Know thyself, then plan thyself
Why contemplation comes before calculation
Sarah sat across from me with a spreadsheet open on her laptop.
“I’ve run the numbers seventeen different ways,” she said.
“Different withdrawal rates. Different investment mixes. Different Social Security strategies. I just need you to tell me which one is right.”
I asked her to close her laptop.
“Before we look at any of those numbers,” I said, “I need to ask you something:
Who do you want to be in retirement?”
She looked confused.
“I don’t understand. I thought we were here to talk about my money.”
“We are,” I said.
“But we can’t build the right plan until you know who you’re building it for.”
A word you’ve probably never thought about
There’s a word that’s been on my mind: contemplate.
We use it all the time.
“I’m contemplating retirement.”
“Let me contemplate that decision.”
But the word means more than we realize.
In Latin, contemplari means “to look closely” or “to observe carefully.”
It comes from templum. That was a sacred space where Roman priests would observe the sky and look for signs.
To contemplate wasn’t just to think.
It was to create a special space for deep observation.
Here’s what hit me: Before you can plan your retirement, you need your own sacred space.
A place to look inward and observe your own life carefully.
Not the rushed checking of your account balance.
Not the anxious comparison to what your friends are doing.
But the kind of quiet thinking that shows you what really matters.
The steps nobody talks about
I wrote a few years ago about an ancient saying: “temet nosce.”
How you can’t make good money decisions without understanding yourself first.
But I’ve been thinking about what comes before knowing yourself.
How do you go about getting to really know yourself?
By first taking time to think deeply.
Here’s how it works:
First, you must contemplate.
Create space. Look carefully. Make room for quiet thinking.
Then, you can begin to know yourself.
Understand what you value. What you fear. What you want.
Only then can you plan.
Match your money to that understanding.
Most people skip to step three.
They want the plan. The projections. The portfolio.
They want me to tell them the “right” answer.
What to do next…
But without quiet thinking, without self-knowledge, the plan doesn’t help anyone.
It might work on paper. The math might be perfect.
But it will feel wrong.
Because it’s not connected to who you are and what you want.
What this looks like in real life
Back to Sarah.
We spent that first meeting not looking at spreadsheets.
I asked questions:
What does a perfect day look like for you?
When you imagine yourself at 75, what do you hope you’ll have done?
What scares you? Not just about money, but about life?
If money weren’t an issue, how would your days be different?
These aren’t typical financial planning questions. But they’re the most important ones we can ask.
Sarah needed space to think deeply before she could know herself. And she needed to know herself before we could build a plan that worked for her.
Three months later, we had her plan. But it looked nothing like those seventeen spreadsheets she brought to our first meeting.
She was working part-time for two more years. Not because she needed the money. Because she wasn’t ready to stop completely.
She was spending more on travel in her 60s. Less in her 70s. Not because a computer model said to. Because that’s what she wanted.
She was keeping more in cash than most advisors recommend. Not because it was most efficient. Because it helped her sleep at night.
The plan worked because it was hers.
Built on deep thinking. Based on self-knowledge.
Creating your space
Here’s what I’ve learned after more than thirty years as a financial advisor:
You can’t outsource this thinking. I can help create space for it. I can ask questions. But only you can do the observing.
And you can’t rush it. Deep thinking takes time and quiet. Two things our world tells us we don’t have.
But without that space to look carefully at your own life? Without the hard work of seeing who you are and what matters?
Any plan I create for you is just a guess. An educated guess, maybe. But a guess.
The first question
So before we talk about withdrawal rates or investments or Social Security, let me ask:
Have you created space for deep thinking?
Have you made room to observe your life without distraction?
Do you know yourself?
Not who you think you should be. Not who you used to be. But who you are now and who you’re becoming?
That’s where really personalized planning starts.
Not with my expertise or your spreadsheets.
But with your willingness to think deeply, know yourself, and then build a plan that fits.
The ancient Greeks said “know thyself.”
But the Romans understood something even more basic: You need space to do the knowing.
Your turn
Where do you do your best thinking?
When you need to make a big decision, what space do you create?
Reply to this email and tell me. I read every response.
And if you’re approaching retirement and stuck in spreadsheets when what you really need is thinking space, let’s talk.
That’s exactly the work I love doing with clients.
Links & things
For more on contemplation, the following article was the inspiration for this week’s essay:
Thank you for reading!
If you ever have any feedback or suggestions for me, simply hit reply or leave a comment and share what’s on your mind…
Merry Christmas to you, your family, and your friends!
Russ