Career optionality in practice

February 23, 2026

"I don't need this job. I'm here because I want to be."

It's a powerful thing to say and actually mean. Most people assume it takes a fortune to have that kind of leverage. It usually doesn't. I’ve heard some version of this from several clients, but one client in particular keeps coming back to me. If you've been reading this newsletter for a while, you might recognize her.

She's the one whose minimum required income turned out to be only $40k, despite a career earning well over $200k. We'll call her Jennifer, although that's not her real name.

Hearing Jennifer say those words...well, that's why I'm in this business.

When having enough doesn't feel like enough

Jennifer grew up believing money was fragile and easily lost. That kind of upbringing tends to create a persistent belief that no matter how much you have it might not be enough.

Ironically, that belief served her well because it made her a disciplined saver. She earned a high income but lived modestly. And her family avoided the lifestyle inflation that traps so many high-earning families. On paper, they were in an exceptionally strong financial position.

But Jennifer couldn't feel it. She could see it in the projections, and I could walk her through every scenario. But the anxiety held.

Then the layoff came.

She'd been at a health-tech startup, and when funding dried up, so did her job. The severance was disappointing. The job market was tight. And the questions keeping her up at night felt impossibly heavy: "Should we sell the house? Move the kids away from their schools and friends? Are we about to make a mistake that permanently changes our future?"

Turning fear into clarity

When we sat down, I could see the worry. From my perspective, she and her family were fine. But knowing this intellectually isn't enough during moments when you feel overwhelmed. You need to feel stability before you can think clearly.

So, we started by zooming out. We ran projections to see what her current savings would look like in retirement. If her future was secure, we could narrow our focus to bridge the gap between now and then.

Jennifer and her husband had accumulated about $285,000 in retirement accounts and roughly $440,000 in bank accounts and taxable investments.

We earmarked roughly $100,000 of their non-retirement assets as a short-term runway, giving Jennifer 10-12 months to live without any earned income. That single step took the immediate pressure off.

Then we combined the remaining $340,000 in non-retirement assets with their retirement accounts, which left about $625,000 invested for growth. Assuming an 8% average annual return, those assets alone could potentially grow to about $2.7 million by age 60.

Their home told a similar story. At the time, it was worth approximately $1.3 million, with the mortgage on track to be fully paid off by that same age. At a conservative 4% annual appreciation rate, it could be worth around $2.5 million by retirement.

Combined, this created a projected retirement nest egg in the $5 million range.

How much is enough?

With retirement all but secured, our next step was to create what I call a "base-case plan." In other words, we identified a worst-case scenario that would keep them on track for retirement, while also meeting their financial goals before that.

Since her husband worked remotely, they had flexibility on where they lived. If necessary, they were willing to sell their home, move to a lower cost-of-living area, and purchase a new home outright using their existing equity.

That would eliminate housing debt entirely. With no mortgage, their monthly expenses would fall to approximately $5,000.

With her husband bringing in about $60,000 annually, and nominal savings withdrawals as needed, Jennifer would only need to earn around $40,000 to $45,000 per year to maintain their lifestyle. Under that scenario, the projections showed they could still cover all their living expenses, take annual family vacations, continue putting money away for retirement and their kids’ college funds, and retire comfortably, Jennifer at 60 and her husband at 67. 

The plan held through age 90 with roughly a 91% probability of success and a median ending portfolio value near $30 million, leaving a sizeable buffer for lifestyle upgrades, legacy goals, or charitable giving.

Once Jennifer saw this, her questions changed. Instead of "Are we going to be okay?" she started asking, "What do we actually want our life to look like?"

What happens when you don't need the paycheck?

For the first time, Jennifer could choose what came next. She considered three very different paths: working part-time as an interior design consultant (a passion of hers), starting her own business, or returning to the corporate world on her own terms.

These weren't desperate backup plans. They were intentional choices.

She ultimately chose to re-enter the job market. But she approached it completely differently, because she had leverage.

Over the span of five months, she turned down three positions that didn't align with what she wanted. Then she landed something better than what she'd lost: better compensation, stronger benefits, a very stable company, and genuinely meaningful work.

And that scarcity mindset she'd carried her whole life? It started loosening. She bought a new car. Started a full kitchen renovation. Purchases she never would have made before.

What would change if you knew your number?

Your numbers will look different from Jennifer's. You might have more saved or less. You might be decades from retirement or just a few years away. But the principle is the same.

Once you know your base-case plan, fear stops driving your decisions. You can walk away from a bad offer, ask for what you're worth, or take time to figure out what you actually want to be doing. That's what financial planning is supposed to do.

You don't have to leave your career to improve your life. Sometimes, simply knowing you could is enough.