Josh Steimle
  • My Story
  • My Companies
  • Blog
  • Speaking
  • Book Coaching

What It Means To Be An Entrepreneur

Update 11 September, 2015: When originally written in 2005, this blog post accurately represented where I was. It’s not where I am today, nor would I endorse many of the choices I made years ago which led to the unfortunate circumstances I, my wife, and my team members went through. I’m not proud of the mistakes I have made, and I only share them so others can avoid them. Some of the experiences are humorous, but many are not. These days I’m happy to say I have reasonable work schedule that allows me to spend plenty of time with my family, be healthy, and run a better business. Now, here’s the original post:

A lot of people think they’ve got entrepreneurial experience. After all, they started or ran a business, and isn’t that what an entrepreneur is? Maybe, if that’s your definition of an entrepreneur. Here my definition.

You might be an entrepreneur if…

1. You’ve maxed out more than $50K in credit cards to fund your business.

2. You’ve taken any money you had in savings and put it into your business.

3. 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.

4. You’ve borrowed money from friends and family.

5. You’ve had to explain to your employees why there’s no money for their paychecks.

6. You’ve had an employee get angry at you for giving someone else their paycheck before them.

7. You’ve gone for two years without receiving any pay in any form from the company you own, despite the fact that you really, really need to get paid.

8. You’ve risked permanent bladder damage because you don’t take time to go to the bathroom.

9. You’ve “borrowed” money from the IRS by not paying your payroll taxes so that you have enough money to pay your employees.

10. In the six years you’ve been married you’ve never taken your wife on any sort of a vacation.

11. Your only source of income over the past two years has come from your wife, and a chunk of the money she brings in you take and put into your business in order to pay your employees.

12. You’ve had to explain to your employees the concept of “no money.”

13. You’ve averaged 80 hours per week of work for the past several years.

14. You’re the lowest paid employee in your company.

15. You’ve had dreams about your employees’ wives yelling at you.

16. 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.”

17. 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.

18. You work for two days straight without sleeping and then feel guilty for buying a hamburger off the dollar menu at McDonald’s because you can’t afford it.

19. 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.

20. You’ve ruined personal relationships over business matters, despite the fact you thought this would never happen to you and you’ve always tried to not do this.

21. You spend 90% of your time feeling like a failure but you keep working anyway.

22. You keep working on your business despite everyone around you telling you it’s a failure and you should just get a real job.

23. 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.

24. You pay all your bills on the last possible day you can, and you know all those dates by heart for each bill.

25. Without trying you’ve succeeded in convincing all your employees to never try to start their own businesses.

26. You hire an accountant and after looking at your books he comes in with a frantically worried look on his face and says “You’re going out of business!” and you calmly smile and say “No, that’s how we’ve been running the business for the past few years. It’s nothing new.”

27. When someone asks you what you’re doing this weekend you say “Working, of course. Just like any other day.”

28. When you see a grown man riding his bike for exercise at 7am while you’re on your way to work you think “How in the world does anyone have time for that?”

29. 6pm feels like 11 am.

30. You get rid of your TV and don’t miss it one bit.

31. Your wife attends family functions by herself, even when it’s your family.

32. You have a plaque on your office wall of a life preserver with the words “sense of humor” written on it.

33. You know which restaurants in the area are open until midnight, and which are open after midnight.

34. You’ve taken out loans on both of your cars.

35. You’ve moved out of the house you were buying and are renting it because you can’t afford to live in it.

36. You live in an apartment that is smaller than the apartment you lived in when you were a student and had just gotten married.

37. Your wife’s car breaks down and since it costs more to fix it than the car is worth, you end up making do with one car because you can’t get a loan on a new car because you already have loans on both cars including the one that is now junk, and you can’t even take that car to the junkyard because that would require paying off the loan, which of course you can’t afford to do, so the car is sitting in someone’s driveway.

38. You wear the same dress shoes to work every day for five years, despite the fact they are scraped up and look horrible.

39. 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 the sole.

40. Your business has brought in millions of dollars of revenue but you have nothing to show for it personally.

41. You feel euphoric just thinking about what it would be like to not owe anyone any money.

42. You’ve had the urge to fill the room with uppercuts when someone says they’re having trouble living on $120,000 per year.

43. You’re not sure why any of your employees continues working for you.

44. You’ve invited someone to lunch and then asked him to pay for it.

45. Every time your credit card works you feel an overwhelming sense of relief.

46. You’ve had to ask your employees for rides to work because you have no money to buy gas for your car.

47. You’ve told someone not to start the same type of business as you, not because you’re afraid of the competition, but because you can’t bear the thought of someone going through what you’ve been through.

48. All your friends tell you they wish they had your job, and you tell them you wish you had their’s.

49. You’ve worked multiple Christmas days.

50. During the past year you’ve paid the federal government more in taxes than you’ve paid yourself in salary.

51. You’re able to get back all the personal taxes you’ve ever paid because you had such a bad year last year.

52. You’ve felt a sense of relief when an employee has quit because now you don’t have to lay him off.

53. You’re an expert on what does and doesn’t count as a business expense.

54. You have the desire to choke anyone who says “And you can just write it off as a business expense!”

55. When your wife gets pregnant rather than being thrilled all you can think about is “How in the world are we going to be able to afford this child?”

56. You’ve considered asking your life insurance agent whether the policy you just took out is still valid if you commit suicide.

57. One of the major things keeping you from killing yourself is the guilt you feel about handing all this mess over to someone else who isn’t nearly as well equipped to handle it as you are since you’ve already been going through it for several years.

58. Despite being Mormon, you’ve wondered if there’s any way to rationalize taking on a tobacco company as a client.

59. You’ve slept on the floor of your office more than once.

60. You’ve slept in your office chair, or possibly a lobby chair (they’re generally more comfortable) overnight.

61. You’ve seriously considered buying a cot for your office.

62. You’ve told politicians that you’ll vote for them if they campaign for a 36-hour day.

63. You wonder if everyone who owns a business and is financially stable is dishonest.

64. You cut your own hair.

65. You haven’t cleaned the inside of your car for over a year because you don’t have the time.

66. You wonder where the last five years went.

67. You’re amazed by how much you’ve learned in the last month, because you weren’t sure a month ago how you could learn anything else after what you’ve learned over the past five years.

68. You’ve gone to that furniture store on Saturdays where they give out free hot dogs in order to save money on meals.

69. You’ve tried to convince your wife to let you cut her hair.

70. You realize your wife must be a very special person because what other woman would put up with all this and still like you?

71. You’re jealous of a school teacher’s salary.

72. You look at a paperclip that costs a slight percentage of one cent and think “I bet the guy running the company that makes these is making a lot more money than I am.”

73. You see all the big houses around you and wonder “What in the world do all these people do?”

74. 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 had actually done it he might stop telling other people to do it.

75. You’re able to write a list like this in a half hour right off the top of your head.

Comments

  1. Dad says

    June 18, 2005 at 5:27 pm

    You know Josh, you might be able to sell this to some magazines, wall street journal, etc.

    They say artists have to suffer. You’ve done that.

    Reply
  2. Zb says

    June 20, 2005 at 1:48 am

    I only got to about number 20 or so before deciding it was not healthy for me to continue reading.

    Reply
  3. Paul says

    June 22, 2005 at 2:59 pm

    That is so hillarious man.

    Reply
  4. Ira says

    November 4, 2005 at 10:50 am

    While not the guy at the top, I have been the code monkey working for a start up like this … I can relate to half of this and I would still jump at the chance to do it again… Perhaps I should seek help.

    Reply
  5. Rita Wilhelm says

    November 4, 2005 at 1:44 pm

    Yep! That would be the life of an entrepreneur- lol

    I was reading INC magazine, and they did a personality test on 250 former and current leaders of Inc 500 companies to see what made them stand out.

    One findig was that these successful entrepreneurs scored 45% higher than their CEOs counterparts in general on ‘performance under pressure’.

    When I read you list I think how it’s really only the entrepreneur that can handle that kind of stress for their vision.

    Thanks for sharing your list.

    Reply
  6. Rita Wilhelm says

    November 5, 2005 at 4:55 pm

    Would you mind if I post this list on my blog. My readers would love it. I will of course give you full credit with a link to your blog

    Reply
  7. donloper says

    November 7, 2005 at 11:17 am

    Sure, you can repost this content anywhere you like as long as you give full credit and a link back. That goes for anyone else who might want to use or link to my content.

    Reply
  8. olivier blanchard says

    December 7, 2005 at 3:49 pm

    I was afraid it would be this way.

    Reply
  9. Natalie Ferguson says

    September 6, 2006 at 12:24 am

    Well I guess that counts me out as I am female and therefore unlikely to ever have a wife 😉

    Reply
  10. Akshaye Madhok says

    November 22, 2006 at 1:14 am

    Oh my… I still have a long way to go… facing the same experiences, minus the ones where a wife is involved, plus im staying with my parents. No smilies for that

    But, there is still this sense of satisfaction as I discover and achieve more… bit-by-bit

    Would be looking forward to hear this coming from u in maybe lesser points, off the top of ur head but sure will fill your heart

    Reply
  11. Elias says

    December 6, 2006 at 12:57 pm

    Hi Don Loper
    I really enjoyed reading this about “What it Means to Be an Entrepreneur”

    Is there a way that you could send me an doc/pdf/odt file with the entire text(from 1-75)
    in it.

    How can I save this.

    Could you send it to info@tavsans.se

    Reply
  12. Joshua Steimle says

    December 6, 2006 at 1:02 pm

    Nope, sorry. But feel free to copy, paste, and reformat it all on your own if you want it for your personal use. I simply don’t have an hour or two to spare to do that.

    Reply
  13. Alan Edmondson says

    January 18, 2007 at 5:51 am

    This is one of the best things i’ve ever read about being an entrepreneur…. 100% true – i’ve been through the same process and like a crazy fool and doing it again.

    Hurrah!

    Reply
  14. Efthymiou Spyros says

    March 1, 2007 at 10:06 am

    Hello, am a 3rd year student in the University of Manchester and i have to make a report of what are the criteria for the best entrepreneur to be chosen. I have read all of the above Its funny although its true but i think if i include that on my assignment am definitely getting a zero.. because is 100% true.

    Reply
  15. Nate says

    April 3, 2007 at 4:23 pm

    Never, I repete never, put yourself before your employee. (Especially when that employee is your wife).

    Great list

    Reply
  16. Bob says

    July 18, 2007 at 7:46 pm

    Damn Josh!

    I had no idea. Sorry about all those times I’ve asked how your business is going and naively added how fun it must be. Wow! you’re my hero!

    Reply
  17. Bob says

    July 18, 2007 at 7:46 pm

    Damn Josh!

    I had no idea. Sorry about all those times I’ve asked how your business is going and naively added how fun it must be. Wow! you’re my hero!

    Reply
  18. Jennifer G says

    August 12, 2007 at 7:00 pm

    Is this remotely serious? Because I’m praying it is….

    If it is that means my business is doing really, really well…and here I was worried everyone else was doing so much better than I was.

    Of course, I didn’t want to say anything to anyone because I was worried that they would say that I was a bad entrepreneur and to shuck it all and go work at McDonalds (they have benefits!)…but if even 10 of the above are true, really true, then I’m an entrepreneural ROCK STAR!

    Thanks for my self-esteem…I’d been wondering where that ran off to!

    Reply
  19. Tyler Mace says

    July 24, 2009 at 12:09 am

    This post brings relief. I’m not the only one.

    Reply
  20. Larry Steimle says

    September 11, 2015 at 3:09 pm

    At this point, can you appreciate having suffered so much? Would you wish a similar experience on your son?

    Reply

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

Recent Posts

I Let AI Fix My Dishwasher for 10 Hours. YouTube Did It in 20 Minutes.

Read more

The Case for Long-Term Agreements With Your Marketing Agency

Read more

One of the Best Metrics for Agency Owners

Read more

Using AI for LinkedIn Content

Read more

PR Is the New SEO: How to Get Your Brand Into AI Search Results

Read more
LinkedinFacebookYoutubeTwitterInstagram
Josh Steimle
LinkedinFacebookYoutubeTwitterInstagram

Success! Now check your email to confirm your subscription.

There was an error submitting your subscription. Please try again.

© Josh Steimle 2026 All Rights Reserved
  • Privacy Policy
  • My Story
  • My Companies
  • Blog
  • Speaking
  • Book Coaching