In 2005 I wrote about what it means to be an entrepreneur and in about an hour came up with a list of 75 characteristics that might mean you’re an entrepreneur. Then I decided to create this section of the blog to add detail to each of those 75 items. Some people have said I should turn this into a book. I’m not sure how to do that yet, but if you’re a publisher feel free to send me a check for $50K and I’ll see what I can do.
This one isn’t on the original list, but I thought it appropriate to add it. Yes, you might be an entrepreneur if you have dreams in which you have dinner with the parents of your contractors. But that’s not even half the story.
Yesterday I was thinking about one of my contractors and thinking “You know, if this contractor…
You might be an entrepreneur if…you’ve felt a sense of relief when an employee has quit because now you don’t have to lay them off.
I remember an SNL skit from about 20 years ago that featured two cruel bosses who made a bet as to who could fire the most employees the fastest as a badge of bossly manliness.…
You might be an entrepreneur if…when someone asks you what you’re doing this weekend you say “Working, of course, just like any other day.”
To weekends you can add holidays, vacations, family reunions, nights, and any other time period, regardless of the location or time of day–I’ve worked them all. Heck, I’ve worked at night on holidays while on a…
You might be an entrepreneur if…without trying you’ve succeeded in convincing all your employees to never try to start their own business.
This isn’t a 100% true statement. I actually do have employees who have left my company to start their own businesses. However, if you include those employees who ran their own businesses prior to working for me and…
You might be an entrepreneur if…you live in an apartment that is smaller than the apartment you lived in when you were a student and had just gotten married.
In the days of our parents the accepted standard of living was quite different than it is today. A couple got married and rented while saving up for a 20% down…
You might be an entrepreneur if…without trying you’ve succeeded in convincing all your employees to never try to start their own business.
After all, for some of you this list along is enough to dissuade you of your entrepreneurial aspirations. But imagine if you had been a first-party witness to such going-ons.
You might be an entrepreneur if…when a life coach tell everyone in the room “Think about what you would do if you had a million dollars in the bank–now go out and do that and don’t worry about the money” you get the impression you’re the only person in history who has actually done this and if the life coach…
You might be an entrepreneur if…you’ve told politicians that you’ll vote for them if they campaign for a 36-hour day.
I really have, but I don’t think he took me seriously.
You might be an entrepreneur if…you’ve slept in your office chair, or possibly a lobby chair (they’re generally more comfortable) overnight.
As an entrepreneur you become an expert on what is the most comfortable object or surface to fall asleep on, other than a bed.
You might be an entrepreneur if…you’re not sure why any of your employees continue working for you.
One of the things I’ve been blessed with over the years, or cursed with depending on how you look at it, is a chain of highly loyal employees. A lot of them have stuck around a lot longer through a lot more than…
You might be an entrepreneur if…your business has brought in more than a million dollars of revenue but you have nothing to show for it personally.
When I was 21 I had a goal to make a million dollars by the time I was 30. I made that goal in a way, in that I owned a business that had…
You might be an entrepreneur if…you’ve slept on the floor of your office more than once.
Heck, I’ve slept on the floor more times than I can remember, although thankfully it’s been a while, plus I work from home now and I’m not so lazy that I can’t make it to the bed.
You might be an entrepreneur if…your wife feels guilty about buying a $9 pair of shoes at Payless even though her shoes are cracked on the bottom and you can see her foot through them.
This happened last winter. I know it was winter because I remember thinking “Her feet have got to be getting cold if she’s got huge…
You might be a shame-faced entrepreneur if…you’ve invited someone to lunch and then asked them to pay for it.
Geez, this is so embarrassing I think I’m repressing the memory and forgetting the details of how it all came about. Kids, don’t do this. I mean, it’s one thing if you forget your wallet, but we actually planned this one…
You might be an entrepreneur if…you’ve taken out loans on both of your cars.
Here’s how it works. “Sweetie, I need to make payroll in two days, and I’m $10K short. Can I make a cash advance on the credit cards?”
“No, they’re all maxed out.”
“What about our personal bank account’s overdraft account?”
“You maxed that out for…
You might be an entrepreneur if…your wife generally attends family functions by herself, even when it’s your family.
Before I dive in, allow me to explain why I haven’t continued writing about this “you might be an entrepreneur if…” topic for a few months. As I’ve mentioned previously, I’m a new man, and as such I’ve been hesitant to…
You might be an entrepreneur if…every time your credit card works in a public place you feel an overwhelming sense of relief.
Of course I’m talking about business credit cards, not personal credit cards. My wife manages our personal finances so those are always in good order. I, however, being of a somewhat riskier nature than my wife, prefer the…
You might be an entrepreneur if…you pay all your bills on the last possible day you can, and you know all those dates by heart for each bill. Here’s a little test, just off the top of my head:
Rent, due on the 1st of each month, but the landlord is pretty lenient and I can usually get away with…
You might be an entrepreneur if…you keep working on your business despite everyone around you telling you it’s a failure and you should just get a real job.
“Have you ever thought about just shutting everything down and going and working for someone else?”
That’s the way people usually phrase it. Oh they mean well, but they don’t understand. I…
You might be an entrepreneur if…you cut your own hair.
I was going to say I don’t think my dad has paid for a haircut since 1949, but I’m not altogether sure he has ever paid for a haircut. I’m positive he hasn’t since I was born. He even installed a large mirror in his bathroom that is on a…
You might be an entrepreneur if…you’ve wondered if there’s any way to rationalize picking up a tobacco company as a client.
There are many types of companies I will never work with, and a tobacco company is just one of them. You can add alcohol, gambling/gaming/lottery, and porn companies as those I would rather than face bankruptcy than do business…
You might be an entrepreneur if…all your friends tell you they wish they had your job, and you tell them you wish you had their’s.
I was visiting with a friend of mine a year or two ago. He had a six or near-six-figure salary, a $650K house that was half paid off, nice cars, a big plasma screen TV,…
You might be an entrepreneur if…you’ve at least considered asking your life insurance agent whether the policy you just took out is still valid if you commit suicide. You know, Jimmy Stewart syndrome.
Ok, first of all, I’m not suicidal. Man, everyone takes things so seriously these days. That’s why I put the line in there referencing It’s a…
You might be an entrepreneur if…you’ve worked multiple Christmas days. And not just Christmas, but every other holiday as well.
There’s a common myth that owning your own business means setting your own hours, making lots of money, taking vacations whenever you want to, etc. The truth is that when you own your own business you are a strange sort…
You might be an entrepreneur if…you’ve had the urge to fill the room with uppercuts when someone says they’re having trouble living on $120,000 per year.
Oh, how I’ve looked forward to writing this post. This is based on an experience I had with a client who was particularly difficult to work with, and who one day, in the course…
You might be an entrepreneur if…you have the desire to choke anyone who says “And you can just write it off as a business expense!”
Apparently 99% of the general population does not understand what “writing off a business expense” means, which is why it qualifies for a humorous exchange between Kramer and Jerry on Seinfeld:
Jerry : So we’re…
You might be an entrepreneur if…you wear the same dress shoes to work every day for five years, despite the fact they are all scraped up and look horrible.
The funny thing about writing these posts is how many of them have improved during the last year. Case in point, I just got new dress shoes after wearing the same…
You might be an entrepreneur if…you’ve moved out of the house you were buying and are renting it because you can’t afford to live in it. But the more interesting part is who we ended up renting our house to and the ensuing chaos. Imagine this: Your renters are a month behind on their payments and you get a call…
You might be an entrepreneur if…you know which restaurants in the area are open until midnight, and which are open after midnight.
By the way, I had a dream last night wherein I was walking around at night and I noticed there were dollar bills all over the place just blowing around on the ground, so I started gathering them…
This hung in the home I grew up in until my dad gave it to me upon my requesting it. I figured I needed it more than he did. I think it’s older than I am because it’s been in our house ever since I can remember.
You might be an entrepreneur if…you hire an accountant and after looking at your books they come in with a frantically worried look on their face and say “You’re going out of business!” and you calmly smile and say “No, that’s just how we’ve been running the business for the past two years, it’s nothing new.”
This is based on…
You might be an entrepreneur if…you can’t afford to shut your business down because if you do you won’t be able to keep up with the debt payments unless you were miraculously able to land a job making $250K per year.
Aside from the question of whether I would do something different if I could (I probably wouldn’t), I don’t…
You might be an entrepreneur if…you spend 90% of your time feeling like a failure but you keep working anyway.
What does persistence have to do with being an entrepreneur? Is it wisdom or foolishness to continue on with something that doesn’t seem to be working out that well? Sometimes you have to know when to fold ‘em,…
TV and I have a love/hate relationship. If I sit down on a Saturday afternoon to watch a few hours of worthless TV, then it’s kind of like eating a half gallon of ice cream in one sitting–momentary satisfaction that turns into a slight case of nausea just prior to more serious regrets due to a feeling of being bloated,…
Good heavens my fingers are sore. I’ve only been golfing once in my life, and I had never been to a driving range until last night. I don’t know if my hands are just out of shape or if I dove into driving with too much relish, but my fingers are incredibly sore this morning. Not the skin, the joints.…
You might be an entrepreneur if…when you see a grown man riding his bike for exercise at 7am when you’re on your way to work you think “How in the world does anyone have time for that?”
Ironically I just started a new exercise regimen and went walking for 50 minutes this morning. But I had to get up at…
You might be an entrepreneur if…you start hoping that you become a victim of identify theft because maybe everyone who is after you to pay your bills will go after the thief.
To introduce this subject let me tell you a bit about my car, which I may have mentioned before, but to which I desire to bring renewed focus…
You might be an entrepreneur if…you work for two days straight without sleeping and then feel guilty for buying a hamburger off the dollar menu at McDonalds because you really can’t afford it.
If you knew me well you’d know I wrote this over a year ago because I haven’t eaten at McDonald’s since I saw Super Size Me. I…
You might be an entrepreneur if…you’ve had to explain to your employees that in order to save up money so that you will never be late on payroll again you have to have at least one month where you make more money than you have to spend to stay in business.
When I’ve been late on payroll I have occasionally…
You might be an entrepreneur if…you have to begin interviews of potential employees by saying “I need you to understand that sometimes I won’t be able to pay you.”
This one is more of a joke. In reality I would never tell a potential employee they might not get paid. I prefer to lie to them.
You might be an entrepreneur if…you’ve had dreams about your employees’ wives yelling at you.
Ah, I’ve been looking forward to this one. This is based on a true experience, that is, a real dream I had.
When I’ve been in danger of being late on payroll I start getting more and more stressed as payday approaches. I tend to…
Yes, you might be an entrepreneur if…you’re the lowest paid employee in your company.
A common misconception amongst the general public is that people with “CEO” or “President” on their business card make lots of money. If the company name on that card is “IBM” or “Ford” then that’s probably true (although if you’re at Ford then you’ve got other…
You might be an entrepreneur if…you’ve averaged 60-80 hours per week of work for the past five years.
When I was a kid I felt like I had been sold into slave labor if I had to do two hours of work in a week. I worked at Little Caesar’s for a few months during high school and putting in…
You might be an entrepreneur if…you’ve had to explain to your employees the concept of “no money”.
In no way do I mean to ever insinuate that employees are not justified in demanding to be paid on time. That’s their right. It’s part of the contractual agreement between employer and employee unless specifically stated otherwise. An employee has every right…
You might be an entrepreneur if…your only source of income over the past three years has come from your wife.
A toast to the spouses of entrepreneurs, we couldn’t do it without them. It’s typical for a male entrepreneur, when asked to give a speech at a business event, to give some token credit to his wife for being supportive,…
You might be an entrepreneur if…in the six years you’ve been married you’ve never taken your wife on a vacation.
It got up to seven years, but right after our seventh anniversary we actually took our first vacation. We went to Oregon for a week and stayed with friends in Portland and Seaside. Hopefully we won’t…
You might be an entrepreneur if…you’ve “borrowed” money from the IRS by not paying your payroll taxes so that you have enough money to pay your employees.
I guess you could say I like knowing where the limits are. How long can I go without making my loan payment before they refer me to the credit division of the bank?…
For those who are getting depressed reading my entries this one will be a breath of fresh air, like receiving a pick-me-up bouquet from Merlin Olsen. You might be an entrepreneur if…you’ve risked permanent bladder damage because you don’t take time to go to the bathroom.
You might be an entrepreneur if…you haven’t been paid in three years.
You’re probably thinking “He’s getting paid somehow, he’s just not taking a standard paycheck is what he means.” This is true, if you count reimbursements as pay. But even the reimbursements I’ve received have been pretty slim compared to what I’ve put in. Other than that I have…
You might be an entrepreneur if…you’ve had an employee get angry at you for giving someone else their paycheck before them.
This is a tough one. There are some things I’ve done as an employer wherein if my employees were to get angry or frustrated I could hardly blame them, and yet there’s not much I can do about the…
You might be an entrepreneur if…you’ve had to explain to your employees why there’s no money for their paychecks.
You might be reading this thinking “This guy doesn’t sound like an entrepreneur, he sounds like a poor businessman.” That may very well be, but if being ill-prepated to make payroll puts me into a certain group of businessmen at least…
You might be an entrepreneur if…you’ve worked overtime, over a weekend, or two consecutive days not so that you could pay your own mortgage, but so that you could get money to pay one of your employees’ mortgages.
Anyone who has started a business knows the working life of an entrepreneur differs dramatically from that of the standard 8 to…
Yes, you might be an entrepreneur if you’ve taken any money you had in savings and put it into your business. Part II in a 75-part series.
Wise people have given the financially sound advice that all households retain one year’s worth of income in a savings account, just in case. I heartily support that advice, although I have…
This is the first in a 75-part series entitled “You might be an entrepreneur if…” that will add details to the list composed a year ago on another post entitled What it Means to Be an Entrepreneur. And so it begins…you might be an entrepreneur if you’ve maxed out more than $50K in credit cards to fund your business.…
