EFP 70: Overcoming Entrepreneurial Self-Doubt, Insecurity, and Unrealistic Expectations

Justin Cooke

November 14, 2013

EFP 70: Overcoming Entrepreneurial Self-Doubt, Insecurity, and Unrealistic Expectations

Entrepreneurs probably doubt themselves more than anyone. Is my idea good? Do people value what I have to offer? The self-doubt goes on and on.

Curing Yourself of Crippling Doubt and Other Mental Garbage

This week we talk about the mental barriers that we see come up over and over again. Even successful entrepreneurs feel like frauds. Hell, Joe and I both do from time to time. Another common worry we see is that families and friends don’t quite understand the unconventional path of “Internet jobs.”

This episode has something for just about everyone. We all doubt ourselves as entrepreneurs and we all feel worried that we could lose it all.

Check Out This Week’s Episode Here:

Direct Download – Right Click, Save As

Topics Discussed This Week Include:

  • Update from Davao and the recent Typhoon Yolanda
  • Overcoming the worry that you’re not good enough as an entrepreneur
  • How to stop worrying about how others view your work
  • The misconception of not needing money
  • Don’t worry about diversification – double down on winners
  • Common team building struggles that you may be facing



  • “Stop looking for permission because you’re not likely to get it.” – Justin – Click To Tweet!
  • “If you never fail or don’t have a history of failing then I have a hard time believing you are successful.” – Joe – Click To Tweet!

Do you find yourself struggling with the same issues we talked about on the podcast? Get in a conversation with us on Twitter, leave us a message on SpeakPipe, or leave us a comment below – we’d love to hear from you!

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  1. JakubHanke says:

    I worry about diversification a lot, because I started invest in shares prior to finding online business :) I want to focus just on three main websites and nothing more, but that’s not so easy especially when browsing Flippa every single day. Glad you have not been hit by the typhoon!

  2. Dan says:

    Hilarious guys! Loved this one cracked up multiple times. Especially love the speech on the entitlement crowd. There’s a few pull quotes in there for sure.

  3. Charles Floate says:

    Hey Justin,

    You remind me a hell of a lot of GrooveHQ! Keep up the awesome tutorials and I’ve just launched my new company, plenty of anxiety over whether It was the right choice over quitting my job… Hopefully I can put my faith and confidence back into myself after a good days work!

  4. Hey guys,

    Thanks for the kind mention in this episode.

    About the typhoon – I actually got a chilling email from one of my oDesk freelancers which explained how the typhoon had affected them. Not long after that, I got the one from oDesk explaining how we could donate via their platform (as Joe explained). I couldn’t resist. I had to send money. I know that what seems like a little bit of money to me will really go a long way over there…

    Everything else you covered in this episode hit home for me. I’m so grateful that you guys continue to produce episodes like this. It really helps keep guys like me motivated and dedicated to moving forward.

  5. Dave Starr says:

    Gangbusters, guys, one of your best ever. I totally agree with the advice about not spending all the time on things like tax avoidance schemes, overseas corporations and bank accounts, etc. Build the damn business and start making a profit first.

    I have a blog reader who has now spent nearly a year doing his “due diligence” for a buisness he plans to set up here in the Philippines. LLC, bank accounts, a banking scheme I don’t even understand, business insurance policies (at least three thta I know if), and lawyers out the ying-yang in three different countries.

    The sad part? He has yet to sell his first product here in the Philippines!

    Talk about the tail wagging the dog.

    • Justin Cooke says:

      Booyah…thanks, Dave!

      Yeah, man…tail wagging the dog, indeed. It’s interesting how common this trap is though, eh? We’ve fallen into it before ourselves, which is why we try to warn about it now, heh.

      • Dave Starr says:

        Of course, everyone has different needs. Example in you and Joe’s case a corporate structure was nearly essential for the foreign business (employees, visas and such) which you were setting up.

        But in most cases, a guy/gal building web sites on their own or with contracted labor, doing affiliate ales, CPC, etc. there is often no need at all for incorporation.

        It may even be very harmful to the individual just trying to earn an honest buck.

        Main point is, though, as you point out, “Eye on the Prize”, not worrying about building a fancy podium for the prize presentation ;-)

        See: Are You Sure You Want to Start a LLC?

  6. PeterTrapasso says:

    Hi Guys,

    In your email that went out about this podcast you mentioned, “Joe and I are safely in the mid-5 figures with our business today.”

    You are making around $50,000 per year in revenue from your business?



  7. Maxime Sincerny says:

    “MEDIOCRE” lolll

  8. Hey Justin & Joe – Glad to hear you guys are okay there. I have family in Manila and that was some kind of storm. wow.

    The point about not worrying how others view your work really hits home. A lot of people don’t quite get what we do online. They might have a narrow view of how people make money online or just don’t really have any context to draw upon. I am finding that if I can provide my friends and family with some actual results they are way more likely to buy in and support me.

    Joe, buddy, I bet you’re a fine salesman – minimally sleazy. I have an engineering background too so I get where you’re coming from.


  9. Hey

    Good to see you guys back in full swing.

    As always I have a lot to agree with here. My divergence is in the details.

    As a business man I believe in the old adage of employing people who are better than you are at a task. Creating the structure and vision and getting the hell out of the way.

    I do agree that a business needs funding and a run way. Where we differ is that employing smart people to leverage your ideas does make sense (Thats as long as they are contractors not hires). Even when money is tight and you can ill afford them, to blast away for hours,days or weeks doing a below par job to save funds is potentially dangerous. Sure put major effort in but identify and eliminate your weaknesses..

    I dont think pure ideas people can make it no. But i think Ideas plus experience and a great team can work.

    Whilst open and transparent business are a great way to learn. Pat’s blog has inspired many as has yours. I feel no need to blog about my ups and downs. Especially when causal effects are outside the business.

    Do i need to be a brand to be successful/happy/or have integrity I think not. Hopeful in a years time Ill make it on the mentions section with my latest attempt :-)

    • Justin Cooke says:

      Hey, Steve…thanks for sharing your thoughts!

      Yes, a business can definitely suffer from “death by a thousand cuts”. Trying to cut core spend can put out a sub-par product/service that will doom you, for sure.

      I’m not entirely sure transparency would work (better) in every industry, but it sure would be interesting to see more try.

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