little changes can mean the difference between making money and losing it.

It’s also critical to stay on top of paperwork, so you’re running the business and the business isn’t running you.

When you start a business, you’re being pulled in multiple directions. It’s easy to become disorganized, then allow bills to go unpaid and obligations to go unmet. If you have a mental block when it comes to numbers, or you’re not the organized type, either get over it or find someone who can fill that role. Unlike quality salespeople, this type of person isn’t so hard to find, or expensive to employ.

It’s tragic to allow an otherwise great business idea to be crippled by a lack of attention to detail.

5. Be willing to keep learning

When I interviewed to become a financial adviser in 1981, I had just passed the CPA exam and considered myself the perfect candidate for a field that was obviously centered around understanding money. Or, so I supposed.

Even after all this time, I can still remember the exact words the branch manager said to me during my first interview: “I’d rather have a used car salesman sitting across the desk from me right now than a CPA.”

Unbeknownst to me at the time, Wall Street investment advisers are primarily asset gatherers — salespeople — not financial analysts. (That’s why I’m not a big fan of that industry.) So, succeeding at that business required learning an entirely new skill set.

When I started regularly appearing on local TV news in 1988, I didn’t know a script from a sound bite. Think it’s embarrassing to screw up as you start a new job? Try doing it in front of 50,000 viewers.

Being an entrepreneur means wearing lots of hats and continually learning new things, often on the fly. And it never ends. Things are always changing, so no matter how big an expert you think you are, in 20 minutes you’re about to be stupid again.

Of course, you can’t know, or even keep up with, everything. I have no idea how a website works or how to edit video. Fortunately, however, I have an engaged and motivated team who are experts at these things and learning more every day.

The point is that you need to be more than just interested in your business; you need to be so obsessed that, try as you might, you can’t stop talking, thinking and learning about it. That will not only allow you to stay ahead, it also will allow you to recognize new opportunities as they arise.

6. Be shopping for your replacement

While there’s nothing wrong with working alone, if you want your company to get bigger, you probably think that somewhere along the line you’ll need to hire people as smart and motivated as you.

Here’s a better idea: Don’t find people as smart as you; find people smarter than you.

Years from now, but not too many, I’ll be retiring. The only way I will possibly be able to do that is by having complete trust and confidence in the people now working with me. I have great writers and brilliant editors; far better than I ever was. I have an enthusiastic marketing manager and a technical team so good I usually can’t understand a word they’re saying.

Building a team, especially a smart, dedicated one, takes time. It is something a new entrepreneur may not be focused on, or at least I wasn’t. Now, however, as I approach anything new, I’m always on the lookout for that person or team who can run my business better than me.

About me

I founded Money Talks News in 1991. I’m a CPA, and have also earned licenses in stocks, commodities, options principal, mutual funds, life insurance, securities supervisor and real estate. If you like what you read here, please share it, then subscribe to our awesome newsletter here. (It only takes a second.)

Disclosure: The information you read here is always objective. However, we sometimes receive compensation when you click links within our stories.

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