The moment you doubt whether you can fly, you cease forever to be able to do it - Peter Pan

Hello there!
I was a bit late with my post last week – it has been a little bit crazy in my world; but I am back on schedule today with my Wednesday posts.  And this one is one of the better ones 🙂
I used to have some major procrastination issues and as I have gained more experience I have been able to overcome my self-doubt and it has made me so much more productive.  And so I hope this post helps you in some small way, too.  Have a wonderful week!


“I don’t believe anyone ever suspects how completely unsure I am of my work and myself.”   — Tennessee Williams

Raise your hand if you’ve ever felt like that during your career. I don’t think there’s anyone who’s ever started a new job, taken on a new role, launched their own company, or taken any kind of real risk in their career who hasn’t thought at least once, “I can’t do this.” (And if they say they haven’t, they’re probably lying.)

Of course, for lots of people that’s just a passing feeling, an unpleasant stepping stone on the way to success. But for plenty more people, the feeling that they’re not quite good enough persists throughout their careers and personal lives, and becomes what drives their decisions.

For me, I’ve always been sure of myself as a programmer; I knew I was smart and I knew I was really good at my job as an engineer. I had clear deliverables and knew what needed to be done to achieve them. But when I started working as a manager and tried to see myself succeeding in this role I’d never envisioned for myself, I struggled with self-doubt.

Especially in a management position, where your daily tasks and deliverables are much less defined (“work on your ‘big picture’ thinking” does not have an especially obvious course of action for self-improvement) it’s easy to assume that when there’s a problem on your team, it’s your fault.

Even as a developer, I used to have a huge problem with procrastination whenever I had a big project I wasn’t sure I could do. I would put off the work until the absolute last second, then work extremely hard and complete the task. I always wished I could apply that kind of last-minute energy all the time, but my lack of confidence got in the way for years.

The point I’m trying to make is, self-doubt happens to all of us in any role, and it most often happens when we step out of our comfort zone and try something new (at least a bit). But whether it controls our actions or stops us from achieving is another thing altogether. And that’s where I want to start.


“The moment you doubt whether you can fly, you cease forever to be able to do it.”   — JM Barrie, Peter Pan


We can all be our own worst enemies. Even if no one else doubts your ability to handle a new role or a big project, there still that little voice inside your head that reminds you that you could fail and finds reasons to convince you to not even try.

And once you go down that road, it can be hard to turn yourself around. Self-doubt compounds on itself when it goes unchecked and can grow in power until it becomes the driving force behind every major decision you make.

One of the trickiest things about it is that it is usually such a private struggle. It’s hard to tell if anyone around you is struggling with their confidence; in fact, it’s easy to assume that everyone around you who’s succeeding is doing so effortlessly and with complete self-assurance.

The moment you doubt whether you can fly, you cease forever to be able to do it - Peter Pan

When I first became a manager at Amazon, I had a mentor who was a VP that had managed people for over a decade and seemed to have it all under control all the time. I remember in a meeting with this person, when I asked them for advice on my own struggles with self-doubt, they replied, “Sometimes I feel like people are going to find out I don’t know what I’m doing.”

It was such a relief to know that I was not alone. Remember, everyone has doubts about their own abilities (even the people you least expect), so if you have them too, it just makes you human.


“If you hear a voice within you say ‘you cannot paint’, then by all means paint and that voice will be silenced.”   — Vincent Van Gogh


The most effective way to conquer self-doubt is to fake it until you make it. Just because your mind is telling you that you might fail doesn’t mean you can’t go after what you want anyway.

And you don’t have to recover all of your confidence overnight to start making progress in spite of your own doubts. The more you succeed in spite of your own doubts, the quieter that nagging, questioning voice will become too.

  • Write it down. If you’ve got a big goal in mind or a small project to complete, writing down your goal in your own words can help make it manageable. Seeing it written down reminds you what you’re working towards and helps you focus your energy.
  • Break it down. Turn your project into a doable, actionable checklist to give yourself specific tasks you know you can accomplish. That way you can turn “build a customer base” which is big and vague into “make 50 cold calls every day” which is specific and achievable.
  • Take small steps. When your confidence is shaken, it’s hard to “turn on” that feeling of kicking down the door and going after what you want. So don’t force it. Make progress is small ways to begin with, and work up your momentum to take big leaps.
  • Get busy. If you keep your head down and get to work, you won’t have time to come up with a million different reasons why you might fail. Taking action – and not stopping – is the best way to silence your inner critic.
  • See it through. Sometimes it feels so good to just get started on a project that it almost feels like you don’t have to finish it or achieve the original goal you set out with. But sticking with it is what will help you build confidence and believe in yourself in the future. Establish a track record of success that your inner critic can’t argue with.

“Success is not final, failure is not fatal: it is the courage to continue that counts.”    — Winston Churchill

Confidence doesn’t come to everyone naturally, so keeping it up takes effort and attention. Especially as you advance through your career, it becomes easier to doubt yourself when you have other people relying on you for leadership and direction.

Personally, I keep a list of what I call “non-negotiables”. This is a list of the goals I have for myself and the things I won’t compromise on. Whenever I’m feeling lost or like I’ve gotten off track, I check in with the list to remind myself of what’s really important to me. Writing these ideas down is a great exercise for putting into words exactly what motivates me, and is also a concrete tool I can always use for guidance when I need it. So how else can you fight self-doubt before it strikes?

  • Recruit a cheering section. I could not have made the huge steps I made early in my career without the support of fantastic mentors and friends who believed in me (even when I didn’t). Who in your life can remind you how great you are when you forget? It can be a spouse, a peer, or a professional coach. Even if you think you can go it alone, having a little back-up is always a good thing.
  • Ask why. If you can identify what causes you to start doubting yourself, you can use that information to avoid wavering confidence in the future. Were you asked to apply a skill you don’t have much experience with? Did you face a fear, like speaking in public or delivering bad news? When you see red flags of doubt on the horizon, you can better prepare to avoid it.
  • Remember: things that are worth doing are rarely easy. Nobody is born with the skills to be a master programmer or CEO. It’s learned. And taking a risk, doing something beyond your normal experience, is what yields the greatest results.The hardest projects and roles are usually the ones that teach you the most, so don’t shy away from them just because they’re daunting.


We choose to go to the moon in this decade and do the other things. Not because they are easy, but because they are hard.”   — John F. Kennedy


When have you faced self-doubt in your career? How did you handle it?

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