Happy Monday, friends!

Well, we actually did it. I ran the NY Marathon yesterday and crushed one of my bucket list dreams. It was the craziest feeling in the world and my body hates me today (feels like I fell off a ten story balcony), but today is not about me.

If you've been reading this newsletter for a while, you know I've been talking about retiring my mom for years. Back in September, I shared that we'd finally made the decision, found her a new apartment, worked through the finances, and were getting ready to make it happen. Well, that day finally arrived. Last Friday, October 30th, was officially her last day of work.

At the time, it still felt like something that was going to happen in the future. We'd made all the plans, had all the conversations, and worked through what the next 25 or 30 years might look like financially. But she was still going to work every morning, and I was still going about my life knowing we had a few more weeks before everything changed.

Well, Friday was her last day. Over the weekend we got her moved into her new apartment, and today my mom is waking up on a Monday without having to go to work.

For the first time since she was 14 years old.

Nearly 50 years of waking up, getting ready, going to work, coming home, and doing it all over again. Raising two boys, losing my dad, dealing with bills, and doing whatever she needed to do to make sure our family was taken care of. And now, after all of that, she gets to wake up today and decide what the hell she wants to do with her day.

I asked her how she was feeling about retirement, and she compared it to being a kid waiting for the last day of school before summer vacation. I thought that was the perfect way to describe it. She's been counting down the days, and now the summer vacation she's been waiting nearly five decades for is finally here.

Knowing my mom, she'll probably have the next six months planned out by Tuesday. She loves the beach, Grateful Dead cover bands, and spending time with my brother Greg and his little guy McCoy. I'm sure there will be plenty of that. Maybe she'll even discover some new hobbies now that she has an extra 40 hours a week to fill.

My only concern is that those extra 40 hours are going to give her a whole lot more time to spend my money.

In all seriousness, I don't think I've ever been more excited about something that was happening to somebody else. I've had some pretty incredible moments in my life over the past few years, but watching my mom finally get to stop working is right up there with the best of them.

The funny thing is, this whole experience has also brought back some memories I haven't thought about in a long time. And one of them involves an $8 cookie.

Last week I was back in SoHo, NYC, checking out the location for our fifth BODY Hot Pilates studio. Lyndsey and I have been building this business together, and it's been an absolute rocketship watching her turn something she was so passionate about into a company that's growing faster than either of us could have imagined.

I've written plenty about how rewarding it is to watch your wife chase her dreams, so I won't go too deep into that again today. But this particular location has a special meaning to me because it's right around the area where I used to work before my life took a very different direction.

I was walking around the neighbourhood when it hit me just how close we were to my old office. And suddenly I started thinking about a woman named Brianna, who used to be my boss back when I was making around $40,000 a year and trying to survive in New York City.

Brianna was one of the good ones. I genuinely loved working for her and learned a ton in the process. Once a week she would take me for a stroll around the block where we would end up at the infamous bakery Balthazar and treat me to a cookie.

An $8 cookie in 2016 (think about the inflation today!)

I know, I know. $8 for a cookie is ridiculous. But back then, I thought this was the biggest little luxury thing in the world. I knew Brianna was making good money, but to see her enjoy the finer things and to create little rituals like this is something I’ve carried with me for the rest of my life.

Meanwhile, I was trying to make my paycheck last until the next one. Between rent, student loans, and the cost of trying to survive in New York City on a $40,000 salary, there wasn’t much left over.

It's funny when I look back at my life and all the incredible experiences over the years. It's the small things, like the routines that you build with your coworkers, the concept off buying a vinyl record every paycheck on the 15th and 30th (racked up over 500 records), phoneless walks with Lyndsey are the things that you actually remember. Not the expensive purchases or lavish trips.

And standing there in SoHo last week, looking at the neighbourhood where I used to worry about things like that, I realized I hadn't spoken to her in more than five years.

So I picked up the phone and FaceTimed her. Imagine the feeling of getting a FaceTime from somebody you haven’t talked to in half a decade.

She was completely shocked to hear from me. I mean, imagine getting a random call from somebody you used to work with more than five years ago, completely out of the blue. But I was right there near the old office, thinking about that period of my life, and it just felt like the right thing to do.

Afterward, she sent me a text that honestly made my day.

"I'm so so so proud of you!!! ❤️❤️❤️ you're really doing the damn thing!"

I responded with about seven hearts because I didn't really know what else to say.

It's such a small interaction, but I haven't stopped thinking about it.

The last time I was working in that neighbourhood, my life looked completely different. I was making barely enough money to get by, and I had no idea what I wanted to do long term other than figure out a way to stop working for somebody else.

If you've been reading for a while, you've heard the story about how that chapter ended. I got fired on a Monday, had almost nothing in my bank account, and ended up sitting on the black metal steps outside an Equinox crying on the phone to my mom because I didn't know how I was going to pay rent.

I genuinely thought my life was falling apart.

And now, nearly a decade later, I'm walking around the same neighbourhood with my wife, getting ready to open our fifth Pilates studio, and calling somebody who used to buy me cookies because I couldn't afford them myself.

What a weird, full-circle moment.

I've spent a lot of time over the past few years thinking about what success actually means to me. When I was younger, I wanted to make money because I was tired of being broke. I wanted to get out of debt, stop working jobs I hated, and finally have some control over my own life.

At 14, I was recycling cans at Price Chopper so I could afford to pay for the internet. I remember electricity bills being late and checks bouncing at the grocery store. Money was always something we had to think about, and I carried that feeling with me long after I moved out and started trying to make a life for myself.

So when I got to New York and started working, the idea of making $100,000 a year felt like the finish line. I honestly thought that if I could just get to that number, everything would be okay. I'd be able to pay my bills, stop stressing about every purchase, and maybe even buy myself a ridiculous cookie whenever I wanted one.

It's funny how much your idea of what constitutes a lot of money changes as you get older. It’s even funnier how the things you want to do with that money change.

When I was building CROSSNET, so much of my motivation came from wanting to change my own circumstances. I was sick of being broke, sick of working jobs I didn't enjoy, and sick of feeling like my future was going to be decided by somebody else. I wanted to build something big enough that I never had to worry about those things again.

Over time, I started thinking more about what I wanted that success to make possible. I fell in love with Lyndsey, we started building a life together, and some of the best moments I’ve experienced have come from watching the people I love reach their own milestones.

Watching Lyndsey open another BODY studio makes me happier than I ever expected. Seeing my brother become a dad and getting to spend time with my little nephew McCoy has been incredible. And now, being able to tell my mom that she doesn't have to go to work anymore is something I genuinely don't have the words to describe.

But there's another side of this that I want to be honest about.

I'm feeling an immense amount of gratitude right now.

And an immense amount of pressure.

When I wrote about retiring my mom back in September, I talked about the financial responsibility of making that commitment. I knew what we were signing up for, and I was more than happy to do it. But now that she's actually finished working, the whole thing feels a lot more real.

This is no longer a goal I'm working toward or something I'm hoping to make happen one day. It's happening. My mom has finished her last shift, she's moving into her new apartment, and I’ve committed to making sure she never has to work again.

I've been an entrepreneur long enough to know how quickly things can change. During the CROSSNET days, I was scrambling to fund inventory and hoping the cash flow would hold together long enough to keep the lights on. We’ve come a long way since then, and I’m incredibly grateful for where we are today. But I also know there are going to be bad moments along the way.

The stakes are different these days. I have a wife, we’re thinking about starting a family, and I’m now responsible for supporting my mom for the next 25 or 30 years. I still love the game, and I don't see myself ever being somebody who just sits around doing nothing. But I'm thinking a lot more about how to hedge against those bad moments so they don’t become bad enough that everything we’ve built goes away.

The funny thing is that I used to think making money would eventually remove the pressure. That there would be some magical number where I could sit back, relax, and stop worrying about the future. Instead, the things I care about have gotten bigger, and the decisions I make affect more people.

One of the things I’ve come to appreciate about building The Founders Club is getting to spend time with entrepreneurs who are at completely different stages of this journey. Some are dealing with the same problems I remember having during the CROSSNET days. Others have built businesses far bigger than anything I’ve ever been involved with, and they're navigating responsibilities I’m only beginning to understand.

And the more time I spend around these people, the more I realize how valuable those conversations are. There’s something incredibly reassuring about being able to talk to somebody who;s already been through the thing you’re trying to figure out, whether that’s scaling a company, managing an exit, or deciding what you actually want to your success to make possible.

I don't mean that as a complaint. I wouldn't trade any of this for the world. I feel incredibly fortunate that I'm even in a position to make this happen for my mom. And right now, the responsibility I feel is to make sure this incredible thing we’ve been able to do for her lasts.

I keep wondering what today is going to feel like for her.

After nearly 50 years of working, does your body just automatically wake up at the same time? Does she get up, make coffee, and start thinking about everything she needs to do before remembering that she doesn't actually have anywhere to be?

Or does she sleep until 10 AM and immediately start living her best life?

Knowing my mom, I wouldn't be surprised if she's already got a full schedule planned. I also wouldn't be surprised if she's bored by Wednesday and starts calling me with ideas for things she wants to do.

But I really hope she gives herself some time to enjoy this.

For so much of her life, there has always been something that needed her attention. A job to get to, bills to pay, kids to raise, and responsibilities that couldn't just be put on hold because she felt like taking a day off.

Now she has an opportunity to figure out what she wants this next chapter to look like.

And I'm excited to watch her do it.

I've been thinking about how strange it is that I spent so much of my twenties chasing the freedom to control my own time. That was the dream. No boss, no schedule somebody else created, no having to ask permission to go on vacation or take a day off.

I wanted to be able to wake up and decide what I wanted to do with my life. And after all these years, one of the most meaningful things I've been able to accomplish is giving some of that same freedom to my mom.

I don't know if younger Chris, the guy who thought an $8 cookie was the height of luxury, would have believed any of this was possible. I certainly don't think the guy sitting outside Equinox crying on the phone would have.

But this morning, my mom gets to wake up and decide what she wants to do with her day.

And Mom, if you're reading this, enjoy your first Monday.

You've earned it.

All the love in the world,
Chris

P.S. If you're a founder doing seven figures in annual revenue and feel like you’re figuring too much of this out on your own, hit reply. I’d love to hear what you’re working through and see if The Founders Club might be a good fit.