How to Build Your Self-Confidence by Memorializing Praise and Rejection


I've had the opportunity to mentor a breadth of product managers through the years as well as entrepreneurs through my work as an advisor to early-stage startups. And in doing so I've spent countless hours working through product challenges, startup challenges, and everything in between. As I work more closely with each individual, their guard starts to come down, they start to open up, and ultimately become willing to share some of their biggest challenges, uncertainties, and fears holding them back.

What's been fascinating to learn is just how many folks struggle with self-confidence. As well as how many suffer from deep-rooted imposter syndrome. This effects so many of us, including folks who are regularly perceived as successful. And this certainly isn't just a female issue. While it flies in the face of the Silicon Valley stereotype of founders having some of the biggest egos out there, I've seen the opposite to be true and think these issues are some of the most pernicious affecting folks from realizing their full potential.

It's a complex set of issues with no silver bullet solution because so many of these inner beliefs stem from pivotal experiences folks have had that have been memorialized into their self-image, whether they realize it or not.

In my own youth I often struggled with my own lack of confidence. It would exhibit itself in so many ways: being afraid to talk to that girl I liked in school, shying away from trying out skiing because I didn't think I could handle it, or always worrying about whether I was going to pass a test that I was undoubtedly over-prepared for. Yet, somehow, over time, I was able to change my inner monologue and reframe my very own beliefs. And eventually even develop a very strong self-confidence that has served me incredibly well in both my professional and personal endeavors ever since.

But I know so many haven't gotten there yet in their own journey. So I wanted to share a couple of techniques that I have used for years now as one small way that I try to continue to control my own inner monologue instead of allowing it to control me. I know it's going to be easy for some of you to look at these techniques and jump to how cheesy they can seem. But I'll remind you that the inner monologue holding you back is all in your own head! And they are effectively games your mind is playing on you that are preventing you from achieving your full potential. So you need to fight back with your own mind games just like I do.

The first technique I use is to judiciously capture every piece of praise anyone has ever bestowed upon me into a praise note in Notejoy. It doesn't matter how small or monumental the praise is, it always goes into my praise note. This serves a few purposes. First, we often don't take the time to appreciate it when someone praises us. We have so much on our mind, worrying about this, that, or the other, that we often just brush off these moments and move on with life. But it's a huge missed opportunity to appreciate someone else as well as to take advantage of a important self-confidence boost! By forcing yourself to capture it, it forces you to take a moment to really memorialize the praise and appreciate yourself for whatever you're being given praise on. It creates a delightful moment that's likely to turn into a highlight of your day. Secondly, it becomes an incredible resource to come back to. When your struggling with your confidence, when your feeling down, or whenever your having doubts, scrolling through your praise note serves as a strong reminder to yourself of what you are capable of and just how much others value you.

I find myself adding to or scrolling through my praise note a couple of times a month. I've captured all sorts of praise in there over the years. Here's just a few recent items in there:

Sachin - nice meeting you as well. I’ve gotten 100% extremely positive feedback from your presentation today. It was outstanding. Thank you for making the time and all the best. - Andy MacMillan, CEO of UserTesting 1.16.19


Wait... you built Notejoy all by yourself?!? I can’t believe that! I thought you had a whole team. I am blown away! That is just amazing. - Dylan Field, CEO of Figma 7.28.18


You have such a beautiful voice. I noticed it as soon as you walked in. - Barista @ b patisserie 10.18.17


So I had an intern start this week and my welcome doc for him was a clone & update of the one you wrote for me back in 2014. I've received multiple people telling me it's the best they've seen and now they're making a version for their interns too. - Steven Kaplan, Group Product Manager, LinkedIn 6.1.17


Now the next technique I use is actually the polar opposite of the first. I also judiciously capture every rejection I've ever had for something I cared about in a rejections note in Notejoy. People are often surprised by this one as it's easy to see this as a potential downer. But I don't use it that way. Memorializing rejection is equally important as praise. The reason this is so important is because it helps you realize that being rejected is not the end of the world. That life goes on. And frankly in many cases, you go on to thrive in so many unexpected ways. The fear of rejection holds so many of us back. And the best thing you can do for yourself is remove that fear's power of you. So what that you are rejected! It's not the end of the world.

I have tons of rejections in my rejections note. Including going all the way back to not being accepted into Stanford University, my top pick for college given my early passion for technology and entrepreneurship. I just had to be out on the West coast where all the entrepreneurial activity was. But alas, I was waitlisted and it ultimately wasn't meant to be. I was absolutely devastated. But I went on to get a fantastic education at the University of Pennsylvania and Wharton. I also ultimately met my wife, Ada, at Wharton, which was absolutely life-changing and I would have missed out on that had I gone to Stanford.

I have other rejections in there as well, including not getting an Associate position at Redpoint Ventures very early in my career when I thought a stint in venture might have been valuable for me. Ultimately didn't get the role despite my best efforts. Again I was bummed. But you know what? I ended up starting Connected instead, a startup that ultimately went on to be acquired by LinkedIn. So things worked out phenomenally. And I also ultimately realized a stint in venture capital early in my career would have actually set me back significantly from my ultimate goals of becoming a product exec and successful startup founder.

Once you learn to reduce the fear of rejection from your life, you can actually unlock incredible opportunity for yourself. I've now gotten to the point where if I'm not adding entries to my rejection file every single year, I'm absolutely doing it wrong. Because it means I'm playing it too safe. I'm not taking enough risks. I'm not putting myself out there. Unless you are taking risks, you'll never know what you are fully capable of. When folks come to me after applying to a few roles and not getting the job, I always tell them, you only need one job! Keep applying! Doesn't matter how many times you are rejected. And when folks come to me excited about getting offers at all the places they interviewed, I tell them they probably didn't set their sights high enough on the kinds of positions they are capable of getting, which is it's own missed opportunity!

I hope you see how these techniques of memorializing both praise and rejection help to modulate your own self-image and thereby improve upon your own self-confidence. I'd encourage you to start your own praise and rejections notes to see if they help you too.
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