I know what you’re probably thinking — a young Millennial known for his hot takes is about to lay down the hammer on the older folks. Well, if that’s what you are hoping for, this probably will disappoint you.

I will certainly be laying out some critiques, but this message overall is meant to inspire and encourage the older generations to be exactly that: the older generations, the heroes we need in our day and age. The heroes that every age needed. But that we are missing at historical levels in our current moment.

Here is a photo with one of my mentors and heroes in life, President Stephen Minnis of Benedictine College.

 

The Context

First, a personal story to help lay the context.

Earlier this year, I attended a Catholic men’s conference in Kansas City. You typically find a few common personas at these men’s conferences:

1. The young, optimistic, hopeful guy who is there to learn more about what it means to be a great Catholic man.

2. The older, wise Catholic man who has managed to successfully live out much of the wisdom that is shared. He has grown faithful children and feels affirmed by what is shared from those holding the microphone.

3. The late convert/revert to the faith — the man who feels as though, whether to a large or small degree, that he has failed his children by his late conversion, neglecting to live out most of the principles shared by the presenters at the conference.

I’d put myself in category 1. The majority of the audience tends to be about a 30/70 split between 2 and 3. The problem is that a great chasm exists in our parishes and society between men in category 1 and those in categories 2 and 3.

This became clear when I was standing in line for confession. The men behind me were talking openly about how their adult children don’t practice the faith, sharing how hard it can be to hear about all the things they wish they’d known in their 20s and 30s.

Hearing this, I get this overwhelming sense that they believe they wasted the time when their kids would have listened to them, and now that they lack that same influence, they feel there is next to nothing they can do. They feel like they have nothing to offer. And so, they go to mass, volunteer where they can, and enjoy their early-morning men’s group meetings, surrounded by other old men with the same frustrations.

You can imagine my surprise when, despite our having just met earlier that day, one of them asked me my opinion on the matter. “Why do you think our adult children won’t listen to us? You’re here today. Why are you still Catholic?”

It’s one of the most common questions I get from dejected parents with adult, secular children. And it’s a fair one. But the truth is that the negative emotions they are feeling are quite valid. Many older parents simply missed the boat on their children. You only have them, and their ear, for so long. Your presence and example matter a LOT when they are small. And if you blow it, you don’t get to just redo it when they’re in their 30s.

But that’s not why we’re here today. We’re here today to discuss the same perspective change that I provided these men on the day of the conference by simply replying to them:

“Man, I don’t know what happened with your adult kids, but I can tell you that there are many young men who could benefit from learning from you and would be eager to listen. I haven’t spoken to my Dad in two years. I have a demanding job. I’ve got two young kids and a wife. And I’m generally just out here navigating it all alone. I’ve almost never had an older man at any parish I’ve belonged to, or even visited, invite me out to lunch or breakfast to get to know me and share some wisdom. You have a lot to offer, even if the ones you most desperately desire to give it to don’t want it.”

You have a lot to offer. There are many people who need it. But you’re so upset that those you want to give the gift to keep rejecting it that you won’t just hand it to the next person standing there with open arms.

I witnessed the light bulb come on. I saw the click. And this is what I want to encourage today.

The Coddling of the American Mind and Soul

Millennials and Gen Zers were raised, for the most part, by parents who coddled them into ineptitude. Regarding faith, we had parents who tried to entirely outsource the responsibility for being our primary educators. We were eagerly dropped off at college—unable to do laundry, cook dinner, or avoid signing up for debt that would financially paralyze us for decades.

We were sent to school for education, but we were never really formed. We now have many women who want to be stay-at-home moms, some of whom were even raised by stay-at-home moms, who have no idea how to run a household. We have men who were never taught by their fathers what it means to be a good husband and father, who were never shown or trained how to provide, protect, and lead.

My mom, like many of my friends’ moms, did almost everything for me when I was younger. I had to occasionally empty the dishwasher or walk the dog, but I certainly wasn’t waking up to long to-do lists on Saturday mornings. And did I complain about this then? Absolutely not. I thought I was living the dream.

My friends mostly thought the same. They enjoyed the helicopter parenting. Mom stayed on top of your upcoming due dates for projects and homework assignments. Even into college, some moms are scheduling every appointment and need for their adult kids. I was blessed that the Army didn’t play that game, so even in ROTC, I had to start taking ownership of my life and growing up.

 

Most, however, didn’t choose to join the military. And they were unburdened of responsibility well into their 20s, unlike the generations before us. And unlike those who came before us, many young people today find themselves unable to cope with everyday life.

And somehow, they are told that this is their fault.

I believe this is the root cause of the intergenerational tension we experience today. For years, the older folks talked about how lazy and entitled millennials were and how emotional and odd Gen Z is. Now, the latter two blame the older generations for creating a political, economic, and familial environment that has put us in a downward spiral we’re unsure we can correct.

See a Need, Fill a Need

Boomers and Gen Xers, we need you. We need you to step up and fill the gap that you or your peers helped create. We need you to stop lamenting the failures of the past and to be involved in making a better future.

Let me give you some examples of what this can look like.

We recently had a friend over for dinner. She and her roommates are all single girls in their mid-20s. She told us about their “wife nights”, where they go over to a woman’s house and learn what it looks like to manage a household. The host is a 45-year-old woman whom they met through Church. She cooks with them, shows them how to plan meals and grocery shop for a family of 7, and how she balances everything that needs to get done in a given week.

When my wife and I were expecting our first, I told her I wanted to have a “Dad party”. As I mentioned earlier, my father and I don’t have the best relationship. Besides, he’s had seven children with five different women, several of whom he hardly raised at all. I wouldn’t say he’s what I aim to be as a father.

Luckily for me, my wife’s family was close to some really amazing Dads in their 40s. My wife contacted one of their wives with the idea. And she and her husband ran with it. He invited about six of his good friends and family members, most of whom I knew, over for a bonfire complete with bourbon and some good food.

We sat around the fire for almost four hours while I asked questions about fatherhood and marriage. What’s amazing is that I think each one of them enjoyed and benefited from it, albeit in different ways, almost as much as I did.

We have bridal showers, baby showers, dress shopping, and all types of things where older and younger women come together to celebrate and shape a woman who is entering a new, hugely important stage of life. And what do men have? Bachelor parties. It’s insufficient and needs to be addressed, especially in light of today’s crisis of masculinity.

Why can’t every church in America do this quarterly for new dads? How much would this simple night change the world?

A man I know has been extremely financially successful. He would fall into category 3 under our definitions above, although he seemed pretty intentional and faithful even when his kids were young. His situation is much more of a mystery to me.

But he takes it upon himself to coach young men with growing families who probably couldn’t afford an executive coach. He volunteers his time to help them with their business/leadership decisions, both at work and at home.

And I don’t think we consider this sort of generosity enough. My wife and I were at a fancy steakhouse in Denver about a year ago, just dreaming about the future. I told her how much I’d love to take young, engaged couples out and just share hard-earned wisdom on marriage and family life with them over an expensive, lovely 3-hour dinner.

We just did this recently, where we had a young couple over for steaks at home. They are expecting their first child this fall, and we thought it would be wonderful to host them, get to know them, and see what we could offer in the realm of the life-altering event that is becoming a parent. It doesn’t have to be fancy or expensive. The most valuable thing you can offer someone is your time and active listening.

Where to go from here

I think people overuse priests as spiritual directors. It wasn’t meant to be this way. Most people don’t need a priest for spiritual direction. What they really need is mentorship from a wise, virtuous person of the same sex who is further down the road than they are. Priests have their place, and it is an extremely important one. But as their population declines, we need them to do the work only they can do.

 

Mentorship is not one of those things. Priests and religious need spiritual directors. People with serious mental health issues need therapy. But most of us just need someone to talk to who can help us feel heard, understood, encouraged, and challenged to be better.

You don’t have to wait to be a mentor and help others. You don’t need to have your life all put together to love someone. Sure, if your life is a blazing dumpster fire, perhaps you aim for more presence and support than providing advice, but even those who may feel like they know a lot more of what not to do than what actually makes for a good life can provide support to young families in numerous ways.

If you’re in college or young adulthood, try to find a high school or college student who could use a listening ear and an older friend.

If you’re in your early 30s like me, find those young dating, engaged, or recently married couples who you can support through these transitions.

If your kids are now all in grade school, find those families at church who are battling toddler tantrums and potty training. Invite them into the busyness of your lives. Have the mom over for coffee or the dad over for a drink. Just talk to them. Build a relationship. Care about who they are and what concerns them. It can literally change a person’s life or save a marriage.

If your kids are now adults, do the same thing with the generation behind you. Get involved. Don’t just sit on the sidelines and pout about the days past. The time is now, and it’s the best time to act.

It is so easy to be selfish. Our society today creates an environment where selfishness is not only tolerated, but promoted and encouraged. It is so easy to think you are too busy, too imperfect, or too stressed to offer your time and resources to others.

But I want you to know that this is a lie from the devil himself. As I mentioned in the example of my “Dad party”, the giver of the gift in these situations is often as inspired and changed by the act of giving as the recipient is.

You’ll find that this crazy thing happens—you’ll feel needed, useful, and have deeper meaning and purpose in your life. You’ll feel appreciated. You will step outside yourself and focus on how to add value to others' lives. It will cause a domino effect of paradigm shifts in your life. You will be a better Christian, better spouse, and better human because of it.

Let me tell you about my weight.

When I was in the Army, I was in the best shape of my life. Preparing for Ranger School does that to you. I graduated from high school at about 185 lbs. After my freshman year of ROTC, I was 195 lbs. I got up to about 207 lbs through my Infantry training and the lead-up to Ranger School. I got to the point where I was running five miles in 35 minutes while being strong enough to handle the heavy, slow movements during missions.

They call it the Army’s elite weight loss program. You come out the other side much leaner than you went in, partly because the program is extraordinarily demanding and partly because they feed you roughly two meals a day while you’re burning an unfathomable amount of calories. I lost twenty pounds in the first twenty-one days. By the end, I had been broken down and rebuilt in ways that went far beyond the physical.

After graduation, I was sent to my first and only assignment at the 82nd Airborne Division in Fort Bragg, North Carolina, where I’d serve as a Platoon Leader. During our deployment to Afghanistan in 2017, I rebuilt my body to the strongest I had ever been. I got my weight up to 225 lbs and was setting personal records on the bench press, deadlift, and squat rack.

Two years later, I transitioned out of the military and into civilian life, and the structure that had kept me disciplined without my having to think about it was suddenly gone. No formation runs. No mandatory PT. No one checking whether you were maintaining standards. Just me, a desk job, and a world full of decisions I had not had to make for myself in years.

My weight has gone up and down nearly every year since. It has fluctuated in ways most don’t pick up on, but enough that I notice. It’s enough that it bothers me. I will build momentum for a few months, get into a real groove, feel like I have finally cracked the code, and then something shifts. My life has been flooded with change post-military: new jobs, new homes, marriage, two babies, promotions at work, you name it. And the fitness habits I thought I had locked in turn out to be more fragile than I believed.

I am telling you this not to confess a failure but to establish a credential. I know exactly what it feels like to start strong and lose all the momentum you’ve built. And because I know that feeling so well, I have spent a lot of time thinking about why it happens and what actually separates those who build lasting habits from those who do not.

What James Clear Got Right

James Clear, the author of Atomic Habits, said something recently on a podcast that was simple yet profound. He said, “A habit must be established before it can be improved. ” And then he said this: the heaviest weight at the gym is the front door.

Both of those sentences are true, and they are worth sitting with.

The first one is a correction to a mistake almost every ambitious person makes. We plan the optimal version before establishing the basic version. We research the perfect workout split before we go to the gym three times in a row. We design the ideal content strategy before we have published ten pieces of anything. We map out the perfect morning routine before we have proven to ourselves that we can get up on time for two weeks running.

Optimization should be a reward for consistency. You ought not do it before you’ve earned it.

The second sentence, about the front door, captures something every person who has ever tried to build a habit already knows intuitively but rarely articulates clearly. The barrier to showing up is almost never the work itself. It is the friction between where you are and where the work happens. It is the gap between the couch and the gym bag. It’s the chasm between the bed and the desk. It’s the intimidating distance that exists between the comfortable and the required.

Clear’s whole system is built around reducing that friction. Make the good behavior easier. Make the bad behavior harder. Stack habits onto existing ones. Start so small that failure becomes almost impossible. It is excellent advice, and it has helped millions of people.

But there is something it does not fully prepare you for. And it is the thing that actually kills most habits.

Nobody Plans for Week Three

The first week of a new habit is almost always fine. You have novelty on your side. The decision is fresh. The motivation is high. You tell people about it, which creates a little social accountability. You feel good about yourself for starting. Week one tends to take care of itself.

Week two is where the first cracks appear. The novelty is wearing off. The motivation has dropped from a ten to maybe a six. You have your first bad day or missed session, and you have to decide whether it is a blip or a trend. Most people who make it this far make it through week two.

Week three is where habits go to die.

By week three, life has reasserted itself. The calendar has filled back up. The kids are sick, or you are sick, or work explodes, or you travel, or you have a brutal week that leaves you with nothing in reserve. And the habit that felt so solid two weeks ago is suddenly just one more thing on a list of things you do not have the energy for.

Here is what almost nobody tells you: this is not a sign that you have failed. It is a sign that you have arrived at the actual test. The early weeks are the entrance exam. Week three is the midterm.

The problem is that most people treat week three as an anomaly. We act like the disruption is the exception and the perfect week is the rule. But life is not made up of perfect weeks. Perfect weeks are the exception. They almost never happen. Disruption, difficulty, and competing demands are the rule. If your habit can only survive ideal conditions, it is not a habit. It is a hobby you do when things are going well.

The Podcast Graveyard

I want to give you a data point that I find both sobering and clarifying.

Approximately 90 percent of podcasts never make it past episode three. Almost half of all shows ever created have been abandoned after just a handful of episodes. Of the podcasts that do make it past the first three episodes, 90 percent of those do not reach episode twenty. Which means that publishing episode twenty-one puts you in the top one percent of all podcasters in the world. One percent. From a bar of twenty-one episodes.

I have published over 400 podcast episodes over almost 6 years.

If you’re reasonable, your response to that shouldn’t be applause or to feel impressed. It should be a prayer that nobody has actually listened to that much of my ramblings. The good news is that most people haven’t. Shout out to the 17 of you who have.

Anyway, I'm not saying that to brag. I say it because those four hundred episodes happened across one of the most turbulent stretches of my life. I recorded episodes while going through a new job. Multiple moves. An engagement. A wedding. The birth of my first child and then my second. The loss of my oldest sister. Seasons of exhaustion where recording felt like the last thing I had the capacity for.

I also recorded episodes that were not very good. Episodes where the audio quality was rough, the content was thin, and the energy was low. I published them anyway. Because I had learned something early on that took me a while to fully internalize: done is better than perfect, and showing up imperfectly is infinitely better than not showing up at all.

The perfect is not just the enemy of the good. It is the most common excuse well-meaning people use to justify quitting.

Playing Hurt vs. Playing Injured

There is a difference between playing hurt and playing injured.

Playing hurt means showing up when conditions are suboptimal. You are tired. You are stressed. Life is not cooperating. The last thing you feel like doing is the thing your habit requires. But you are functional. You are capable. You are choosing comfort over commitment when you stay home, and you know it.

Playing injured means showing up when doing so would actually make things worse. You have the flu, and you are considering going to the gym because you do not want to break your streak. You are running on two hours of sleep and wondering whether skipping your morning routine counts as a failure. These are not the same situations.

When I had the flu recently and my whole family was sick at the same time, I did not go to the gym. That was not weakness. That was wisdom. Your body is not going to benefit from a workout when it is fighting a virus. Your immune system needs the resources you would spend on the barbell. Resting when you are genuinely ill is not an excuse. It is the prudent choice.

But here is the other side of that coin: choosing to stay out late on a Tuesday night and then using exhaustion as a reason to skip your Wednesday morning workout is not the same thing. You made a choice. That choice had a cost. Pretending the cost does not exist is not self-love. It is self-deception.

One of the most clarifying questions I have learned to ask myself in these moments is: Am I actually unable to do this, or am I just unwilling? Those are completely different situations, and they require completely different responses. Inability deserves grace, but unwillingness deserves honesty and accountability.

The goal is not to white-knuckle through every hard moment regardless of your actual condition. The goal is to develop the self-awareness to distinguish between the two. And to stop letting the legitimate excuses cover for the illegitimate ones.

The Habit That Exposes Me Most

I want to get personal for a moment about the habit that exposes the gap between my intentions and my execution more than any other.

My prayer life falls apart when I travel.

At home, I have a rhythm. I know when I pray, where I pray, and roughly what that time looks like. The habit is anchored to a place and a routine that holds it in place. But when I travel, all of those anchors disappear. Travel brings a ton of chaotic unknowns: different time zones, different schedules, dinners that run late, and early-morning flights. Hotel rooms never quite feel like places where prayer happens naturally.

This is not a new problem. In the Army, deployed to Afghanistan, I went weeks between opportunities to attend Mass. In Ranger School, I had Mass once over the course of thirteen weeks. The external structures that support your routines are not always available. Life is hard, and this shouldn’t be news.

And yet, I have not fully solved this. I will be honest about that. But I have gotten better at it. What helps me most is accepting in advance that travel is a disruption and building a minimal version of my prayer habit that is specifically designed for disrupted conditions. It is not the ideal version, but rather the survival version. The version that keeps the thread from breaking entirely, even when the conditions are not perfect.

A decade ago, I would have told you that a five-minute rosary in a hotel room was a failure compared to my normal hour of prayer. Now I understand it as a victory. It is the thing that keeps the habit alive when the habit wants to die. And a habit that is alive, even barely, is much easier to maintain. A dead habit has to be rebuilt from scratch.

The System That Has Kept Me Honest

The single practice that has done more to keep my habits alive than anything else is not a productivity hack or a motivational framework. It is something far simpler and far less glamorous.

I review my goals every day, every week, and every month.

Daily, I look at what I said I was going to do and check it against what I actually did.

Weekly, I do a broader review of the week: where I showed up, where I fell short, and what I am going to do differently.

Monthly, I look at the bigger picture, at whether I am making progress on the things that matter most, and at the gap between where I am and where I said I wanted to be.

This practice is uncomfortable and often exposing. And that's the whole point.

When I skip workouts, the daily review makes me look at the skipped workouts. When my prayer life has fallen off, the weekly review makes me sit with that fact rather than let it quietly become the new normal. When I am drifting from the person I said I wanted to be, the monthly review shows me the drift before it becomes a chasm.

Most people avoid this kind of honest accountability because it requires them to confront failure. But failure that is confronted is failure that can be corrected. Failure that is avoided just compounds quietly in the background until the gap between who you are and who you intended to be is so large it feels insurmountable.

I have failed at a lot of goals over the years. My weight, as I said, has fluctuated in ways that frustrate me. There are habits I have built and lost more than once. There are commitments I have made to myself that I have not kept as fully as I intended. The review practice does not prevent those failures. What it does is force me to own them, learn from them, and get back on track faster than I would otherwise.

The goal is not a perfect record. It is an honest one. And an honest record is what allows you to make real improvements instead of just feeling vaguely bad about where you are.

What Actually Works: A Framework for Getting Past Week Three

First, design your habit around your worst week, not your best. Most people design habits around the version of their life where everything is going well. That version of your life is rare. Design for the version where you are tired, traveling, and overwhelmed, and ask what the minimum viable version of this habit looks like under those conditions. That minimum viable version is your survival protocol. Use it as a baseline.

Second, decide in advance what constitutes a legitimate excuse and what does not. Before you need to make the call under pressure, decide where your lines are. Genuine illness: legitimate. Genuine family emergency: legitimate. Tired because you stayed up too late: not legitimate. Busy because you did not manage your time well: not legitimate. When the moment comes, you will not have to decide. You already decided.

Third, never miss twice. This is the rule that has saved more of my habits than any other. One missed day is a blip. Two missed days are the beginning of a pattern. Three missed days and the habit is on life support. If you miss once, the only thing that matters is what you do next. Show up the following day, even if the session is shorter, messier, and less impressive than you wanted it to be. The streak you are protecting is not the unbroken one. It is the one you always come back to.

Fourth, review honestly and regularly. Daily, weekly, monthly. Make failure visible. Make progress visible. Keep the gap between your intentions and your actions somewhere you have to look at it. The discomfort of that visibility is the mechanism that drives correction.

Fifth, and perhaps most importantly, remember why you started. The habits worth building are not ends in themselves. They are the means by which you become the person you are trying to become. The workout is not the point. The father, the leader, the man of faith, the person of genuine excellence, who is formed by consistent physical discipline, that is the point. When week three is hard, come back to that. Not to motivation. Return to your purpose.

Getting Past the Front Door Is Only the Beginning

James Clear is right. The heaviest weight at the gym is the front door. Getting started is hard, and anything that helps you reduce the friction of beginning is genuinely useful.

But the front door is not the finish line. It is the starting line. And the race that begins on the other side of it is longer, harder, and more demanding than any motivational framework fully prepares you for.

Four hundred episodes in five and a half years. New jobs, new cities, new children, grief, exhaustion, and more imperfect weeks than I can count. The podcast did not survive because conditions were always favorable. It survived because I decided early on that conditions were not the variable. My response to conditions was the variable.

That decision, made once and then made again and again in every hard moment that followed, is the only thing that separates the person who publishes episode four hundred from the person who published episode three and stopped.

Establish the habit first. Survive week three. Play hurt when you have to. Rest when you are injured. Review honestly. Come back when you fall off. And keep coming back.

That is the whole thing. It is not complicated. It is just hard.

Do it anyway.

“You have the coolest job in the world.”

I know I do. And I’m very blessed to have it. Today, I want to share with you my journey of coming to Hallow, what the last five years have been like, what I love, what I don’t love, and where I hope it goes from here.

 

For those who don’t know, Hallow is the #1 prayer app in the world. With over 1.5 BILLION prayers prayed through the app, it has had an immense impact on the life of the Church and the world at large.

 

My Journey to Hallow

My journey to Hallow really began when I was 13 years old, which was 11 years before Hallow was founded. In 8th grade, I decided to join the Catholic Church, becoming the first Catholic in either of my families. I went from my Catholic grade school to my Catholic high school, where I met a boy who would become one of my best friends for life.

His name was Alessandro DiSanto, the Italian stallion of my high school friend group. Alessandro, or Sandro as we called him, was at the top of our class (#2 to be exact, a fact we don’t let him forget), played soccer, played music, and was a favorite of all of our teachers.

I, on the other hand, earned myself 21 detentions in the first two years of high school, along with an in-school suspension to top it off. This all paled in comparison to the legal trouble I risked getting myself in on a regular basis. From taking illegal drugs to school to joyriding without a license, I was living on the wild side while Alessandro studied hard and spent summers at programs for prospective students at Harvard.

And yet, in our free time, we spent a lot of time together. More and more every year, leading to a deep bond that continued through college and beyond.

 

We visited each other at our respective colleges and in our early careers in the heart of Manhattan and at Fort Benning, GA. I’ll let you guess who went where.

We served as groomsmen in each other’s weddings and are now honored to be godfathers to each other’s children. I think few people are blessed with the type of friendship that he and I have, and it is not one that I take for granted.

I know this isn’t a reflection on friendship, but I’m going somewhere with this.

 

I began my career in the Infantry. Alessandro attended my Ranger School graduation. Then I went on to serve in the historically awesome 82nd Airborne Division in Fort Bragg, North Carolina. I deployed to Afghanistan, and we stayed in touch. Upon returning from deployment, I remember Alessandro floating the idea of starting a prayer app with me during a casual phone call.

I thought it was awesome—something that could really impact a lot of people’s lives. After all, my journey from a habitual rule-breaking teenager to a faithful Catholic was made possible largely due to the gift of prayer. It absolutely changed my life. And I knew most people did not know how to do it, especially in any meaningful or transformative way.

He goes on to quit his job to go all in on this thing—an idea that we all thought was crazy at the time. I decided that year, in late 2018, to get out of the Army the following year. Hallow launched in December of 2018, and they were off to the races. At this point, I never thought working for Hallow would be in my future.

I took a job as a Parish Consultant at the Dynamic Catholic Institute. I absolutely loved it and thought I’d work there until my death. Funny enough, I never made it to my one-year anniversary. This was mostly because of two reasons:

1. The Dynamic Parish program was ending as we knew it. I was offered a job in Development or a severance package. I took the latter because

2. I met a very special lady who would become my wife. She lived in Atchison, KS (yikes), and I knew if I took the Development role there was a high likelihood that I’d rarely get to see her, let alone actually discern marriage.

This led to my greatest act of sacrificial love in my lifetime—moving to Kansas to date my future wife in person. I took a job at the incredible Benedictine College, which came with a generous 53% paycut. The downgrade from my beloved Cincinnati apartment to a rugged combination of freshman dorm rooms, wrongly referred to as an apartment in Newman Hall, was the greater sacrifice. But now I have kids, and we’re happily married, and yada yada yada, it worked out :)

But it most certainly was not my long-term career. I love Benedictine College, but that year was the worst year of my life since Ranger School. I missed the two weeks of training due to my start date, Covid rules had to be enforced, I missed homecoming for Alessandro’s wedding (worth it, did you see the photo?), and tore my achilles playing basketball with students in January.

After those wonderful six months, I was ready for my next move. I applied to the Augustine Institute and was offered a full scholarship and a job. Finally, it felt like my future Catholic career was back on track. I called Alessandro to give him an update on my life. He suggested a phone call with Alex Jones, CEO of Hallow, whom I had met several times by now.

Alex is incredibly to the point. After a few minutes, he hit me with, “Why don’t you just come work for us?”

I paused, utterly confused. “Uhh, and do what?” I said in reply. Mind you, at this point in my life, I’m an Infantry Officer with 18 months of experience in ministry. I have no idea how a start-up works, no knowledge of software development, and a voice not nearly as sexy as Francis’ (if you know you know). Therefore, I have no clue what I could possibly contribute.

“We’re starting a sales team”, he told me. And I immediately lit up. Now THAT I can do!! I was over the moon. Luckily for me, Hallow was still very uncertain and just crawling out of the “only our friends want to work here” stage. I don’t think I’d ever get hired here today, especially not just off the street like I was then.

So that’s how it began—I was the first Sales Lead (now Partnership Executive) at Hallow, starting in July of 2021. I was the 18th employee at the company and the third on the B2B Team (the other two pictured below). Alessandro became my boss. And our goal was to partner with schools and parishes to accelerate both Hallow's business growth and its mission.

 

My Career at Hallow

The last five years have been nothing if not insane. I had an unfathomable number of things to learn. What is ARR? How do you best structure a sales call? And what in the hell is an illo? Hallow seemed to have its own language—mirroring the Army's culture. But here, there was no ROTC or any real onboarding. I was immediately seen as a leader, especially after we started hiring more people in the coming months, who looked to me as a veteran on the team despite not being halfway to my one-year anniversary.

We had some solid growth in the first two quarters, then got absolutely annihilated for two quarters. I started updating my resumé and casually applying to places. I even had an interview. We were seriously wondering if this whole B2B sales thing would work at all.

The panic was followed by great success in the second half of 2022. Things were really picking up steam. We made some incredible hires in 2023. We started working more intentionally with parishes. Then, in 2024, my role really began to change.

I was promoted first to Senior Partnership Executive. That summer, I was made the Associate Sales Manager. I held that role for about 9 months before being promoted to Sales Manager and entering full-time leadership. About 9 months after that, I was promoted to my current role as Senior Sales Manager, where I now manage Regional Sales Leaders, who manage Partnership Executives and the overall sales of their region.

One of my greatest career desires has been to do something only a small percentage of people can do. Anyone can take orders at McDonald’s. Most people can do basic corporate jobs. Even after a few years as an Infantry Officer, I came to realize that our time of war was coming to an end and that the Army didn’t really need Nathan Crankfield.

In contrast, my current position fully checks that box. I’m certainly not the only person who could do it, but I think I’m one of only a few who could do it well. It requires a unique combination of leadership skills, passion for the Church and her mission, and a love for sales and business development.

That is not something I take for granted.

The B2B team of 3 has grown to 70, with much more expansion ahead of us.

 

The Good, The Bad, and The Ugly of Working Here

First, I’ll answer the general and most common question I receive, which is: What has been your experience working at Hallow?

Then I’ll hit you with some more rapid-fire FAQs.

I do not exaggerate when I say that Hallow is the greatest company in the world. While the two men pictured above (Alessandro and Alex) drive me absolutely nuts sometimes, they, along with the third cofounder, Erich Kerekes, have built an absolutely incredible company. Their leadership, vision, and example have created a culture that I believe to be second to none.

They seek to create a job that will be “the best job you’ve ever had and the hardest job you’ve ever had”. Alex has made it very clear to the team over the years that he did not seek to make the best Catholic app in the world, but rather one of the best apps in the world, period. We don’t want to just be the best Catholic company in the world, but the best company in the world.

Plenty of people will say we are not that, but it is the goal. And while I haven’t worked at every company in the world, I do believe Hallow is the best company for me and for people like me.

What I love

I chose to join the Army because I wanted to become an Infantryman. I chose to become an Infantryman because I wanted to go to Ranger School. And I wanted to go to Ranger School to see if I had what it takes to be elite.

Most veterans struggle in their post-military careers because they lose their sense of mission, purpose, and teamwork. And many of us miss working with a fully dedicated team that seeks to maintain really high standards. I am blessed to have found all of these things at Hallow.

Our mission is to help people pray. And we’ve been able to, by the grace of God, do that on a really large scale and in a really deep, sometimes life-saving way. We’ve received countless testimonies and hundreds of thousands of five-star reviews that recount how Hallow has helped save marriages, break addictions, and end suicidal thoughts.

We have kids who tell us they now believe God is real as a result of praying with Hallow in their classroom. We have parents who say they’ve never felt closer to God and to their children since learning how to pray with them through the app. One parish reported to us that 25% of their OCIA class this year said they were there because of Hallow.

Outside of the priesthood, I don’t know how I could have found more meaning and purpose in my work.

That being said, you can do great work for the Gospel and for people in many roles in the Church. What sets Hallow apart is our true commitment to excellence. Many ministries and parts of the Church operate more as a government bureaucracy than a fast-moving startup dedicated to success. It’s the difference between being in the Army Rangers and working for the IRS. Both are government jobs. One is ruthlessly committed to high standards and accomplishing the mission, while the other is a place where many people go to collect a paycheck.

Don’t get me wrong, there are many incredible people doing amazing things in the Church. But some of you who have worked for the Church or a nonprofit know exactly what I mean. Dynamic Catholic, in my opinion, is in a pretty high tier in this regard. It was hard work there, but it wasn’t this hard. And I really like hard work, which is part of why I really like Hallow.

Lastly, the culture that this creates is also really amazing. This is especially true on our sales team. We can earn a great income from our work while serving an incredibly important mission. Usually, people see those two as opposing each other and accept that they have to choose one or the other.

One bonus one: I can’t lie, I love the prestige of it all. Hallow is the New York Yankees, the Los Angeles Lakers, or the Dallas Cowboys of Catholic organizations. When I worked for Dynamic Catholic, most practicing Catholics knew of the organization or of Matthew Kelly, its founder. But roughly 13 non-Catholics are aware of the company.

Working for Hallow is in another statosphere. Whether it’s at the gym, on a flight, or at the barber shop, it seems like half the population perks up with recognition when I tell them where I work. It’s awesome.

What I don’t love

I have a love-hate relationship with working for a startup. If you’ve ever watched the dramatic television shows or movies about the early days at Spotify, Apple, or Uber, you get a sense of how hectic life at a startup can be.

Many jobs say they’re fast-paced, but few really mean it to this extent. Going from a 250-year-old organization like the Army, filled with rules, regulations, and set expectations, to something like this has been the ultimate whirlwind. I love it for all the reasons I listed above, but it’s not without its challenges.

Some people simply don’t like that we don’t have everything figured out. We change A LOT of things very frequently. These constant pivots can cause emotional and mental whiplash, which can be quite unpleasant. We constantly face new problems and communication breakdowns. We scale too fast and still have pretty crappy onboarding after all these years.

Hallow expects a lot out of you. This is not a place to come get a remote job and coast. We don’t track your hours or see if you’re constantly online from 9-5. It’s an organization for adults. We expect great work from you, which, especially on the B2B team, is pretty easy to measure by your results.

If you simply love Jesus and want to work somewhere that “aligns with your values”, this probably isn’t for you any more than Navy SEALs’ hell week is for people who love the beach.

 

Frequently Asked Questions

Do I have to be Catholic to work at Hallow?

No, you do not! We actually have a pretty diverse team when it comes to religion. Most are Christian, but there are certainly non-Catholics! Should you become Catholic? Yes, but that’s a topic for another time :)

How does Hallow’s mission show up in the day-to-day work culture, or does it just live in the marketing?

We pray together. We celebrate Mass together when we’re in person. We have daily rosaries together — all of which are optional. We also have an annual spiritual development stipend, which is extremely generous. We get free tickets to the bi-annual Summit. Hallow offers exceptional benefits, including baby bonuses, unlimited PTO, caretaker leave, bereavement leave, and more.

Is this a stable company or an early-stage startup where my job could disappear in six months?

Nobody has ever lost their job in six months except for serious underperformance. At a startup, the future is definitely unknown. But that’s true at any company or in any industry. I feel very comfortable in my job security and think most strong performers feel the same.

What does compensation look like compared to a non-mission-driven tech company? Am I taking a pay cut to work here?

I think it’s true that many people here could make more money elsewhere in the secular world and that very few, if any of us, would make more in the Catholic world. Software developers at X make more than ours, and probably work 3x as many hours. Most people working in parish life probably make less than our parish leads. So it’s somewhere in that range. Illinois law requires we post the pay scale of each role in the listing, so it’s never a secret!

Is this a remote, hybrid, or in-office environment, and where is the team actually based?

We have an office in Chicago, but nearly every role is offered remotely. The exceptions to this are most commonly on the international team, where you do need to live in the country you serve most of the time. Our B2B team is national, but we becoming more intentional at hiring people who live in the region where they will work.

What does growth and career development look like here? Is there a real path upward, or does the small team limit that?

It is my personal belief that we are just getting started. I think there is plenty of room for growth at Hallow, but that also looks different for every role. On B2B, we have a long way to go and many leadership opportunities. If anything, we’re trying to avoid promoting people far before they are ready for more responsibility. And we heavily prefer to promote from within.

What is the leadership team actually like to work for day to day? How accessible are the founders?

When I worked at Dynamic Catholic, I was legitimately never introduced to Matthew Kelly. At Hallow, every one of my employees has a monthly meeting with our CEO and our team of 15 to share their learnings and concerns, or ask questions. Our Head of Sales and CFO are also extremely accessible. Everyone is reachable via Slack if one prefers a private conversation.

How do you balance the commercial pressure of being a venture-backed startup with staying true to the mission?

This really isn’t as hard as some make it out to be. When we accomplish our mission of helping more people pray, we also grow as a business. I am personally a big proponent of morally strong Capitalism. I think that people with well-formed consciences can do great things for the world while becoming extremely profitable. The two don’t often contradict each other.

But they might sometimes. Hallow is most often criticized for trying new things—and we will never get it 100% right. You have many Monday morning quarterbacks who evaluate a decision long after it has been made and deem it unacceptable. Hallow tries new things to carry out the New Evangelization. Mistakes are inevitable, and we always strive to learn and improve from them.

Can you connect me with “x” person at the company?

Honestly, probably not. We receive a lot of applications. Like, an insane amount of applications. I recently went on our applicant management system and saw this:

 

48,000 applications all time. That works out to 6,400 per year — and they really didn’t hire anybody for the first 2.5 years, so it’s closer to 9,600 per year. That’s about 26 a day. It’s an amazing gift, but it makes hiring really hard. I appreciate your effort to reach out via LinkedIn, email, or text to those you know.

We really aren’t trying to be rude when we decline your request for a call or connection. One summer, we had 7,000 applicants. I legit could’ve made a full-time out of the requests I got for 30-minute phone calls to learn about my experience at Hallow. That’s why I spent 2-hours writing this article to help save the several hours a month I spend on those phone calls.

How do I make my application stand out?

If you majored in the Psychology of Sea Turtles and have worked at Starbucks the last few years since graduation, I really don’t know what to tell you.

If you have relevant experience and a real desire to work in the role you applied to, here is what I honestly think helps people stand out when I’m sorting through 500 applications:

There are two questions at the top of each application. The first is “Why do you want to work at Hallow?” The second is “Why are you a good fit for this role?”

This is my personal perspective, but I see the first question being about what draws you to Hallow’s mission, culture, and structure. If you just list things about you, then you’re kind of missing the boat. It’s a place, especially when applying to a sales role, to sell me on your love for Hallow. This will drive your success in sales, so it’s very important.

The second question (again, just my opinion) is where you begin to sell yourself. Why are you a good fit for this specific role? The question is not “why are you a good fit to work at a Catholic company?” Therefore, telling me about how important your faith is to you is insufficient. That’s a great thing to hear, but that doesn’t necessarily make you a strong fit for a sales role. I want to build an elite sales team. There are many faithful, wonderful Christians who are not a good fit for sales. Convince me that you are not one of them.

Conclusion

Working at Hallow is amazing. If you’re interested, apply. The best way to discern if something is for you is to take a shot at it. If you don’t apply, please don’t ask any employee to take the time to learn about the company. I know it sounds tough, but most of us really do work about 1.5 jobs at a time to keep this going with such a small team.

If you don’t want to take the time to fill out the application, we probably don’t want to take the time to talk you through all the things you already know about the company. I, however, am not the official spokesperson for all employees. And yet, I’ve never really found anyone who feels differently about this.

Apply! Give it a go. If you’re amazing, we’d love to have you. I hope this was helpful. If you have questions, leave them in the comments!

God bless you on your career journey. And please, pray for us!