The Upside of the Midlife Crisis

“Seriously, Peter, I will take a massive paycut right now for the opportunity to get to do work that is meaningful”

“I’ve been dragging myself to work for years. I feel hopeless and trapped”

The other week I was having lunch with yet another person sharing with me his dissatisfaction with work. And it’s not just your typical had-a-bad-day-at-work chat. This was deeper. Teary-eyed-grown-men deep.

The funny thing is, ever since the start of this year, I’ve easily had more than 25 chats with people experiencing some deep existential angst.

There are clear common threads:

  • Almost everyone is at 40 or near 40
  • There is a clear dissatisfaction (and being stuck) not only with work, but with their careers
  • Everyone mentions the longing to do something meaningful
  • A lot of people mention the willingness to sacrifice: getting “massive” paycuts
  • A good number of them are externally successful in what they do: a couple are CEO’s and a lot of high level executives, a couple are successful entrepreneurs

Mind you, this isn’t a norm for me. I don’t go around looking to talk to mid-lifers. It usually just starts with a catch-up over coffee, and then it goes deeper, and deeper.

I told my wife Pauline I think God is telling me something. I also figured, perhaps my friends and natural network know me as the guy who quit corporate work to on a startup very early on (mid 2000’s), and perhaps they want to explore what that’s like.

For whatever reason, logical or otherwise, I’ve had the privilege and honor of hearing the stories of a lot of people undergoing midlife crises. I find myself arriving at one conclusion:

All midlife crises are spiritual.

Hear me out.

In all my chats, I’ve asked the person to “go back” and recall their entire careers with me, asking them to look for clues with me as to where this dissatisfaction could’ve come from.

In ALL cases, there are compromises involved:

  • A practical decision to stay in a situation they knew sucked their souls.
  • Conforming to the expectations of someone who influences them greatly. Very typically parents.
  • The feeling of giving up trying to change a situation because they feel it’s too late now, they’ve invested so much in one path.

My own spiritual-influenced definition of the midlife crisis is this:

It’s when there’s a growing gap between who we are and who God wants us to be, and our souls are crying out that we need to do something about it.

I guess this also applies to the quarter-life variety, the midlife version just cuts deeper – because the dissatisfaction has been there longer, and because we already can feel a bit of our mortality.

The type of job does not matter.

I tell the people I talk to that as an entrepreneur who’s basically designed his job, I’ve felt this dissatisfaction too. And it’s because I’ve also made haphazard choices without the benefit of deeper discernment.

It’s very obvious the money doesn’t matter as well. I’ve heard enough “I’ll take a paycut to do something meaningful.” to reach this conclusion.

What matters then?

That term: meaning, is an often-used term in my conversations. The problem starts methinks when this is ignored.

There was one person I talked to who was shocked by the question, “what activity or work gives you meaning?”

He muttered the question several times, and couldn’t give a ready answer. It appeared to me that he had a hard time even processing the question, because all his life, work has been “just work.”

But work is never just work. For a lot of us it occupies most of our waking hours. We typically define ourselves first by our jobs. I’m a doctor. A lawyer. A brand manager. An entrepreneur.

Okay, so what’s the upside?

I always tell the person I’m talking to: you know, it feels sucky, but this is actually a very Blessed time.

That gnawing feeling? That restlessness of the soul? You know what that is?

God is calling you to act, He is trying to lead and nudge you into what can truly make you joyful.

Don’t waste it. Listen to it. Use it.

What to do?

Do not ignore it. The very LAST thing you should do it to ignore the crisis you’re feeling. Believe me, it’s a GOOD thing. Face and process it.

I remember talking to someone a couple of years ago. She wanted to leave her longtime career in HR to pursue something that would tap into her creative side. At one point, she said, “I think I’m good. Let me stay where I am for another year or two and see if this feeling is still there.”

Recently we met and yes, it’s the same old feelings back. With a vengeance.

Again, I think it’s an opportunity. Don’t spend the rest of your life ignoring it. It is disturbing to think of how many people are in their graves now who spent their entire lives not fulfilling the promise of who they were meant to be.

Talk to someone about it. I think


Stop compromising.

The Compass, The Anchor, and The Propeller


When we moved into our new office, we were in a momentary quandary about what to do with a good-sized room that was right smack in the middle of the layout.

We could turn it into another meeting room – you could never have enough of those.

Or perhaps a designated interview room?

Incubate a startup idea (or two)? (such a temptation!)

Then, it hit Pao and I at the same time – we just HAVE to turn it into a prayer room.

It’s obviously not the bottom line-friendly alternative, but knowing our history, it just made too much sense to put a prayer room in the middle of the office. This was our little way of honoring the God who has been so faithful to us and our journey.

Prayer has been absolutely essential in my life as an entrepreneur.

I know “prayer” and “entrepreneurship” don’t really mix that well in the eyes of some people, but for me the opposite is quite true – I think prayer is absolutely critical in the life of the (believing) entrepreneur.



“I want to be the CAPTAIN of my own ship!”

This was my battle cry all those years in corporate. Then, one day, I made it happen  –  the big leap.

Then I felt it.

It was very clear to me from day 1 as a “captain.”

…I felt that I had NO CLUE whatsoever on how and where to steer the ship.

That was a HUGE adjustment I had to make. In corporate, everything was (mostly) laid out for me. I had a boss. He had goals and objectives for me. The company had overall goals I had to align myself with. There was an accepted method of doing things.

As an entrepreneur though, everything was MY CALL.

This amount of freedom – without any accountability – is very dangerous.

Sure, you can lead your firm to quick profitability and success, but if you don’t watch it, the subtle costs can lead you to be someone you don’t want to be.

I remember years ago, at a time when we were just starting to turn it around as a startup, we got an opportunity to service a motel chain.

We certainly needed the cash, but after going back and forth on the matter, we declined.

I would probably get a lot of flak from that decision from most entrepreneurial experts (an employee actually questioned me about this), but ultimately, my prayer led me to the conclusion that it wasn’t a project aligned to what I wanted the company to stand for, and ultimately, to what I wanted to stand for.

There are many, many, many other morally ambiguous items which you would have to decide on when you run a firm. These ultimately will have an impact on the company culture you create, and perhaps, more importantly, to who you become. (our decisions make us, after all)

Tread carefully.

This is where prayer has really come in handy for me as a discernment medium. As a much-needed COMPASS, prayer helps me navigate the sea of infinite choices and options I find myself in.



I’m not so sure if I blogged about this before, but I remember many many years ago when I happened to find myself doing some work for one of the richest men in the country.

As I would come to know after a few months working with him, he was – bar none – the most power/money hungry person I’ve ever met.

What I remember mostly were his eyes. There was something about them. Even before I knew about how he was, I remember looking at his blank eyes and finding something off.

They were soulless.

I remember vowing to myself NEVER to walk that path, never to love money that much.

This isn’t easy. It’s an incredibly slippery slope.

When most of an entrepreneur’s time is spent safeguarding and ensuring “bottom line”, it’s very, very difficult not to obsess over it and make it the ONLY target.

This is where prayer comes in as a much-needed anchor. Prayer has helped me, over and over and over, realize that my worth does not lie in money…nor in my startup, for that matter.

It lies with the fact that I am God’s child.

Prayer helps me put things into perspective.

But it does more than that.

I realize now that prayer has become my propeller.


Without prayer, I would still be in corporate. Without prayer, I wouldn’t have had the right amount of serenity to realize there was a call for me to give back and encourage other people to take their own leaps. Without prayer, there would be no blogging. No JGL.

Prayer is where I draw the necessary strength (the secret – it isn’t mine) to do big, hairy leaps.

The Grand Design

So, my friends and fellow entrepreneurs, never forget and take prayer for granted.


Fight for your prayer time. Don’t pray much? Start. Don’t pray much in conjunction to your work as an entrepreneur? Start the integration.

Do you believe we all have a specific purpose here in earth? I do. I believe in a Grand Design. This is why I am so excited about today’s entrepreneur-friendly world. I think we can pursue our truest passions (inextricably linked to our purpose) in a much easier way than it ever was. I think it is much easier now to stop compromising and live up to what OUR grand design is.

The MOST efficient and effective way to figure this out?

Talking often with the Grand Designer.


Forget Your Career And Pursue Your Vocation


My So-called Career Development

For the most part of my adult life, I thought I knew what I had wanted to do.

I wanted to pursue a career in HR. I wanted to make money. I wanted to make my resume as impressive as I could possible make it.

And so I tried my very best to achieve these. I knew they would make me happy.

At particular points, I would find myself dissatisfied with certain facets. So, I just decided on changing some things along the way.

Not enough money? Join a better-paying firm.

Resume not impressive enough? Get an advanced degree.

Still not happy? Party and go out with friends.

In my fourth company, Chikka, I became extremely confused.

I was doing well.

It was a dynamic firm. I had a great boss. I made key decisions in my function. I was paid well. It was fun.

I SHOULD be happy, I thought. So I pretended a bit, trying to ignore my restlessness.

But I just wasn’t happy.

Almost instinctively, I thought of leaving for another firm. But I knew one thing which bothered me to the core: after 3-4 months, the novelty would fade away in my theoretical new firm, and I would be left with the same dissatisfaction I had wanted to escape from.

Was this how life is? Just trudging from one place to another like a plodding headless chicken? 

Could I start anew in another field?! No! How can I just waste a decade of my life and start from scratch?

This was how effective my “career management” endeavors ended up being. My own decisions brought me to the brink of desperation.


Finding My Vocation

In How God Founded Our Startup, I talk about how God intervened at this particular point in my life.

It wasn’t an instant thing.

I think I really only found Him around two years before that fateful leap.

Prior to that, I had no prayer life whatsoever (except maybe when I needed something, then I’d say a short prayer), I did what I wanted when I wanted. I would usually skip Mass. In retrospect, I never let Him be a part of my life nor of my decisions.

When I decided to really follow and love God – and get to know Him and talk to Him more consistently in prayer, things slowly started to change. I learned I needed to let go of the wheel and surrender. Very tough for someone as independent as me.

Little did I know that 2 years after, God would ask of me all that I found important in the world – money, titles, security, clarity, control – in making my great leap.

I had never imagined in my wildest dreams that I would be an entrepreneur, much, much, less a helper of entrepreneurs. It was never, ever a career option.

Up until I wrote the first Juan Great Leap post, blogging was something very very foreign for me. I never in my wildest dreams thought: “I want to start an entrepreneurial blog and a build a community of entreps who help one another.”

Yet, this is precisely where God has led me.

Only He could have designed something that fits me perfectly in so many profound ways, I cannot even begin to describe. I have found my vocation, and my soul cannot stop celebrating.

Career versus Vocation

When we speak of “vocation,” it is usually reserved for just describing someone entering the priesthood or the convent.

No way.

All of us are missioned. God has a purpose for EACH one of us, and until we find that purpose, our souls become restless. We may try to numb this restlessness with money, power, control, or even relationships, but until we find that purpose, I believe getting rid of this restlessness will be elusive.

Vocation hails from the latin word vocātiō, meaning a call or a summons. Quite literally, vocation means being were we are called by God.


Heeding our vocation  –  which connotes seeking and following what His will is for us – is quite a different process from developing our careers – which frequently involve mental decision making.

The goals of a career are quite different from what the goals of a vocation are as well. The goal of a developing a career will likely revolve around some of the things I mentioned earlier: money, power, security, control.

The goal of a vocation, meanwhile, is to find our place and God’s purpose for us.

Careers are typically goal-based. We try to find jobs that pay us x amount per month let’s say, or will allow us to travel to countries, or will give us a certain title, or a certain type of car. There’s an endgame.

Vocations, on the other hand, to quote Fr. Ramon Bautista, SJ, in a retreat I had earlier today, “are never ‘mission-accomplished'”

Putting it most bluntly: careers don’t usually involve God. It seeks satisfaction in the external, specifically, that which we do not have.

“My dream job is out there. I need to keep looking.”

Vocation, on the other hand, makes you look at your interior self.

How has God moved in my life? What are my deepest desires? What are the gifts God gave me? How and where can I use them best for Him?

These internal questions, which I now so often use when I discern, are so different from the questions I used to ask, when I decided: 

What field will I be happy in? How much will my minimum salary be? Are the benefits comparable? Is my boss cool? What is the salary increase rate here? How fast will I get promoted? 

For lasting happiness and fulfillment, I think it’s pretty easy to see here what to pursue. You’d be glad to know following God has a practical angle as well: God’s plan will surely involve developing the best you that you can possibly be, maximizing your gifts and talents. When this happens, opportunity abounds. (In the end though, the bottom-line is this, if you surrender to God, don’t you think He will be faithful and take care of you?)

My social media spat

I got a note from someone around a year ago who said something like:

“Religious faith has no place business decisions. I would understand things like ‘having faith in the company,’ but religious faith? I fail to see how that can help any business.”

After everything that happened to me, I felt like going nuclear on the guy.

But then I realized that I felt the same way just a couple of years ago. Come to think of it, I NEVER involved God before in my career decisions. In fact, it was a little weird to mix “careers” and “God” in the same sentence for me.

I’m sure a lot of us still feel the same way.

So perhaps its best to start with something most of us can agree with: God loves us so very much.

Incredibly. Uniquely. Infinitely.

If you believe He loves us this much, then surely, You have to believe He must have a unique plan for each of us. A purpose.

If we believe He does have a plan then doesn’t it make sense to begin the process of trying to find out what it is?

The Dangers of a Fragmented Life, Part 2

(This is the second of a two-part post, the first of which could be found here.)

In 2004, I decided to try to live on my own. There is nothing wrong with living on your own – my mistake was that I allowed the situation to further isolate myself from my family and friends. This accentuated the fragmentation my life was already experiencing. The circles in my life were separated even more profoundly. Who I was in my condo, at home with my parents, with different sets of friends, at work, in graduate school – all were different people.

Leading this sort of life meant having virtually no rules for myself. I was willing to try anything or be anyone to fulfill the expectations of whatever group I was in.

Not knowing who I exactly was, I stood for nothing. And as a friend once said, if you stand for nothing, you will fall for everything.

So with bad decision after bad decision, I spiraled.

I had a good paying job, my own place, my own car, and whatever niceties I was able to afford. But I didn’t really know who I was, work was meaningless, I was doing things people who loved me would not approve of, and I felt really alone. Yes, a lot of people knew me from my different circles, but no one really knew me. In retrospect, I didn’t even think there was any reason to change. I thought that was how life really was.

Things started to change when I attended this retreat where I found God. I had attended dozens of retreats before, so I wasn’t expecting lasting change in this one, but this was different.

In a moment of spectacular clarity, I asked myself, if I truly believed in God, if I loved him – then what was I doing with myself? Why was I so intent on pleasing these other people?  On doing “cool” stuff?

If I believed in God, and if I loved Him – then shouldn’t everything revolve around following Him? And if I believed that God created me for a specific reason, and He has the absolute best intentions for me, then shouldn’t I stop pretending to know what’s best for me and instead just listen? (something very challenging for my very independent self)

Oh, and is there any sense in stalling? 

I then went on with my life with renewed vigor – I started discerning instead of deciding. Reclaiming my life was going to be difficult, but I had found my needed Anchor. In finding God, I had found myself. (And you know what, I think it’s the absolute quickest way to do so.) I suddenly knew who I was and very importantly, who I wasn’t. 

One by one, my horcruxes disappeared. It wasn’t something instant or even something I was consciously aware of. It was a long process. But one day, I suddenly found myself thinking: hey, you know what – there’s little need for me to pretend anymore! Suddenly I realized, who I was at home was the same person I was with my friends. There was no tension felt when my worlds collided. I could do stuff like share my faith freely at work (or write about it in my entrepreneur-centric blog) or in meetings.

It was liberating. Wherever I was, I was me.

I realize that I also have to fight the tendency to create silos and fragments. I do my best to talk to my wife about everything, even with the powerful man-tendency to solve problems on my own. I just don’t want to create other universes which she isn’t part of the equation. (I think this is where a lot of problems begin) At the same time, I can freely share with my STORM partner Pao the things at home which might affect stuff at work. I share with people in my spiritual community how I am with everything. That’s a lot of sharing for someone who’s intrinsically very, very private, but holding myself accountable to people I love and respect helps a lot in ensuring I live one, integrated life.

Is following God a strategic career move?

Do we, really?

I had always believed and said to people that God was at the center of my life.

Only, I realize now that for most of my adult life, that was mostly just lip-service.

Yes, I would go to Mass every Sunday, quickly pray before sleeping (especially when I needed something), and always tried to do the right thing. Me and God were “good,” I thought.

In the meantime, the decisions I made in my life never involved Him. I would go from job to job never thinking about what God would want from me. I formed relationships in my life with nary a thought on faith. I had always been fiercely independent, leaving my parents’ house to forge my own path as soon as I could’ve. This would partly explain why decision after decision would involve only what I alone felt and thought. I would buy what I want, spend my time doing what I wanted, did what I want. It wasn’t really God who was at the center of my life, eh?

Not that I thought there was anything wrong with how I was doing things. This was no prodigal son story, right? I mean, I wasn’t really doing anything inherently wrong. But when I think of it, I ended up straying from the right path anyway. I was so intent on following my own way I just went around in circles. I conquered my corporate professional dreams, but felt empty. Left to my own devices, I found myself alone, frustrated, and confused.  No, I wasn’t leading a ruinous life. I was, however, leading a mediocre one.

In some ways, I think this can even be more dangerous because mediocrity tends to subtly creep up on you. I can see how some people would only realize one’s presence in the mediocrity mire after decades have gone by – but you can even chalk up this late realization as a blessing. Some people never get it.

I guess life phase-triggered crises occur when we realize that the decisions we have made has resulted in a life that’s missing something, and existential desperation sets in. You can call it a search for meaning, or purpose, or pagmemeron, or saysay, or happiness, or joy, or peace, or even searching for yourself.

All along though, I realized I was searching for God. My infinite hole could only be filled by something, someone infinite.

It was only a few years ago that I truly, fully realized this. It was when my heart caught up with my head. So I resolved not to waste any more time. (why do we waste so much time?)

I had always heard holy people on TV say repetitively “Do you have a personal relationship with God?!” It was only recently that I truly understood this.

If I talked all the time with my close friends, got to know them better, and read their updates, I figured I would do the same thing with God. I endeavored to talk to God everyday during prayer, get to know Him more, and read His teachings.

I endeavored to make Him the center of my life. As in REALLY make Him the center of everything in my life.

This of course, includes career choices.

At first I thought, huh? Really? Careers and God don’t seem to mix. I had never encountered God in the corporations I had been in, save perhaps for the obligatory prayer said before Christmas parties. No one has ever told me to “pray,” when I asked for career advice.

But aren’t “careers” so inextricably linked to WHY GOD PUT US HERE ON EARTH?

God uniquely made each of us, endowed us with a specific set of gifts, for a purpose. And you know what? I bet that if you just find that purpose, more than anything, it would make you incredibly happy. So I prayed to God fervently to lead me to that purpose.

My big mouth.

One day, I found myself in a very difficult career decision point (detailed here) that put everything that I had resolved to do for Him against everything I held dear. It was one of the two most difficult decisions I’ve ever had to do.

In my gut, I knew it was a seminal moment. The decision I made here will determine how the rest of my life would unravel. To the world, it was a blatantly clear decision. To my God, it was a clear decision as well: Take the leap. I will take care of you.

It took guts which I didn’t have, but I took the leap no other career advisor would have recommended.

It was difficult going through that process, but God showed me a career path I never would have thought of in a million years – building startups. And oh boy, I can’t tell you how wonderful the fit is between what I do and who I am. In finding God, I had found myself.

Another interesting side effect is that my life was suddenly integrated. You see, before I would live a life divided into silos. I had my life at work, my family life, my love life, my life with my friends, and so forth. I noticed I was a different person in each silo. So during the times when worlds collided, I would feel very uncomfortable at the risk of being “discovered.” I don’t know if this makes sense to you. I didn’t do anything wrong, but I was projecting a different self, probably because I was trying to live in accordance to what each “world” expected of me. This has all changed. I am now one person. I feel integrated, complete. And the necessary foundation for this was and is, God.

A couple of weeks back, I posted this on a particular online forum. I was told by a reader that he had trouble believing how faith can determine the success and failure of a business endeavor. Friends, my whole happiness with where I am career-wise is a result of my faith and nothing else. The whole “business endeavor” would not even have existed if God had not intervened.

Not only can faith and work mix, but I would posit that NOT doing so would lead to something incomplete. The easiest, most direct way to find yourself is through God.

Of course, you can always do something part-time for God, like build houses, or help street kids, and stuff. This is all good, right? Think about that phrase though: part-time for God.

Hey God, you are my everything! I would give PART of my time to you!

Why not the alternative? I mean, you don’t necessarily have to be a priest or something, right? Why not be a full-time politician for God? An full-time entrepreneur for God? A full-time lawyer for God? A full-time website designer for God? The important thing is you follow that voice which calls within. Then you can still build houses and minister to street children in your spare time.

So, how exactly do you know what God wills for you? Three quick suggestions: One, it would help if you TALK to Him for starters, right?! Take a designated 30 minutes (say, 6:00am-6:30am) of your morning to pray. Everyday. Can’t overemphasize this. Second, search within yourself for your DEEPEST desires. I can guarantee it isn’t money. Our deepest, most intimate desires were put there by God. He sometimes can talk to us through our desires. Third, notice what sort of work you do makes time speed up remarkably fast. Notice what work you do brings you complete joy that you can do it for free, that you would PAY someone for you to do it. What did God put in your DNA?

Be warned though, that oftentimes in your journey, you will find that there will be a conflict arising between what God wants and what can bring in money.

So is following God truly strategic then?

It will depend on what you determine to be your ultimate end goal is.

In the end, what race are you really running?