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Do The Weird Things Now While You Still Can

I’ll be honest. I’ve done some weird things in my life.

I’ve donated bone marrow for stem cell research (and money). Six times. I’ve crashed on couches, vacationed in Iowa, and many other things for which others might be ashamed. OK, the Iowa one is kind of shameful for me, too.

There’s a time and a place to do weird things, and our side-hustling attorney friend Kevin is realizing that now is not the time. Perhaps he’ll be back to his weirdly-behaving self as an empty-nester one day. Time will tell.

This Friday Feature was originally published on Financial Panther.



This past year has been one of the craziest of my life – not just because of the pandemic, but also because of how much my life has changed.

Of course, I’ve had big life changes before. Graduating from law school, starting my first job, getting married, quitting my job to pursue self-employment – all of these were big events. On a practical level though, these events didn’t really change my life that much.

Sure, I might have had a new job or a new living situation, but for the most part, my lifestyle didn’t change. I was still out there doing what I was doing. And importantly, the way I thought about my life didn’t change.

Last year, however, my wife and I had our first kid. There’s probably nothing more life-changing than having children. Before kids, I only had to think about myself. But when you have children, in a way, your needs become secondary. You end up molding your life, not for you, but rather for what you think is best for your children.

And molding my lifestyle to fit someone else means an end to a lot of the weird things I once did. For most of my twenties and early thirties, I lived in a way that I think was different from most. I picked up side hustles when I didn’t need them, doing gig economy work that most people would consider beneath someone with my educational and work background. I kept living like a student and avoided lifestyle inflation for a long time. When I moved into a house, I house hacked by renting out a room in my house on Airbnb.

The weird things I did throughout my 20s and early 30s gave me a financial advantage. It made it so I could save more money and put me in a position where I had a good nest egg at a young age. The weird things gave me a mental advantage too, proving that I could live comfortably even if my living situation wasn’t normal.

Doing weird things can be helpful. But you have to do them when you can because one day, you might not be able to do those weird things anymore.


The Weird Things Get Harder To Do Later


I’ve done things differently for most of my adult life. I house hacked using Airbnb for over four years, both by renting out a room in my house and by renting out my entire house when I traveled. Most months, I was able to cover my mortgage solely from the income I earned from Airbnb. The trade-off was that I had to let strangers into my house. When I was a 20-something with no kids, opening my home to strangers wasn’t so difficult. But once I had a kid, the idea of letting a stranger into my house became untenable for me.

I was also able to live lean for most of my adult life. I lived in modest apartments for almost all of my 20s. When I lived in a house, I house hacked and dramatically reduced my housing expenses. My transportation costs were almost nothing too because I didn’t drive a car. And I kept my food costs low by taking advantage of secret shopping apps.

When no one else relied on me to take care of them, it was much easier to live life outside of the ordinary. But having a kid changed all of that. I’m not comfortable with sharing my space with strangers anymore. I still bike everywhere with my kid, but there’s no doubt that I probably have to drive more than if I only had to transport myself.

And of course, living lean is a lot harder when you have to pay for childcare and all the other expenses that come with a kid.

A lot of the living situations that we see online – quitting your job to go out on your own or doing the digital nomad thing and traveling the world – are only possible when you’re in a particular stage of life. Realistically, lifestyles like this are only possible when few people rely on you. It’s not to say that you can’t do things like this if you do have kids. It just becomes much harder.

It’s why you need to do the weird things when you can. You never know what your future will look like, but more likely than not, it’ll get harder to live life out of the ordinary as your life gets more complicated.


Some Of The Weird Things You Can Do Now That You Can’t Do Later


So what are some of the weird things you can do now that you might not be able to do later? Consider the following:


House Hacking

House hacking is one of the big things that come to mind when it comes to things that are much more difficult to do later in life, especially if you have kids.

Almost all of us have had weird living situations at some point in our lives, most likely in the form of roommates. In college, I lived in a house with 4 other guys so that I could save money.

When my wife was in school, she house hacked by buying a house and renting out the other bedrooms to students. It worked out well for her because she was able to essentially live for free, but there was a trade-off because she had to live with roommates.

Finally, when my wife and I were in our late 20s and early 30s, we rented out a room in our house on Airbnb. It covered our mortgage most months, but it also meant we had to live with strangers throughout the year.

House hacking often requires you to accept a weird living situation. You can have these sorts of weird living situations when you’re young and don’t have anyone else to worry about. It gets much harder to do that though when you add other people into your life.

That’s not to say you can’t house hack even when you have kids. But it’s natural to want your kids to live in the most comfortable space you can provide them. I definitely could continue to Airbnb a room in my house. I’m just not so comfortable doing it now versus when I didn’t have a kid to think about.


Living Like A Student

One of the best things you can do for your finances is to live like a student for as long as you can. It doesn’t mean you have to do it forever, but living like a student for at least a few years can give you a huge head start when it comes to building your nest egg. If you do it for long enough, you can even reach Coast FI and put yourself in a position where saving money becomes less important going forward.

Living like a student means living on less. It also often means living differently than most. Like with house hacking, it’s easier to do that when you don’t have to think about anyone else. I could probably continue to live like a student, and in some ways, I still do. I still don’t have my own car. When I need to get my son to daycare each morning, I bike him there, either with a kid’s seat that I have on my bike or with a bike trailer.

But I’m not willing to live like a student in most aspects of my life anymore. Life has gotten more expensive because my priorities have changed.


I've got my 2 acres of non-leveraged, crop-producing, cashflowing farmland via AcreTrader. Get yours.


Side Hustling

Side hustling is a great way to improve your finances. It’s something I’ve done my entire working life, even when I was working as a big shot attorney. The beauty of side hustling is that the money you earn is bonus money. If it’s a true side hustle, you shouldn’t need the money to cover any bills and that means you can save all of it. Making a few extra thousand dollars per year doesn’t take much work. And it can make a huge impact on your financial life (thanks to a concept I like to call The Reverse Latte Factor).

But side hustling also requires time. And when you have kids or as your life starts to get more complicated, time can become a commodity that you can’t waste.

Before I had my first kid, I often spent an hour around the dinner rush doing deliveries before I came home. It let me maximize my earnings because most people order food around 6-7 pm. These days though, my time around 6-7 pm is booked up. My son needs to eat dinner and get ready for bed right in that time frame. It means I’m never able to side hustle during those peak dinner hours anymore.



Traveling is another thing that I think is worth mentioning, especially since I’ve traveled a few times now with my son. It’s not impossible, but it’s more work compared to traveling when it’s just yourself and a friend or significant other.

You see a lot of YouTubers and bloggers showing off these glamorous travel lifestyles, moving around an airport with just a single bag. Kids on the other hand require a lot more stuff to get them traveling – strollers, pack and plays, food, etc.

It’s a night and day difference between traveling on your own and traveling with kids. This means if you want to take a few months off to travel the world, you need to do it now before it gets much harder later.


Final Thoughts


You can set yourself up financially if you’re willing to do the weird things. I’m in a position now where even if I stopped aggressively saving, I’d still likely have enough money set aside to live a decent life if I retire at 65.

I did this through a combination of things. I made good money because I went to law school and got a good job. And I was fortunate enough to come from a family that was able to pay for my undergraduate education and give me a safety net if I needed it.

But I also did it by living life differently compared to most. I earned extra money whenever I could. I had living situations that most people wouldn’t do outside of college. And I kept living like a student even when I didn’t need to anymore.

Life is a lot more expensive for me now that I have a kid that relies on me. And it can’t be as weird as it once was. It makes me glad I did the weird things when I could.



What weird things have you done? How have you benefited financially from doing the “weird” things? Tell us about it below!


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4 thoughts on “Do The Weird Things Now While You Still Can”

  1. I can so relate to your comment about travelling with children! Before having a kid, all we had to do was pack a small bag and head out. Now – even on a day trip we ending up bringing multiple bags (toys, a change of clothes, etc). We didn’t have to worry about WHEN we travelled – even when your kid is a baby or a toddler – you can go anytime. But once your kid is in school – nope! You plan around school vacations. Before kids, we never thought twice about eating out. Now – between bringing snacks and finding restaurants that can cater to our son’s food allergies – eating out requires a lot of planning! Overall, even though travelling looks a little different now – we still do travel and really enjoy it!

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  3. Another aspect of travel is the decline of physical abilities with aging, tolerance for high altitude, etc.
    If one has some bucket list destinations that will be more taxing than others, it’s a thought to get those knocked out at an early age. There MAY be some 70 year-olds climbing Mt. Kilimanjaro, but I suspect not a lot.

  4. Your article brought back a lot of memories and reminded me how weird we were. We traveled to Hawaii at age 21 in 1979 with only $350 cash to last a week after pre-paying our room and flight. Even back then that meant 1 meal a day if not careful. We Island hopped from Oahu to Kauai for one day ($99) and when boarding the plane each end given 50% off next flight coupons. Stood in front of their air terminal the next day and hocked them to people approaching to purchase a flight. Made back my $99 plus more. We accepted time-share offers early mornings to get free rental cars and dinners on Oahu. Now empty nesters our weirdness freedom is back but different. It comes in not having to conform to social norms in the way we dress, live, play. No longer have to play the game of showing a perceived conformity for us/kids to fit in.

  5. This article made me chuckle. I remember the shock and awe that having the first baby brought to my previously pretty free and sometimes weird lifestyle. He is thirteen now.


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