When Lost, Ask Your 95-Year-Old Self

“Life has been a haze… Everything feels like a side quest, but not in an inspiring way… I have infinite freedom, yet I don’t know what to do with it.”

The co-founder of Loom wrote this a year after selling his company for such a huge amount of cash that he decided it wasn’t worth it to stick around with the acquirer for another two years and $60 million dollars. Unfortunately for him, he’s yet to figure out what is worth it.

Over 1.4 million people saw his tweet. Thousands offered advice:

• “Stop thinking and go do something useful.”
• “Embrace the purposelessness.”
• “Start a robotics company.”
• “Go into venture capital.”
• “Read this book/article.”
• “Have a kid.”
• “Find God.”

But not a single commenter posed the simple question:

What would your 95-year-old self want you to do?

What Every 95-Year-Old Self Wants

Though every 95-year-old has unique desires, there are two things none of them would ever complain about:

1. Feeling they gave their best to life. Doing what they’re naturally good at in ways that help others. 
2. Feeling they got the best from life. Enjoying relationships, experiences, and the roses along the way.

This presents a challenge to us not-yet-95-year-olds: How do you have your cake and bake a beautiful one, too?

Some people give, give, give – aka work, work, work. But even if what they worked on was their calling, they often regret ignoring their families and enjoying the spoils of their labor.

Other people get, get, get. But even if they manage to fill their lives with hedonism, they often end up feeling hollow. “I wonder what I could’ve done if I’d applied myself.” 

Most people accomplish neither. They follow society’s stream, working too hard in ways that hardly use their gifts, and wasting non-work time on distractions.

This gloomy Loom guy? He “won” society’s race along the stream. Now he’s in a swanky eddy, going in circles without clarity on what to give or what’s worth getting.

Defining an Extraordinary Life

In 2013, I had just 0.1% of his wealth but 100% of his questions. After a decade of researching, experimenting, and soul-searching, I realized the first step in figuring out what to do with life is defining what your 95- (as well as 65- and 45-) year-old self wants it to look like.

My definition:

An extraordinary life – aka “true success” – is giving your best to life, getting the best from it, and inspiring others.

The third part—inspiring others—comes naturally when you do the first two.  You’ve seen people like this. They’re thriving at work and outside it, even if in a humble setting. They’re in their element. You can tell they’ll be deeply satisfied at 95.

We see them and think, “I want that, too.” But then we try to copy their path instead of crafting our own. It never works. You can’t copy extraordinary.

Systematic Obstacles Call for Systematic Solutions

We’re fortunate to live in a time when we have the freedom to engineer extraordinary lives. Yet few people do.

Why? 

Because both society and our evolutionary wiring push us to give what they want and get what they value. These forces almost never align with our 95-year-old selves’ desires. Ironically, if we fulfill our future selves, we’ll not only thrive personally but also help create a more extraordinary society—and make “extraordinary” easier for everyone.

But how do we overcome these systematic obstacles? By implementing systematic solutions. 

I see four pillars to living extraordinarily:

1. Keep your foundation solid. Health, relationships, habits, finances—prevent these from causing unnecessary friction. 
2. Hone in on your “gift.” What role would an all-knowing CEO of the Universe assign to you?
3. Own your story. We act according to the stories we tell ourselves, so make yours a good one.
4. Steer systematically. Have a practice that keeps your inner saboteur at bay so you can focus on giving and getting your best.

Back to the Loom co-founder:

• He’s got his basics covered, with plenty of money to spend on staying solid.
• He has obvious talents, proven by Loom’s success and other projects.
• But he lacks clarity on his gifts, the values his future self wants him to fulfill, and the problem he wants to solve to live a great story.

No reason he can’t figure these out and get on an extraordinary path his 95-year-old self will thank him for. I’ve done it (I think). And I believe you can too.

An Agent at Your Door

In 2024, I honed my own gift: “engineering extraordinariness.” That clarity fueled a bold vision: to help create 1 billion extraordinary lives by 2080. That means rethinking how society educates youth, develops talent, and defines success.

Where to start? By assuming a new role:

I am an agent sent on behalf of your 95-year-old self. 

I don’t work for you; I work for them. My job is to help you apply systems to give your best to life and get the best from it, so that when you’re on your porch at 95, you can say, “That was awesome.” And your loved ones will agree, following your lead to forge extraordinary paths of their own.

Want to Start?

If your foundation is solid, you’ve succeeded in conventional ways, but now you’re ready to get on an extraordinary trajectory, I invite you to:

Join me as a beta tester for my new ARC program. 

We’ll work one-on-one to strengthen those four pillars: foundation, gift, story, and system. 

You’ll find more info here: thezag.com/arc/.  

More Stuff Your 95-Year-Old Self Wants You to Read

• The Next Best Thing You Can Do Is Broaden Your View of Time: How to escape short-term thinking and make decisions your future self will celebrate.
• The Ultimate Guide to Befriending Your Future Self: Transform your relationship with your future self from stranger to trusted advisor.
• Don’t Minimize Regrets. Maximize Your Anti-Regrets: Stop playing defense against regret and start creating moments your future self will treasure.
• How to Find Your (Not-So-)Superpower: Discover the unique gift that lets you contribute meaningfully while energizing yourself.