Leaving Work Behind

How to Defeat Self Doubt [in 5 Steps]

Written by Tom Ewer on May 14, 2013. 34 Comments

Our doubts are traitors, and make us lose the good we oft might win, by fearing to attempt ~ William Shakespeare (tweet this)

Photo Credit: Dom Dada

Photo Credit: Dom Dada

If you’re just starting out on the road to leaving work behind then one of the biggest issues you’re likely to face in the coming weeks and months is doubt. Doubt that your plans will succeed. Doubt that you have what it takes. Doubt that you’re capable of really quitting your job and building a successful business.

I know this because I had that same self doubt when I started out. It is a common theme in many of my early posts here on LWB such as How to Combat a Loss of Enthusiasm, The Importance of Mindset, and What Cricket Can Teach You About Blogging.

When I wrote those posts back in mid-2011 I had achieved nothing in the world of making money online. I can tell a different story today, but only because I fought and defeated the doubts I had in myself. And that’s what I want to help you with in this post.

Step 1: Recognize and Understand Your Doubt

Self doubt is not always a bad thing. I doubt my ability to survive jumping off the roof of a ten storey building, so I don’t do it. That’s a sensible doubt. It is the doubts that prevent us from fulfilling our unrealized potential that do the damage.

Therefore, before you can defeat destructive self doubt you must see it for what it is. That may sound obvious, but self doubt for many of us is as natural as breathing and might just as easily go unnoticed.

So ask yourself: what is it that you doubt? Do you doubt your ability to succeed in building a successful online business? If so, what is at the root of your doubt? Do you feel that you do not have necessary ability, experience, willpower, money, time, energy?

Write down what you believe is stopping you from the success you crave.

Step 2: Accept the Inevitability of Success

There are over 315 million people living in the United States and over seven billion people in the world. That means a many great things, but for our purposes I want to focus on just one simple fact: there is almost nothing you can achieve that someone hasn’t already achieved under greater hardship and with fewer resources.

Do you know what that means? I means that if you persist for long enough, you will meet your goals (assuming they are not wildly unreasonable). You do not exist under some unique set of circumstances that prevent you from attaining the level of success you desire. You launching a modestly successful online business is a drop of water in the ocean of human achievement.

Some things are impossible, or so unlikely as to be not worth pursuing. I’ll probably never walk on Mars or be a professional soccer player. I’ll never live in Buckingham Palace. But in saying what you think you could definitely never do, you suddenly realize what you might be able to do if you put your mind to it.

My favorite excuse that I often hear people use when telling me how they absolutely cannot achieve something is that they don’t have the time. Sorry guys — I’m calling bullshit on that one. How many waking hours do you spend doing things you need to do, as opposed to things you like to do? With the greatest respect to those who do have a lot on their plate, for every single mother of one complaining that she doesn’t have enough time to launch a business on the side, there’s a single mother of three who made the time.

For most of us, success is a journey with different paths but no dead ends — if you persist for long enough you’ll eventually reach your destination. The only decision you need to make is whether to take the journey or not.

Step 3: Take Baby Steps

In a post here on LWB titled Why You Shouldn’t Chase Your Dreams, I wrote the following:

…if you’re going to shoot for the stars, you best learn how to build a spaceship first. You’re going to need a space program for that too. What I’m saying is this – don’t chase your dreams; build towards them.

In another post titled How to Succeed I wrote this:

Visualise your success as a series of cracks in the ground. If they are just small cracks, then you can step over them and in time you will reach your target. However, if those cracks grow into chasms, you can no longer move forwards. One of the keys to success is to eradicate the impassable chasms, so you can step over the cracks with relative ease.

I’m sure you’re seeing the common theme here: nothing is more conducive to self doubt than trying to do too much too quickly. It is so easy to attempt the impossible and then tell yourself you’re capable of nothing when you fail. Yet that mindset is utterly absurd: failing in an attempt to do the impossible teaches you nothing about your capabilities.

With that in mind, don’t be afraid to take baby steps towards success. This thinking should be applied at all levels of your business. For instance, I initially had dreams of passive income success but eventually fell back onto freelancing, which has ended up being an extremely lucrative endeavour for me. The less likely path to success ended up being the best one. Similarly, don’t try to write an eBook by literally sitting down and attempting to write it. Start by producing an outline, then work on it chapter by chapter, in manageable chunks.

Turn those chasms into cracks.

Step 4: Don’t Feed Your Doubt

I am a huge fan of goal setting — I don’t know where I would be without my goals. I have covered goal setting here on LWB in posts such as How to Set Goals and Motivate Yourself to Actually Achieve Them and The Benefits of Goal Setting (Why I Disagree with Leo Babauta). So of course I am going to tell you to set goals. However, I urge you to do so with the following in mind:

  1. Prepare to adjust your goals based upon changing circumstances
  2. Never use your goals as an excuse to fail

One of my favorite online business and entrepreneurship books of all time is Rework, and one of my favorite chapters in that book is Planning is Guessing. Here’s an excerpt from that chapter:

Unless you’re a fortune-teller, long-term business planning is a fantasy. There are just too many factors that are out of your hands: market conditions, competitors, customers, the economy, etc. Writing a plan makes you feel in control of things you can’t actually control.

If you replaced “business planning” with “goal setting” in the above paragraph, you wouldn’t be too far from the truth. And yet goal setting is something that I urge you do. Let me explain.

The first personal goal I ever published on this blog was to quit my job by 23rd May 2012. At the time of writing that goal (July 4th 2011) it seemed like a complete fantasy. In a way it was — I had no clear means of achieving that goal. But I did in fact beat that goal by some distance — I quit my job effective 31st December 2011. Not only that, but I did it in an entirely different way to how I initially managed.

My goals were helpful in giving me direction, but I did not like them direct me mindlessly. Goals should be adaptable to the changing environment in which you work. As it says in Rework:

…you have to be able to improvise…Sometimes you need to say, “We’re going in a new direction because that’s what makes sense today.

To bring us back to the topic of this post, I mean to say that goals should fuel your drive and determination, not your doubt. Don’t let a failure to reach a goal affect your ego. Don’t respond to a failure to reach a goal with, “Well I knew I wouldn’t be able to do it anyway.”

Goals are not your enemy — they are temporary milestones that should be adjusted to suit your own internal progress as well as external influences. Treat them accordingly.

Step 5: Record Positives and Achievements

I am an avid amateur cricket player and I recently started having lessons with a professional coach. In a recent session I was recounting how fed up I was with my performance in a recent game and he gave me some simple yet effective advice: no matter how bad a situation, try to think of three positives that came out of it. Although it was a struggle, I did manage it. And then I felt a lot better.

There is always a silver lining to every cloud, and reminding yourself of your positive achievements in response to doubt and/or failure is a powerful weapon that you should utilize generously.

If you take the time to list your positive achievements you may surprise yourself. Consider for example the fact that I made no money for about the first six months of my efforts to launch a successful online business. In fact, I lost nearly $1,000. And yet I knew that I had learned a great deal in that time, and that if I persevered, my efforts would eventually pay off.

If on the other hand I had just reflected upon six months of failure, I may well have given up. All the potential was there; I just needed to employ the kind of patience that would allow me to succeed in time.

Finally, one of my favorite things to do is turn a negative into a positive. Take for instance the very first website I built. I spent hours and hours on it only to see it crushed by Google after four months of hard work. Although that first project was a complete failure, it taught me an enormous amount about various aspects of blogging and SEO. I used that newly-found knowledge in future projects to much better effect — the things I learned in building that first site set the foundation for what I do now.

Be openminded and optimistic about what you do, and see the benefits of both your successes and your failures. Don’t let self doubt creep in — there is no place for it.

Over to You

The worst thing anyone can do is give up. If you’re doing something — anything — then you have a chance of success (no matter how small). If you’re doing nothing then you have a zero chance of succeeding. Remember that and never strop trying!

If you are struggling with self doubt then I hope the above has helped you. If you have any questions or comments please do not hesitate to leave them below. I hate to think of anyone giving up on their dream to quit their job and build a successful online business and I would love to help you succeed. Good luck!

Make Your Start as a Beginner Freelance Writer

We're sure you've had enough of hollow promises and get-rich-quick schemes.

We don't buy into that stuff; it's never worked for us. Instead, we create profitable online businesses through nothing other than hard work and persistence.

Enter your email address below to get our best tips for getting a head start on the learning curve with our ebook "How to Make Your Start as a Beginner Freelance Writer" right away! Learn 10 ways to make money, how to set income expectations, and choose your niche in this comprehensive guide.

34 Responses to “How to Defeat Self Doubt [in 5 Steps]”

  1. Mike Collins
    May 14, 2013 at 3:58 pm

    Self-doubt can be a difficult monster to tame and it can undermine you and drive you off-course. I like your tip about taking baby steps and recognizing the small victories along the way. In the past I’ve been guilty of biting off more than I can chew and reaching for the stars without first building a working spaceship. Have to remind myself to take it one step at a time.

    • Tom Ewer
      May 15, 2013 at 1:02 pm

      That is the key…it’s amazing how far we can travel if we just focus on putting one foot in front of the other.

  2. Joe
    May 14, 2013 at 4:44 pm

    Another great post. Keep them coming!

    Recognising and recording successes, no matter how small is something I’ve been made aware of before but always forget. Will try and get back into the habit of doing so again.

    • Tom Ewer
      May 15, 2013 at 1:03 pm

      Hey Joe,

      Thanks! It’s not something that everyone needs to do but if you’re riddled with self doubt then I consider it a must.



  3. stephaniearsoska
    May 14, 2013 at 6:23 pm

    Thank you for this, exactly what I needed to read right now! My blog has recently started and I have been in a panic this week about putting myself out there and feeling very exposed and vulnerable. Sometimes you just need to dig in and hold on despite the discomfort, thank you for reminding me of this!

  4. Sibo
    May 14, 2013 at 9:22 pm

    Great thoughts, Tom. I was struggling with quitting my daily job for longer than 6 months because I never learned how important a goal is. I don’t know personally how long it took you to understand all of above. For me, I spent over 8 months on training programs, reading books. The process was not fun, but I went through it. Did I feel on my journey, many times, but I fail quickly and learn something from it.



  5. Bree Brouwer
    May 14, 2013 at 10:01 pm

    Love your “turn a negative into a positive” step. This is essentially what I’m doing now, when I realized my blog and freelance goals were not working.

    Instead of viewing the last 6 months as a failure, I’m looking on them as a learning exercise so I can better my chances for success this time around.

  6. Kathy Sullivan
    May 15, 2013 at 3:10 am

    Excellent post, Tom! Great tips. This sentence really struck home for me – “You launching a modestly successful online business is a drop of water in the ocean of human achievement.” That really puts things in perspective. My goals don’t seem quite so outrageous when I think of the whole of human achievement! In comparison!

  7. jonthan jacob
    May 15, 2013 at 9:05 am

    “The worst thing anyone can do is give up. If you’re doing something — anything — then you have a chance of success (no matter how small).”

    Thanks for that.

  8. Joe
    May 16, 2013 at 3:24 pm

    Excellent post Tom!

    We all struggle with self-doubt and your article was very helpful and encouraging. I really liked the comment about never giving up and eventually reaching our goals if we just don’t quit!

    Keep up the good work!

  9. thepotatohead
    May 18, 2013 at 1:07 am

    Excellent post Tom. I’m just starting out in blogging and decided to do a co-blog with a buddy of mine. I figure it will be easier to motivate ourselves during these periods of doubt if we have each others back and can bounce ideas off each other. It also gives me a sense of me needing to work just as hard if I see him working hard so it’s good for both of us to stay on task.

    • Tom Ewer
      May 20, 2013 at 10:36 pm

      Best of luck with that — my only concern would be that the blog will only move as fast as the least eager partner. If you can keep each other motivated then that’d be great.

  10. schellert
    May 19, 2013 at 11:30 pm


    I really love your post. Stopped by because you orginally followed me on twitter.

    I am starting to make a living online but had many times in the begining with doubt. Can remember working every night after I got home from work and on weekends to make a few hundred dollars. Also had a few months where I lost money too.

    Doubt is really destructive and so first step in the process is believing you can and then taking the steps to improve and get better.

    There will be bumps in the road but over time you learn to pick better tools, write good copy that creates interest and continue to move forward to where it eventually it starts to turn around.

    I want to point out you will not get rich overnight but you can make steps. The Guru’s that tell you they are quite often do not have a paycheck that supports their claim.

    I tell everyone give it a solid year of real effort is what it take and most take up to two years.
    If you quite then you have no chance of success!

    Few businesses make money overnight but never has their been better tools available to increase your chances of real success and do some of the heavy lifting. The challange is finding the right method for the novice.

    Well written….


    Steve Schellert

  11. John Banks
    May 21, 2013 at 12:46 pm

    “You launching a modestly successful online business is a drop of water in the ocean of human achievement.” – Really awesome post Tom. This has inspired me a lot, especially at a tough time.

  12. Christian Slagter - Slagter Media
    May 22, 2013 at 2:40 pm

    Thanks for the inspiring words, ecellent post. I sometimes get negative energy from clients who are not happy with the results. They don’t see the value of my effort. That’s why I’m gonna focus more on my own projects.

    I like to write so that’s a way of living. The goalsetting is very useful and like you say, you never know what the future will be.

    • Tom Ewer
      May 23, 2013 at 3:17 pm

      Hi Christian,

      Negative energy can be used to further yourself — do you take time to consider why your clients are unhappy? If I were to be cold I would say that the value of the end product is going to be far more of interest to them than the value of your effort. That’s why I always say that you should write to the client’s standards rather than your own.



      • Christian Slagter - Slagter Media
        May 28, 2013 at 12:40 pm

        Thanks for the reply Tom! I” dig into this approach because I see value in it for both parties :).

  13. Sarah Li Cain
    May 24, 2013 at 9:11 am

    I think too many people are afraid of failure. I remember someone telling me that they wouldn’t trust an entrepreneur if they haven’t failed at least a few times. I know I doubt myself too much at times, but I use that anger I have towards myself to find a solution to whatever is bothering me. I too am on a path to self-employment and it won’t be easy, but I think it’s totally worth it because I want it that badly.

  14. star
    August 25, 2013 at 5:12 pm

    I’ve just done the “Classic Mistake” (or what everyone around me feels like is a mistake anyway), of dropping out of college to pursue my music career. I feel pretty certain that as you put it my success is inevitable, however sometimes I hear myself thinking “you can’t do this”, out of no where when I’m planning or making music. This one small thought somehow overpowers all my certainty and confidence, is there anyway I can push this out of my head and keep it out?

    • Tom Ewer
      August 27, 2013 at 12:20 pm

      Yes — taking action. That thought won’t go away until you prove to yourself that you’re capable. Until then you need to be dismissive of it and focus on the positive aspects of your mindset. Good luck!

  15. Abhishek
    February 21, 2014 at 12:40 pm

    Hi Tom,
    From the past 3 years I have been trying to clear an exam but I have been failing miserably . I don’t know where I am going wrong.I even opted for guidance . Initially
    I feel motivated but as time passes the past shadows of failure start to haunt me.
    I gave up everything for the sake of clearing this time. Now I am feeling drained and worthless. I am feeling afraid to take a step fearing I will fail again.
    Hoping you can help.

    • Tom Ewer
      February 24, 2014 at 2:02 pm

      Hi Abhishek,

      You need to find out where you’re going wrong. Trying again, with everything at stake, without knowing this is not what I would recommend. You need to pour your energies into understanding why things haven’t been working out.



Leave a Reply

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