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2 Lessons From People Who Will Work Until They Die

I have friends and family who are going to work until they die. I’ve learned two massively important lessons from their lives.

Lesson 1: On Choice

Some of these friends have no choice. Their finances are: no work = no money, and no money = no life.

This quickly brings us to the first lesson.

Lesson 1: Your goal should be flexibility.

In everything you do, ask: is this adding to my choices or reducing my choices?

No – don’t buy every t-shirt you see. You don’t need to maximize your “wardrobe choice.” That’s not what I mean, here. Too much choice can be paralyzing, let alone bad for your wallet.

Instead, I want you to maximize your financial choice and time choice. Are you giving yourself the money and the time to choose your future?

You don’t have to examine your decisions every hour or every day. But you should check in on a regular basis. Did your past month increase your financial and time flexibility? Did 2021 help or hurt? Will your goals in 2022 help or hurt?

The easiest ways to increase financial and time choice?

  • Spend less
  • Save more
  • Invest what you can
  • Say “no” to things that will waste your time

In short, develop a bimodal mindset.

Those friends I mentioned before…I don’t know all the details of their lives. But I do know they made choices in their lives that reduced their flexibility.

And now they work.

They have no choice.  

Lesson 2: On Passion

I have other friends who are multi-millionaires (…I’m estimating. Because they’d never flaunt their wealth).

They are in their 60s, 70s, 80s. And they continue to work full days and full weeks.

They’re meetings with clients. Answering emails. Grabbing lunch to mentor eager youth like me.

These people don’t have to. They want to. And that’s the second lesson.

Lesson 2: Find something you want to do!!

Easier said than done. I know. And it’s cliché to boot. “Do what you love, and you’ll never work a day in your life.” Yeah, ok Confucius.

It’s difficult because there’s a narrow crossover between “Make money, increase flexibility” and “Do what you love.”

But you can try to find that crossover zone. Or at least move towards it. Progress is better than resignation.

Can you make your current job more enjoyable? Can you find a similar job that you’d enjoy more? Another employer, or a shift in duties?

The Stoics would say that happiness is rooted in your own mind, regardless of your job. Can you progressively practice a shift in mindset?

Is there another career path you want to be on? What can you do now to begin shifting in that direction? I didn’t know that starting The Best Interest in 2018 would shift my career path. But I pursued something fun, productive, skill-building…and it increased my future flexibility.

Will I work until I’m 80? I don’t know. But I do know these two lessons.

  1. I want to have the flexibility to retire if I choose to.
  2. And I want to live a life too enjoyable to retire from.

Both are easier said than done. But I’m trying.

Thank you for reading! If you enjoyed this article, Subscribe to get future articles emailed to your inbox.

-Jesse

P.S – I wrote a book! Check out the ebook here and the physical Amazon book here.

4 thoughts on “2 Lessons From People Who Will Work Until They Die”

  1. So, what does a “too enjoyable to retire from” look like?

    Mine tumbles somewhere around having the time and energy to draw, read, juggle, and but still work with a cause that helps people and nature. Wow, if that doesn’t scream millennial, I don’t know what does! 😆

    1. Hey BLL – great question! I’m going to steal the famous words of Potter Stewart: “I know it when I see it.”

      It sounds like you already have a pretty good idea what it looks like for you. That’s awesome!

      PS – you juggle?!

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