This Labor Day Can Mean Different Things to Different People
As we head into another Labor Day weekend, I want to take a moment to do something the financial media may never do:
Celebrate you.
Not the stock market. Not the economy. Not interest rates or inflation data or whatever crisis is dominating the headlines this week.
You.
Specifically, I want to celebrate every person reading this who has done the hard, unglamorous, decades-long work of living below their means, saving consistently, and building a life that no longer depends on a paycheck to sustain it.
If that’s you, if you have reached the point where work is a choice rather than a financial necessity, take a genuine moment to appreciate what you’ve accomplished. Not a polite nod, but a real moment of reflection because what you have achieved is, historically speaking, extraordinary.
How Rare This Actually Is
Prior to the mid-20th century, “retirement” as we think of it today simply didn’t exist for the vast majority of people. You worked until you physically couldn’t, and then your family supported you. The concept of spending 20, 25, or 30 years living comfortably without depending on a paycheck from your labor was reserved for the Rockefellers and Carnegies of the world.
That began to change with Social Security in 1935, the rise of corporate pensions in the postwar era, and the gradual democratization of investing through IRAs and 401(k)s. But even today, with all of those tools available, the number of Americans who build enough in their retirement portfolio and pensions to support their desired lifestyle for the rest of their lives without needing to work remains a distinct minority.
You may be in that minority. If you’ve just crossed that threshold this year, or if you’re within striking distance of it, I want you to fully grasp what you’ve done.
You have given yourself something that, unfortunately, most people never have: a choice.
The choice of what to do with your time. The choice of whether to keep working or stop. The choice of where to live, how to spend your days, and with whom, free of financial obligation driving those decisions.
You are in the catbird seat, and getting yourself there deserves to be celebrated, not glossed over in a rush to the next goal.
If You’re Still Working — Which Group Are You In?
Now, if you’re still working, I have a question for you:
Are you working because you want to, or because you believe you have to?
That distinction matters more than almost anything else in your financial life right now, and the answer is not always as obvious as it might seem.
Group One: Working Because You Want To
The first group is made up of people who have done the homework. They know their numbers cold. They’ve run their retirement forecasts. They’ve modeled their spending, their investment returns, their Social Security timing, and their tax situation, and they know, likely with confidence, that they don’t need a paycheck anymore.
They’re still working because they choose to, and that changes everything about the experience of work.
This plays out in dozens of ways.
Some keep doing exactly what they’ve always done, but quietly redefine the terms. They stop commuting five days a week. They work from home, or from their place on Cape Cod in the summer, or from their condo in Naples from January through April. The work is the same. The freedom around it is entirely different.
Others go half time, or restructure their professional lives in ways that would have seemed impossible when a paycheck was a necessity. They leave one career and launch something entirely new, sometimes in the same field, and sometimes in a completely different direction, simply because they can afford to follow their curiosity rather than the market.
Still others take their decades of expertise and redirect it entirely. They sit on boards. They mentor younger professionals. They consult on their own terms, taking the engagements that interest them and declining the ones that don’t. They apply their skills to charitable organizations that align with their values.
Some hire a landscaping service because they never want to do yard work again. Others mow their own grass into their eighties because they genuinely love the exercise and the solitude.
The common thread is not what they’re doing. It’s why they’re doing it, and it’s not “because I have to.”
Group Two: Working Because You Believe You Have To
The second group is larger than most people realize, and it’s the group I want to speak to most directly today.
These are dedicated, disciplined people who are still grinding it out every day, not because they genuinely want to, but because they believe they still need to. And here is the question I always ask when I meet someone in this group:
How do you actually know?
Not what do you feel, or what do you assume, or what did someone tell you twenty years ago. How do you know, based on careful, personalized analysis of your actual numbers, that you still need to work?
In my experience, the answer is often: they don’t. Not with any real confidence.
What they have instead is usually a collection of conditioning, rules of thumb and inherited beliefs that have calcified into what feel like facts but are actually just assumptions. Things like:
“You can’t retire if you still have a mortgage.”
“You have to wait until 67 to collect your full Social Security benefit.”
“You can’t retire until you have $2 million. Or $3 million. Or $4 million.”
“You have to wait until you’re eligible for Medicare because nobody can afford private health insurance.”
I hear these constantly, and my answer is always the same: maybe. Maybe they’re true for you, and maybe they’re not. None of these is a universal truth. Every single one of them depends entirely on your personal numbers, your spending, your assets, your priorities, and your timeline.
Over 37 years I have sat across from people who were absolutely convinced they needed to work another three to five years, only to discover, once we looked carefully at their numbers together, that their assumptions about retirement timing deserved to be tested. They had been giving years of their lives, years of their health, their energy, their time with the people they love, to a financial obligation that may not exist.
Think about how significant that is!
If you are 60 years old today and you could have retired at 58 but didn’t know it, you may have already given away two years. Two years of mornings with no alarm clock. Two years of being present for your grandchildren on ordinary Tuesday afternoons. Two years of the trip you keep saying you’ll take when things settle down.
Things don’t settle down. The calendar keeps moving.
The Question Worth Asking This Weekend
Labor Day is one of only a handful of moments in the year when most of us actually pause long enough to reflect, so I want to leave you with one question to sit with this weekend — not while you’re checking your email or half-watching the news, but in a genuine quiet moment:
Do I know, with real confidence, based on actual numbers, whether I could stop working today if I chose to?
If the honest answer is yes, if you’ve done the analysis and you know where you stand, then whatever you decide about work, you are making an informed choice. And an informed choice, even if it’s the same choice you would have made anyway, feels entirely different than a conditioned assumption.
If the honest answer is no, if you’re not actually sure, or if your “numbers” are a rough mental estimate rather than a carefully constructed retirement forecast, then the most important thing you can do before this weekend is over is commit to finding out.
Not because the answer will necessarily tell you to stop working. It might tell you to keep going for a few more years. But you deserve a clear view of your own situation so that whatever you do next, you’re doing it by choice and not by default.
Because as anyone who has built meaningful financial independence can tell you: knowing that you don’t need to work for a paycheck can change everything.
Not just your finances. Everything.
If you would like help discovering where you stand, we invite you to begin having a conversation and schedule a complimentary Retirement Strategy Assessment.
This is intended for informational purposes only. You should not assume that any discussion or information contained in this document serves as the receipt of, or as a substitute for, personalized investment advice from Savant. Please consult your investment professional regarding your unique situation. at any discussion or information contained in this document serves as the receipt of, or as a substitute for, personalized investment advice from Savant. Please consult your investment professional regarding your unique situation.
Jack Phelps
Managing Partner / Financial Advisor