The Next Big Thing

Mike Tyson once said that everybody has a plan until they get punched in the month. Every future parent has a plan until they actually become one.

Every now and then, the inertia of your life coalesces into a singular moment that makes you feel like you’re on the verge of your personal next big thing.

I was hit by one of these lightning bolts on the open roads of Connecticut's Merritt Parkway. Around that invisible area where the tri-state area cedes to New England. Where it’s acceptable to be either a Yankee or a Sox fan and the Boston underdog mentality and the New York directness are blended into a rich, Italian-American sauce. It was June 2023, and my wife and I were traveling from our new temporary home in Westchester to Maine for what the kids commonly call a babymoon.

We were expecting our first child a few months later, and were under contract on a house that we’d move into 3 weeks before our daughter was born. When it comes to major millennial life moments, it was all happening. .

But I was over the moon about something else. Right before we left I checked the mail and opened up the following letter:

Depending on the the level at which you knew me in the preceding 33 years, you’d either be completely shocked, or it would have immediately clicked. Home Inspection?

**

A little rewind.

For 10 years, I pursued standup comedy with a seriousness that was not at all funny. I was out at open mics every night, then booked shows, then finally paid spots and gigs on the road. I was very dedicated and effectively squandered the many high-earning career options I accrued by virtue of graduating from a very good college.

But ultimately, I didn't go the “full loser”¹ that is necessary to really succeed in standup. I kept a 9-5 job in marketing and communications, where I did a solid enough job to never raise eyebrows. I turned down an opportunity opening for a more established comedian because I had a family member’s wedding. And most notably, I realized that the best thing I had going for me was my relationship with my girlfriend, now wife.

These are the types of things you eventually have to give up, or at the very least deprioritize, in order to “make it” in standup. So that you can one day perform to a sold out crowd at a theatre, and celebrate afterwards by spending the evening on your phone at a diner.

I also may have only been sorta funny, but we can ignore that part.

**

During COVID, my wife and I began to seriously think about the next phase of our lives. One that didn’t consist of having 11:00 pm dinners on the Lower East Side after my shows were over. Or living directly above a car service that blasted music all hours of the night. Over time I began to realize that standup, which for years was the primary fulcrum by which my life revolved around, would become a hindrance to our larger, shared goals.

Yet by many respects, standup was also my career. Sure, I had a day job. But I had always viewed it as just that. I spent years resisting advancement at my job in service of telling jokes about grocery stores to Norwegian tourists, taking random days off work to go perform at a firehouse near Annapolis or at the Sons of Italy in Binghamton.

Walking away from standup was an extremely tough decision, albeit very clearly the right one. But with this major life shift there was suddenly a huge, gaping void in the balding form of my career and identity.

Who was I? What is the thing that I do?

I needed to figure out my next big thing.

***

In the summer of 2021, as interest rates taunted the world and my wife and I entered our early 30s, we became obsessed with real estate. Sensing this was what was the pursuit that would fill the energy I had been channeling toward standup, I started diving headfirst into books, podcasts, and YouTube videos. Things like Capital Expenditures, Jerome Powell, and Financial Freedom suddenly became important parts of my life. In the spring of 2022, we came close to buying a house in Rhode Island that we’d turn into an AirBnB.

But ultimately, we got cold feet. As interest rates climbed back up and the prospect of having kids went from being hypothetical to totally in play, the methodical, risk-averse planner in me decided we’d best be served by buying a primary residence. Traveling to Rhode Island every weekend to fix up a house so that it’d be ready for the following summer was ultimately not the best use of our time. Not to mention the looming feeling that this AirBnB thing was at its peak mania with COVID receding.

So the real estate investing dream was put on hold. But one aspect of the bug successfully bit me.

**

At some point, I listened to BiggerPockets Real Estate Rookie Episode 11 featuring a home inspector². Immediately I was hooked. Home inspection seemed to exist at the intersection of many things I love and believed I was good at. Continuous, deep learning about complex topics, seeing and communicating the big picture, being a “tour guide” of sorts, and best of all, risk management and preparing for future problems in a comically long-term manner.

I was primed to hear this podcast at this exact moment in my life. After many conversations with my wife, this felt not just something that would be cool to do. But rather, something I should do.

With her high-earning W-2 providing stability, we thought it always made sense for me to do something a bit more high risk-and-high-reward; whether it was standup, a few random side-ventures I had done, or taking the lead on this hypothetical AirBnB project. Home inspection seemed like a great way to get plugged into the real estate world while starting my own business.

Plus, after further researching the market, it seemed like every current home inspector was a boomer in their late 60s on the precipice of a double knee replacement. It felt like the market was crying out for a millennial in the same way that Chopped judge Geoffrey Zakarian might say that a dish was crying out for some acid. If I got in the game now, I’d be positioned incredibly well for the Boomer retirement wealth transfer.³

So in October 2022, I enrolled in a licensing course. By April of 2023 I had completed the course and the required fieldwork, and signed up to take the NYS licensing test in May. In a few short months, I had gone from a person who somewhat knew about homes to someone qualified enough to become a New York State home inspector. While I knew I still had a lot to learn, I was growing confident in my skills and spent much of my free time learning about zip sheathing, category IV furnaces, and polybutylene pipes.

Driving on the Merritt Parkway that June, it finally felt like my next destination–after a few years of dead ends and confusing traffic circles–was firmly in view.

**

Our daughter was born in late August, 2023. They say you can’t really prepare for parenting, and “they” are absolutely right.

My wife and I had spent the previous few months doing the sorts of things first time parents in stable relationships tend to do. We attended a CPR class in a pothole-filled strip mall. We had discussions about bassinets and snoos during commercial breaks of Top Chef. Overall, we exhibited a general unearned confidence about our strategies for parenting.

Then, in what was simultaneously a very long time coming and all at once, our lives completely changed. A few days in the hospital, accentuated by the indescribable jolt of meeting your new family member, and we were suddenly on the other side.

It’s hard to quantify all the differences of life before and after a child is born. How vastly the day-to-day changes, how much you evolve over the long term, and all the little things you don’t even account for.

One small example. When we made the offer on our house, we had no thought whatsoever about how creaky the floors were. In fact, we barely noticed they creaked at all. There was no infant to punish us for the evening if we stepped in the wrong spot, so why would we?

But mostly, we didn’t know the infinite joy that comes from bringing a new life into the world. How fascinated we’d be by her every movement, her quirks, and as I’m writing this, the peek-a-boo-style practical jokes she’s starting to play on us as an 18 month old. The way she insists on washing her hands in the sink as if it's a 9-11 level emergency, or squeals in delight upon seeing her Elmo doll.

It’s a sense of meaning and purpose that dwarfs the rush of getting laughs on stage a million times over. I now have a hard time believing, and am retrospectively embarrassed by the fact that pursuing comedy at the expense of being present in my daughter’s life is something I legitimately considered for many years.

**

In those first few months, I existed on two planes. On the main floor of our house I was a devoted and heavily involved parent. Down in the office basement I was, pun intended, laying the foundation for my home inspection business.

I bought hats, shirts, and tools. I worked on a marketing strategy. I watched a few too many Alex Hormozi videos⁴ and built a website. I opened a bank account and slowly started to spread the word. Some of my friends and family reacted enthusiastically, excited for this next chapter. Others looked at me like I had five heads. Or in some cases, pretended that my new career didn’t exist given that it didn’t align with their existing perception of me.

I also existed in a sort of career purgatory. I was at my marketing and communications job, albeit on a 3 month parental leave. The plan was to return to my job, have our childcare situation settled, and solidify a more permanent transition to home inspection in spring 2024.

It was exciting gearing up, and beginning to feel real.

**

Yet, it wasn’t all positive. For the first time since embarking on this venture, I began to feel a slight pit in my stomach that threatened to expand ever-wider.

The housing market had screeched to a halt. One of the downsides of this abrupt career transition is that I lacked any sort of career capital⁵ in the field. Sure I embraced routine apartment maintenance and considered myself exponentially more handy than anyone in my Jewish family. But that is sort of like dominating the Little League World Series as a sixteen year-old.

I had no official background in construction, almost no prior contacts in the industry, and having moved to an area 90 minutes away from where I grew up, I didn’t have a hyperlocal built-in network of realtors, homeowners, and families that I could initially rely on.

My wife and I were clear about the fact that I’d be starting this from basically nothing.

This wasn’t something I was afraid of. In comedy, I did terrible open mics nearly every day for almost a year before being booked on my first real show. And despite walking away in year 10, I still outlasted the vast majority of comics I started out with.

So it wasn’t the plunge into the unknown I was scared of. It was something else, that I couldn’t yet put my finger on. Mike Tyson once said that everybody has a plan until they get punched in the month. Every future parent has a plan until they actually become one.

***

I returned to my job in December. Winter ceded to spring, and our daughter was turning into an amazing little person. One morning on the couch, she started hooting and pointing outside our window, as if to say she was thrilled to be consciously joining the world. A diet of strictly milk turned into one that also included yogurt and avocados.

We went to the diner and I gave her fries for the first time. She was confused, and possibly offended by them. She was much more interested in watching the action at the diner counter, enraptured as I was that someone would actually order a danish that had been sitting there for possibly several days.

Our childcare situation hadn’t been fully figured out. We knew it would be expensive. But in all of my diligent planning, I found a gap between our expected childcare costs and the actual, truly insane price tag⁶. Our monthly expenditures, which had been relatively static over the past few years, shot up exponentially with the prospect of baby college tuition (AKA childcare), a mortgage, and a new $200 a month budget to support our daughter’s blueberry and strawberry habit.

I wasn’t our family's primary earner. But I was the proud architect of our household's financial model. One that was predicated on living well within our means first, and taking calculated risks second. I knew my spreadsheets were going to change drastically, but the change was finally making its way into the cells of the google sheets⁷.

Even so, the numbers still said that home inspection was workable. Some of the entrepreneurial types that had infiltrated my ears through podcasts might have even argued that I couldn’t afford not to start my home inspection business given all of the potential earnings I’d be leaving on the table.

But as I was beginning to realize, the numbers were just one component.

***

I spent spring 2024 in soft-launch mode. I performed inspections for friends who generously let me inside their homes, usually free of charge in exchange for a google review. I joined the local chapter of the American Society of Home Inspectors and met the most accomplished professionals in the area. I soaked in their every word during our monthly meetings in the private back room of an Italian restaurant. I was one of the few inspectors who actually took notes during presentations about gravity furnaces and step flashing.

I teamed up with a friend from my home inspection class, doing inspections with him as his assistant. We made a great team with his many decades of knowledge, and my ability to write quality reports and not throw out my back.

As a thank you for my services, he once gave me a giant bag of bacon he smoked himself. Not only was it possibly the best bacon I ever had, but cooking this bounty a few days later, I felt that this was a place and career where I could not only find my professional calling, but actually bring home the bacon.

Meanwhile, the rest of our life was coming into view. My wife would start a new job in May, one that was a lot more flexible and enabled her to spend more time with our daughter than she otherwise would have. We had a permanent childcare situation set up to start in September, with a temporary one for the summer.

Although my initial plan was to launch the business in the spring, September suddenly made a lot more sense. I could build some more experience with my soft launch and ongoing partnership, get a license to fly drones–something that, once in the field, I realized was a huge value add–and get the business going at a time when the market was hopefully a little bit more active.

My various plans and calendars shifted to September. I told myself I wasn’t putting off the inevitable.

***

Part of our summer childcare plan involved me. I took off work the vast majority of Fridays and spent the entire day taking our daughter to the park, on long walks, and reading her books. We occasionally faced off in a battle of wills when she refused to nap.

It was a truly great time. I loved watching how excited she’d get when I plopped her down on the swings. How she now said “Dada” with conviction, or how she’d house an entire plate of mac and cheese. The days were often long and weren’t without their stressful moments, but I mostly understood how lucky I was. That I was able to get this time with my daughter that most people, mothers or fathers, did not typically have.

Watching her grow so quickly I knew I’d come to deeply miss these moments, but I was getting beyond excited for what the future would hold. Weekends at sports games. Excursions to the city for food that my wife would rather not eat. Having real, intellectual dialogue about what she was learning about in school.

One day, as we were walking back to the house from the park, I absentmindedly started thinking about going to her soccer games–or whatever activity she gravitates toward–on the weekends. How fun that would be.

Then, out of nowhere, something hit me and the pit in my stomach grew ever so slightly.

On the weekends.

Through comedy and my tour guide business, I had always been accustomed to working when other people weren’t–nights, weekends, none of it bothered me. I actually sort of loved it, feeling like I was using this time well. Watching half the people at my comedy shows being dragged there, having a terrible time or spending too much money on something they didn’t totally enjoy, I often felt sorry for them.

Working during these odd hours gave me a sense of control and structure over my life. It was something I naturally assumed would remain true as I transitioned into the home inspection world.

But, again, in all of my diligent planning, there was a major oversight so embarrassing I could hardly believe that I made it, even though it was the exact reason I walked away from comedy.

Now, we were a family. This was the structure. The sun in which we’d all revolve around. There was and probably will be a time to fully optimize my life around bold career pursuits. But as I was realizing with each passing moment, this was not that time.

*

Since my daughter was born, I’ve constantly thought about what it meant to be a father, and how to be a good father. With this conversation taking shape on the national stage–the election later in the fall, it turned out, was arguably a referendum on the democratic party’s inability to provide a roadmap of purpose to men, particularly young men–I began to seriously juxtapose my own experiences with what I was reading and observing around me.

I noticed that in some family arrangements, the dad was rarely around, likely due to work. In some of these situations, this was obviously the agreement. Husband goes out to make money to support the family, and the wife takes care of the child. The traditional arrangement.

But in approximately 45% of opposite sex marriages, wives are now either the primary breadwinner or make roughly the same amount as their husbands⁸. An even greater number of families are reliant on dual incomes⁹. Based on trends in higher education and academic performance¹⁰, it seems very likely that family unit dependence on women’s income will only increase.

Yet, women are still expected to do more of everything else. The stats¹¹ say that on average wives are spending more than double the amount of time on housework than men, and almost two hours more per week caregiving. My observational evidence says that when it comes to an event at daycare or an event involving our children, the wives are the ones expected to leave work in the middle of the day to attend. To bake the zucchini bread for the party, or plant a nature garden. Or take the child to the doctor if they are sick.

If they are absent from these things, there is a societal subtext that implies they are a bad mother. Men, on the other hand, spend three and a half more hours per week on leisure activities.

**

As the traditional role of father as breadwinner becomes less and less of an obvious or even practical reality, the role of men is undergoing a drastic change that we as a society have yet to fully grapple with. As I began to think about my personal situation, and my role as a father, I myself was confronted with a reality specific to my own circumstance.

My role as a father within the context of our family unit was not to go out and start a risky venture, and never be around both physically and emotionally.

My role, rather, was to be dependable and reliable. To be in charge of seemingly small things like making grocery lists and planning our weeknight dinners, or to manage household projects like our roof replacement or the organization of our garage. To understand where the gaps are, and how to fill them without fanfare. To lift heavy things. To make jokes when jokes are needed. To do well professionally and earn a good income that contributes to our household, even if it’s not as much as my wife’s.

And probably most importantly, my role was to play an active, present role in raising our daughter at such a crucial age. To be a present husband, and provide practical and emotional support for my wife. To be 50% of the ongoing work and dialogue that is running a household and family, without actually measuring that percentage.

Parenting, it turns out, is very hard. My initial thought that my wife would take care of our daughter and home while I was out doing inspections and drumming up business all the time was short-sighted at best, insulting at worst. My wife is an incredible mom and has intelligently centered her own life around our growing family while still earning a very good income, but doing that so I could go out and build a home inspection business started to seem less like a great idea and more like me going out to play-act entrepreneur while my wife did all the real work. It felt childish. The opposite of how a man should behave.

**

The first week of September, I was supposed to have launched my home inspection business, notifying my full-time job what I was doing, and possibly going part-time there. While I wasn’t quite ready to officially call the home inspection business quits, I now knew that this launch was not going to happen anytime soon. If at all.

That Thursday morning I sat on the floor playing with my daughter, who was about to attend her third day of daycare. My wife came out to join us. She had taken the transition hard, naturally pained to see our daughter cry and scream for large chunks of the day (daycare streaming cameras are a blessing and a curse).

But her demeanor seemed completely changed from the day prior. Calmly, she explained that she now understood why she was having a much harder time adjusting than she anticipated.

She held out a wand. This wand had two solid pink lines.

Taken by complete surprise I screamed in delight, scaring our daughter, who started crying.

About an hour later we drove home from dropoff. It had gone much better on her third day. It was one of those September mornings where you wish you could just capture the weather in perpetuity. The sun warming our bodies through the car, not a cloud in the sky. Neither of us said anything, but were both obviously thinking about how crazy our life was going to be starting next spring.

It was abundantly clear that the next big thing was right in front of my face this whole time.

I started to think about how I couldn’t wait to take us all on a family vacation. Maybe we’d drive on the Merritt Parkway, ending up somewhere in New England. At least in our family, I’m still the driver.

Photo by Valentina Locatelli on Unsplash

1. See point #9 in 10 Thoughts About 10 Years in Standup

2. See:

3. This statement was made under the assumption that Boomers will actually retire and not just drop dead in their office chair

4. If you are interested in starting a business and/or better understanding sales (my weak spot) I would highly recommend these videos, but make sure to consume responsibly

5. According to google’s AI overview, Career Capital is “refers to the skills, knowledge, credentials, connections, and financial resources you accumulate that allow you to achieve greater impact and autonomy in your career and life.” It was a concept first proposed by academics Robert Defillippi and Michael Arthur in the 1990s.

6. Since 1990, child care costs have risen 214 percent, while the average family income has increased by 143 percent. The increase significantly outpaces other major expenses like housing, groceries, and well, pretty much everything.

7. This is how you know I am a self-taught spreadsheet person, as I’ve increasingly gotten the vibe that true spreadsheet people use excel.

8. The math on this is taken from the stats in this article: https://www.npr.org/2023/04/13/1168961388/pew-earnings-gender-wage-gap-housework-chores-child-care

9. I imagine these numbers are particularly high in high cost of living areas, where the cost of live has largely outpaced wages in many jobs, causing a phenomenon in which Americans are moving away from opportunity towards affordability, thus limiting the opportunities of their children: https://www.theatlantic.com/magazine/archive/2025/03/american-geographic-social-mobility/681439/

10. https://www.brookings.edu/articles/boys-left-behind-education-gender-gaps-across-the-us/

11. All stats cited in this section from the same article in footnote 8: https://www.brookings.edu/articles/boys-left-behind-education-gender-gaps-across-the-us/