If I Had to Start Over With My Finances, These Are the First Five Things I'd Do

If I woke up tomorrow and had to completely start over with my finances, I wouldn't begin with a fancy plan. I'd begin with information. I'm on track to retire by 40, and none of that happened because I guessed — it happened because I knew my numbers.

So the first thing I'd do is track exactly where my money is going for an entire year. Everything coming in, everything going out. Not a week, not a month. A full year.

A month of data tells you what a month looked like. A year tells you the truth, because a year includes the birthdays, the car repair, the holidays, the random trip you forgot you take every summer. That's the version of your spending that actually shows up in your life.

Once I could see the whole picture, I'd finally be able to tell what's actually possible with my money instead of arguing with myself about it. Every decision after this one gets easier when you're working from real numbers.

Next I'd zoom in on what I call my big three expenses: housing, transportation, and food. For most of us, that's where the majority of our income goes.

I'd rather have one uncomfortable conversation with myself about rent than fifty tiny ones about coffee. The question I'd ask is simple: what sacrifices could I make in these three areas to lower the cost?

That question has different answers for different people. A roommate, a smaller place, a longer commute, a cheaper car, dropping to one car, cooking more, eating out less. I'm not going to pretend any of those are painless — they're trade-offs, and which ones are worth it depends entirely on your life. But this is the category where a single change moves real money, month after month, without you having to think about it again.

Then I'd write down every single debt I have. Balance, minimum payment, and interest rate for each one. All of it in one place, even the parts I'd rather not look at.

From there I'd pick a debt payoff strategy and stick to it, and I'd figure out my actual debt-free date. Having a date changes how the whole thing feels. It stops being a fog and becomes a deadline.

My personal rule: any debt above 7% APR has got to go immediately. That's the line where, for me, the interest is doing enough damage that paying it off jumps to the front of the list ahead of almost everything else. Below that, I'd think harder about it and weigh it against my other goals.

APR just means annual percentage rate — the yearly cost of carrying that balance. It's the number I'd sort my list by, because it tells me which debt is quietly costing me the most.

This is the step people skip, and it's free money sitting in a drawer.

I'd go through my benefits package line by line and take advantage of as much as I possibly can:

• Get my full employer match on retirement contributions
• Take the discount on employer stock, up to whatever the limit is
• Actually go to the eye doctor — my insurance gives $150 a year toward contacts or glasses
• Use the free therapy, which a lot of companies offer and almost nobody uses
• Check whether they cover a gym membership

None of this requires earning more or spending less. It's compensation I've already been offered. If I were starting over, I'd read the whole benefits guide, boring as it is, and claim everything I qualify for.

The fifth thing on my list would be opening a Roth IRA. Here's how it works: you contribute money you've already paid taxes on, then you invest that money, and your investments grow tax-free until retirement.

Two things I like about it. First, there's a cap on how much you can put in each year, which I've always taken as a nudge — you can't make up a missed year later, so it's worth contributing when you can.

Second, it's one of the most flexible retirement accounts out there. Anything you contribute, you can take back out without penalty, even before retirement age. Knowing that made it much easier for me to start putting money in early, because it never felt like the money was locked behind a door.

Those are the first five things off the top of my head, and the sequence isn't random. Tracking gives me the facts. The big three is where the biggest savings live. Debt inventory tells me what's urgent. Benefits are money I'm already owed. And the Roth IRA is where the long game happens.

Would I do it in exactly this order every time? Probably not — if I had a 24% credit card, that's jumping the line. But this is the shape of the plan I'd rebuild from, and it's roughly the shape of the one that has me on track to retire by 40.

What would you add?