How to Make Better Life Decisions

Over the past 2 years since the pandemic started, I made some life decisions that altered the trajectory of my work and personal life. Internally debating what to do could have set me on a mental tailspin.

But oddly, although living with those decisions are at times difficult, the process of making the decisions were straightforward. Clear.

I credit it to clearly knowing my personal values, but also to the process I’m about to share.

Life decisions are rarely easy. They're typically decisions with either:

• Two extremely good options (or conversely two extremely horrible options)

Or

• One option that makes logical sense. The other option that is intrinsically illogical but your heart wants to pursue it.

What do we do? My suggestion…start with the end in mind.

I have two mental tools to introduce to you today:

• Regret Minimization Framework

• The Top 5 Regrets of the Dying

We’re Wired to Avoid Pain

Regret can be a powerful thing. Regret can also be painful. Daniel Pink wrote a whole book on it called The Power of Regret. It chronicles and categorizes the types of regrets people have had in their life and what they wish they had done if they had a do-over.

My personal takeaway from the book was to anticipate regret and use it as a tool for good. For better life decisions. Daniel’s quote concisely captures this for me.

“When we handle it properly, regret can make us better. Understanding its effects hones our decisions, boosts our performance, and bestows a deeper sense of meaning.” - Daniel Pink

But how do we make better life decisions? How do we avoid regretting those decisions?

Jeff Bezos has the answer.

The Nerdy But Useful Regret Minimization Framework

Have you heard of the Regret Minimization Framework? It was developed by Jeff Bezos early in his career as a Wall Street analyst when he was faced with the significant life decision to give up his lucrative Wall Street job to pursue his crazy startup idea of an online book store.

Jeff clearly made the right decision for himself with this framework. So there’s a good possibility it could work for you & I.

When faced with a difficult life decision, this framework helps you identify whether something is the right fit for you by forcing you to face the end of your life.

1. Picture yourself at 80+ years old on your death bed

2. Think of a decision you’re struggling with today.

3. On your death bed, ask yourself:

4. Would you regret not pursuing this opportunity?

5. Would you be satisfied you pursued this opportunity even if you failed?

6. Would you feel the same way about the alternative option?

It’s such a simple framework, but one that can guide you to a better path.

I used this framework early in my career in my 20’s when I took a 40% pay cut with a Fortune 500 company to pursue a career path that was better suited for me. I haven’t regretted that decisions since.

The Top 5 Regrets of the Dying

From a longer term lens, this is another mental tool that’s good to have in your toolbelt.

I’d like to think that we all want to have a complete & fulfilling life. One that’s filled us up in every possible way, with little to no regret. A life that didn’t end in…”I wish I had…”.

Bronnie Ware, a palliative care nurse, wrote a book called The Top Five Regrets of the Dying. In her career, as she cared for her terminally ill patients, she faced death regularly.

She documented the life regrets of her patients and found the five following themes:

1. I wish I'd had the courage to live a life true to myself, not the life others expected of me.

2. I wish I hadn't worked so hard.

3. I wish I'd had the courage to express my feelings.

4. I wish I had stayed in touch with my friends.

5. I wish that I had let myself be happier.

When I read this list, it spoke to me. I could see myself in every single one of those regrets. And I didn’t like the path that I was on.

Even if for some reason we don’t know what we want, we typically know what we want to avoid. These are extremely powerful when you overlay them on your current life path.

I credit this list as one of the mental filters I used to transform the trajectory of my personal life.

Which one of these resonates with you? Could you confidently check-off on every single one of these?

Your One Action Item This Week

With all this in mind. I’d like you to pick at least 1 of the Top 5 Regrets of the Dying that resonates with you the most.

One that you want to avoid when you’re on your death bed.

Your action Item: What is 1 thing you will do this week to avoid that regret?

If you’re open to it, I’d like to hear thoughts. What are you going to work on this week?