Random referrals, awkward calls, not sure who’s legit, not sure who’s a fit. Habits fixes that.

They match you with vetted advisors who already work with people in your situation, same age, same income range, same stage of life.

It takes 30 seconds to get started, and you stay in the driver seat the whole time.

My favorite part about Threads, is that my profile doesn’t even have 1,000 followers, yet my dashboard claims to have (on average) 400k+ views per month.

Nonetheless, here are some of my favorites from the past few weeks.

I work from home full time, and I have a love hate relationship with it.

On one hand, I’m probably 100x more productive at home than I ever was in an office. It’s not that people are distractions, but it’s a lot easier to get things done when you can mute Slack, throw on headphones, and know nobody is going to tap you on the shoulder asking if you have a minute.

There’s a level of control that comes with working from home that’s hard to give up once you get used to it.

And I didn’t always have that luxury. I started my career wearing a suit every day for about 5 years. Alarm at 6, commute, badge into the building, same desk, same routine. After that I spent a couple years basically living out of a travel bag. Airbnb to Airbnb, city to city, the full digital nomad phase that everyone convinced themselves was the dream after Covid.

So I’ve seen both sides.

And as much as I hate to admit it, there are parts of office life I actually miss.

The repetitive conversations about your weekend. The random happy hours you didn’t plan. Venting about the same bullshit with the same people. Brainstorming in real time instead of over Zoom. Even just the feeling of being around other humans doing the same thing as you.

Working from home is convenient. It’s efficient. It’s comfortable.

It’s also very easy to realize that comfort and happiness are not the same thing.

Convenience makes life easier. It doesn’t always make it better.

One thing I’ve noticed as I’ve gotten older is that almost every great memory I have started with doing something I didn’t really feel like doing.

College trips. Moving to a new city. Traveling somewhere random. Taking a job that made no sense on paper. Starting a business. Trying hobbies I had no business trying. Meeting people I wouldn’t normally meet.

Nearly all of them started with a moment where I decided to step outside my comfort zone. And the older you get, the harder that becomes.

When you’re 20, your whole life is uncomfortable. You don’t know what you’re doing, you don’t know where you’re going, you don’t have money, and every decision feels like a risk anyway. Trying new things is the default.

When you’re 30 or 40, comfort starts to win.

You have a routine. You have a job. You have bills. You have responsibilities. You have a couch you like, a gym you like, restaurants you like, the same 5 people you talk to, the same places you go.

You don’t have to step outside your comfort zone anymore. Which is exactly why you probably should.

The older you get, the more intentional you have to be about doing new things.

At the start of this year I made a quiet resolution that I didn’t really tell anyone about. I wanted to do more things that made me slightly uncomfortable. Not extreme stuff. Not reckless stuff. Just things that felt new.

For context, I’m not someone who’s afraid of trying things. I’ve lived in 5 cities in the last 12 years. My first internship was in Shanghai. I studied abroad in Marseille because I wanted to be somewhere where I might be the only American. I left a pretty traditional path early in my career to do something different. I started a company. I make content on the internet for a living, which in itself feels slightly insane some days.

So I wouldn’t say I struggle with stepping outside my comfort zone. But I do struggle with defaulting to comfort.

This weekend, Remington and I did a Spartan race.

If you’ve never done one, picture a military obstacle course mixed with a mud run. A few miles of running, 20 plus obstacles, climbing ropes, monkey bars, walls, sandbags, crawling under barbed wire, throwing a spear, and every time you fail something you either run extra or do 30 burpees while people behind you are waiting.

At one point I remember thinking, I paid $160 to do this?

An hour later you’re covered in dust, mud, sweat, maybe a little blood from a scrape, completely exhausted, and somehow glad you did it. What really got me though wasn’t the race itself. It was looking around and realizing there were people out there who had to be in their 60s doing the same thing.

Not fast. Not perfect. Just out there doing it.

And I remember thinking, this is cool, but this isn’t actually what stepping outside your comfort zone feels like anymore. It was fun. It was physical. It was different.

But it didn’t make me nervous.

Real growth usually starts with the things that make you feel slightly out of place.

A few weeks ago I did something that definitely wasn’t on my 2026 bingo card.

I joined a soccer league.

We moved close to a small pitch and I kept seeing games there every night. Rain, cold, didn’t matter. People were always playing. One night I walked over like a kid and asked someone how to join. He gave me a number. I texted the number. Got a link. Paid $80 through a portal that honestly looked like it could have been a phishing scam.

Next thing I know I’m showing up on a Tuesday at 9pm in freezing weather with 6 strangers in a group chat I had been added to.

For context, I’m not that good at soccer. I played a couple years in high school because a teammate dared me to try out. Played a little club in college where I was easily the worst player on the field most of the time. I love the sport, but I’m not exactly built for a competitive adult league.

Then I found out this league is legit. Former D1 players. People who grew up playing their whole life. People who actually know what they’re doing. First couple weeks I could tell I wasn’t just one of the weaker players on my team. I might have been one of the weaker players in the league.

I scored a couple early goals and then spent the rest of the season volunteering to sub out, trying not to mess up in big moments, getting frustrated, getting competitive, getting way too into games that ultimately don’t matter.

And earlier this week something funny happened.

One of my teammates was wearing Arkansas soccer gear. We started talking. Somehow connected the dots that one of her old teammates is married to someone I knew in Chicago. Someone I used to (funny enough) play in a kickball league with years ago. Which is literally the last and only other time I participated in one of these evening rec leagues. Hundreds of miles away. Totally different stage of life. Random Tuesday night. Small world moment.

And it hit me walking home. If I didn’t walk over to that field one night and ask a stranger how to play, none of that happens. No new people. No random connections. No stories. Just another night at home.

Most of the things that make life interesting start with doing something slightly uncomfortable.

I think about this a lot now, especially when it comes to money and life decisions.

Buying a house. Starting a family. Changing jobs. Moving cities. Spending money on experiences. Paying for things that don’t make sense on paper. These are the conversations I have with my financial advisor more than anything else.

Not stock picks. Not tax strategies. Timing. Because a lot of my goals right now aren’t about maximizing wealth. They’re about doing things I probably won’t have the appetite to do at 50.

Playing in random soccer leagues. Signing up for races. Traveling when it’s inconvenient. Saying yes when it would be easier to say no. Not because it’s optimal. Because it’s alive.

And the weird part about getting older is that comfort becomes easier to afford, but harder to escape. Which is exactly why you have to keep choosing things that make you a little nervous.

Even if it’s just walking over to a field and asking a stranger how to join the game.

You don’t lose your appetite for new things because you get older. You lose it because you stop practicing it.

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