Change Your Life by Understanding Yourself

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Sid Yadav is the co-founder and CEO of Circle, a community platform for creators. Before Circle, Sid was the third hire and first designer/front-end engineer at Teachable, where he grew into the VP of Product. At Teachable, he built a product team of 8 and helped scale the company from $0 to $22m ARR. He grew up in Queenstown, New Zealand, and now lives in New York City.

Biggest fuck up?

In a previous job, I was promoted to a VP role way too early in my career and had to learn everything from how to hire and manage people to how to plan your calendar as an executive in a very short amount of time. I wrote about some of the lessons I learned in a blog post

Key takeaways:

  • Don’t be afraid to step up, given such an opportunity, even if you see a mountain ahead of you. I never once regretted stepping into it, and it taught me so many lessons, more than any success I’ve ever had.
  • Don’t be arrogant. Learn to be extremely humble, and be an information sponge. If you’re humble and giving it your best, people will generally be nice and patient with you even if they know you’re failing.
  • If you ever get promoted to an executive role, you’ll be very tempted to add processes and checks and balances to justify your position. Avoid as much of it at all costs. Being a manager or a VP isn’t about “process”. It’s about doing the right thing for the current scale of the company, which at times are very unscalable things. This was probably the biggest lesson for me.


What really gets to me is the need for everyone to be right all the time, especially when presented with evidence on the contrary. I love this quote:

“if you want to be right all the time, you should be the first person to admit when you’re wrong — if you keep doing that, you’ll never be wrong!”

If you look at most problems in the world today, they probably stem from someone who, deep inside, knows they’re wrong but won’t ever confront it.

Useful Advice 

When it comes to truly changing your life, I think most people should avoid “prescriptions” in books, podcasts, and even articles like these! Those are great for entertainment and finding inspiration but very rarely lead to actual life-changing outcomes.

Instead, I find that if you block out some time, even just once, to really do an audit of some of these questions and focus on understanding yourself, you may have much better luck (credit to Jerry Colona for some of these):

  • What is the truth behind what motivates me to act in the ways I do?
  • How am I complicit in creating the conditions of my life that I say I don’t want?
  • What am I not saying that needs to be said?
  • What’s being said that I’m not hearing?
  • What am I saying that’s not being heard?


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