Dive 100: Why I don’t wish I started this sooner

What was cannot change. There's no value dwelling on what could have been.

Hey, it’s Alvin!

Whether you’re new here or you’ve stuck around since the first dive, I’d like to thank you for reading. After all, this is the 100^th dive of my newsletter, Below the Surface. You make this tight-knit community special. And you’re the reason I have so much fun writing every edition of my newsletter. So, you have my gratitude from the bottom of my heart.

I never expected more than a handful of people to be interested in anything I had to say. Especially for a newsletter with no niche. So, to have over 500 subscribers two years in, far surpassed my expectations.

Sometimes when people succeed in something, I’ll hear them say,

“I wish I started this sooner.”

For example, I’ve heard YouTubers with hundreds of thousands of subscribers say, “I wish I started making YouTube videos sooner.”

I don’t share this sentiment.

I just find this to be an unproductive way of thinking. You can also sense the regret. If you’ve followed me long enough, you know regret is an unhealthy source of motivation.

This frame of mind makes questionable assumptions. But if we Flip this Frame, we’ll uncover a way to grow towards your goals without being held down by “what could have been.”

Despite the success of my newsletter, I don’t wish I started this sooner.

This only sounds wrong… on the surface…

If only…

Upon success, it’s tempting to assume that shifting the timeline back must mean that the same kind and level of success would have been achieved sooner. But this assumption is the product of a limited imagination.

It could’ve also been worse.

Would I have achieved the same level of success if I started my newsletter sooner?

Maybe.

Maybe not.

But it would be absurd for me to assume that a single factor (starting sooner) would’ve made all the difference if we consider that most success stories have multiple contributing factors.

I didn’t start my newsletter sooner because I was working on other projects a few years ago. If I split my attention among more projects, would my newsletter have been as successful as it is today? Hard to say.

I publish my newsletter on Substack. Substack didn’t exist until 2017. If I started before 2017, I would have been publishing on other platforms. Would I have found the same level of success on other platforms? Maybe. Maybe not.

If I published on Substack in its early days, maybe I would’ve had a “first-mover advantage.” On the other hand, the platform would’ve had fewer readers, too. So, that could’ve been a disadvantage.

If I started Below the Surface sooner, I would’ve had fewer experiences to share. I would’ve had less credibility in my field of software development since I would’ve been a junior or intermediate developer. Although maybe I would have written about other topics that would’ve garnered more views. Maybe. Maybe not.

So, would I have achieved the same success sooner if I started sooner?

Maybe.

Maybe not.

The truth is… I have no idea how my newsletter would’ve done if I began it earlier.

It could’ve done better.

It could’ve done worse.

It could’ve done just as well, but differently.

Any scenario I’m imagining in my mind is just a fiction of my imagination. At best, it’s a story that has no impact on me now since the alternative didn’t happen. At worst, it’s hindsight bias that makes me feel regretful and hopeless because I can’t go back in time to change anything.

So, why do we bother focusing on “what could have been?” It turns out the answer to this question can be super valuable for personal growth. But only if it’s asked with a specific intent…

What if…

Imagining “what could have been” is what psychologists call counterfactual thinking.

There are 2 types of counterfactuals:

Downward counterfactuals explore how things could’ve been worse. They make us feel better about our current situation.

I could’ve been struck by a cyclist. I wasn’t. Thank goodness.

Upward counterfactuals explore how things could’ve been better. They leave us feeling worse about ourselves because they instill regret—a longing for a better present and future. And that can sound bad, but…

Upward counterfactuals are powerful if we draw lessons from them and apply those lessons to self-improvement.

I work as a software developer. My team and I do this all the time. There was one time I broke software used by thousands of users around the world. I thought I’d be fired. Instead, our team got together to understand all the errors that led to the outage. And we explored what each of us could have done differently to prevent a similar incident in the future.

Upward counterfactuals helped me and my team improve. But the counterfactuals were only valuable because we asked “what could we do better” with the goal of finding lessons to grow stronger. We didn’t just dwell on some alternate reality where the incident didn’t happen.

Where do we go from here?

So, despite how amazing it’s been, do I wish I could have started my newsletter sooner?

Not really.

There’s no guarantee how it would’ve gone if I did. It could’ve done better. It could’ve done worse. Either way, I can’t go back and start sooner. In fact, we can’t start anything earlier than “now.” So, I see no value dwelling on how things could’ve turned out if I started sooner.

Since I have a choice, I’d rather think my newsletter started at the exact right time—the time it was meant to start. This unshackles me from the torment of dwelling on what could have been.

I also like to think about what I could have done differently with each edition to make each dive better than the previous ones. At least I can extract lessons from these upward counterfactuals that I can apply to improve current and future editions of my newsletter for you and every other reader out there.

I can reach out for feedback on additive upward counterfactuals to find out what I can do to make Below the Surface better.

And I can explore subtractive upward counterfactuals to find out what I can stop doing to improve it.

Let’s avoid dwelling on what could have been, and focus on figuring out our next best step forward from here on out.

For personal growth. And mental health.

Thank you for reading the 100^th dive of Below the Surface. Once again, I appreciate all of you who have stuck around. And I welcome those of you new to this newsletter. I hope you all enjoy and get something from it. I can’t wait to dive into other life topics that mean the world to me.

Reply to belowthesurfacetop@gmail.com if you have questions or comments. As always, I’d love the hear from you. I’d love to explore counterfactuals with you.

Thank you for reading. Leverage those counterfactuals. And I’ll see you in the next one.

Cheers!