How do you know if your “someday” is already here?

You probably have a version of “someday” in mind. Someday you’ll work less, or finally take a longer trip. You plan for it and save toward it, but how do you know when it’s already here?

Recently, I was in a room with women in the middle of life transitions. Some were stepping back from work to care for parents or spend more time with their kids. Others were recovering from burnout or taking a break because they could afford to. They were grateful to have the choice, but figuring out what to do with their time and who they were outside work wasn’t always easy.

For me, optionality means having real choices about how I spend my days. I can choose the work I want to do, or choose not to work. Even so, figuring out what I wanted next took me almost eight months.

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Turning “someday” into today starts with knowing your numbers: what you need to live on each year, including health care, insurance, and taxes, and what you have invested today.

To get a starting estimate, multiply the annual expenses your investments need to cover by 25. If a pension, investment income or Social Security will cover some of your spending, account for that income when it begins.

The 25-times estimate comes from the 4% rule. You withdraw 4% of your starting portfolio in the first year, then adjust that dollar amount for inflation each year after. Bill Bengen, the financial planner whose research created the 4% rule, updated his work in 2025 and now suggests 4.7% may be sustainable with a more diversified portfolio.

Historically, this approach supported 30-year retirements in the portfolios studied. Think of it as a starting point. If you’re stepping away early, your money may need to last a lot longer than 30 years, so you may want a bigger cushion.

Here’s what that looks like:

Your yearly spending is one piece. Then there’s the bigger stuff you may want to help with. Your kid’s wedding, or a down payment on their first home. Maybe care for a parent. Those costs aren’t in your everyday budget, but they still need a spot in your plan.

I’d keep that money in its own bucket, so you’re not counting on the same dollars to cover your groceries and the wedding.

If you’ll need it in the next few years, keep it in cash or a high-yield savings account, so it’s there when the bill shows up. If it’s further out, you could invest it, as long as you could wait or spend a little less if the market drops right before you need it.

If you’re looking at that number and thinking, “Well, that’s not happening anytime soon,” I’d start by looking at what you’re spending today. Will you need to spend that much forever?

Maybe your mortgage has another ten years to go. Your kids will eventually be off your payroll. You may not want or need as much stuff anymore. You still need to cover those expenses until they go away, but you don’t necessarily need to plan for them for the rest of your life.

Some expenses, like health care or helping family, could grow, so I’d look at both what might end and what might increase.

You can also choose to cut certain expenses now. Using the 25-times estimate, every $1,000 a year you no longer need lowers your target by $25,000.

If the gap is still wide, financial independence doesn't have to be all or nothing. FIRE, short for Financial Independence, Retire Early, comes in different degrees.

I wouldn’t get too caught up in the labels. Coast and Barista FIRE are especially worth a look in your 40s and 50s, since either could make working less possible sooner.

Even if the numbers make sense, stepping back can still feel hard. After years of putting money away, you’re now considering using it.

Work also gives you a role, a routine, and an easy answer when someone asks what you do. There’s always another paycheck or bonus that makes staying another year seem sensible. If you leave, what will you do with your time?

I had to figure that out after a layoff in 2023. At first, I enjoyed the freedom. I woke up when I wanted and got around to the house projects I’d been putting off.

“Then, I organized the drawers for the fifth time, and the freedom started to feel like boredom.”

My first layoff had taught me not to build my whole identity around my job. I cared about my work and being a parent, but I have also made time for interests and relationships outside those roles.

Still, knowing who I was didn’t mean I knew what to do next. I loved working in tech, but I also wanted to build something of my own. 

I tried an exercise often associated with ikigai: looking at what I enjoy, what I’m good at, what people need, and what they might pay me for. I wrote it all down and started trying things, keeping track of how I felt about each one. Along the way, I kept asking myself, “Would I still be happy doing this at 80?”

It took almost eight months to settle on continuing to invest in real estate and starting this newsletter.

So if you know you want a change but can’t quite say what comes next, I understand. Give yourself time to try things and see what you want to keep doing.