Why I set milestones instead of a quit date
I'm thinking about quitting my job. Not tomorrow, not dramatically — but it's a real thing I'm working toward, and I didn't want the plan to be a feeling.
So instead of circling a date on the calendar and hoping the money worked itself out, I set money milestones. The rule I gave myself is simple: the milestones decide when I go, not the other way around. If I hit them sooner, I go sooner. If it takes longer, it takes longer.
The reason I like it this way is that a date is something you can talk yourself into. A number sitting in an account either exists or it doesn't. It takes the negotiation out of it, which is helpful, because on a bad week at work I am extremely good at negotiating with myself.
It also changes what I do day to day. A quit date makes you count down. Milestones make you build. Every paycheck between now and then has a job, and that's a much less anxious way to live inside a big decision.
What money milestones usually have to cover
I'm not going to tell anyone what their numbers should be, because they depend entirely on your life — where you live, who depends on you, what your fixed costs look like, what kind of work you'd be walking into. But if you're building your own version of this, these are the categories the milestones tend to land in:
- Runway. How many months of your actual spending you can cover with no income at all. Not your ideal budget — the real one, the one with the annoying subscriptions in it.
- Fixed costs. Rent or mortgage, utilities, loan payments, insurance. The bills that don't care whether you have a job.
- Health coverage. If your insurance comes through work, leaving means finding and paying for something else. That's a number worth knowing before you give notice, not after.
- A cushion that isn't runway. Runway is what you live on. A cushion is what absorbs the surprise — the car, the tooth, the flight home. If one emergency can eat your runway, you didn't have as much runway as you thought.
- Debt payments. Anything with a required monthly minimum belongs in your spending number, not in a separate mental category.
Writing these down was the least fun part and by far the most useful. A vague sense that I need "more saved" is not a plan. A list of specific things the money has to cover is.
How I'm treating the money while I'm counting up
The part I didn't expect is how much this changed my relationship with ordinary spending. When money has a job — get me to a milestone — I make different calls, and not in a miserable way. I'm cooking at home a lot more, and I genuinely like it. The recipe I was making while I filmed this is from the Love and Lemons cookbook, which has been doing heavy lifting in my kitchen lately.
For me it's less about restriction and more about direction. Every dollar I don't spend moves the milestone closer, and that's a much better motivator than guilt.
The other thing I care about is where this money sits. Money I might need in the first month after quitting is not money I want tied up or exposed to a market swing, so I keep my runway money somewhere boring and easy to get to. The whole point is that it's there on the day I need it.
And I keep the cushion mentally separate from the runway. Same idea, different job: the runway is the months of living, the cushion I don't touch is what keeps one bad surprise from resetting the whole plan.
I'm not at the finish line yet. But I know exactly what the finish line is, which is a completely different feeling from just being tired of your job and wishing.