You’re Earning More Than Ever. Should You Keep Working?

You’re earning more than ever. Your savings are strong, your investments are on track, and your financial plan could probably weather a long retirement.

So why does walking away still feel like the wrong financial decision?

For many career professionals with higher income, the temptation to work “just one more year” is hard to resist. You tell yourself another bonus, another vesting cycle, or another deal will create a larger cushion — maybe even unlock the next tier of financial freedom. And with major expenses like college tuition or the mortgage finally easing up, the math could look too good to ignore.

But is it necessary? And more importantly — is it worth the opportunity cost?

This guide helps unpack those questions, exploring the financial, emotional, and lifestyle trade-offs of continuing to work when you may already have “enough.”

Revisit Your Financial Readiness

It’s natural to assume that working longer can only help. And in some cases, it can — extra retirement savings, extended benefits, and delayed withdrawals can be impactful. But there’s a fine line between bolstering financial security and delaying financial freedom.

So, how much does one more year move the needle?

Let’s assess where you actually stand.

Your inputs (gather these first)

• Annual spending in retirement (today’s dollars). In addition to essentials, include travel, hobbies, gifts, and any other “fun money.”
• Investable assets. Taxable accounts + retirement accounts (e.g., IRAs, 401(k)s) + cash reserves.
• Planned Social Security age (and ballpark benefit), pensions, rental income, or other retirement benefits.
• Current savings while working (how much you’re adding each year).
• Health care coverage plan pre-Medicare (if you stop now) and after 65.
• Estimated lifetimes for you and your spouse (life expectancy drives the time horizon).

Use a free planner to run two scenarios

You don’t need to build a model from scratch. Most brokerage platforms, including Fidelity, Vanguard, and Schwab, offer calculators that approximate Monte Carlo simulations.

In case you’re unfamiliar, a Monte Carlo simulator runs your retirement plan through a range of best- and worst-case market scenarios to estimate your probability of success — typically expressed as a percentage (e.g., 90% chance your money lasts 30 years).

Your preferred brokerage platform likely offers some form of a calculator, but if not, there are free tools like Portfolio Visualizer. Then set reasonable assumptions:

Now compare two cases:

1. Retire now
2. Work one more year (keep contributing, no withdrawals for that year, delay Social Security and Medicare transitions accordingly)

Look at the tool’s output for probability of success and projected ending balances. If your success probability is already ≥ 90% with today’s assets, and “one more year” only raises it a few points, there isn’t much of a financial case for working longer, at least not from a numbers standpoint.

Keep in mind, anything less than 100% does not imply failure. It just means there’s a certain percentage chance that adjustments will be needed along the way — you may need to lower living expenses temporarily, withdraw differently, or make small course corrections in particular market conditions.

Back-of-napkin estimate

You can also estimate the order of magnitude impact of one more year with a simple formula:

Your one-more-year “delta” ≈ (net portfolio growth) + (new savings) – (withdrawals avoided this year)

Let’s see what this looks like with an example scenario. For simplicity, we’re going to assume a standard investment strategy (60/40 portfolio) and ignore Social Security and taxes.

With these parameters, your net portfolio growth is the difference between what your portfolio would earn with and without your $120,000 annual withdrawal.

• Keep working: $3 million x 7% = $210,000
• Retire: $2.88 million (less the withdrawal) x 7% = $201,600
• Net portfolio growth = $8,400

Adding this to new savings ($75,000) and the avoided withdrawal ($120,000), your one-more-year delta is $203,400.

What could you do with that extra money?

Fund a once-in-a-lifetime trip. Provide seed capital to launch a passion project. Gift meaningful assets to family or charity. Pay for a major home remodel or vacation home. Or maybe just enjoy a little more cash flow each month.

There are plenty of options.

But how influential are these funds versus a year of freedom to pursue whatever it is you please? A couple hundred thousand dollars sounds nice today, but what about down the road?

A different perspective can help. With a steady 7% return, 4% withdrawal rate, and 3% inflation, your end portfolio balance rises from about $1.8 million to $2 million with an extra year of work — and one less year of retirement.

Is it worth it? That depends.

Emotional Readiness: Are You Actually Ready to Stop?

The math says you’re free to walk away, but the next question is, “Do I want to?”

For many high achievers, work is more than an income stream. It’s structure and identity — a source of purpose as much as productivity. Which is why, even after financial independence, the idea of stopping can seem unsettling.

Examine What “Enough” Means Beyond the Numbers

You already know what enough looks like financially — you’ve modeled it, planned for it, earned it. But emotional enough is harder to define. It’s not a number; it’s a feeling of congruence between how you spend your time and what you value most.

Ask yourself:

• Do I still feel challenged?
• Do I feel energized by my workdays, or merely occupied?
• If I had one more free day each week, what would I do with it?
• What activities or causes have I consistently postponed because of work?
• What am I curious about that I’ve never had time to explore?
• Who in my life deserves more of my time, and what would that look like weekly?

If those answers come quickly and clearly, you’re probably ready for your Life After Work. If they don’t, that’s okay — clarity tends to appear only after creating space to reflect.

Test-Drive Your Next Chapter

Instead of leaping into retirement, sample it. Think of this phase as a “trial run” for your next act.

Try taking extended time off — three weeks, then a month, just to see how your days unfold without the usual structure.

If you’re still working, consider downshifting before departing. Find ways to cut your schedule to four days a week, decline new projects, or step into an advisory or consulting capacity. This partial slowdown can surface how much of your identity is tied to your job title and whether you’d miss the work itself or simply the routine.

Many clients we work with discover they don’t need to stop working altogether; they just need to work differently. Consulting, teaching, philanthropy, or mentoring can preserve the satisfaction of working.

Don’t Forget About Other Retirement Planning Variables

The financial equation is fairly straightforward: how much additional security or opportunity would another year of income actually buy? When you model your personal finances, the difference often isn’t as dramatic as it feels.

Still, it’s essential to account for the details that can influence your financial situation and your retirement income timeline:

Social Security benefits: Each year you delay benefits past full retirement age increases your monthly payout by about 8%, up to age 70.

Medicare eligibility: If you’re younger than 65 years old, you’ll have to bridge the insurance gap if you retire. You have options, but this needs to be factored into the decision.

Taxes: Working longer may raise your current tax liability, but it can also open a future window for Roth conversions or tax-efficient withdrawals in the early retirement years.

Moreover, try modeling what happens if you retire now versus in one, three, or five years — or if you scale back into part-time work instead of stepping away completely. Test how an immediate market downturn, higher inflation, or delayed Social Security could alter your projections and downside risk.

The more information you have, the easier it is to make a definitive decision.

Making the Decision: What’s the Real ROI of Delaying Retirement?

It’s a matter of weighing what you’d gain (and lose) with one more year. A financial advisor can help you not only test how the above levers interact over the next 20 or 30 years of your life but also talk through the psychological variables (well-being, relationships, and sense of purpose).

Financial independence doesn’t mean you have to stop working. It simply means you get to choose what work is worth your time, whether that’s full-time, part-time, or something entirely new.

At BEW, we call this stage Life After Work — a post-retirement phase defined not by endings, but by the freedom to choose what comes next.

If you’re ready to test your plan, refine your timeline, and see what “enough” truly looks like, download our free guide, Retirement Redefined: Your Guide to Life After Work.

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