Seeking Excellence
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Dare we Hope that Hell is Empty?
Pulling from the saints, the Catechism, and other sources to answer one of the most common questions of our time
January 20, 2024
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Isn’t it interesting that, time and time again, death comes as a surprise?

One could argue that it’s really the only guaranteed thing in life; the death rate for humans is 100%. We all know it’s coming, but we still manage to take most days for granted. Death is perhaps the most significant and vital transition we will ever make, and yet we don’t spend much time planning or preparing for it. Think of all the time we allot for planning and preparing to get out of the military, for moving into a new home, or for a wedding day. We are so intentional and deliberate when planning for these times of change in our lives – we know that the less prepared we are for any big transition, the more anxiety we have. I think the fear of death comes from a general misunderstanding of it and a huge lack of preparation. We often have our priorities mixed up, focusing solely on the here and now when the other side of eternity awaits in our not so distant future.

Preparing for marriage is actually a great example of how we let our priorities grow overly focused on the urgent, rather than the important. In order to get married in the Catholic Church, you have to go through marriage prep courses; however, most couples are far more invested in planning for the wedding day than they are about getting ready for every day that follows. Consider this – we put so much time and so many resources into a 5-hour event, and widely choose to neglect preparing for the time, most likely decades, that fills the space between the wedding day and death. That leads many people to having an awesome 5 hours of ceremony and celebration followed by a draining and unfulfilling marriage for the next 5, 10, or even 50 years.

So it is with how we spend our lives on earth solely focused on earthly things, neglecting eternity. This comparison of a wedding and marriage here on earth to the after-life may be relevant, but it won’t ever be sufficient.  A 5-hour to 50-year comparison is conceivable.  A 50 year to eternity comparison isn’t possible to wrap our minds around because eternity, in a certain sense, is still a mystery to the time-bound human mind.   We cannot fully conceptualize the difference between 50 years and eternity, because we cannot understand eternity.

The mystery of eternity partially explains our apathy toward preparing for it, but I think the cause is a deeper, more philosophical issue. I believe it has to do with our beliefs, or better yet, our assumptions about judgement, God, and the afterlife. Do most people go to heaven? That's a question that only makes sense to the believer.

Lacking intentionality in preparing to meet God face to face would be reasonable for the atheist. We know there is a growing trend toward atheism and away from religion in the West, but the truth is that majority of us do profess a belief in God, or at least in the afterlife.  An NBC News article cites a 2016 study that showed from the 1980’s to the 2010’s, there was a significant increase in the number of people who had serious doubts about the existence of God. There was a significant decrease in those who considered themselves to be very religious. However, the percentage of people who believe in some form of afterlife actually increased. Belief in God and the afterlife are what allow us to lead a meaningful life. In The Brothers Karamazov, Dostoevsky summarizes the effects of destroying the idea of everlasting life in society,

“If you were to destroy in mankind the belief in immortality, not only love but every living force maintaining the life of the world would at once be dried up. Moreover, nothing then would be immoral, everything would be permissible, even cannibalism.”

And while an increase in belief in the afterlife is undoubtedly a good thing, this belief separate from a belief in God that is grounded in the Truth and context of the Church signifies some dangerous (and heretical) thinking.

Do Most People Go to Heaven?

Similar to my incredulity toward people's surprised attitude toward death, I’ve always been amazed at the thing that typically follows, most commonly at funerals:  the assumption of salvation and heaven for the deceased. Almost every time you hear people, including many preachers, console a grieving family or friend, they assure them that the person who has passed is now "in a better place". I don’t mean to be a downer, but is it remotely possible that this is really true for every person? From a biblical perspective, it seems clear that not every person goes to Heaven. In Matthew 7:13, among other places, Jesus Himself confirms this, “for the gate is wide and the way is easy that leads to destruction, and those who enter by it are many. For the gate is narrow and the way is hard, that leads to life, and those who find it are few".

I think this is a very important, but often forgotten, truth: Heaven and Hell both exist and there are likely many, many people in both places. To me, this truth isn’t meant just to scare us into going to church on Sunday or to repent of our sins strictly out of fear, but to move us to be bolder and more courageous in sharing our faith with others and to live holier lives ourselves.

The problem with assuming that everyone we know gets into Heaven is that it generates lukewarmness of faith in our own lives. After all, we usually knew the people whose bodies lie in the caskets at funerals. We knew their strengths and their weaknesses. We are, by nature, judgmental creatures. These ideas combine to make us think that if a person, who in some instances we know was heavily disengaged from their faith life by all knowable standards is assumed to have made it into heaven, then we also can be saved by doing the bare minimum of subjectively "trying to be a good person".

Admittedly, we can’t know the inner workings of someone’s heart, and we are certainly not the ultimate judge of who is saved and who is not. Therefore, I’m not championing that we loudly proclaim at a funeral that the deceased won’t make the cut into heaven, the point is that we just don’t know. The uncertainty is tremendous. And it's okay to express hope rather than conviction when talking about the deceased's eternal destination.  

The Catholic response to this ambiguity is just another reason that I love being Catholic. In a video by Fr. Mike Schmitz on this topic, he states that we typically have three major reasons for wanting to attend a funeral:  to say a final goodbye, for closure and grieving, and to celebrate the life of the person. But these are each contrary to the main purpose of a Catholic funeral. The reason we gather is to offer the sacrifice on the mass on behalf of the person who has passed away. The main problem with assuming someone is in Heaven is that we fail to pray for their salvation and for their soul in purgatory. Hope moves us to action through prayer and sacrifice on their behalf while conviction leads us to wrongly assume that the work of salvation is complete. 

I’ve noticed this in my own life as well. Many times when someone dies, I’m asked to pray for the family. While the family is certainly in need of prayers and God’s love, our main focus should be praying for the soul of the individual who died, asking for their salvation, and offering sacrifices on their behalf.

The same is true when someone is in the process of dying. The focus of most "thoughts and prayers" are for the recovery of the sick and for peace in the hearts of grieving loved ones. Both of these things are good desires, but they are not the most pressing need. Praying for the continued conversion and work of salvation to be brought to its completion is by far the most important thing you can do in such a situation. 

Fr. Mike makes another interesting point. We are often told that we shouldn’t judge people while they’re on earth, but we are quick to judge them once they leave this world by declaring where they will spend eternity. Canonizing (i.e. making the person a 'saint' by declaring with certainty that they are in heaven) the person who died is not the role of family or friends, and certainly not the purpose of a funeral. This happy go lucky idea of not judging others unless it’s pleasant and convenient comes from a few flawed, yet mainstream, beliefs:

Belief #1: God doesn’t really send people to hell

One of the most deceiving and misleading teachings circling around in Christianity today is that hell and the devil do not exist. I do understand the difficulty of reconciling an all merciful and all loving God with this concept of hell, but I don’t understand how you can profess to believe the Holy Bible and the teachings of the Catholic Church yet say that hell doesn’t exist or that it exists but is empty.

Now, many of you may think that I’m exaggerating this problem. Not that many people actually doubt the existence of hell or believe that it is empty. You might be able to convince me that few people actually outright state that belief, but isn’t it obvious that we don’t believe in it based on the way we live? In our personal lives we often demonstrate this belief by having a passive or lazy approach to developing our relationship with God.

In our evangelization efforts, I think it’s even more common. Do you share the Gospel with people as if their eternity depended on it? Or do you tend to be more focused on preserving your relationship and your reputation by avoiding what could be a “touchy subject”?

Further, do most Christians go to Heaven? I guess it depends on the definition of “Christian.” We know the Catholic Church does not teach the popular evangelical maxim that you are “once saved, always saved.”  If to be Christian is to be a member of the Church, that is the Body of Christ, then presumably yes, all Christians would go to Heaven where they continue this incorporation as a member of the Body of Christ for all eternity. 

However, that is quite different than saying every person who claims to be a Christian is going to Heaven.  Contrary to popular belief, simply stating something does not automatically make it true. You can claim to be something you are not, but that doesn’t change reality. The Church believes that everybody who is in a state of grace and has not cut themselves off from God through mortal sin at the point of their death goes to Heaven. A plain reading of the New Testament confirms that many believers and baptized Christians will abandon the faith and thereby likely forfeit their own salvation through their beliefs, words, and actions.

Belief #2: Ignorance is a free pass

Another common objection to hell is the hypothetical (although probably common for most of Church history) situation of someone who never gets exposed to the faith and dies without ever getting baptized or professing belief in Christ. It’s a good question and an interesting one to discuss. But it’s utterly irrelevant to the vast majority of people alive today. Jesus said, “The harvest is plentiful, but the laborers are few. Pray then to the Lord of the harvest that he will send more laborers into the harvest” (Matthew 9:37). The harvest around us is certainly plentiful each and every day. We are not interacting with people who have no access to information about Jesus. In modern day America, essentially every person has access to free resources about anything and everything. I must drive past 12 churches on my ten minute commute to work. The people you know who are unbelievers or disengaged in their faith are not that way because they are deprived of the opportunity to learn the truth. This ignorance is most frequently a result of choice. And while we can’t save everyone, we do have an immense responsibility to lead people closer to God and his Church through our prayers, words, and actions.

The well-formed Catholic might ask how the idea of ignorance applies to Protestants, Mormans, Muslims, and people of other various religions. After all, you may recall the old Latin phrase, extra Ecclesiam nulla salus, i.e. "outside the Church there is no salvation." This is an infallible teaching of the Church, meaning Catholics must accept this as the truth. 

I’ve recently done a lot of thinking on the topic of non-Catholics being saved. I’m currently reading Will Many be Saved? By Ralph Martin, who is one of my favorite Catholic authors. He argues that Vatican II did in fact make some adjustments to the way the Church now views our “separated brethren” (referring to Protestants) and that those changes were needed based on new context after the passing of several centuries. After all, it is quite different to be raised Lutheran in Minnesota today than it would have been to choose to leave the Catholic Church follow a schismatic Martin Luther in the early 16th Century when the Protestant Reformation first began. 

The idea is that those who were raised believing forms of Christianity that lack the fullness of faith found only in Catholicism are not as culpable as those who initiated the breaking away from the Church in the first place. 

The problem we have today, as Ralph Martin repeatedly stresses, is that so many leaders in the Church promoted the idea that salvation for Protestants, as well as members of other non-Christian religions, was not only possible, but actually probable. 

This I believe is the root of the first issue I named - the assumption of salvation. This “salvation optimism” permeated the Church and has become extremely popular in so many Protestant denominations who teach a watered down Gospel and a nice, always tolerant caricature of Jesus. 

I believe there are two main attractions to this lie. The first is that it gives us false security that we can go to Heaven no matter what we believe and regardless of how we live.  Why strive for sainthood when mediocrity will take you to the same location for all eternity? It allows us to choose lukewarmness and apathy rather than self-denial, repentance, and dependence on God. 

The second attraction is that it presents a wholly acceptable option to neglect evangelization. There’s no need to have those tough conversations about getting married in the Church, living chastely, abortion, etc. if you believe your ideological opponent is guaranteed a spot in heaven regardless of what they believe and do. 

Ultimately, it gives us the excuse to ignore the command of Jesus Himself to make disciples of all nations, especially disciples who know and follow His commands. Rather, operating on these false beliefs, we can simply make disciples who are warm to the idea of Christianity and think highly of Jesus as a good teacher and positive influence.

Belief #3: Just be a good person

We have this vague belief floating around today that if you are just a ‘good person’ you will be good to go in the long run. That’s ridiculous. The idea of a “good person” has as many definitions as there are people who claim to be one. Almost everyone fancies themselves a good person, even some serial killers and dictators.

According to our faith, getting to Heaven requires more than avoiding being a horrific human being. It’s typically the holiest among us who identify themselves more as a sinner than a saint. Why is that? Because the closer you get to the light of Jesus, the darker you find yourself to be. When compared to true perfection, you find yourself to be small, wretched, and hopeless without His mercy and love. Conversely, when we are far from God, we tend to compare ourselves to the most evil among us, and we shine in this juxtaposition with Hitler and Stalin. People truly think that because they are not committing grotesque sins on a daily basis that they are deemed ‘good' in the eyes of God.

This conclusion doesn’t come from any sort of logic; it simply flows from laziness. People who don’t want to change or put effort into their spiritual health are quick to lower the standards that we are called to. You see this happen as many churches today drift further and further from the fullness of the faith that Jesus originally intended for us. People reject absolute truth or high standards because it challenges them to actually live their lives differently. And even those of us who are engaged members of the Church often fail to live our lives with enough conviction, joy, and zeal to actually make them give faith a chance. I think one of the main causes of this problem is that we fail to remember death.

Remember Death

Memento Mori is a Latin phrase that means “remember death.” As Fr Mike explains, the meaning is actually two-fold. It serves as a reminder of our impending death, but also serves to call to mind the fact that we have already died to sin through Baptism and are risen to a new life in Jesus Christ. The phrase used to be extremely common among Catholics. At times it was even used as a greeting. One of my best reminders of death comes when I’m on a plane that is about to land. I always think of just how little a mistake could cause us to crash. No, this thought doesn’t invoke fear and anxiety. Instead, it causes me to evaluate my life up to this point:

Am I happy with how I’ve lived? 

Am I happy with how people would remember me? 

What would my eulogy sound like? 

Who did I not reconcile with who could be left feeling empty and without closure? 

Do people know how I feel about them? 

Do they know how grateful I am for what they’ve done for me? 

Have I done my best to know Jesus and to make Him known?

I come off each flight motivated to live my life. For many, though, the thought of death doesn’t bring about inspiration to live life to the fullest. Instead, it draws, from within the deepest parts of their being, serious fear, worry, and anxiety. I know that in my own life few things give me more anxiety than procrastinating on something vitally important. I believe that a lot of anxiety and depression comes from not having a proper understanding of death along with a lack of preparedness for it. Think about how hard it would be to near the end of a life you know you are currently wasting.

Most of us fall somewhere in between one of two categories:

1) Knowing God exists and striving to live completely for Him

2) Knowing God exists and ignoring that fact, distancing ourselves more and more from Him with each passing day

Many people unknowingly move closer and closer to that second category. For almost a decade now, I have been intrigued by what I now know is many Catholics' misinterpretation of Church teaching in their neglect for evangelization stemming from their lack of concern about their own salvation or the salvation of others. 

Ralph Martin continues to address the Vatican II documents in a way especially interesting to me; one such point is the following: 

“All children of the Church should nevertheless remember that their exalted condition results, not from their own merits, but from the grace of Christ. If they fail to respond in thought, word and deed to that grace, not only shall they not be saved, but they shall be the more severely judged” 

And yet another quote reads: 

“Whosoever knowing that the Catholic Church was made necessary by God through Jesus Christ, would refuse to enter her or remain in her could not be saved” 

It seems like most holy men and women have believed that we really underestimate the culpability of those who willingly choose to be ignorant, as St. John Chrysostom points out: 

“One should not think that ignorance excuses the non-believer…When you are ignorant of what can easily be known, you have to suffer the penalty…When we do all that is in our power, in matters where we lack knowledge, God will give us his hand, but if we do not do what we can, we do not enjoy God’s help either…

 

So do not say: ‘How is it that God has neglected this sincere and honest pagan?’ You will find that he has not really been diligent in seeking the truth, since what concerns the truth is now clearer than the sun. How shall they obtain pardon who, when they see the doctrine of truth spread before them, make no effort to come to know it?...

 

It is impossible that anyone who is vigilant in seeking the truth should be condemned by God… ‘but how is it,’ you ask, ‘that they have not believed?’  It is because they did not wish to. And yet Christ did his part on their behalf; his passion bears witness to that.”

 

The line that hit me especially hard, because of my constant struggle with this very question, was the following: 

“But how is it” you ask, “that they have not believed?” 

It is because they did not wish to. 

A great fictional depiction of this choice can be found in C.S. Lewis’ work The Great Divorce. 

He does an amazing job of showing that people really do choose hell for themselves rather than being arbitrarily sent there by God. Many people, despite access to so much information and ability to seek the truth, decide not to do so. 

Others know the truth and choose to reject it anyway. 

____________________________

 

How We View Death, and in turn, Heaven

Peace, hope, and joy are virtues that come through grace. When our life has no meaning or greater purpose, when we lack the love of God in our lives, what else is there but sadness?

Matt Walsh explains it well in his new book Church of Cowards,

“We are told that despair – or depression, as we call it today – is a mental illness. But how can we call someone ill for being in despair when he has so many good reasons for that despair. . .We do nothing for a despairing man by numbing his sadness while leaving him to his empty, miserable existence. . . Life moves always on to death. Every step we take is a step closer to it. If death is a plunge into nothingness, if it is the cessation of all being, then what is there but despair?”

We are called to draw people out of that despair. One of the necessary marks of a Christian is hope. This hope, when fully present, doesn’t allow for there to be fear of death. We have hope in God’s mercy and goodness, trusting that our wholehearted pursuit of God’s presence here on earth will be finally made fully possible in heaven. Contrast Matt’s description of the unbeliever’s despair, life and the view of death with C.S. Lewis’ view of the afterlife for a believer in Till We Have Faces,

“The sweetest thing in all my life has been the longing – to reach the Mountain, to find the place where all the beauty came from – my country, the place where I ought to have been born. Do you think it all meant nothing, all the longing? The longing for home? For indeed it now feels not like going, but like going back.”

 

Death is our journey home to worship God for all eternity.

A healthy view of death along with a serious intentionality around trying to be prepared for it allows you to be fully alive. The best athletes are those who play like it could be their last game ever. The best concerts are those where you see someone perform like it could be their last one. In a similar way, the best lives are those lived in a way that doesn’t take time here for granted. I want you to love your life and to live like it’s almost the end. This means spending time being truly present with people, forgiving people, loving others with all your heart, and being bold in your faith. It means tenaciously seeking out your purpose in life and then pursuing it with all your heart.

Knowing that there is an end allows us to understand the urgency of now. You may not understand why just yet, but God created you in this particular time in history, in this particular place, for a particular reason. Your life will go on forever, but your time here on earth is finite. The most important thing we can do in this finite time is know Jesus and make Him known.

Are you spending your limited time wisely and intentionally? I hope so, because your eternity and the eternity of many others will likely depend on it.

“Many great things depend, don’t you forget, on whether or not you and I live our lives as God wants.” –St. Josemaria Escriva

 

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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.

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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 :)

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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?”

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“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!

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Why I'm Giving Up People Pleasing For The Month of May (And Maybe You Should Too)

I'm giving up at the end of this month. I know it sounds dramatic, but I've reached a dramatic point in my life.

It's been a tough year so far. Work has been very demanding, my son has been battling whooping cough for some 75+ days now, we have a teething baby, and we're still struggling to build community in our new city.

 

I started the year off strong, filled with that optimism and energy that hits every January 1st. My plan was to rejoin the 5am club, go deeper in my prayer life, and finally lose the weight I gained some five years ago when I tore my left achilles.

It was a great plan that got almost immediately upended. I got promoted at work, and was promptly told I needed to hire 7 new people. This meant Q1 went from being status quo to total chaos by the end of the first Monday of the new year. On top of that, several work trips got added to my schedule.

Whooping cough, along with stomach bugs and maybe the flu(?), also absolutely destroyed my agenda. I got so exhausted at one point in March that I thought it was borderline imprudent/illegal for me to be driving.

Life is hard - but that's honestly not the core of the issue when it comes to my seriously increased stress levels and unhappiness.

 



The truth is that I've let the secondary things drain time away from the primary things. I've failed to keep the main things the main things.

I've never considered myself too much of a people pleaser. How could I be one, when I so frequently (and sometimes intentionally) piss people off? I’m intentionally not nice. I aim to be kind, but I am not someone who walks around afraid to offend people. I still have that combination of East Coast ruggedness topped off with the US Army Infantry’s approach to dealing with people.

When the topic of people pleasing has come up in the past, I usually tune out. I don’t really care about being liked, or so I thought. After all, I am the man who does and says the hard things. And I am genuinely at peace knowing that there are people at the parish, at work, and online who dislike me for my allegiance to excellence and the truth.

But trying to be liked isn't the only form of people pleasing. I've learned that I am very defensive around my reputation in some ways. I've become a yes man and I hadn't even noticed in until now. I may think that I don’t care if people don’t like me, but that’s only true in certain circumstances. Let me explain.

Every year I set out a goal to say "no" more often. I simply get asked to do way too many things. This happens all the time in life, and especially within the Church. The same volunteers run every event. You help out at youth group, then you’re asked to coach basketball, then help with OCIA, then speak at the school and the parish, then run a men’s group — that’s the real story of my experience at our last parish.

The worst part is that every year I get better at saying no, but the demand increases as well. So while I'm accumulating reps of "no" at exponential rates, the requests are also growing at a number that outpaces my skill in rejection. And therefore, my busyness increases rather than decreases.

And nothing stresses me out more than spending time doing things that aren’t the primary things I know I am supposed to be doing. But apparently, I’m willing to misalign my priorities for the sake of pleasing others, even strangers.

 

I seem to really be bothered by the idea of people thinking any of the following:

-I am unwilling to make time for them

-I am incapable of doing more than I currently do

-I am unwilling to help them (or think I’m too good/important to help them)

But the reality is that, while the internet can do many great things, it also makes us way over connected and exposed. Speakers in the past never had 20 follow up DMs from people wanting more of their time. Back in the day, when people applied at a company in high demand, they just had to submit an application and try networking at events or through relationships. There was no LinkedIn and requests for 30 minute/phone zoom calls to “learn how to stand out”.

With all of these things, I am simply overwhelmed. Maybe it is that I have a lower capacity than I’d like to imagine. Perhaps I am selfish. Or maybe I’m just not managing my time well. I’m honestly not sure. I just know I’m stressed out, under-prayed, and overweight. And I’m tired of all of that.

So I'm taking a sabbatical this month. I'm going to focus on three main things outside of work:
1) my faith
2) my family
3) my fitness and my health

Every yes I give to a request for 30 minutes of my time to a stranger takes away 30 minutes of time I could spend in prayer, at the gym, or playing with my kids.

And frankly, I'm tired of watching my goals, purpose, and my happiness fade away to please people I've never met, will never meet, and oftentimes, can't really even help.

It feels selfish to say these things. It feels even more selfish to post it on the internet. But I want to encourage others out there fighting this same fight, because I know I'm not alone. I have friends, coworkers, and internet peers who I know are doing the same things. The burnout is real, even though we try so very hard to ignore it.

The Negativity Fast: Proven Techniques to Increase Positivity, Reduce Fear,and Boost Success: Iannarino, Anthony: 9781119985884: Amazon.com: Books
 

Here’s the full detail of my plan to reset my life in the month of May. I am primarily fasting from three things:

  1. Negativity - I recently read the book The Negativity Fast by Anthony Iannarino. It’s a secular book that is filled with many profoundly basic insights to create a more positive life. One of the key ingredients of that is what leads to number 2.

  2. Social media - specifically Instagram and X. This is pretty self-explanatory, but these apps generally suck and make my life worse.

  3. Extra-curricular activities - this is anything outside my primary grades, aka the six pillars of excellence. That means anything that doesn’t contribute to the growth of my mind, body, soul, career, money, or key relationships is a no go if I do not sincerely want to do it. That last part is the important one. I can still have fun. I am just releasing the false sense of obligation to do things I don’t want to do in place of things I ought to do.

So to my beloved internet peeps - no, I do not have time in May to chat. I don't have time to connect. I don't have time to review things you'd like me to review. I'll (probably) be back in June - and I will still be posting here on Substack and on LinkedIn. I’ll still have podcasts dropping here and there. But no random phone calls or zoom chats.

I need to talk with God. I need to call my grandparents. And I need to make it to the gym and home in time for dinner with my wife and kids. I hope you’ll understand, but it’s okay if you don’t.

For these 31 days, I'm going to reorder my life and put first things first. I'm sorry that you're second, but I need Jesus, good health, and my family more than I want to make you happy. And it's time my calendar reflected that reality.

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The Call of Duty Delusion: Why Responsibility Is What Makes You Fully Alive

There is a lie spreading through our culture that sounds reasonable enough on the surface. It goes something like this: less sacrifice and less suffering = more happiness. 

I got a message recently from a man in his early thirties. He told me he did not have kids yet, but he was an uncle. He repeated the belief I’ve heard many times – being an aunt or uncle is actually superior. Have a good time with the nieces and nephews then send them back to their parents for the hard stuff, like discipline, baths, and bedtime routines. You get the fun without the responsibility. He seemed genuinely pleased with himself for having figured this out.

I did not respond with anger. I responded with something closer to sadness. Because I recognized in his message something I have seen in dozens of conversations with men over the years: a man who has convinced himself that the absence of burden is the presence of fulfillment. That opting out of hard things is the same as winning. That fun and ease are superior to purpose.

They are not. And deep down, I think he already knows that.

The Call of Duty Problem

When I was an infantry officer in the United States Army, I had a nephew who was obsessed with Call of Duty. He had logged hundreds of hours in virtual combat. He knew the maps, the weapons, the tactics. He could play for hours on end and hoped to become a pro one day.

He genuinely seemed to believe that his virtual experience bore some meaningful resemblance to my real-life military training.

It did not. And I do not say that to be cruel. I say it because the gap between simulation and reality is precisely the gap between the man who carries responsibility and the man who watches from a comfortable distance. One of them is being formed by the experience. The other is being entertained by it.

This is the Call of Duty problem. We have built an entire culture that applauds taking the easy route, and even goes so far as to claim it is equal or superior to the road less traveled. We want the experience of things without the consequences, such is the case with rampant fornication and abortion. We want things to be given to us for free and for our debts to be paid by others. We want to normalize co-parenting – another word for part-time parenting that still allows for plenty of “me time”. We want marriage but with the opportunity for divorce without cause if we feel it doesn’t benefit us any longer. 

Being a great uncle is a wonderful thing. I mean that genuinely. Uncles matter. They have a unique role in a child's life, and they can do genuine good. But it is not fatherhood. Just as playing Call of Duty is not war. And living together before marriage is not the covenant of matrimony. These are not equivalent experiences with the same transformative power. They are simulations. And simulations, by definition, cannot do what the real thing does to you.

The Data on a Generation Opting Out

This is not just anecdotal. The data on young men in America right now is sobering.

As of August 2024, labor force participation among men aged 25 to 34 had fallen to 89 percent, representing over 700,000 fewer young men working compared to 2004 levels. One in three adults between the ages of 18 and 34 now lives with at least one parent, the highest rate in over a century. Twenty percent of men in the 25 to 34 age range were still living at home in 2023, compared to only 12 percent of women. The median age at first marriage for men has climbed to 29, the highest in recorded history.

Richard Reeves, whose book Of Boys and Men documents this crisis in exhaustive detail, put it plainly when he said that many young men today feel "not sure that they are needed or that they are going to be needed by their families, by their communities, by society." Leonard Sax's Boys Adrift makes a similar case, documenting the specific ways our culture has systematically removed the incentives and rites of passage that historically pulled boys toward manhood.

Jordan Peterson's extraordinary reach, with millions of young men consuming his lectures and interviews, tells you something important. It tells you that young men are starving for someone to look them in the eye and say: Your life can mean something. You are capable of more than this. Pick up your cross and carry it.

They respond to that message not because it is new, but because it is true. And because almost nobody else is saying it to them anymore.

What Responsibility Actually Does to You

I want to be specific about something, because I think it gets lost in these conversations. The argument for responsibility is not that suffering is good in itself. It is not that difficulty is something to be pursued for its own sake. The argument is simpler and more powerful than that.

Responsibility forms you in ways that nothing else can.

I am proud of a lot of things in my life. But when I think about what has actually shaped my character, strengthened my identity, and produced in me something I genuinely respect, the list is not made up of fun experiences. It is made up of hard ones.

Earning my Ranger Tab was not transformative because Ranger School was enjoyable. It was a life-changing experience because it nearly broke me, and I kept going anyway. Ranger School stripped everything comfortable away: food, sleep, warmth, and any illusion I had about who I was when shit hit the fan. What was left when they were done was something more real than what went in. It was both humbling and empowering. It exposed both serious cracks in the armor of my mind and an inner depth I didn’t know was there. 

Fatherhood is doing the same thing to me right now, just more slowly and with more temper tantrums. Every time I come home exhausted and choose to engage instead of check out, something is being built in me. Every time I hold the line with my son, when letting it go would be easier, I am becoming more of the man I want him to grow up to be. Every hard conversation with my wife, every budget review, every early morning, every moment of choosing my family over my comfort, these things are forming me.

You cannot get that from being an uncle. You cannot get it from a video game. You cannot get it from a relationship that costs you nothing because you have structured it that way. 

The growth cannot be separated from the sacrifice. 

The Cohabitation Trap and the Broader Pattern

The uncle mentality shows up in more places than just fatherhood. It is the same logic that drives the cohabitation epidemic.

Living together before marriage is sold as a trial run. A way to get the experience without the commitment. A sensible, modern approach to something that used to require you to actually decide. But decades of research tell a different story. Couples who cohabitate before marriage have consistently higher rates of divorce than those who do not. The relationship that costs you nothing to leave is the relationship you treat like it costs nothing to lose.

This is not an accident. It is a feature of how human beings actually work. We rise to the level of our commitments. When the commitment is absolute, something in us becomes capable of meeting it. When the exit door is always propped open, some part of us never fully walks through the entrance.

The same pattern plays out in careers, in communities, in churches. The person who volunteers for the hard assignment grows. The person who always finds a reason to stay on the sidelines stays exactly where they are. The parishioner who commits to a parish, who sees its problems as their problems, who gives their time and money and energy to something larger than themselves, that person is being shaped. The one who church-hops to avoid obligation remains a spiritual tourist and misses the opportunity to experience true belonging and community.

Responsibility and commitment are the foundations. Sacrifice is the natural fruit of those two things. And fulfillment is the ultimate end that can’t be found without a powerful combination of those three. 

The Leadership Call That Most People Ignore

I want to broaden this beyond masculinity for a moment, because I think the principle applies to every person reading this.

Every one of us is called to lead somewhere. In your home. In your workplace. In your parish or community. Leadership is not a title. It is a decision to take responsibility for something beyond yourself and to accept the weight that comes with it.

Most people never fully answer that call. Not because they lack the capacity, but because answering it is uncomfortable. It requires you to care about outcomes you do not fully control. To have hard conversations you would rather avoid. To be present when absence would be easier. To hold a standard when lowering it would buy you peace.

The person who answers the call anyway, who steps into the difficulty rather than engineering their life around avoiding it, that person becomes someone. They develop the kind of character that can only be forged under load. And they discover something that the person on the sidelines never will: that the weight they were afraid of is actually what they were made for.

This is not a modern insight. It is ancient. The greatest spiritual traditions in human history have understood that suffering embraced for a worthy purpose is not merely tolerable. It is sanctifying. It makes you more fully human. It strips away the parts of you that are soft in the wrong ways and builds something harder and truer in their place.

Jesus did not model a life of comfort and self-protection. He modeled a life of radical responsibility for others, freely taken on at enormous personal cost and fueled entirely by love. Whatever your faith tradition, the pattern is clear. The people who have lived most fully have almost universally been those who gave themselves most fully.

Grow Where You Are Planted

I want to close with something important, because I do not want this to land as a condemnation of anyone who is not yet a parent, or who is unmarried, or who is in a season of life that looks different from mine. There are aunts and uncles out there who make great sacrifices for their families. There are boyfriends and girlfriends who really dedicate themselves to working hard to serve their significant other, as Emily did for me when I tore my achilles while we were dating. 

The call to responsibility is not a call to a specific life arrangement. It is a call to a posture. To show up fully wherever you are. To stop treating the absence of obligation as the presence of freedom. To find the thing in your current life that is asking something of you and to give it everything you have.

If you are an uncle, be the best uncle those kids have ever seen. Sacrifice for them. Show up consistently. Be the man in their life who demonstrates what it looks like to be someone of character. That is a real calling, and it is worth everything you bring to it.

If you are single, stop treating that season as a waiting room. Your life is happening right now. Your church needs you. Your community needs you. The people around you need a leader who is present, invested, and willing to carry something for them. Be that person.

If you are in a marriage that is hard, do not engineer your way out of the difficulty. Grow into it. The hardest seasons of marriage are often the ones that produce the deepest intimacy, if you refuse to quit.

The point is not that any one path is the only path. The point is that wherever you are, there is a version of your life that requires more of you than you are currently giving. And the gap between what you are giving and what you are capable of is exactly the space where the best version of you is waiting to be forged.

You Were Not Made for the Sidelines

The man who messaged me about being an uncle is not a bad person. He is a person who has been told, by a culture that is deeply confused about what constitutes a good life, that minimizing his exposure to difficulty is a form of wisdom. That fun without responsibility is the better way.

It is not. It is the lesser thing dressed up in the language of freedom.

Real freedom is not the absence of obligation. It is the capacity to choose something worthy and give yourself to it completely. That kind of freedom is only available to people who are willing to carry something heavy. And the people who carry it, who do not set it down when it gets hard, who keep showing up for the people and the purposes that depend on them, those are the people who, at the end of their lives, will look back and recognize that they were fully alive.

The ranger tab is not the point. Fatherhood is not the point. The marriage is not the point.

The point is the person you become when you refuse to take the easy way out. 

That person is worth becoming. And you already have everything you need to start.

Where in your life are you currently choosing the simulation over the real thing? Drop your thoughts in the comments.

 

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