Tim Denning Asked Me to Define Retirement. I Had to Think About It.
It's time we all defined what our 'retirement' looks like. Hint: It's got nothing to do with work. Or age.

I am not a friend of Tim Denning. Don’t get me wrong, I’m sure we’d be all buddy-buddy if we knew each other. I’d bounce his kid on my knee. We’d sing carols. Make S’mores. Drink lots of water.
But we don’t know each other.
I have rolled through a few of his classes. All well-structured. All informative. All relevant to the current marketplace.
I mean, he doesn’t actually do the work for you. Gotta do that yourself. So that’s frustrating. But he knows his shit. You’ll learn. You’ll improve. And you’ll make some friends along the way.
Probably not Tim though.
We do have lots of deep and meaningful conversation.
Right here. On Substack. In Notes.
I like to say hi. Leave a comment or two on his articles. Reply to his Notes.
It’s fun.
Until he responds. Oh, crap. Now, I have to come up with a smart and humorous reply. He asked me what I thought retirement was. Oh, man. Do I know? Better think about it?
Come up with something good.
If I screw this up, I’m toast. I’ll never make it. Online or anywhere else. So I thought about it for at least 15 minutes.
This is what I came up with.
My totally thoughtful, researched, and acted upon definition of retirement (heavily influenced by my still foggy Covid-brain).
The first thought was freedom. Retirement is freedom. The freedom to do what I want when I want. I want to be like Mel Gibson - well, not really Mel, but more like William Wallace - yelling freedom at the top of my lungs in Braveheart.
But without the disembowelment and torture.
It seems like torture sometimes. Trying to craft a life of responsibility and joy.
We all have freedom though. If we’re willing to pay the price. We can make the difficult choice. Stand out. Do what we think is right. Just ante up. It’s there if you want it. You may get your guts ripped out, metaphorically, but you can always push them back in. Start again. It’s a choice you have.
So no, freedom isn’t part of my definition of retirement.
How about ability?
Ability, as it relates to retirement, at least in my screwed up ‘Jeff Dictionary’, means we’ve prepared ourselves to face life’s challenges. The ones we choose to accept and the ones that slap us in the face.
You’re going to get smacked down by life. You need to have prepared for it. Think of it as an emergency hurricane kit for life. Have you prepared yourself to deal with everything? Anything? Do you have the ability to thrive?
Retirement is?
The ability to follow your interests - Our interests lead us to our purpose. An interest leads to talent. Talent is nothing without effort and purpose. We learn. We try. We fail. We evaluate. We correct. We apply effort once again.
Effort turns an interest into a talent and into a purpose.
Rinse and repeat.
These interests will change over the course of a life time. A new interest is sparked by a problem. Solve the problem and move on to the next problem.
It may be as simple as that. Solve each problem as they arise.
To do this you must create a life free of detritus. Free of waste. Shit gets in the way. Fear stops us. Comfort stops us.
Acquiring talent by following our interests prepares us for obstacles.
The ability to educate yourself - self development and self education should continue for your entire life. Learn how to work and to train yourself. This means embracing the uncomfortable. Read. Then apply. Or do. It’s action that creates learning.
Take a course. Then take action.
Start a business. Everyone should start a business at least once in their life. It’s a practical education.
The ability to support yourself, your family, your friends, and your causes, financially, and emotionally - Money is important. Don’t let anyone tell you differently. You’ll need money to lead a healthy life. Rich people live longer. You’ll need money to address emergencies, to eat right, to sleep right, to exercise right. Money affords you time. Reduce anxiety. Stress. Increases happiness.
Money makes it easier to help others. Yes, help and support can come in many shapes and sizes. But money constraints limit your time. Limit your assets. Limit your mental capacity to think clearly.
It limits your ability to help.
But we’re not talking Lamborghini money. We’re talking multiple streams of income. Revenue that keeps coming whether you show up for work or not. You’ll need to understand and have developed the ability to manage your money and maintain an income source throughout your life.
Hopefully, this stream of revenue has come as a result of following your interests. Educating yourself on the topic. And implementing a strategy that creates a full-time income.
Think of your interests as a business.
It’s one reason you pursue them. It’s one reason you educate yourself.
Think investment account. Think income producing business. Think spending less than you make; always.
The ability to direct your own time and schedule - Your life is made up of time. It’s finite. Not time. It goes on. But your allotment of time doesn’t. It’s scarce.
The ability to financially support yourself allows you to manage your time. It allows you to choose your interests and educate yourself.
If I’ve mastered these skills, I’m retired. I can handle anything.
Let’s wrap it up
Retirement is simple. Do what I want when I want. Have the confidence to know I can meet any challenge through self-education and self-development. And have the financial resources to support my goals in life.
It has nothing to do with work. I’ll always work. I’ll always follow my interests. I’ll always be building a business of some type.
Until my time is up.
Think about it…
What’d I miss? What does your ‘retirement’ look like? Is it the end goal of a lifetime quest? Or is it a continual refinement of a daily process?
Self development?
Do it…
Watch: Today, season 4 of The Umbrella Academy drops on Netflix. It’s insanely fun. Each season has gotten progressively better. And weirder. Enjoy.
Eat it: In honor of my son who is now living in Japan and has settled into his apartment, I’m making and eating Ramen this weekend. It’s easy and tasty. Check out this recipe.
Read it: I’m a huge fan of Ryan Holiday. His books are filled with well researched stories about cool people doing cool things. Or bad things. Plus, I always find multiple books to add to my reading list after checking out the bibliographies included with all his books. His latest, Right Thing Right Now, may be his best. It’s certainly his most timely. And needed. And as a companion, I re-read Joan Didion’s article, which originally appeared in Vogue magazine in 1961. On Self Respect.
Quote:
The aim of life is self-development. To realise one's nature perfectly-that is what each of us is here for. People are afraid of themselves, nowadays. They have forgotten the highest of all duties, the duty that one owes to one's self. Of course they are charitable. They feed the hungry, and clothe the beggar. But their own souls starve, and are naked.”
― Oscar Wilde, The Picture of Dorian Gray
If you want to check out some great reading list and see which books have influenced, surprised, educated, and entertained me, check out my book shop here. The lists grow monthly and I don’t recommend any books I haven’t personally read. Or use my book recommendation engine and specific author chatbots. Check it out. It’s fun.