What would you have done differently?

Knowing what you know today, if you could go back and time and do that thing again, how would you approach it the second time around?

This a helpful exercise to gain insight into our weaknesses and address our shortcomings. It’s not about regret or dwelling on the past, rather, considering how much you’ve grown since then, and leveraging those learnings to spiral up.

Because the reality is, life rarely if ever turns out the way we would have liked. Less than ideal outcomes are par for the course. The secret is evaluating our experiences with an iterative lens. Using our experience and data and feedback and identify what worked and what didn’t, and then incorporating those learnings back into future efforts.

That way, every decision an experiment to be tested. We work flexibly and dynamically.

Now, if this sounds like the job description for a computer engineer at an agile startup, you’re right. You hear that word iteration a lot in the tech world.

But the principle behind the word can be applied to ritually anything. Hell, human life is a complex iterative model. Everything that happens today forms for the basis of what can happen tomorrow.

Let’s explore a few examples and benefits of this mindset.

The first one is efficiency.

When you approach things iteratively, you embrace trial and error. You try stuff. Lots of stuff. Early and often. You fail quickly and quietly. All of which move you towards a desired results faster.

I find this aspect of the iterative process to be highly efficient. Compared to some people, who prefer to work on coming up with the final product without trying new ideas along the way, I believe it’s easier and smarter to bias towards action.

You start before you’re ready, before it’s perfect, before you have enough information and reassurance, and let the process teach and guide you.

I think back to the first corporate resume I ever made. Having spent the first ten years of my career as an entrepreneur, the major challenge was translating my experiences from running my own publishing business to a talent stack that companies would find valuable, and then visually communicate that story in a unique and creative way.

To be fair, my version one wasn’t awful. But considering how far I’ve come since then, looking at it today makes me want to facepalm.

What the hell was I thinking? What company in their right mind would have hired me?

The language was vague, superfluous and unconvincing. Plus, there was no job experience listed on my resume. Just a bunch of bullet points about my skills.

I don’t beat myself up about it, because I did end up landing a job. More importantly, I have iterated on that resume multiple times since then. And now it’s one hell of an efficient calling card.

Another upside to the iterative mindset is adaptability.

I find it useful to view my brain as an artificial intelligence fighting machine that corrects its own mistakes by collecting information on the opponents it encounters. That way, every subsequent model improves upon the previous one by correcting the flaws discovered during fights.

With every experience comes modifications, and as a result, my intellectual mechanism becomes more capable against challenges, solving more problems and fending off potential threats to its plans.

Now, such a visual might sound absurd, cold or robotic to you, but to me, it’s joyful and motivation.

Because I love learning. Curiosity motivates me. Testing something out and then tweaking my iteration to hit my goals is fun.

Especially when I end up doing something I didn’t expect at the start of the process.

As an example of adaptability, let’s continue with the job search analogy. When I’m looking for a new gig, I apply for fifty to a hundred jobs every day. I will typically do between eight and twelve interviews every week. And I’ll continue that process until offers start coming in.

Many of these jobs I’m excited about, some of them are moderately interesting, and some of these positions sound downright since the product is pointless and the pay is dogshit.

But you better believe I do interviews with every single one of them.

Remember, I’m a learning robot. My artificial intelligence is here to iterate. To practice. To improve my skills and improve its adaptability.

The more hiring managers I talk to, the more market feedback I get, and the more I can tweak my pitch, materials and strategies.

Like a software designer, I’m continuously scraping away at elements that may be clouding my process with cognitive friction.

In addition to efficiency and adaptability, here’s a final benefit to maintaining the iterative mindset.

Compassion and humility.

When you iterate on anything, you’re doing the best you can with the information you have. You’re not trying to get it perfect on the first go. You do what you can with what you’ve got. And once you finish something, you use that information to take another, more educated stab at it.

I’ve worked with many software engineers in my career, and I like how they think of iteration as a succession of approximations. Each one builds on the one preceding to achieve a desired degree of quality.

This attitude has a high degree of humility and compassion, because you’re accepting the fact that you don’t really know what you’re doing, and that’s okay. Because you trust the people and the process. You surrender to them. And you know that whatever happens will happen, and you’ll figure out a way to leverage the learnings for your benefit.

Allow me to share one final career related example for this final benefit.

I have a friend who’s worked the same job for twenty years. He’s an amazing scientist I have deep admiration for his intellectual gifts.

Meanwhile, I’ve worked no less than ten jobs in my career. Now, neither of us is better or worse than the other. It’s simply to different career paths.

But for my purposes, I’m glad I’ve had so many career iterations. I’m grateful that I’ve been laid off from various jobs because of cutbacks, recessions, fundraising failures and whatnot.

Sure, being shit canned sucks in the moment and you feel rejected and lonely and angry.

The upside is, my vesper of humility is now finely tuned. I’ve had continuous practice being compassionate to myself during trying times. And that’s a priceless asset.

Sometimes I think that’s my real career. Learning how to be resilient in the face of disappointment, failure and rejection.

Matter of fact, maybe I should write that on my resume.

Okay, enough telling you how much I’ve suffered.

In summary, the mindset of iteration affords us the opportunity to gain efficiency, adaptability and humility. And the best part is, we don’t have to know how to program computers to do it. Iteration only requires a willingness to experiment, a desire to grow, and a commitment to loving ourselves during the process.

Knowing what you know today, if you could go back and time and do that thing again, how would you approach it the second time around?