How are you supposed make big choices when there are so many what-ifs?

When Aya booked her first get-to-know-me call, she was 52 years old. Even though the call was on Zoom, I could still see the particular exhaustion that lines the face of someone who’s been having the same conversation with herself for two years.

Aya had been together with her wife, Priya, for fifteen years; they’d been married for eight.

Fifteen years is a long time, long enough to have built an entire world with, and around, someone—a home with its particular smell, a shared shorthand, a wordless way of moving through a Sunday morning.

But sometime in the last few years, that world had curdled. And then she met Daniel, who was everything Priya wasn’t.

This month: Should Aya stay? Should she go? How does she choose when there are so many what ifs?

Back when I worked as a full-time doctor, I’d slip into a mental tailspin every Sunday night. Monday loomed, and I would dread going to work. Like a kid resisting his broccoli, I’d internally protest the impending 4:30 am alarm, the scrubs, the stethoscope, the white coat. Every time.

These days, there’s a word for that feeling: the Sunday scaries—that feeling of dread that creeps over you on Sunday nights, as a weekend away from work comes to an end, and you start to realize that you’ll have to wake up the next day to a job that you’re barely enduring. 

If you consistently dread going to work, two things you should know right off the bat.

First, you’re not alone.

And second: there’s a way out.

Want to know why what you actually want and what you say you want aren’t the same thing?

In this week’s post, we explore the difference between “stated preferences” (that is, what you say you want) and “revealed preferences” (that is, how you actually act).

And we explore the Arrival Fallacy, the part of our psychological immune system that assures us that our suffering is only temporary, that there’s good on the other side of it.

Both of these work hand-in-hand to turn dream jobs into nightmares, dream relationships into despair. (Don’t worry…there’s a way to counteract them!)

Want to know why what you actually want and what you say you want aren’t the same thing?

In this week’s post, we explore the difference between “stated preferences” (that is, what you say you want) and “revealed preferences” (that is, how you actually act).

And we explore the Arrival Fallacy, the part of our psychological immune system that assures us that our suffering is only temporary, that there’s good on the other side of it.

Both of these work hand-in-hand to turn dream jobs into nightmares, dream relationships into despair. (Don’t worry…there’s a way to counteract them!)

This week's blog post was tough to write. It forced me to publicly, vulnerably excavate a somewhat difficult period, one where I made some mistakes.

Deep breath…Here we go…

Back in the Before Times™, before a global pandemic changed everything about the way we work, I was offered my dream job.

It came right on time, too. I'd just started to feel stuck where I was; I couldn't see a path for my career that wasn't stagnant. And this job...it showed up, unexpected. Like a gift I didn't even know I was looking for.

It was everything that I'd been saying I wanted, for my entire freaking career. Literally, this job ticked ALL the boxes.

...And it was a nightmare.

Financial insecurity—or at least, the fear of financial insecurity—is the single biggest barrier keeping people from making decisions that will improve their lives. It was (heck, still is) for me, and it has been for every one of my clients.

And it doesn't matter the decision either. This fear is there, whatever the life decision is: I’ve seen financial fear stymie consequential career moves, convince so many good people to stay in bad relationships for years past their expiration dates, and prevent others from pursuing their big city dreams.

So, if it feels like you’re stuck on the path you’re on because of financial insecurity, or the fear of it, then this post is for you →

I use a budgeting app. Chances are, you do too.

And by “use,” I often mean “look at that open tab on my browser, tell myself I’m going to look at what I spent this month, and then promptly ignore it.”

I’ve tried everything to stay more on top of my budget—putting it on my to-do list every day, allowing myself a piece of chocolate every time I reconcile my transactions—and, a week or two later, I’m back to sticking my head in the sand.

Remember Josh from last week? The surgeon who couldn’t figure out his budget and ended up not taking a $3 million a month job?

There’s something that unites us both.

It’s called the Ostrich Effect →

Josh is a surgeon and has been one for 7 years when I first meet him. He’s from San Francisco; born, bred, trained, and now working in one of the most expensive cities in the nation.

He doesn’t like his job.

Why, I ask him, is he still doing something he hates with a purple passion?

“Look Mark, I make $400,000 a year—and honestly that’s just not enough. I need to be making even more than that.”

“Say more?” I prompted.

“I really feel like, to be middle class in San Francisco, you need to make a million dollars a year or more.”

About six months later, Josh was offered a job that would pay him three million dollars. He didn’t take it. Because he couldn’t bring himself to figure out his finances.

What happened? →

I spent the holidays thinking a lot about the idea of discernment. What does it mean for us to feel in our bones, to know that a decision is good? And how do we know that we can trust that feeling?

Discernment is a complicated thing. It’s hard to pin down because it’s so…nebulous. So today, let’s talk about what a friend of mine calls “the ‘woo’ of decision-making.”

What’s the role of the unconscious mind in decision-making? How do you tap into it? And how do you know when to trust it?

Let me tell you a divorce story.

Longtime readers of my blog know that I got a divorce in the early part of the 2020s. It’s hard to pin down the exact date, because the gap between our separation and our divorce was nearly five years. Part of that was the court systems getting gummed up by Covid—and part of it was because it took us a long time even to be sure that that was the path we wanted to take.

This blog is about the second part.

It’s about those decisions that we sit on for months, years even, because we’re waiting for discernment. Because we want to find the right answer to the really big crossroads in our lives…

Hey friends! Welcome to 2026! Let me tell you what’s in store for you at Solving for Why® this year.

In addition to moving to a new platform, I’m changing the format of my posts this year, all in an effort to make your experience so much more predictable (and easily digestible).

Each month, expect three blog posts, emails, and videos, all around a central theme. The blog posts will come out the first three Thursdays of the month, and they’ll be shorter than the ones I’ve written for the last two years—some of those ran upwards of 3000 words!

Here’s what each month will look like →

In the last few years, as I’ve talked to countless clients and, more importantly, potential clients about navigating burnout, stuckness, or a midlife shift, the single most common thing I hear about why they stay stuck is, “I can’t afford to change.”

So, today, let’s talk about exactly how to deal with that. Financial insecurity is a huge, and very valid, fear (especially these days)—but it may not be as big an issue as you think.

Here’s how to figure it out for yourself…

As I was starting my coaching business, I paid a guy $15,000 because he promised to bring me clients, whenever I wanted, on demand. And I took that claim as gospel.

In fact, I was so concerned by the “on-demand” nature of the thing he was helping me build that I worried I’d have too many clients—more than I knew what to do with.

“But what if,” I asked his salesperson, “I’m on one of my trips to Africa and I can’t handle all those clients?”

“Don’t worry,” she responded. “You can just turn off the tap.”

Should I have known a promise like that was too good to be true? Absolutely. I have more letters after my name than I have in it, and I still believed him.

And now I’m $15,000 poorer. There’s a reason for that…

I used to stand in the shower every morning and mutter to myself, “Two more. Two more.”

Two more what? No clue. It was just “two more.”

Yes, it’s as weird as it sounds.

Weird or not, I had those daily two more conversations at two distinct periods in my life. The first was when I was a full-time doctor, something I’ve written about a lot.

The second was for the three years that I worked my “dream job,” a job which ended up being so soul-destroying I still get PTSD any time I see my former boss’s name.

I literally had a timer app on my phone counting down to completely arbitrary self-imposed goals. 

“6 days since my boss last yelled at me.” 

“84 more days till I hit my nine-month mark.” 

“285 days until I’ve been here for 3 years.”

I was absolutely miserable. 

—

Fifteen years later, I’m writing this blog while sitting in my window on a hospital ship in Sierra Leone. I’ve built a career I adore—one that lets me work on the things I want to work on, and still get paid to do it.

There’s a way to go from there to here. Read more →

“You absolutely should not do this,” my boss told me. 

I had just informed him that I was considering taking a year off from surgery to travel the world. 

He was, to put it mildly, concerned. 

“This is the absolute wrong time to make a decision like this. No job will take you seriously. They’ll think you’re a flake.”

“Just finish fellowship,” he continued, “get your practice going, and then, once you’re established, you can take some time off. You don’t want to mess up your career before it’s even started!”

I didn’t listen. I took the year off anyway. 

And, you know what? Pat was right. It messed up my career.

In the best way possible.

God, I hate the feeling of not being able to help a patient. Hate staring at a CT scan and knowing that there’s nothing left for the surgeon to do.

Hate it.

Because...It isn’t just disease those of us in healthcare fight against. It’s also the systemic barriers too, the insurance, the bureaucracy, the financial hardship—none of it within our power to fix, and yet we feel responsible for the outcomes.

This dread used to beat me down when I was a full-time surgeon, engulf me in a heavy blanket of powerlessness. My lone efforts were insufficient, my surgical expertise flaccid against the onslaught of forces that were completely out of my hands. 

There’s a name for that feeling.

For the last year, I’ve written weekly about the science of decision-making. We’ve unpacked cognitive biases—those shortcuts our brains take to save energy, even if they sometimes lead to worse choices—and explored Nobel Prize-winning decision science research. We’ve covered decision models, dissected the math behind choices, and discussed techniques to help us make more objective, rational decisions.

But. 

In all this intellectual exploration, there’s one fundamental element I’ve overlooked.

And it’s time I addressed it.

was a deeply mediocre grade-school student. Except in penmanship. I almost failed that. Drunk crickets trace neater paths through sand than I do with pen on paper.

Sister Viola P, of the Incarnate Word and Blessed Sacrament—a nun who believed in punishing grade-school evildoers by stuffing their butts in wastebaskets—sent my parents desperate entreaties to fix their son’s handwriting. 

Thankfully, cursive skill doesn’t play the role in my life they said it would.

To my parents and their friends, though, my penmanship was proof of one very important thing: their son was destined for medicine.

“No!” I’d respond. “I don’t want to be a doctor. I want to be a rock star!”

I became a doctor anyway.

What happens when your purpose is subjugated to your path?

On September 19th, the President of the United States signed an executive order, one that effectively guts the immigration of many high-skilled workers* into the US—including in healthcare.

According to the order, unless an employer is willing to foot an extra hundred grand, no one can come into the US to work in a “specialty occupation” —including healthcare.

For those of us in healthcare, this is going to hit. 

Hard. 

Your burnout’s about to get much worse. Are you prepared to weather this storm?

Since Charlie Kirk was killed by a 22-year-old kid in Utah on September 10, the internet has been at each other’s throats. “How could you speak ill of the dead” people have been speaking ill of “But have you heard the things he said?” people.

It’s been a mess.

It’s also been one of the clearest examples of confirmation bias I think I’ve ever seen