Kickstart your bucket list before you kick the bucket
How to spend without guilt, give with confidence, and retire without regret
“Will I be alright?”
“Can I afford to stop working?”
“What happens if...?”
If questions like these keep popping into your head, you’re not alone.
They’re some of the most common — and most important — questions I hear from women approaching retirement.
And even after you’ve retired, “will I be alright?” and “what happens if…?” often persist.
But answering them requires more than just crunching numbers.
It means taking a step back and looking at the bigger picture.
Not just what you have, but what you want your life to look like, and how your money can support that life — today and for the rest of your years.
Let me show you a simple way I like to think about this.
The bucket
I’ve written about buckets before, but today let’s try something different…
Imagine your financial life is a bucket.
Everything in that bucket — and everything that flows into or out of it — represents your ability to live the life you want, with confidence and peace of mind.
Here’s what’s already in your bucket right now:
Checking, savings, brokerage and retirement accounts, your 401k — any liquid assets you can access within about a week, if needed
And here’s what flows into your bucket:
Current income like a paycheck, bonus income, dividends, interest, and more
Future income sources like Social Security, pension payments, or part-time income
Proceeds from downsizing your home, selling a business, or receiving an inheritance
And here’s what stays outside your bucket, for now:
Your home (you can’t spend bricks and mortar — though downsizing may one day change that)
Your business (unless and until you sell it)
Your vehicle(s)
Your personal property
Everything else?
It’s future potential, not present-day liquidity.
And then there’s the tap
Every day, money is flowing out the bottom of your bucket.
That’s the tap.
Or spigot.
Or what I’ve always called a “spicket.”
Right now, that tap might be wide open — covering the cost of your current lifestyle:
Maintaining your home
Gassing up and driving your car
Taking trips
Supporting adult kids or grandkids
Enjoying dinner out with friends
And anything else that costs money for you to live
When you retire, the source of the inflow changes — but the tap is still open and running.
And for many women I work with, the early years of retirement aren’t about slowing down.
They’re about finally having the time and freedom to do all the things they’ve been putting off.
That means the tap might flow more freely once you retire.
Eventually, your priorities will shift.
Travel may slow.
The calendar gets quieter.
The tap flows more toward comfort, health, and security.
And one day, it - and you - stops altogether.
But along the way, there may be some surprise outflows too:
Helping out a granchild with a wedding, education, or a down payment
Supporting an aging parent
Finally taking that 2-week cruise in the Mediterranean
Deciding to spend a couple of months at the beach this winter
These are meaningful, joyful things.
But they can drain the bucket quickly if we haven’t planned for them.
So what’s the goal?
It’s not just to make sure the bucket doesn’t run dry, though clearly that’s important.
It’s also to make sure it doesn’t overflow.
Let me explain.
So many women spend decades doing everything right — saving and watching their expenses - only to find they’ve filled their bucket with more than they’ll ever use.
And they risk real regret about missed opportunities and experiences.
They never took that trip.
Never left the job they dreaded to pursue something more meaningful.
Never helped the kids when it would’ve made a difference.
Never fully enjoyed the wealth they worked so hard to build.
And now they can’t go back and do it over.
Real financial planning = more than just math
The truth is, managing your money well isn't just about ensuring you don’t run out.
It’s about helping you:
Enjoy and protect your lifestyle today
Retire early enough to enjoy your freedom while you're fit and able
Stay secure as your needs shift later in life
Make confident decisions about when to give, spend, enjoy, and relax
And to do all of that without fear.
Fear of markets, fear of the unknown, or fear of “what if I get this wrong?”
I can help
My job isn’t to tell you what you should want.
It’s to help you get really clear about what you do want — and then build a personalized strategy around that.
A plan that says:
“Yes, you can afford to stop working.”
“Yes, you can help your granddaughter with that wedding.”
“Yes, you can book that trip you’ve been dreaming about for 20 years.”
“Yes, you’re going to be okay.”
Because that’s what real financial planning is:
Helping you live the life you’ve dreamt of — without running out of money OR dying with too much of it.
If that sounds like the kind of financial partnership you’ve been looking for, I’d love to talk.
As you might imagine, the bucket idea above might be better explained with some visuals.
If this is something you’d be interested in, please let me know and I’ll put something together.
Note: you likely received a “bonus” essay yesterday afternoon via email.
I sent this mistakenly while I was republishing several older essays.
You can always browse and search among all 440+ essays here at your convenience.
And my old podcast episodes too.
I appreciate your continued readership.
Please let me know if you have any feedback or suggestions for future essays.
Until next Wednesday,
Russ