Feeling Uncertain Doesn’t Make You Weak, Weird, or Unqualified

I have two stories to tell you.

Story Number One

I was in a bar in New York City and I was trying to convince a stranger to fly to Buenos Aires. I had never been there, but I knew it was the right place for him.

This man told me that his dream was to run a soccer camp for kids in South America. After tossing out a few possible locations, we both agreed that Buenos Aires would be the perfect place to start.

I asked if he would move there if he had the chance or if there was something keeping him in New York.

“Absolutely, I would move,” he said. “I don’t have family or friends or anything keeping me tied down here.”

We talked about whether he could save up enough money to fly down there. He could, and so I pressed him further.

“Perfect,” I said, “Here’s what I would do, if I were you. Once you have the money saved up, buy a one-way ticket to Buenos Aires. Make sure you have enough to buy a ticket back as well. Get down there and hit the scene hard for as long as you can afford it. If for some reason you can’t make it work by the time your money runs up, then buy your ticket back to NYC and you’re back where you started.”

He smiled, but shook his head and said, “Well, that’s just a dream.”

Story Number Two

I spent a long time preparing to launch my first business. I was drawing sketches of the website on a whiteboard for 4 years before I launched it. Basically, I was in perpetual planning mode.

Eventually, I ran out of excuses, put some money where my mouth was, and launched it. In total, it cost me $1,600 to get a prototype built (I had to pay for some programmers to work on things because I didn’t know how to code).

What happened? That business idea made me a grand total of $118.05. For those of you planning to do this at home, this is the opposite of what profitable businesses do. (Thankfully, I figured this out when I quickly moved on to other business ideas.)

What’s the point of these two stories?


I get what it’s like to feel uncertain and unsure about your abilities. I understand how it feels to finally work up the courage to do that thing you wanted to do … and then fall flat on your face.

Thankfully, I kept pushing, continued to experiment with different business ideas, and I’ve been a full-time entrepreneur for over 3 years now. Becoming an entrepreneur was one of the best decisions I’ve ever made. But it wasn’t easy in the beginning. There was a lot of self-doubt and fear. And there were plenty of reasons to feel that way.

I’ve noticed similar feelings in other areas. I wrote for over a year in a private document before I finally worked up the courage to start writing these Monday and Thursday articles. Now look at this place. We have over 47,000 members in our little community.

These fears and uncertainties are everywhere. We feel them with little things like going to the gym. (Will people judge me? What do I look like?) We feel them with big things like moving to a new country. (That’s just a dream. I could never drop everything and make it work.)

The Bottom Line

But, and this is the main point of all this, I want you to know that I’m going through it with you. I’ve said this many times, but I don’t have all the answers. I’m just learning along the way like everyone else and sharing what comes up during the journey. But I have no plans of just becoming someone who writes about it and doesn’t practice it.

How easy would it be for me to sit here and say, “That guy in the bar was an idiot! He has the money. He has the freedom. He should follow his dreams!”

And I think he should follow them, but have you ever embraced that kind of uncertainty with open arms? Change is hard, but oftentimes the hardest part isn’t knowing what steps to take or figuring out what is important to you. The hard part is handling your own psychology, getting over your own fears, and finding the grit to make something happen.

If I could see that stranger again, I’d tell him two things.

First, I’ve been there man. I get it. You’re uncertain and unsure and you doubt that you can make it all work. That’s normal. I felt unsure when I moved to a new country. I felt uncertain when I started my first business. I felt like an amateur when I started writing publicly. It doesn’t make you weak or weird or unqualified. It’s normal.

And second, keep pushing. Don’t chalk things up to “just a dream.” It can be something small like making it to the gym or something big like buying that one-way ticket to Buenos Aires, but if you keep pushing enough, it’s going to be a reality instead of a dream.

If you are lucky enough to find a way of life you love, you have to find the courage to live it.
-John Irving


  1. Clarity is power!

    Uncertainty is part of life and fear of failure is what stops 97% of us from becoming the best we can be! This is my year to STOP IT. What is the worst that can happen?

    Exactly — it wont kill me.

    Thanks James. It is said when you are ready, the teacher will appear. I am and there you are. Cheers.

    • Procrastination has been one of my biggest faults and has cost me in the past. 2014 and that is behind me now. Your article is very timely and has brought home to me here in New Zealand that we can do things anywhere in the world. Looking forward to future articles.


  2. Hi James,

    I want to thank you for the article about feeling uncertainty. I am a grandmother and a widow, starting my own permaculture farm. There are so many decisions to take and I’ve been going at it in baby steps, because of uncertainty. I have some knowledge and no experience, but I have a vision in my mind and heart. Still, it has been hard not to feel self-criticism or despair.

    By the way, you said that you felt like an amateur when you started writing publicly. Well, that’s a great place to start from, because amateur comes from the word “love” in Latin. You obviously love what you are doing. Thank you for writing. I always find your articles helpful and supportive.

    • Thank you Rose. I am a amatuer and thanks to your comments, that word now means love to me…. what a great different perspective.

    • Hi Rose — have you tried to hook up w/ any college classes that do permaculture? There is a LOT of interest in it among some of the college age folks — and they have energy too! There are also online certificates in it, I believe. Hugs, from a fellow gardener/orchardist.

  3. James – this was EXACTLY what I needed to read today. Thank you! I am basically at the same place as the guy you mentioned in Story #1 — but the details of HOW to start the new adventure eludes me. I’m not giving up though. :)

  4. I’ve jumped out of my comfort zone quite a bit now and I can say with all honesty it’s those experiences that’ve made me the resilient and independent person I am now. Yep, I still get scared when change is on the horizon (especially when I feel like I can’t control it) but if you can’t stop it, embrace it. As I’ve gotten older I’ve gotten bolder, so now I think ‘What’s the worst thing that can happen if I try this?’. Usually it’s something you can plan around and it’s also not that bad. I say go for it!

  5. Great post on uncertainty. It’s something I struggle to accept sometimes – to accept that my circumstances will have to be uncertain, but if I want it bad enough, I’ve got the balls to push through it and realise my goals.

  6. James,
    I am a big fan of your work. I love your writing style! This article comes right on time for me. I have my struggles sometimes with my project, and I am thankful for the way you explain things so simply yet so eloquently. I appreciate this article!

  7. This is just what I needed to hear. I’ve been wanting to move out of state for a while. I did once for a bit but some bad choices led to my return. I’ve learned and grown but my family is apprehensive about me leaving (I’m single, no kids or anything), while my friends are all for me adventuring off and fulfilling some dreams. The more I linger around with my fam the more uncertain I feel but after reading this I think that’s fine and normal! If things don’t work, I can always come back (I hope they work though). Thanks for the inspiration!

  8. Hi James,

    Life begins at the edge of your comfort zone. Uncertainty sucks but not as much as looking back on a life unlived.

    Thanks for the inspiration.


  9. Yeah! And here I am on the other side of the world doing it and still scared sometimes. There is no ‘going home’ for me, I’ve been nomadic since 2004.

  10. Thanks for the reminder James.

    I have nothing to add but only one thing – uncertainty is a part of our life and rather we like it or not, we need to live with it.

  11. James,

    I’m confused. I get the point of Story #1, but I don’t get Story #2. You finally put the money up, took action, and it’s only made a very small amount of money. Are you saying the guy was right not to go to Buenos Aires? Or are you saying that if he goes, and only accomplishes a very tiny bit, at least he WENT, and turned his dream into at least *$118.05* worth of reality?

    I guess the confusion comes in the fact that in one breath you say you’ve been a full time entrepreneur for three years now, and in another you say the company you launched has only made $118.05. Maybe that company is only one of many. (Not sure I’ll get a response if you have 47,000 followers, but it’s worth a try.)

    Thanks for these messages.


    • Hi Tina,

      Sorry for the confusion. I definitely could have explained that better. Yes, my first business idea flopped. I have started many others since then, some of which have paid for my lifestyle the last 3+ years.

      Tn story number one, the man I met decided not to go because he faced fear, uncertainty, and self-doubt. In story number two, I was simply trying to say that I get what he is feeling and I also understand how hard it can be to work through those things and make the dream a reality. In some cases, you’ll fall flat on your face (like I did with my first business idea). However, and this is the point of the whole article, if you’re willing to embrace that uncertainty, see the failures and setbacks as an opportunity for growth rather than a defining result, then you can work through the difficulties, master your own psychology and make it work.

      Bottom line: fear strikes all of us, working through it isn’t easy, but it is possible.

      I was just hoping to share the lessons learned from my own experience. Thanks for reading!

  12. Good inspiration – I too am caught up in my own uncertainty, frozen like a deer in headlights and wasting precious time, always thinking tomorrow, next week, next month, I will make a decision and the longer this pattern goes on, the harder it is get going. Thanks for this timely reminder, James.

  13. I wish I could bottle just one ounce of your insight! I am so thankful I stumbled upon your website. Thank you for your desire to make a difference and for
    for challenging us to do the same.

  14. I believe that the problem, for most of people, it’s not about failing but losing the dream.

    The best thing about a dream, someone said, it’s the chance to become real. If one fails trying, then not only loses the dream but hope to. They aren’t only afraid of failing but afraid of not having anything left to live for, to hope for, instead of feeling some closure. Not risking is the middle term to the best and the worst that can happen.

    I’m not saying that I agree, but I do understand the need to have hope.

  15. I’ve been in both situations.

    I passed up a potentially great job opportunity in Australia when I was 19 and I’ve had a couple of career choices and business ventures that ended with myself in the red.

    I’m planning on launching a new business/career venture in the summer and what I keep coming back to are the two questions of “What can I afford to loose?” and “What could failure cost me?”.

    I am still deciding if the answer to the first question is more than the answer to the second.

  16. Loved this James, thank you! Sometimes uncertainty makes me feel like Im lazy. Deep down I know Im not lazy or unmotivated. Im learning to trust my gut more and stop listening to that little voice. For me, fear takes a while for me to push through. Its frustrating, but easier when I accept that and just keep on pushing:)

  17. I’ve been there lately.

    And suddenly I came up with a question that makes everything clear for me: “If that’s what must be done, then why do I have to fear anymore?” Because it’s the thing that must be done, so I’m going to do it anyway. Then why fear? Why anxious? There’s just no reason for that.

  18. Words that came DIRECTLY after an evening of internal strife. Getting over our psychology is exactly the issue. Good luck to us all. And thank you for the words.

  19. James – Thanks for the reminders. I have tried and failed, but I am going to keep on trying. I am more afraid of quitting than trying and failing. Keep encouraging us.

  20. Quite perfect for me today. Glad to know that others have faced similar feelings and have made them work to their benefit. :)

  21. I’ve always told people when you start your own business, your demons come out – and that’s a good thing. These demons are the limiting beliefs that held us back in our comfortable – but unsatisfying – lives. The beliefs could be “I’m not smart enough”, “I don’t have enough money”, “What if I fail?”…

    These are all fears we drummed up in our heads. Like one post said, fear won’t kill us. I believe when we don’t follow our dreams, we beat our soul into deeper, false beliefs of limitations. To me, that’s crueler than death.

    After 15 years of starting different companies, demons still surface. But each time they do, I just embrace them as one more belief to acknowledge, and consciously ignore. Then I replace it with what I believe to be true. We are all awesome. We are all limitless.

    Fear is your soul letting you know you’re expanding. Move past the fear. The fear is temporary, while the expansion you gain from moving forward will bring more joy than you can imagine. Jump. Just jump and know you’re safe and you’re more than capable of success, no matter what you think now. Jump.

  22. Great article, James, thanks a lot! You are right, change is hard but the most difficult part is handling your own psychology. Excessive self-criticism and the fear of being not good enough, not professional enough (I have a whole list of not…enoughs)is what keeps me from achieving my goals. To me, changing of mindset is the key priority for having a better life, let alone reaching your highest potential, and living your dream.

  23. Uncertainty is a big obstacle. What is most frustrating is that realizing that, doesn’t necessarily help in overcoming it. It is the first step in choosing to overcome it I suppose. I’ve just recently overcome some of my own uncertainty and started something I never thought I would…We will see if it pays off.

  24. James! I’m not sure how you do this but each one of your
    email I receive, ALWAYS fits with my weekly personal development
    question (do you have spies on me man? ;)) Seriously, I enjoy each
    one of your posts and I read them as my bible. If in a rush, I make
    sure to star it and get back to it later. That said, you’ve touched
    a serious point when you said “feeling amateur when starting to
    write publicly”. I’ve been wanting to start that blog. I did
    actually. It felt good. But I got pushed back by my own judgement
    and now it’s sitting on ice. I’m back to the drawing boards about
    deciding on which subject I’d feel comfortable to write about (and
    be the best at it too). I feel like I’m making excuses to push it
    back every time. This post didn’t go unnoticed. Thanks (again) for
    this inspiring message.

  25. Tonight I was researching how to create a marketing plan on Entrepreneur.com and saw your bio at the bottom. One click and here I am, relating directly to this article. I wanted to start my business almost a year ago but I stalled out… mainly because of fear. I made excuse after excuse, but the timing really was right. However, I decided to try it again and I have a launch date of March 2014. My nerves are starting to get the best of me and fear of failure is creeping in. Why is it so hard to take the leap? I don t know, but this time I’m going to do it. And I’m glad I’m not alone. :)

  26. Once again a phenomenal article that speaks directly to me. Thank you for having the courage to work past your uncertainties, you have tremendously helped me, and I know you are helping so many other people!

  27. Inspirational piece, thank you.

    Reminds me that every time I make a decision despite my doubts, I’ve NEVER felt more alive and ALWAYS learnt something.

    Someone wise person once said, ” A rut is just a grave with the ends knocked out”.

  28. There is a saying of Hazrat Ali A.S. the brother of Prophet Muhammad PBUH… “No-one can increase the money written for you and nothing can make the death earlier”, So up-to us to try without any fear!!

  29. I grew up surrounded by military culture. I believe in traveling light and acting swiftly. General George S. Patton, Jr. once said the worst thing that can happen is for someone to say, “Ready, aim, aim, aim. Somebody has got to shoot.” Last year I had an idea to put unemployed, disenfranchised people back to work in a temp to hire ‘second chance’ model. Incorporated the LLC in two hours; approached a major manufacturer that had a social conscience and found a ready opportunity. Found a payroll funder and showed them the contract. Grabbed and customized the employee application and handbook from ‘boiler plate’ on the Internet. Called a social advocate that I knew in the region around the factory, who connected me with 5 nonprofit referrers who now refer candidates. Bought a sound school bus to transport people to work. Secured insurance on pay as you go plan. All in four weeks. Billed $80K the first week; now billing $80-90K consistently and talking to the international manufacturer about repeating program at 9 other locations. The fly in the ointment? None. But I do have at least two dozen dead concepts on the junk pile that never got their wings. Thanks for this affirming blog, Mr. Clear. People need to be challenged to take aim and shoot.

  30. Wow… the uncertainty has been stopping me in my tracks lately. It’s so wonderful how your words can help me so much. Thank you, Thank you, Thank you.

  31. Hi James,

    Awesome article! I have started a new career and am filled with self doubt but I will put into practice your tips! I can do it I just have to believe in myself and guess what — I don’t know what I don’t know,so I will feel unsure!

    Thanks for the pep talk. You ROCK.

  32. I’m trying to move to another county to live and work for several years. I also feel uncertain about the future and I even’t can’t make sure I can get a job there. But I’m trying. There’s no failure before I give up. I’ll do my best to get there.

  33. James — uncertainty, fear, or whatever moniker you want to give the feeling has paralyzed so many and allowed greatness in the form of projects, symphonies, songs, ideas and inventions to lie dormant within them. This article is SOOOOOO on point and speaks to what I have wrestled with for over a decade. Thanks man for having the courage to continue to take steps in a direction that you feel is right.

  34. Hi James,

    Thank you so much for your articles! I always enjoy reading them.

    I recently stumbled upon this quote and it is my new motivation for this year:

    “If your dreams do not scare you, they are not big enough.” -― Ellen Johnson Sirleaf

    Your article really resonated with that quote and just reinforced everything you said.

    Keep up the great work!!! :)

  35. I am moving temporarily to another country for work leaving my husband behind. We have agreed it is for the best (no household income for some time now) and we will see each other etc. Twice I should have been on a plane but HR haven’t got the paperwork sorted. Each of those days and on other days I have become so anxious, horrible sick feelings. I want to be able to accept my situation and not let these debilitating emotions override the good stuff. I do all the usual stuff, Tai Chi, breathing etc. How do I learn to accept what is?

  36. Wow… what a wonderful message. I found you, James, because I read a post on Rebelle Society that you wrote about Dr. Suess and I loved it. I just finished reading The Alchemist by Paulo Coelho. It seems to be a recurring theme in my life right now. Don’t give up the dream. Your writing style is very personable. I like it a lot and I thank you for sharing these thoughts. As they spoke a truth into my heart that just keeps confirming… DON’T ever give up!

Leave a comment Share your knowledge and experience.