You Asked What You're Struggling With. Here's What I'm Learning

Good morning {{first_name|Reader}}.

First, thank you to the veterans who responded to last week's poll. My wife and I both served, and seeing over 60 of you are veterans means a lot. Thank you for your service.

Second, I asked what decision you're struggling with right now, and two answers tied for first place:

These are the exact questions my wife and I wrestle with every single day. So let's talk about both.

— Ian

(see what watch I’m wearing today)

Our number is $500k in four years.

But here's the thing: that's not our "retire forever and never work again" number. It's a milestone.

With $500k, we can buy and pay off a house (in the right place). No mortgage. Just property taxes. And we can live with that. Literally and figuratively.

Right now, our mortgage is $3,000 per month. Add utilities (everything is expensive in Alaska), and housing costs eat up a massive chunk of our income. Once we have a paid-off house, we'd only be paying $500-600 per month in property taxes.

That changes everything.

With no mortgage, our options open up. We can take lower-stress, lower-commitment jobs. We can say no to things we don't want to do. We can spend more time with our kids, work on our own projects, and build something that's ours.

That's what "enough" means to us. Not infinite money. Not never working again. But freedom to make choices we've never been able to make before.

We didn't use the 4% rule or some fancy formula.

We know our expenses. We've tracked them for years. YEARS!!! We know exactly how much we need to spend each month to live comfortably, outside of mortgage or rent payments.

Once housing is handled, the rest is manageable. That's our calculation.

This is a pretty new thought process for us. Five years ago, our "enough" number would have been way lower. But we weren't thinking about work optional back then. We were just trying to save and get by. Three kids under three and a a different world looked very different to us.

Now we're aggressive. Intentional. We know what we're building toward.

Honestly? Not much, but also, everything.

We both plan on still working. This isn't about quitting everything and sitting on a beach forever. It's about paying off a house and then taking jobs that give us more freedom.

That makes the number feel achievable. We're not trying to have $2 million in the bank. We're trying to eliminate the biggest financial burden in our lives so we can breathe.

My wife and I created this goal together. We're on the same page. That helps. But there is always a fear of the unknown and as someone who has been raised in a risk-averse environment, it’s scary.

If you're asking "how do I figure out my number?" here's where to start:

How much are you spending per month? Like, do you REALLY know?

Most people think they do. They don't. They significantly underestimate or conveniently leave out expenses that they don’t want to face.

Track every dollar for three months. All of it. Groceries, subscriptions, coffee, gas, everything.

Once you know your actual expenses, you can build your number from there.

Until then, you're guessing. And guessing doesn't get you to work optional.

Learn Our Real Numbers

Upgrade to Get More In-Depth Numbers

Want to see our real, no shit numbers? Upgrade to unlock a new section of the newsletter where you see our actual investment accounts and portfolio. For $10 per month, you get a behind the scenes look and help support the newsletter.

Sponsored

Wealthfront: Where We Park Our Monthly Investments

Automated investing with tax-loss harvesting that can save thousands. High-yield cash accounts. No minimum balance. No advisory fees on your first $10k. This is the platform serious investors use when they're tired of managing it themselves.

Start Building Wealth →

The two questions that tied in the poll aren't separate. They're connected.

You can't figure out "how much is enough" without knowing your expenses. And you can't balance enjoying life now with future freedom unless you're intentional about both.

That's what this whole thing is about. Not deprivation. Not YOLO spending. Just knowing what you want and making deliberate choices to get there.

My wife and I are figuring this out in real time. We don't have all the answers. But we're on track. And we're sharing the whole journey—the wins, the struggles, the daily "no" decisions that add up.

If you're wrestling with these same questions, you're not alone. Take the poll below and let me know how you feel.

Thanks for reading,

Ian

Thanks for reading,

Ian