Confidence development

You’re good at what you do. You like to think so. But it’s one thing to think you’re great and another to believe you’re great.

The app you made is amazing and helps people every day. And yet, you know it has bugs and the design makes you cringe.

You love to write and you want to write a book, but you’re too embarrassed or scared to write anything and share it with the world.

What you feel like, instead, is an imposter (ala Imposter Syndrome). You feel shame: both in not being able to exercise your abilities effectively and not being able to believe in yourself (recursive shame!).

Am I good enough to call myself that?

Here’s an incomplete list of roles I’ve bestowed upon myself over the years. In each of them, I’ve experienced moments of self-doubt and shame in my lack of ability to be skilled in the role:

Working at Bebo, even though I’d been hired specifically for my experience with mobile platforms combined with my interest in the then-budding world of social networking sites, I still often asked myself, “Am I qualified to do this? Am I good enough?”

Others may tell you you’re great, but that isn’t necessarily enough to convince you. You think they’re just being nice, or they’re words from your friends, so they don’t hold as much sway (which, BTW, is utter bullshit, but that’s a topic for another day). This is not confidence or belief in yourself: this is insecurity and seeking of validation.

Belief in yourself is not binary: walk before running

I can confidently call myself a software developer now. But this belief did not happen overnight. It took time, and it took work: some of it intentional and some of it not.

The important part is that you have to start somewhere, and you start with baby steps.

And at the beginning, it would be unwise to expect too much out of yourself. If you’re starting out and believe in yourself as a great violinist but go to audition for the San Francisco Symphony and end up crashing and burning, you can falsely lead you to believe that the experience you’ve built up so far was invalid.


I was once at a bar chatting with someone about Japanese grammar (thrilling, I know). She was telling me something that I knew to be wrong. I let her know that I did not think she was correct, and she insisted on her viewpoint. I decided not to pull out the “I actually have a Bachelor’s in Japanese Language and Culture” card that day, but my years of study and speaking with native speakers had built up a foundation of confidence to know that I knew what I was talking about.

I was confident in what I knew based on experience.

For me, confidence is not classified as an emotion, so it is not an expression from your body that’s telling you the state of things. Confidence is, however, something that can be grown, built, and developed with experience.

Once you’ve developed some confidence, you can continue honing it and growing it. You hold it within yourself based on your experience that you built up over time.

But how do you gain this experience?

Confidence development

In order to develop your confidence, you need to understand how you’re growing. And to get to that understanding, I find it easiest to find feedback loops.

Here are some feedback loops that have helped me:

  • Teaching and mentoring others: At Hipmunk, I had the joy of hiring and mentoring interns. Not only was it satisfying to share my own experience and knowledge, it solidified my own believe that the experienced I had was worthwhile. Similarly, pairing sessions I have with Mike Watts on Little Countdown bring up a lot of great questions and help reinforce my skills with another experienced developer.
  • Connecting with my tribe: Going to Defcon and talking with my fellow nerds let me reflect my own experiences with them. When I went to MicroConf, my eyes were opened to how far along (but also behind) in my journey as an entrepreneur.
  • Keeping a journal: Writing every day and looking back at where I’ve been, I’ve been able to notice how far I’ve come in my journey for personal growth. When I read old memories where I felt insecure about not being a good enough boyfriend compared to where I am now, I can feel both proud of myself for my progress and confidence in my ability to be a good partner for my wife.
  • Blogging: Much like mentoring or connecting with my tribe, blogging gives me a medium in which I can help others who are on their own journey of growth. By writing ideas down, structuring a post, and sharing, I make my own experience concrete and ultimately helps to develop my confidence in what I’m writing about. When I get comments about my posts, I get a feedback loop back to let me know that my experience is valid.
  • Setting goals: By setting goals, reflecting back on them, and seeing how much I’ve accomplished, I give myself a feedback loop to let me very viscerally see that improvements I’ve made in the progress of my skills.

With all of the above, I have to make myself vulnerable and honestly accept where I am on my journey of growth. Only then can I step back and take actionable steps on improving and developing confidence.

Compassion for yourself

Shame has no power when it’s been exposed.

When comparing your abilities to those who are elites in their area, of course you’re going to feel like you’re not good enough. Is this how you would talk to your friends if they were learning a new skill? That they’re not as good as Michael Jordan so they should stop trying to dunk?

Of course you wouldn’t, and when you speak with yourself about both your abilities and the confidence in your abilities, I encourage you to speak with yourself with compassion.

You’re doing great, and you’re making great progress.

Inspired by a cynefin99’s post in /r/aspiepositivity.