The Cowardly Lion’s Guide to Conquering Your Entrepreneurial Fears

The Cowardly Lion’s Guide to Conquering Your Entrepreneurial Fears

Reader Comments (161)

  1. #1 is spot-on: Get disgusted with yourself. I know in our new-age pursuit of balance, harmony and self-affirmation, this probably isn’t a popular notion. But it’s very effective. Thanks for the kick in the ass, Jon. My grandfather would like you.

    • Self disgust could be a really great motivator. This whole list could read as ‘How to Motivate Yourself’ and personally, I like #4. There is nothing like fighting for someone else to get a person fired up.

    • Dr. Cox said it best on [Scrubs]: “My entire workout philosophy centers around one truth: I hate my body.” … “The moment you’re okay with how you look, baby, you’ve just lost the battle.”

      While it’s a little weird to think of in our current culture, it works.

  2. Jonathan:

    There’s a few other lessons from the Wizard of Oz

    1. Neither the lion, Dorothy, the Scare Crow, or the Tin Man, could make it on their own. But they did band together into a mastermind group.

    2. They also thought they could get help from the final knowledge source – the Wizard of Oz. But the Wizard turned out to just another misfit.

    3. When they were all given external recognition by the Wizard (i.e. diploma, etc.), it awakened their inner resources.

    Can anyone else think of business lessons, from the Wizard of Oz?

    Good post today.


    • 4. Don’t be fake. When the gang found out the Wizard was nothing more than a little man, they felt betrayed. Yes, they saw in the end that his intentions were well placed, but that’s an anomaly in this short-attention-span society. Don’t be fake. Be genuine and you’ll sleep better at night knowing you made the best decisions you could for your self.

      • True. The only alternative is to never let anyone see behind the curtain, and that’s getting harder and harder to do.

      • Love that one and totally agree. It seems so easy to fudge things behind the “curtain” of the blogosphere, but critically important to remain genuine and true.

      • And be generous. Dorothy et al didn’t burn the Wizard at the stake. They forgave. Rather than getting stuck in retribution, they moved on to be

    • Here’s another lesson for you guys that you can take from the Wizard of Oz:

      If the group would focus on what happened last (finding out the Wizard was a random douche behind a curtain), they would have given up on everything they had learned on their way there.

      And THAT’S one of the most important lessons in business: it’s not about the destination, it’s always about the journey. Success is a journey, not a destination. And because of that, your mindset is your most important business asset.

      After all, if you start seeing your business as a road? Then you don’t mind traveling another 5 miles (persistence), then you start enjoying the ride more, etc.

  3. I act because if i don’t then I will not achieve my goals..and my goals are big and not doing something isn’t acceptable..

    “Black Seo Guy “Signing Off”

  4. This is a terrific post. What it always comes down to me in my internal monologue is this: doing something is better than doing nothing. Sure, it isn’t always true, and sometimes you will fail/get embarrassed/be filled with regret but, if you tap into a stream of internal confidence you can overcome those petty feelings. You lived. You learned. You moved on. You got better.

    • Right on. Sadly, I don’t think most people realize those are the only two choices. They believe there is a third option: do it later. They go through their entire lives thinking, “I can’t deal with this right now. I’ll do it when things get better at work/my kids stop driving me crazy/I have more energy.” But that never happens, and they never realize the game they’re playing.

      • Very well said Jon! Sometimes, I regret the way that I started my own business. I basically just jumped off the deep end and did it, because I was so fed up with my current situation. I ditched the junk that kept me in my day job, as Sonia said 🙂 But after the fact, I would wonder if things would have been better if I had taken more time to prepare, to research etc… Had I done that though, I probably would have gotten so scared and overwhelmed by what was ahead of me that I would have delayed and delayed until it was the right time. There is never a right time. There is only now.

        • I think you’re right. Pretty much every entrepreneur I know screwed up the first few times, ruined everything, and then had to start over again. It’s painful, sure, but it’s better than sitting in a cubicle when you’re 65 years old, wondering what the hell happened to your life.

          • I doubt you would be in a cubicle at 65, you would have been laid off long before 65. Reason # 398 to go out on your own

  5. If you continue to think like you always thought, you’ll always get what you always got..I’m sure the person that said this in an AA meeting borrowed it from someone else, but it’s true.

    Thanks for the great post, it’s nice to know we don’t live desperate lives all alone.

  6. This is a very good article Johnathan. Applying some good and direct suggestions that can make us all better in our business and in life.

    Thank you for sharing this with us!

  7. Jon,

    This was an encouraging post. Even for someone who has started a half dozen start-ups it’s good to be honest about the fear and the courage we must choose to have each day.

  8. This one really pulled at my entrepreneurial heartstrings! As someone who has launched several businesses (some of which sizzled, some of which fizzled), I kept thinking as I was reading: yes… mmmhmm….yes… DEFINITELY! You’ve hit it dead on – thanks for such a fantastic post!

    • Not a fan of the Wizard of Oz? My God, woman! You can’t admit something like that in public. You’ll never live it down.


  9. Well thanks, Jon,
    I think you really got the point… I see so many people striving into the web business field, and getting so little.
    For sure the right mindset is the core point for a definitive solution.
    In fact, that’s the same as in all others fields of life, and there’s no reson why it should be different…

    • That’s true. It’s fun to believe the web is new and revolutionary and changing the way everything works, but the older I get, the more I realize it’s nothing new at all. It’s just the same old principles wrapped in a shiny new package.

  10. I was talking about his same topic with some friends yesterday. You really captured the dilemma of running your business – it’s scary but you need to embrace the fear and do it anyway. Thanks for a terrific post.

  11. Great. Many things you say here I have come to me awhile ago.

    Luckily I was able to overcome my fears and now I am focusing my efforts on being an entrepreneur.

    Thanks for this article that gives me strength to keep going.

    Best Regards.


  12. Great post!

    In the end it all comes down to you. A coach will help but they’re usually not there holding your head when you’re vomiting instead of pushing the send button to launch your first big product. A mastermind group will help – but you’ve still got to pull what you need out from deep inside yourself.

    Excellent comments too. Yes, Paul, being real and true to yourself is paramount. Thanks for the inspiration.

  13. Excellent post!

    Personally launched my second company in six months and I’m still scared to death every day! Thank you for the notion that it’s not just me and that every situation can be overcome.


    James H.

  14. Well done Jon! Since I’m relatively new in business I especially appreciate your lines: “The fear never goes away.
    You just get better at dealing with it. I was just as afraid when I started my fifth company as I was when I started my first one. In fact, I was probably more afraid, because I understood how truly difficult it is to build a business from scratch.”

  15. This post sparked a lot of fire in me. Not because I believe I am a cowardly lion but because I feel compelled to mention that if you don’t naturally have the mindset of an entrepreneur or a go-getter you aren’t going to make it. I was playing poker at a local Casino the other night and shooting the bull with this kid whose in his third year in college, he told me he is going for his MBA and is “very interested in entrepreneurship….”

    That baffled me!

    Entrepreneur-ism is NOT something you fall into or become interested in. It’s not a job or a career and it’s definitely not something you proactively work at to develop the correct mindset for. Entrepreneur-ism is a way of life. It’s who you are as a person. It’s your frame of mind with regards to business, finance, life and leadership.

    Sure you must develop the mindset of only focusing on the things that you do which are right and which work and squash all the other made up assumptions but to truly succeed as a leader in your niche, if you’re under the guise that you can just become an entrepreneur by reading Copyblogger or by taking a course or reading a How-To book etc. you are sadly, sadly mistaken!

    I was 9 years old when I began selling my Dad’s leather goods at the Flea Market. I was 12 years old when I started my first business. I was 14 when I started my first MLM company. I was 16 when I began teaching other kids how to make money with fundraising etc..

    I was born an entrepreneur. There’s no mindset you can develop to be this way, you either walk in the light of a leader or you spend all your life reading blogs, newsletters, ebooks, articles etc. to get that needle in the vein feel for the day so you can go on believing your an entrepreneur, when truthfully your not!

    Good post. 🙂

    • I don’t believe that. I never had much of an entrepreneurial mindset — it always intimidated me — until I was royally fed up with working for people who were dumber and more arrogant than I was.

      I know the mindset can be developed. I believe it’s our natural mindset, we just have to unlearn a lot of the junk that keeps us in day jobs.

      • I’ve always been a care provider (from babysitter to nurse to nurse-midwife) and I’ve always been happy to show up and provide care.

        I never thought I’d be an entrepreneur because I hated the idea of the “selling part.” I’m grateful for the examples of Sonia, Brian and Jon (and many others here) that showed me that marketing is just communication and based on relationships, which I enjoy very much. That realization was like Glinda telling Dorothy, “You had the power all along.” and gave me the courage to build my own business.

        (All time favorite quote form the Wizard of Oz: When Dorothy asks the Wizard if he was scared, and he says, “Frightened? Child, you’re talking to a man who’s laughed in the face of death, sneered at doom, and chuckled at catastrophe… I was petrified.”)

      • Sonia,

        I always listen to you and Brian and I read all of your content. You write very good copy and your mindset is very similar to mind but it’s not the same. You might be an entrepreneur in the sense that you’ve founded a business and have led it to higher heights but as long as you work for someone else and
        get a paycheck from another entity, that is not entrepreneur-ism and it’s not what I’m talking about.

        I too believe that a mindset can be developed for as Jon is talking about only focusing on the things
        we do that are right and working and to prove to ourselves that we can accomplish our goals or be
        who we want to become but you’re either born with a sense of greatness or your not.

        I had a group of buddies growing up. Out of 20 kids only 2 of us had the natural mindset and the rest were just daydreamers. While they ended up working day jobs and trading hours for dollars, my friend and I went on to build companies before we even reached highschool.

        Now as for me, I struggled to find support in my entrepreneurial life and thank goodness for Copyblogger because I do feel support through your copywriting and content marketing but my friend was a 6th grade when he got an idea that would later make him millions in Real Estate Investing.

        6th grade!!! He didn’t need mindset development, it was natural and he naturally made millions!

        Thanks for your time.


        • Well, I do consider founding my business and leading it to greater things to be what makes me an entrepreneur. So perhaps we have different definitions.

    • I think some people are born that way, but others, like Sonia said, figure out at some point they are “unemployable” when it comes to working for others anymore.

      I went through college and law school without a clue as to what I wanted to do, other than “attorney” sounded good to me. Once I started practicing, I realized I hated it. But then I realized something deeper — I hated working for anyone, no matter what I was doing. I wanted to do what I wanted, the way I wanted.

      Thus, an entrepreneur was born (at 30).

      • And for that Brian I applaud you and I totally agree. I do believe that people are born with this inner inability to work with and for others and only get along by themselves making their own rules. I have been that way since preschool and even to this day I despise others telling me what to do, when to go on break and how much money I am allowed to make per day and for that I am proud of my entrepreneur-ism.

        People who spend their lives enjoying working for others until they reach a bump and then go looking for the latest thing that will make them rich or make them money from home etc, that’s not entrepreneurial anything, that’s desperation.

    • The more I think about it, the more I believe entrepreneurship is a like a disease. Some people are born with it. Others catch it accidentally sometime during their life. Still others surround themselves with others who are infected, HOPING they’ll catch it.

      I also think there are different strains. Felix Dennis and Donald Trump have an entirely different strain of the disease than people like Steve Jobs and Walt Disney. The end result is the same, but the symptoms are different.

      If you’re not careful, I think it can kill you, too. Unchecked, it will use up everything inside of you and leave you broken, empty, and ready to die. Smart entrepreneurs realize this and deliberately schedule time for “relaxation therapy.”

      It’s actually scary how well the metaphor works.

      • Entrepreneur: one who organizes, manages, and assumes the risks of a business or enterprise.
        ~Merriam-Webster online dictionary

        You can be a shipping clerk. If you organize, manage, and assume the risks that might arise from your actions, you’re an entrepreneur.

        I believe corporations would work better if they valued the entrepreneurial spirit: and allowed people to organize, manage, and take risks.

        But they would have to trust their employees. Probably a bad idea: they might do something innovative. And their employees would have to trust them. Probably a bad idea: they might get fired.

        Where’s Jon? I hope he didn’t wander off into his maze of metaphor and get himself lost.


  16. @Jon: Your articles are two lessons in one. Lesson one is what you mention in the post. Lesson two is in studying how you executed lesson one. Classic Morrow Open & Close. 😉

  17. Love this blog. I have always been one of those people who stands just a bit to the side and waits to see what will happen. Too shy for my own good, too ambitious to give in to it, too stubborn to give up. Thanks for the pep talk, I’ve taken it to heart.

  18. Jon,
    I don’t have anything of true insight or value to say at the moment. Just that I truly needed this post today, and I thank you for taking the time and putting in the effort to write it for me. Not for the other 138,000+ readers, but for me.

  19. I really needed to read this today. You have NO idea of how scared I am to actually take my next step. Mindset is sooo important. And sometimes, you just gotta leap and hope a net appears. Or that you’ll learn to fly.

    Great post.

  20. Thanks for such a wonderfully written article. As a small business owner I am constantly doubting my abilities and questioning the tangible realities of my purpose in the marketplace. Although I can swagger with confidence I can also cower in shame when tasks and project deadlines pile on top of me. I really appreciated reading these words and how they relate to the cowardly lion. From now on I will remind myself of this connection when I feel the pang of fear!

    From Here To There,


  21. This was very timely. I occasionally get wracked with self doubt. I can’t do it. I am not good enough. I am just fooling everyone. Who do I think I am. But I think that is par for the course. These are my fears giving themselves a voice in a way that I would easily internalize, self doubt. Sometimes you have to tell yourself to shut-up.

    • I agree. Sometimes, success isn’t so much about positive thinking as learning to recognize the voices in our heads and selectively ignore them. 🙂

  22. That was awesome. I have been wanting to for a long time to jump in so to speak as far as getting something going on line and off. I know I have my fears but you did a great job of helping me face them a little better. I know that I have done a lot of things anf jobs others would not even try and was able to accomplish, so the only thing now to do is take the courage I used to do those to make some other things a reality. I guess the worst part is fear is generated from within not from the outside, but I will get through this. I just need to get better at telling the voice in my head to be quiet and let me get this done. Thx

  23. Jon,

    Thank you. For those just starting out you have expertly described what for many will be their #1 impediment to success – themselves and their fears.

    For those who have been in the entrepreneurial game for a while, you statement that the “fear never goes away,” is an excellent reminder to keep your edge and work on what is most important, not on what has become easiest. The easy path is usually the path around your fears and not through them.

  24. Finding the right mentor is key. Actually I feel that you need a minimum of two mentors. One that is someone that knows a lot about the industry that you are in and the other one that knows nothing about what you do, but provides motivation and insight into important business decisions that you make.

    • That’s true. Personally, I make the point of talking with at least one reader every week, just to remind myself what they’re going through, where they’re struggling, and where they need help, and I think that awareness helps me write posts that resonate with people. Mentorship from the bottom up is a great way to think about it.

  25. Wow, I can’t believe how much this one really hit home.

    I’ve never heard it presented like this, but it’s absolutely spot on with the way I feel some days. Thanks for posting this Jonathan. I’ll be reading this whenever I’m feeling Lion-ey.

  26. You guys and girls at Copyblogger are fantastic! It’s very meaningful and highly useful posts like these that keep me coming back, again and again. This post says so much. Yes, it is sometimes scary, but to know your situation and concerns are in a general sense, shared by so many, gives us added strength to keep moving forward. Thank You!

  27. Right on! That’s what I call Moxie – the conviction to BE REAL, BE HEARD and BE WILLING to BE VULNERABLE (and here’s the key…….) No Matter What!

    It’s about the willingless to acknowledge and honor your fear by stepping right into it. That’s freaks the little bugger out like nothing else. Engage a professional to coach you through the nuggets of fear that are buried deep within you that you can’t see. There there – in any place you’re stuck.

    On those days where fear has you by the short hairs don’t move. Sit on the pot and really stink up the place. While you’re there, make no major decisions, take no significant action. If you do, you won’t like the outcome. When you’re done, Flush. Suck it up, cupcake, and take one bold step into what scares the shit out of you.

  28. “They’re willing to do the unpopular thing and for everyone to think they’re an ass.”

    Thank you for reminding me of this.

    Even tho’ I’m working in a bit of an unusual subject, the feeling is not unique to me or my business.

    I really needed to read this today.

    Now, onward!!! :>

    PS – Thnx also for pointing out that it’s a human thing to do for others what you won’t do for yourself. Needed to hear that too.

  29. Great post. It’s exactly how I felt today. Of course, this is better than yesterday when I was feeling like the Scare Crow.

  30. Great analogy Jon. All your points work.

    Don’t you wonder what happened to the excowardly lion after Dorothy went back to Kansas? I figure the Scarecrow probably became the new mayor of Oz, but don’t know about the Tin Man and Lion. They must have set up businesses of some sort.

    The Lion, maybe head of the Law Enforement/military? Roar…

  31. This article is AWESOME! You explained very well the mindsets and beliefs of successful people. And I really enjoy the way you write. Storytelling is definitely your strength! Write MORE articles of this kind!

  32. Just the thing I needed today, been running my own little business for 6 months, no other job the timing was not so good but I scoffed and did it anyway its gotten quite hard now and as a client sacked me they said what they thought would ease my worrying; time to get a real job this is affecting your performance, honestly considered it for two days. But I can’t its not like me to let fear eat me whole it can gnaw at me but that’s as far as I’m willing to let fear go, I hate being a hamster MoRE!

  33. I discussed this very subject with a friend of mine once. We came to the conclusion that what we consider to be ‘fear of failure’ is sometimes ‘fear of success’. After all, success is a frightening thing, what with all the responsibility and expectation that people have of you now that you’re established.

    Personally, the fear of failing has never been as great as the fear of being faced with the idea that what I’m doing might actually make me successful. Cheers.

  34. Dear CopyBlogger,
    Will you please continue to be my mentor??? This spoke AT me!
    Fear is the absolute worst! It will hold you back from doing things that you actually want to do. It will tell you lies about not being good enough & failing (before you even begin to try), and before you know it…life is passing you by while you wait on the “perfect time” to get started.
    Thank you for the reminder that there is no “perfect time” to start doing what needs to be done to reach your entrepreneurship dreams!
    Sometimes after reading an article here, I feel quite silly because you (consistently) make it all sound so simple. Thank you!

  35. This article made my day! Thanks for writing it. I just started to receive the daily emails and I’m very glad I signed up for them. Thanks.

  36. Of all the posts I’ve read here and on related blogs (most from links on this one or Leo’s), THIS is the advice I’ve needed most — and never knew it.

    Time to read this again from the beginning, and get passed simple fear. Tick tock.

  37. When I saw the title, I wondered “The cowardly lion? How’s Jon going to pull this one off?”

    I should never have doubted. A masterful story with some terrific lessons woven in. Your message doesn’t feel like copy at all, just a friendly voice offering wisdom and guidance.

    Joe 😀

  38. I think #3 is crucial. How many times do you hear people saying, “I’m just not good at that” or “I just don’t have the genes for X.” You live with a trait so long you think it can’t be fixed. It’s the classic mistake of bemoaning a lack of attibutes when what they’re really struggling with is attitude.

    I do believe there are attributes that can make you a more successful entrepreneur than the average bear, but research clearly shows that attitude can overcome nearly all deficiencies you were born with. These suggestions will go a long way in helping folks overcome their fear.

    I’m predicting one the “Best of 2011” right here. Nice job, Jon!

  39. Finding a mentor is so important. When you can meet with someone who understands where you are and where you want to be, you can move forward in your business more quickly.

    I never knew there was so much value in that old classic!

  40. Going back to read, but just a quick comment. The first sentence knocked my on my butt. Cowardly, fear, uncertainty, doubt. Interesting is that I write about this stuff often. More interesting and not so good, I still let it get to me. Closer I get to developing a product or approaching someone to do a guest post, the more I want to (and often do) cower.

  41. This is a really fun post that also has great insights into the courage it takes to be an entrepreneur. The discussion of this particular character, the Cowardly Lion, also points out yet another way to conquer fears: change the story. In truth, the Cowardly Lion was only that character in Oz. In Kansas, he had a whole different story. I think if we take ourselves out the context of our old story, which is as much fantasy as the Land of Oz is anyway, we can create a whole new context where it’s easy to be courageous and powerful.

    For example, must of us fledgling entrepreneurs put ourselves in the land of I-Don’t-Know-How-To-Do-This-I’m-Just-A-Nobody and we could create a new story space called I-Am-Learning-Fast-And-I-Have-Much-Value-To-Offer. The story we tell can deplete us or empower us, as the Wizard of Oz so beautifully demonstrates. So thanks for reminding me to choose a good land to be in. 🙂

    • That’s a very deep insight, Ande. Most people aren’t even aware they have a life narrative, much less awareness of how to change it, but I think you’re right. The story we tell ourselves is a huge part of who we become.

  42. So the fear never goes away huh? Could be my biggest enemy if I don’t learn how to deal with it. Confirms my notion – I need to persist with the projects in my biz and stop letting fear be my enemy.

    Learning to deal with it!

    By the way, networking with friends/like-minded ppl – is a great help in dealing with the fear.

  43. Of all the days that I could have read this inspirational post, today was the ideal day! I recently quit my full-time job to focus on my art career – something that I love and I believe in. I had my doubts as to whether or not I could succeed, but after reading this post I will continue to stay positive about my ambitions.

    I am definitely a procrastinator who prefers to wait for the perfect opportunity to take action. But through recent experiences I have discovered that I will be waiting a lifetime for that ideal moment. You are absolutely right about misery being a useful tool. Being frustrated about ones current situation is just as motivating as having the perfect opportunity to make that change, and we should all push ourselves to fulfill our dreams no matter what obstacles we face.

    It is also very comforting to believe that we all possess fear to some extent, even successful and seemingly fearless entrepreneurs. But what differentiates these successful entrepreneurs is the fact that they can look past their naturally existing anxieties and achieve greatness.

    Thanks again for this wonderful post!

  44. Having a mentor is something that I’ve been really thinking about for a while now. I don’t have one but believe it would help a lot however I don’t even know where to begin finding one. Are there people available who want to mentor other entreprenuers?

  45. Great post, at least I’ve taken action an created my own product. So now it’s time for some SEO and link building to drive traffic to the site. People how thinks online business is easy are completely wrong, it’s all hard work

  46. Thanks so much. I was feeling like such a loser. Here I am at 60 trying to start a new consulting business. I already am working as a volunteer executive director with our family owned non profit. However we have limited funds and frankly I am broke. I am taking an Entreprenurial Training Class with Operation Hope. I have been working on my business plan and feeling encouraged one day and hopeless the next. I am going to share this blog with my fellow classmates tonight. I still feel like crying, however after I re-read your words of encouragement, so how I am going to find the courage to take this battle on as well. I just wish that I did not always allow money to cause me such great anxiety. I am brave enough to face this one too.

    God Bless You Jurline

    • Jurline, money is often a very difficult and stressful matter. This is why so many people get fed up and think, wow, if I can work so hard for someone else, why don’t I do it for myself and reep the benefits? I know how hard it can be trying to build yourself up from nothing while worrying about money, however, you only have one way to go, and that is forward. Find the strength to get through the difficult times and better days are waiting for you. Good luck on your journey, you are in my ‘doua’ (prayers). — Ahlam

  47. Jon, this reminds me of a great lesson I was taught by one of the mentors in my life: feel the fear and do it anyway.

    It also reminds me of a book she recommended back in the 90s: You’ll See it When You Believe It, by Wayne Dyer. It’s about the importance of our attitude … just like you said, @Jen Gresham.

    Thanks for the post, Jon. The perfect reminder at the perfect time!

  48. I grew up in an entrepreneurial family and at the beginning, had no qualms about starting or owning a small business. Unfortunately, after College, I thought bigger was better and joined the ranks of the fortune 500 employees, which was great until the market I was in, started to compress.

    Those years, though, got me into a cycle of thinking that only big business could get through the tough times and did a very good job of convincing me that originality and thinking out of the box was a problem, not an asset.

    Although I did finally get out of the corporate “rat race” and into the small business owner one, it took a long time to get my head straight as to what it really took to be successful. I finally realized that the things that made for a good manager of an already successful big business, was almost exactly the opposite of what it takes to start and grow one. It was no wonder, that when thing became difficult, the big companies bought other ones (and in many cases, destroyed what made them successful competitors of the bigger company.

    I may be a slow learner, but I think it’s taken me a good 5 years to feel comfortable in my own shoes as an entrepreneur and just do what I know I have to do, without unnecessarily worry about competitors, money, friends, family and others who think they know more about being successful in business than I.

    Don’t give up. You can do it. Just put one foot in front of the other and keep going. It really does get easier!

  49. Jon this post is inspiring.

    It reminds me of both times I tried working for myself, and the major difference.

    The first time I tried working for myself, I was head strong. Foolish, I thought that by simply sitting in front of the computer all day, I would be able to make magic happen and find a paying client.

    Of course that was wrong, and after a few months of thinking that it was just “going to happen” I lost my girlfriend, my apartment, and a ton of respect from my friends.

    I hit bottom. I ended up working for the gas station across the street because there were no other opportunities within walking distance.

    Flash forward two years later…

    I stopped working for $9.00/hr at the gas station to $12/hr selling cell phones. What a step up!
    The job was alright, but in the end, I had gotten fired over a pair of pants…

    This disgusted me. I figured I could either pound the pavement and find another job and put myself in another position where I could get fired for some stupid bullshit reason, OR I could put the same amount of effort into working for myself…

    I worked, I studied, I kept my eyes on my screen for 12 – 16 hour days absorbing as much content as I could and I came across some some common themes. “Be compelling, create awesome content, and above all else be interesting”

    So I Googled… “How to be interesting”

    and low and behold, I found the post that changed my life…

    A week later, I got my first client. I looked at what they did from the inside out. I helped them become more interesting.

    A few months later, I started working with a start up agency. They paid me $750/ month and I made them and their clients more interesting.

    I stopped working with them after a year and I started to make myself more interesting.

    I have a fiancée, and a new baby. I am the sole source of income for my house. We live off of my passion and they keep me motivated.

    So thank you Jon. Thank you for helping me to no longer be a coward. Thank you for writing a post that ultimately became the foundation for how I conduct my business. Thank you for teaching me those two years ago how to be interesting and thank you now for reminding me why it’s OK to be afraid sometimes, as long as you keep pushing to move forward.

  50. Jon, this is a GREAT post and so timely. I run a self-employment program for women and we just finished our last workshop … they are ready to fly on their own, yet the fear is paralyzing them. Be assured that your post is being circulated to all these women and I KNOW they will all be INSPIRED. I could not have said it better. Thanks for making my job easier.

  51. First of all, holy comments! You know you have something good when subscribers have to scroll and scroll to get to the bottom and add their own comment. The post itself was great and I loved reading the dialogue that followed. Fear is definitely a motivator–it’s what got me where I am in my business today and keeps me moving forward. I look forward to reading more of your posts.

  52. I’ve just ditched my well paid day job, and am using up all my long service leave (which will give me a small income) for a year to work on some things that I’ve been “meaning” to do for some time. Write. Teach myself things that I can’t find courses for in my country (which means I can’t officially be a student, and get the support that entails). Improve my skills.

    It doesn’t make sense in the ways we normally measure success, and the stuff I am working on is going to be very challenging and likely unpopular with a lot of people – but its necessary and important. More important than sitting in work meetings thinking ‘I could be doing x’.

    I am still trying to get it through to people that I am not ‘taking a year off’!! Everyone thinks its a holiday. It’s not. It’s buying myself the breathing space and doing the work I really want to do, even if it is unpaid (people don’t get that either!), living at home with parents so I can afford to, not going out because getting this material in place by a certain time is more important. Available time DOES make a difference – we all only have 24 hours in the day. And you can either spend it at your day job, or at the pub – or doing the things that will progress what you want to achieve. One way or another, it involves some kind of sacrifice of spending time in one area, and rechanneling it into what you are passionate about.

    And being ruthless about boundaries, your time – as a yes-person and people-pleaser, learning the word ‘no’ has been very powerful for me. It makes it easier to say no, and spend your time according to YOUR priorities when you are buying your own time back at considerable expense 🙂

    I’ve stopped feeling so angry and frustrated that I can’t get to stuff I feel strongly about, and am now making progress working virtually with others. I am a little anxious about what I am going to do when the money from my long service leave runs out, but I felt so much better once I had made the decision that it must be right!

    Right now, this site is for the flagship film of the initiative I am part of – but watch this space for a web launch in February! http:///

    • I completely understand I did the same thing January 2010 and my little income has run out compounding the fear, but I have a great cheering section helping and supporting me. Makes a huge difference!

  53. I’m a struggling Internet entrepreneur even though I’ve been into this business for over 3 years straight. The challenges are extreme, be it infrastructural or resources deployment. I had a pretty bad day only yesterday and I found this post out of no where. Now, I feel motivated big time. Keep writing good stuff and doing the rest of the world a big favor. Great stuff!

  54. Wow, if you read all the way down to this comment you are not cowardly, lol. Usually I am too cowardly to post comments but this one really hit home. I just came back from a trade show that was a total bust. It was hard to come home to my friends and family all waiting to know how it went. Now, I was sitting here try to redouble my efforts rather than cry when I read your post and it really help- thanks. (shout out to the other l lawyers who jumped ship)

  55. Amazing read. This is the type of motivational thing that can help so many people overcome the fears they have of continuing in the face of adversity. I can completely relate to the part about being even more scared the 5th time around, because once you know what you’re getting into, you know the challenges that you’re up against, but you are at least more prepared. Bravo again for this post.

  56. Dam you’re good Jon! You got me in the first few sentences. 😉 Although I have to say, I’ve gotten MUCH better in taking action in spite of fear. It’s a muscle that took a long time to work out; now it only get’s sore once in a while.

    P.S. Very clever how you sneaked in Robert Scoble in there. 😉

  57. Awesome, awesome, awesome!

    I don’t think I have ever read these thoughts put so well, so concisely, so perceptively, so…well, you get my drift.

    I have problems with anxiety anyway (long story) so this is where I live. And yet…I continue to challenge myself and do things that seem to be a lot of work for nothing (because I have a vision!) Among other things, at the age of 49 I have gone back to college (again) and this time I am determined to finish my Bachelor’s degree and believe me I will PROUDLY wear those letters after my name.

    Thanks for a great post, Jon!

  58. Jon, fantastic stuff here. I spend so much time in my business working to convince people of what is possible. I often find that us humans tend to focus on the problem instead of the possible. We get caught up in the pursuit of perfection when we should be doing.

    And by doing, I mean just taking that first step of action. A quote I always says is that, “Life rewards those who take action, not those who take notes.”

    That’s what makes the difference between the successful and the “regular” folk. They took action when they weren’t 100% prepared and tweaked their efforts on the way to the top.

  59. It really does have to do with mindset. I think when Dorothy gave the medal to the lion, she inspired him with confidence because he felt worthy of getting a prize. Often, conquering one’s fears takes that same mindset. It just takes a small confidence builder to start conquering fears.

  60. This touched a nerve within me, and it did so because its true. I’ve often being disgusted with myself for either giving up far too early, or for quitting because someone told me to. I guess I’m acting out Step 1 right now.

    I like Step 2 though, because its something I really need to do. I’ve never had a mentor, and I get the vibes that now might be a good time. If it helps the cowardly lion within me, then it’s worth it, no question.

    It’s not how loud or how long you roar, it’s how you roar after you get knocked down.

  61. Wow Jon.. cool post. I can see myself in much of what you said. It’s so easy to let the fear surround you, engulf your thoughts and stop you in your tracks. I am convinced that what many call procrastination is actually fear of failing in many cases.

    In fact, I bet there’s a little of the Cowardly Lion in all of us.

    Thanks for the post Jon.

  62. Goodness gracious, Jon… this post speaks directly to me. Are you in my head?! 🙂

    I have moments (too many) when I am flat out terrified of making the next move. Truth is, I am disgusted (and surprised) with how cowardly I have been acting in my business lately.

    It helps to know that other entrepreneurs (including some of the most successful) all experience fear but have developed a mindset that helps them push through it. That tells me I too can develop that mindset and learn how to harness its power.

    By the way, I don’t recall ever watching (or reading) the Wizard of Oz. After reading this post and checking out the comments, that will change very soon. 🙂

    Thank you for another great read. Inspirational indeed!

  63. How apropos this story…
    I sometimes am faced with my own demons of fear and discouragement. Being an entrepreneur, to me, was never a choice, it was the fiber of my soul. I couldn’t help it! I evolved into this entrepreneur who didn’t have a clue what to expect in the journey. Deciding to take this path comes with uncertainty and even though it’s scary, what’s scarier is not doing what I love! I feel that the best thing that could happen in the journey of entreprenuerialism is those periods of lack of courage or fear…it forces you to dig deep — find it and grow beyond the point of fear. It’s an exhilarating feeling! Having people in your corner is important and there are some who will gravitate because of the energy you have and support you and protect you. Those are the ones you hold near and dear to your heart. This is story is a great analogy of finding the strength to persevere and win in the game of life.

  64. How did you know? lol I’ve been freaking out about EVERYTHING lately, but through the little bits of work I’ve done here and there I’ve been getting enough recognition from outside sources which gives me confidence to continue to grow and expand.


  65. This was a post I needed to read, even when I wasn’t looking for it. I’m at the stage where I failed once, almost hit bottom (from a start-up point of view), and am seeking the courage to overcome my fear in the face of another launch. Here I am, peddling through in the face of my fears. It sounds as though I am on the right entrepreneurial track….but boy can it be frightening. Gotta love it.

  66. Great post! I particularly liked what you said about surrounding yourself with people who motivate you and doing seminars, etc. I do a lot of reading and webinars, and even when there isn’t much new info, it’s still really helpful to reinforce stuff I already know but have pushed off my radar screen, and to allow myself to get re-inspired.

    There’s a pretty funny line in Oz, which could also be interpreted in business terms. When the Witch agrees to give Toto back to Dorothy if she can have the shoes, and she tries to grab them, her fingers are zapped with electricity. Dorothy’s response is, “I didn’t do it. Can I still have my dog back?” I don’t know if a business lesson was intended, but I think it says something about being ultimately responsible and accepting that accountability, even if you yourself weren’t directly responsible for a mistake.

    And for my fellow “Lost” fans, Hurley MUST have represented the Lion, don’tcha think?! Especially the hair. Other more blatant references to Oz on the show, too.

  67. Great story, saw my self reflected on the lion.
    What happens when you become a secure or fearless salesman?, I´ve found that traditional old school bosses, tent to see this self confidence atitude,as arrogancy. they preffer to have zombies or robotized employees.
    Ps: Any comments regarding “the naked emperor syndrome”, will be gladly appreciated; Thanks.

  68. Thank you, Jon, your words come at the right time, thank you for sharing your insights, what an inspiration and a motivational push in the right direction.

  69. By far the best post I’ve read in a LONG time about having the courage to start and run a business.

    It’s all about mindset, willpower, tenacity in the face of adversity, making the right decisions under pressure, and most of all, going for it! Taking the leap of faith regardless of how it will turn out. Taking calculated risks for the reward of success. That success could really be anything you set your mind to. Your goals are what make you you, and going for it separates the “9 to 5’ers” from the true entrepreneurs. (nothing wrong with working a 9 to 5, it just isn’t for me)

    The ability to face the fear of failure is one thing, but to face continued opposition, resounding ridicule, and failure over and over again without giving up or giving in to your fear is pure courage. It’s not foolhardy, nor is it irresponsible or “crazy” as misunderstanding family and friends tell you. They don’t say these things out of anger they say it because they are afraid, and more times than not they wish they had the courage to step up and step out of their own comfort zone.

    Standing up in the face of adversity and staring it down might make you look like an ass to some, as they may be ignorant to your goals and vision. Not ignorance meaning stupid, but ignorance meaning they just don’t know.

    You do. You know what it takes, you’re the one who knows, you can see the future, and the future looks bright. Who cares if you fail?! If you never tried, you’d never fail, but if you quit, you’ll never know what you can be, who you can be, or what successes might be out there for you.

    Never quit, never surrender. Never give in to your fear. As Franklin D. Roosevelt said in his inaugural address, “the only thing we have to fear is fear itself.”

    Fear is temporary, courage is forever!

  70. As a 29 year old man who left a career and pent house, moved into an affordable dorm on a college campus to make my start-up dreams a reality, I say this post is spot-on!

    Not to mention my website mascot was partially inspired by the Cowardly Lion himself.

  71. Thanks so much for this story. After a year of planning I am now transitioning from a good, safe job to opening my own business and achieving a better work life balance. I’m committed and confident in my plan and my fears are motivating, not debilitating. Stories like this keep my going, and channel my energy and fears. And the reader comments were motivating, too – I realize I’m not alone in this journey !

  72. Yes! Oz himself turned out to be all bark and no bite. So it is in the Emerald City of busines: The loudest and most aggresive types will come up with a whisper when push comes to shove! Thanks, Evan

  73. Terrific post. It reminds me that it isn’t just me, but that we all have to overcome obstacles in order to succeed and that overcoming these obstacles can be mighty uncomfortable, if not outright painful at times. Thank you.

  74. I love how we can take a character from a movie like the Wizard of Oz and reveal how it relates to some of us in such a profound way. It’s amazing how his character can relate to in this case an entrepreneur in such an exact way.

    It really makes you wonder if the writers have these things in mind while they’re creating characters like this.

  75. Great, great post! It really was applicable to me and a coupla friends. I’ll be sure to reference it when that fear bug starts creeping back up! Thanks for the awesome, awesome insights!

  76. Jon,

    As a graphic designer with over 20 years experience I see this in myself all the time.

    In fact I had a big attack of the cowardly gremlins last year just before deciding to jump into the blog world.

    But I pushed through this feeling of self-doubt & finally started the blog a couple of weeks ago.

    On my blog I hope to help young graphic designers who want to go out on their own and push through their own self doubt. I’ve had good traffic so far and my analytics is telling me that people are reading it from all kinds of different places.

    While I hope to make a bit of money, my greatest hope is to provide some wisdom to graphic designers who want to go out on their own.

  77. This is an awesome post Jon!

    The Wizard of Oz has been my favorite movie for as long as I can remember, and it holds many business and personal messages.

    Each of the characters have their own messages to convey, and I think you have been spot on with the business lessons imparted by the great lion. Fear is typically at the heart of most of the things we do not do, and you are absolutely right when you say that everyone is afraid, even if they won’t admit it to themselves.

    However, when someone takes that step and does the thing of which they are most afraid, they cast off a bit of that original fear and make it easier to take the next step.

    After doing this enough, it gets a lot easier to remember how to roar each morning!

  78. There was a reason the wizard hid behind the curtain….He was afraid also.

    He was afraid of his success and that he would not be accepted, respected unless he had a great and powerful facade.

    So go on out and be Dorthy .


  79. Boy, do I identify with this. I just finished reading Art and Fear and it also spoke volumes. One thing I came to understand was that fear can make you drag your feet and go verrrryyyy slowwwwwwwlyyy. It seems like you work at something all day and at the end of the day you only got a tiny bit done. Still you are exhausted. Pushing through fear is like swimming through mud.

  80. You know, as a tennis teaching professional and senior tournament player, the one thing that all top- players have to do at times is “act”.

    There’s just always the potential for a player to get in their own way, you know those little voices, and for me, there are times when I have to act like someone else out there on the court.

    As a full time blogger now, acting may not be a good thing because we want and need to be genuine, however, I will think to myself “What would the guys over at Copyblogger do?” in this situation.

    Thinking of what someone else might do helps me break through the fear of publishing garbage and gives me confidence to just be myself.


  81. Great article. I could use this reminder every once in awhile. I get so stuck on whether the path I’m taking is the correct one and end up redirecting my efforts, only to have it all fall short. Persistence is key with anything really, anything truly good in life takes time and effort. You just have to keep at it. 🙂

  82. I am so swept with emotions atm. I have just found you in this cyberland. I have just read through your blogs on How to quit your job,move to paradise and get paid to change the world and this one I am commenting on. You are truly a gift in this world. I wanted to acknowledge that fact. Also, I want to say thank you for your courage and finding a way to speak with all of us that need a clear voice. I have been searching for many years a way to make money doing what I do but I have never considered blogging along with what I do. Also, you have opened my eyes to some of why etc. I can do it.I make art in many mediums. I have been outside the job realm for over a decade but now find myself back in the arena again. I want to work for something more than minimum wage or money/I want to inspire and help and I know my talents possess the ability if I can find my way. I just want to say thank you for the strength and devotion to others you have poured into the world. I will continue reading your blog daily now. I will send you mine when I figure out where and what it will be. I am not sure I can say it will be about one thing. Is there a good place just for a blog about whatever but a serious one? well sorta I am funny sometimes 🙂 Any suggestions on this matter would be greatly appreciated. Thanks again! I wish I could express here better what your words mean to me today. All I can say is it gives me Hope and a fresh perspective I needed. I hope maybe I can find a way to return that out that somehow.Thanks so very much~Mars

  83. This is my first time visiting this blog, but I’m glad I found it! What a great comparison, and something I needed to hear. The idea that we all have everything we need already inside of us is one that I hear a lot, but it takes constant affirmation and pushing through fears to make it into a belief. Thanks for illustrating it in another way for me. I will be back!

  84. I’ve read all your other blog posts here at Copyblogger, but I found this one to be the most inspirational and beautiful. Well aside from your post about your mom’s dedication and strength.

    Nice work, Jon Morrow.

  85. Excellent article. I like it your way of telling to the readers. Easy and effective. What attracted more is the image of your blog post 🙂

    It’s really look amazing LOL

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