Confessions of an Entrepreneur: We All Need a Lucky Break

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Some people will say that “the harder they work, the luckier they get.” There may be some truth to that old adage. On the other hand, sometimes you just get lucky, and you didn’t really do anything to deserve it. 

Either way, if you become successful, odds are that somewhere along the way you got lucky. I am well-aware that I got lucky, and more than once. I got my first real job at a bike shop at age 12 or 13 because it was one of the few times I ever listened to my father’s advice.  

He told me to go down there and offer to work for free for a month and if they liked me, they could pay me $1 an hour. Instead, they hired me on the spot for $1 an hour and then raised me to $1.25 by the end of the month. I got lucky and from then on had a job working in bike shops that eventually paid me three times what my friends made. 

Good luck runs in my family. My dad was lucky to have survived the landing at Normandy and multiple bouts of hand-to-hand combat in Europe in WWII, and to have gotten his first job in advertising after the war, getting him out of factory work for the rest of his life.

Then he got lucky and married my mom whom he had known and loved since they were little kids on the playground in elementary school. 

My older brother was lucky to have survived being shot at as PT boat crewman in Vietnam, and then later he survived a terrible heart infection he got over there that has 50% death rate. My older sister was lucky to have bought a Chinese artifact for $100 at a yard sale years ago that she eventually sold for millions of dollars at a Sotheby’s auction years later. 

I could go on but won’t. We have good luck. Some of it may be random and some of it isn’t.  

If you feel like you are due for a spate of good luck, here are some things you can do that might increase your odds of experiencing it.

1.  Be born into the right family.

That is pure luck by any means! But it sure helps keep you being lucky. I am, without question, the beneficiary of white privilege. And while I most certainly did not get everything bought for me, I at least had everything I needed. We never went to bed hungry or had tooth problems we couldn’t get fixed at the dentist. We had a nice house and cars that were reliable. I was also fortunate to grow up with parents who expected me to get my college education at a minimum. And they also told me regularly that I could do anything I set my mind to.

Hard to beat that kind of luck. 

2. Get your education.

Sure, you can make a good living if you become a plumber or welder or airplane mechanic, and you don’t need a college degree to do any of them. But don’t you think a lot more doors will open up to you if do get a degree in computer science or business or engineering than if you didn’t?

You can always go be a plumber if you choose to do so.

And what about grad school on top of that? Is it lucky to be 27 and making $150,000 a year or did that MBA increase your odds of getting and keeping that job? Of course it did. Get your education and see if your luck doesn’t improve.

There are so many online programs now and so many different ways to finance it and with the increased flexibility many have in terms of where and when they work, you can probably keep your job while doing so. 

3. Follow the rules.

Pay your bills on time without failure. Don’t drink and drive. Don’t speed in your car. Don’t mix prescription drugs you shouldn’t mix. If you ride a motorcycle or scooter, wear a helmet. File your tax return by the deadline. Balance your checkbook. Do what you are supposed to do in your job on time. If you are a student, go to class and turn in your assignments on time. Wear a mask and maintain your distance from others in a pandemic.

If you follow all the rules that you are supposed to follow, odds are you will have less “bad luck” and overall, your luck is going to improve. 

4. Watch who you associate with.

Who is in your friend circle? Are they smart people? Are they successful? Are they living good lives and doing the right thing? Do they have good luck?

Or are most of your friends people with a lot of problems who probably aren’t doing what they should be on a daily basis?  

Here’s the truth: If you hang out around the right people, odds are your luck will improve. And I am not even going to touch who you pick as your boyfriend or girlfriend or spouse or significant other. A good choice here will most definitely improve your luck!

5. Get really good at doing something.

It’s funny how being really good at doing something improves your luck. You just get more “breaks” when you are.

Of course, most of the time that probably means working hard at it and following the process required to actually excel at doing something. It usually takes time, work and self-discipline to develop a real skill at doing something, at least in my experience.

For example, I have a friend who knows a tremendous amount about antique cars and what they are worth. Not a week goes by he doesn’t seem to be able to find something to buy for a lot less than it’s worth. He makes a half million a year and has a lot of fun doing it. It’s because he knows the value of everything in that world.

Maybe there is some truth to “the harder you work, the luckier you get” after all?

6. Don’t do anything that creates enemies.

What am I talking about? How about posting lots of political stuff on social media that insults and alienates everyone who doesn’t agree with you? That’s a good place to start creating enemies when you live in a polarized society like we do today.

Or how about regularly calling the police on your neighbors? Or gossiping in your workplace? Or going around your boss at work to complain about them to their boss?

I won’t say I never did any of these things myself, but the older I got the more I became aware of the aftermath of doing so and guess what?  My luck improved. 

7. Live in the right place.



Are you living in a place that doesn’t have a lot of air or water pollution? If not, you increase your odds of getting sick. Do you live somewhere that may not be so cool but has a low crime rate? You reduce your odds of being a crime victim if so. Do you live somewhere with a good school system? If so, you increase the odds your kids will be successful in school.

Sure, I know that some of these “good places” to live cost more than some others, but not always. The choices you make about where you live influence your luck. 

So sure. Some things in life are not within our control and that could mean good or bad luck. But many things are — probably more than we may at first realize — and those, too, affect our luck.

How lucky are you? Are you doing everything you can to improve your chances for getting “lucky?”