Life doesn't wait for your plan
What a client's story reminded me about time
My friend and Chicago-area colleague Brian Plain sent his most recent email newsletter with a link to a podcast I’d been meaning to listen to.
It’s a lengthy conversation with Jason Fried, cofounder of 37signals, on the Founders podcast with David Senra.
I replied to Brian and told him I had the same episode already saved to listen to later.
He wrote back that he thought I’d enjoy it, and mentioned — with a hint of pride — that he’d listened at 1x speed instead of 1.5x or 2x like most of us do these days. That’s high praise!
And he was absolutely right.
It was worth slowing down for.
I’d encourage you to check it out.
Jason talks about life and business, but the ideas he shares — about simplicity, about “enough,” about living in the present rather than mapping out every step — got me thinking about something much closer to home.
Planning.
Why we plan
If you’ve followed my writing for any length of time, you know I believe in planning.
It’s a core part of what I do. Who I am.
And what I work on with my clients every day.
Planning encompasses your income, your taxes, investments, your estate, your goals, and more. All while doing what we can to make sure the future you’re building toward is actually within reach.
But here’s something I’ve been thinking on lately.
A client mentioned to me just last week that a longtime work colleague had passed away.
He was 50 years old.
He’d had a serious health scare, made what looked like a strong recovery, and then, unexpectedly, he was gone.
He left behind a wife and children.
By all accounts, they were well prepared financially. The foundation they’d built would take care of them.
But think about everything else.
The plans they had together.
The trips, the milestones, the ordinary Tuesdays and the big vacations they’d talked about.
The future they’d been building toward — into their 50s, 60s, 70s, and beyond.
They never got there.
And it made an impact on my client who was his friend and coworker.
The cost of only looking ahead
I don’t share that story to be dark.
I share it because it’s real, and because most of us can think of someone like him.
We’ve all heard about people who worked hard, saved diligently, and deferred everything, including Social Security to maximize their benefit at age 70, only to face a health crisis at 66 or 68 or 69 that changed everything.
The benefit they spent years waiting for never fully arrived.
The retirement they’d imagined never looked the way they’d pictured it.
This isn’t an argument against planning.
Please don’t hear it that way.
It’s a reminder that the present is more certain than the future.
What’s in front of you today is real.
The trip you keep postponing, the people you keep meaning to spend more time with, the thing you’ve been waiting to do “once everything settles down” — those all matter now.
The closer we stay to the present, the more certain the ground beneath us.
The further we project, the more we’re guessing.
A client shared this poem with me in an email (thanks again, John). It’s something that Lou Holtz asked all his players to memorize:
I love the ending:
”…because the future is just a whole string of nows.”
Length, depth, and breadth
When I think about what I want for the people I work with, it’s not just a long retirement.
It’s a full one.
Not just the length of your years, but the depth and breadth of them too.
That means having a real plan — one we revisit regularly and build around and into your actual life.
And it also means giving yourself permission to live now.
To spend on what brings you joy.
To say yes to the trip.
To make the call.
To show up for the people and causes that matter to you.
A plan is simply a tool.
It’s meant to give you confidence so you can live more freely — not something you spend your whole life trying to reach.
Planning for the future is smart.
But please don’t do it at the cost of today.
A few questions worth sitting with
Is there something you’ve been waiting to do until the “right time”?
Are there people in your life you’ve been meaning to spend more time with?
What would you do differently if you knew your finances were truly secure?
That last one might tell you more than any spreadsheet.
Bottom line: planning matters.
But so does today.
If our work together only helps you feel prepared for tomorrow, I haven’t done enough.
I want you to feel free to live now — with confidence, not just caution.
I’m curious how this lands for you.
Hit reply and share your thoughts...
Thank you for reading!
If you’re not a client and would like my advice, simply reply to this email with your questions and I’ll be happy to respond with my thoughts…
Until next Wednesday,
Russ
The Social Security point lands hard. Deferring to 70 makes perfect sense on a spreadsheet. It makes less sense when you factor in the probability of actually collecting enough to justify the wait. The plan optimizes for a future that isn't guaranteed. The present always is.