DIARY ENTRY #2
House Hack Diaries
What’s the most powerful word in the English language?
Hint: it only has two letters.
Hearing “no” is often enough to stop you before you ever get started—especially when it comes from a spouse or partner. If your partner doesn’t understand why you want to house hack or isn’t comfortable with the idea, it can quietly derail your entire investing journey.
But it doesn’t have to.
There are plenty of reasons to house hack. You just need to present them the right way. I wrote an article for BiggerPockets about how couples can make real estate decisions together. This version is less about mechanics and more about the conversations that actually turn hesitation into buy-in.
Don’t let your dreams die. Try this instead.
We need to live somewhere anyway
You need somewhere to live. Why not build equity?
I’ve heard some real estate influencers and financial pundits say that they rent instead of own. The reasons are usually framed as avoiding maintenance headaches or homeownership being a poor investment compared to renting in expensive markets.
I don’t know about you, but I wouldn’t buy a car from a car dealer who walked to work. The same is true when it comes to housing. For most median-income earners, their primary residence is the only property they own and it makes up the largest share of their net worth.
Why?
If you look at American real estate over the last 60+ years, you can see the value skyrocket over time. All you have to do is show your significant other this graph from the Federal Reserve to see that point.
Who’s richer after any amount of years: the person who rented or the person who house hacked? More often than not, the person who owns real estate builds more wealth.
There’s a version that fits our lifestyle
“I don’t want to live with roommates.”
If you’ve ever brought up house hacking with friends, family, or a significant other, this is usually the first objection you hear. The pushback almost always has something to do with lifestyle.
Remind them that there are many ways to house hack that can be adapted to fit your lifestyle and comfort level.
Some people rent by the room, others add an ADU, buy a multi-family, or use short-term rentals like Airbnb if they enjoy hosting but don’t want full-time tenants. When my wife and I started family planning, we knew sharing walls wasn’t for us. So instead of renting out space, we bought a fixer-upper single-family home and created value through a live-in flip.
The point isn’t one “right” way to house hack. It’s choosing a strategy that’s congruent with your life, not fighting against it.
Make the decision easier
Ever been to the Cheesecake Factory?
There are so many options that deciding what to order can feel overwhelming and take forever to make a decision. On the other hand, at restaurants with smaller menus, the decision is easy because the choices are intentionally constrained.
The same goes for house hacking: choose for them. Research the markets, narrow the property types, choose a strategy, find an agent, and get pre-approved. When everything is lined up for them and you seem confident because you’ve put in the work, the decision becomes simple.
Don’t leave this up to luck. Do the work.
Temporary discomfort for permanent optionality
Dave Ramsey has a great quote:
“If you will live like no one else now, later you can live and give like no one else!"
Think back to where you were five years ago.
Chances are your life looks different today. You make more or less money. You’re in better or worse shape. You’ve picked up new skills, habits, or priorities. Change happens whether you plan for it or not.
House hacking is a way to be intentional about that change.
Done thoughtfully, it can meaningfully improve your finances and expand your options over time. That’s why getting your significant other on board matters. This isn’t about short-term discomfort for its own sake. It’s about making a temporary, intentional decision that creates lasting flexibility and freedom.
Other couples have done this. Why not us?
The reason I started this newsletter was to share what I’m learning and highlight what others are doing in hopes that it inspires you to start or keep going.
It can feel intimidating if you think you’re the only one navigating these decisions. You’re not. Plenty of people have gone down this path before, learned as they went, and built momentum over time. The real risk isn’t doing it imperfectly, it’s not doing it at all.
If others can do it, why can’t you?
I want to hear from you: reply to this email and tell me your biggest hesitation.