Effective in Minimizing Regret

I want to thank everyone for the kind words I received after announcing my departure from Amazon. I have finally decided to take a pause from climbing the corporate ladder and focus on scaling what I have been doing on the side for over a decade. Am I done with the corporate world? Not really, but I believe it’s a good time to formally build on my passion project. Below, I explain the frameworks I used to make this decision and share more about how this applies to my next chapter after Amazon. (Read beyond the signature for more details)

The Theory

The Regret Minimization Framework was created by Jeff Bezos to justify his decision to leave a VP-level job on Wall Street to launch an online bookstore. Bezos imagined himself at age 80, looking back on his life and realizing he would regret not seizing the internet opportunity more than leaving his high-paying job. This eventually led him to leave his stable job, move to Seattle, and found Amazon. His framework highlights the importance of considering future regrets to make bold, life-changing decisions, even if that means jeopardizing short-term security (well, we all know this worked out well for him).

We overestimate the effect of potential losses and then regret our decisions later. This phenomenon is extensively covered by Kahneman and Tversky's Prospect Theory. It outlines that people weigh potential losses more heavily than equivalent gains; however, evidence also suggests that most people regret inaction more than potential failure. In "The Top Five Regrets of the Dying," it is revealed that many people, in their final moments, express profound regret over not having the courage to live true to their dreams. This insight aligns with psychological studies, suggesting that the pain of “what could have been” often follows us until the end of our lives.

Our default mode is to just keep the current course. As previously mentioned, we all have Two Selves, and if we don't do the proper (hard) self-reflection, it is easy for our Doer-self to make the decisions, as opposed to our Planner-self. Our Doer-self doesn't like uncertainty and will likely focus on not rocking the boat if "things are going well."

My Personal Thoughts

If you follow your dreams, you better have a good backup plan. I believe there is a tendency to idolize stories like Jeff Bezos' and disregard some important facts. In Jeff's case, he had a VP-level Wall Street job he left on good terms, a degree in computer science from Princeton, was still young (30), and is estimated to have a really high IQ. This is not to minimize the fact that he took a risk but to point out that, if he failed, he still had many opportunities to fall back on.

How to Put This into Practice

So, should you just drop everything and follow your dreams? Well, it’s complicated. My recommendation, as usual, is to "break the lion into small kittens", avoiding drastic and passionate decisions and playing the long game by following the steps below:

Step 1: Discover the thing you are likely to regret not acting on (aka Your Lion). Reflect on the things you constantly think about or that you enjoy doing in your spare time.

Step 2: Break the lion into small kittens and act on one. Break this big project into as many parts as you can think of and find the lowest hanging fruit you can act on.

Step 3: Once you nail that, add the next kitten.

Step 4: Keep going until you get to 20% of your time. The Mayo Clinic suggest that fulfillment is maximized when you spend 20% of your time working on your passion; beyond that, the rest starts to be marginal increases [I propose how to carve out time in this post].

Step 5: Keep scaling until you feel comfortable making the jump. When you get to Step 4, you'll probably either confirm your aspirations or burst your bubble. So, this final jump might never come, and that’s OK (at least you won’t regret it at 80 anyways). If you do decide to take this step, make sure you have validated your idea and also something to fall back on.

Effectively,

Jorge Luis Pando

PS-Bonus section: Sharing how this applies to my personal story

In previous posts, I've often wrapped up around this point, aiming for a concise read of about 2-3 minutes. However, as promised in my last update, I'm sharing my own journey and my next steps.

My own journey:

Step 1: Unveiling my Passion: Back in 2016, I wasn’t really doing much about my love for public speaking and developing others.

Step 2: Low hanging fruit: Fast forward to 2017, I reserved a meeting space at Seattle's Apollo building and initiated a training series. What began with a modest audience of 20, grew into sessions with up to 400 participants.

Step 3: I automated my presentations. By 2021, after delivering countless presentations, the repetitive nature was reducing my enthusiasm. This lead me to pivot towards automation and tailor-made workshops for teams.

Step 4: I built a newsletter. In 2023, acknowledging the opportunity from having an untapped email list, I launched a newsletter, scaling back workshops to still allocate 20% of my time.

Step 5: The time is now. I have validated my idea by saving countless hours for thousands and having an engaged subscriber base. I also have a contingency plan in place with a robust network that I can (hopefully) use to go back to the corporate world. So, I am ready to make the jump and try to avoid regretting it when I am 80.

What am I offering now:

I just created a new company, "Effective LLC," to start offering what used to be my side gig to everyone. My main goal is to ensure people are building the right foundations for a successful career, making them feel in control of their own journey. Here’s what’s on offer:

1. This newsletter: I will keep posting every Friday. Share it with others using the referral link at the bottom of this email. [Subscribed: 3k+]

2. Sign up to be a Founding Member. Be an early adopter of what I am currently building, a program focused on having strong foundations for a successful professional career. [Requests Received: 100+]

3. Request to train your team. Reply to this email if you want to elevate your team's effectiveness with training sessions that can help participants reclaim 2.75 hours weekly. [Requests Received: 5]

4. Book a 1:1 session with me. If you consider that your needs require immediate attention, you can reply to this email with your request [Requests Received: 2]

If you read this far, thanks! I think you would be a great founding member… think about it.

"Whenever you see a successful business, someone once made a courageous decision" - Peter F. Drucker