7 Easy Steps to Have the Guts to Become and Entrerpreneur

I regularly get e-mails from people asking how did I have the guts to become an entrepreneur. They are asking because they’ve thought about starting their own company (or side hustle) like I did with JibberJobber, or do something crazy like write a book (I’ve written three) or create a bunch of online courses. Here’s an email from a friend I met many years ago:

I am glad to hear your business is doing well. I wish I had your skills to go out and start my own business, but I am too big of a chicken.

I have always wanted to own my own business, but I wasn’t on the path to do it. My schooling was geared towards a rich, fun corporate life, where I could climb the ladder and retire after a rewarding career 🙂

I didn’t think I would ever come up with “the better mousetrap,” or be in a position to actually execute on an excellent idea. So just how did I get to where I’m at (disclaimer: I’m not saying “where I’m at is my definition of success,” but I sure do love what I do!)? Here’s how I responded to this very good friend who is climbing the corporate ladder:

My 7-step formula to have the guts to become an entrepreneur:

  1. Focus 150% on your career, give your life and time and thoughts to the company.
  2. Get laid off because of any lame reason (usually something out of your control).
  3. Work 60 hours a week looking for a job.
  4. Have a great looking resume that has some ghost problem (something that is a problem but you can’t figure it out – and no one can tell you).
  5. Have an aha moment that is “wow, this would be really cool!!”
  6. Continue to not be able to get a job (much less a couple of interviews)
  7. Figure that going forward on your own business is going to be more fruitful than spinning the job search wheels (this happened to me months into the job search)
  8. Being okay with giving up all of the corporate perks (steady paycheck, bonus, holidays, sick leave, cheap health insurance, etc.)

There you go. That’s one way to have the guts.

There’s my guts. Where are yours?

how to have the guts to become an entrepreneur

This is one of my favorite blog posts. People think you have to be lucky, or have good timing, or have funding, or something similar to get started. All I needed was a swift kick in the pants, out the door, and to the unemployment line. I hope you need something less drastic to have the guts you are looking for.

And look at me now. Trust me, that’s not an ego-trip statement, I still think I’m a pretty normal guy. I just kind of wear my guts on my sleeve.

YOU HAVE THE GUTS. I bet more than 1/2 of my readers now will get that swift kick in the pants in the next few years… if you don’t believe me that you have the guts now, you will prove it to yourself later.

8 thoughts on “7 Easy Steps to Have the Guts to Become and Entrerpreneur”


    I always say “Hesitation breeds doubt”; the more you wait, the more you doubt your chances of success.

    On Sunday, I will turn 27 and as I look back (I know some of you will say that 27 is soooo young (at least that’s what older women tell me…but I digress) , but, trust me, it’s been a rough ride 😀 ), on my life, I know that I want to live knowing that I created, started and owned something of significance!

    I just hope that my businesses continue to grow so I NEVER have to worry about working for “the man”.

    Great blog posting!

  2. Fear comes in both rational and irrational forms. When it comes to starting a business, there’s usually too much of the irrational fear and not enough of the rational kind, IMHO.

    Entrepreneurial success is IMHO a table with four legs: strategy, execution, funding, and luck. Maximum success comes when all are well-matched to each other. Where I find most people stumbling is understanding the interaction between strategy and execution. This determines the level of funding needed to obtain a certain probability of survival. Luck, however, still gets to cast a vote. There were a lot of very sound businesses started in late 1999 that were simply crushed by the changing market conditions.

    While my own journey into this game came about as part of a sequence of events not unlike your own, I actually feel this is a very dangerous path to take. When starting or running a business, you really need to separate it entirely from your feelings about yourself. The business is either ready to support you full-time, or its not; it cares nothing how desperately you need a new job. In the end, I made the move when my then-employer folded up, and emotionally it was not a moment too soon, but in hindsight I think life would have been a lot easier if it had happened six or nine months later.

    Last, my experience is that you hear a lot more from those who were very lucky than from those who were very unlucky, and the very lucky not infrequently ascribe their success to their method, and not the universe’s madness. People who “defied all the rules and succeeded” make for great copy, but they make very bad examples for people who have yet to develop a good sense of the four factors I mentioned above.

    If I had to give one piece of simple advice, I’d say to people that they should look for businesses where it is possible to “fail small,” and better still if you can also fail fast.

    In other words, find something where you can start out putting in 10-20 hours a week on the side, and not more money than you’d be willing to play on blackjack in Vegas, and get it to the point where you can find out whether someone is willing to pay something for it. A large majority of businesses fail before they reach this point, so you should try to get there as quickly and as cheaply as possible.

  3. I was scanning your post when my eye caught the picture. I couldn’t figure out what it was, so I decided to engage in reading the post. My, my, my….

    What a powerful, visual image for the equally powerfully written post. I feel the foot kicking me….

    I have some ideas, I will share with you off line. I am working towards generating a serious income so that I can stop working for others and work exclusively for myself. It amazes me continually that you see yourself as a normal guy. I think normal doesn’t come close to what you are Jason…. but you already know how I feel about you. You are an inspiration. What you have done with JibberJobber is not normal at least not by my estimation! Keep writing, and kicking, and…

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