What would you say to your 2016 self?

What would you say to your 2016 self?

Founder's Notes

natalie eng

January 26, 2026

Many of you might have seen the 2016 trend, where we look back at where we were 10 years ago.

Looking back at my 2016, I realized I don’t have that many photos I actually want to post. It’s not that I didn’t take them – I did and still do take many pictures to help me remember my days better – but scrolling through now, most of them just don’t feel right to share.

I was wondering why and I think it was because 2016 represented a major shift in my life that I was trying to adapt to.

2016 was when I graduated. I was so excited to start working, mostly because I knew the management consulting job that I worked hard to get into would let me travel to places like India, Shanghai, Brazil.

Coming straight out of the structured bubble of school, that felt like success. Like I’d figured it out.

Back then, 2016 Nat had this very specific idea of what success looked like: climb the corporate ladder, get the promotions, do the thing everyone says you’re supposed to do and everything would be good. That was the plan.

So if you’d gone back and told 2016 Nat that she’d eventually get to join her dream company Google and leave it 4 years after to start her own company? I would have been like… what? Why would anyone do that? Google felt like the peak. The endpoint. What Nat always wanted. Why would you walk away from that?

I think the thing is 2016 Nat was chasing someone else’s definition of success that she thought was hers. She thought she knew what the path looked like. She thought if she could just climb the ladder fast, she would get what she wanted, be happy and all her hard work would be worth it.

She forgot that she would evolve as a person and become more acutely aware of what she truly wanted, instead of adopting societal definitions and metrics. She forgot that she also needed to constantly check if it was still the right ladder to climb for herself.

I don’t have a camera roll full of milestone moments from that year like some people do. But maybe the real milestone was just that shift – leaving the structure of school and stepping into everything that came after, even though I had no clue where it would actually lead. And realizing that I could either walk the path of others or figure my path out for myself.

If I could tell 2016 Nat anything, it’d be this: The right path for you isn’t going to look anything like you think. And that’s the whole point. After all, would we really enjoy the movie as much if we knew the ending?

I have a feeling that 2036 Nat might also tell 2026 Nat the same thing.

What would you tell your 2016 self?

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