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!

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.

 

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.