“OK, but really. Where did I go wrong?” Josh asked.

It was a Wednesday in April, in the middle of an oppressively hot fake-summer day in New York City. Too early for the buildings to switch over from winter heating to air conditioning—and rightly so; the mercury would drop fifty degrees within the next week.

Even through Zoom, I could hear the tumult of sirens that serves as the soundtrack to this city, blaring through Josh’s open windows. I’m sure he could hear the ones coming through mine, if, that is, he could get past the white noise from the two fans I had pointing at my face.

“Where did I go wrong?” he said again.

How did Josh make all the right choices and get to a job he hated? Read more…

I won’t sugarcoat it. Coaching is an investment. So let’s talk about it—let’s talk about the investment, the return, and whether it’s worth it.

Because coaching shouldn’t be any different from other cost decisions in your life: You know what your time costs. You know what your business decisions are worth. You have a sense of what a wrong turn in a personal decision may cost (in dollars and years).

So when you research the cost of executive coaching, you're really asking whether it can produce a return that justifies the line item on your life’s P&L.

Here’s how to figure it out

Welcome back to a month of answering reader questions!

Remember, if you’d like me to answer your questions about making big career and life decisions, leave a comment below or send me an email. Readers who ask my favorite questions get a signed copy of Solving for Why.

This week’s question, like last week’s, comes from Ali, who wrote:

How do you convince others that the decision they think you made about a huge life changing event being completely out of left field is actually rational, thought through, and OK. Is it their insecurities or is that decision completely barking mad!!

In last week’s post, we covered what to do when the decision is yours and other people don’t like it. When you own a decision, then naysayers provide important information. But they don’t have veto power.

On the other hand, sometimes the pushback isn’t pushback. Sometimes it’s a co-decider who’s exercising their legitimate decision rights. So for this week’s question, let’s talk about

How are you supposed to co-decide with someone else, especially if you don’t agree?

Welcome back to a month of answering reader questions! Remember, if you’d like me to answer your questions about making big career and life decisions, leave a comment below or send me an email. Readers who ask my favorite questions get a signed copy of Solving for Why.

This week’s question comes from Ali, who writes: “How do you convince others that the decision they think you made about a huge life changing event being completely out of left field is actually rational, thought through, and OK. Is it their insecurities or is that decision completely barking mad!!”

I love this question. So much so that I’m actually going to break it up into two questions. Next week, we’ll talk about how to incorporate others into your big decision. But for this week:

What are you supposed to do when everyone thinks you’ve lost your mind?

This month, I’m answering some reader-submitted questions I’ve gotten over the course of the year.

Today’s question was submitted by Farhad. He asked:

How do you know if you’ve made a good decision or a bad one? Does poor decision-making have a “look” to it?

To answer Farhad’s question, let me tell you about Margaret.

Long story short, Margaret landed her dream job, the job that she felt like she'd been preparing for her entire life.

Like, every other job, every other interview, and heck even some of her relationships, all felt like they were pointing to this one. She even went so far as to tell people she'd felt called.

Two years later, her boss restructured and her job evaporated.

For months after, Margaret would lie awake at 2am, running and rerunning what happened. The excitement she’d felt when the offer letter was signed. The other opportunities she’d turned down to take this one. The colleague who warned her that leadership was unstable, but the (misplaced) confidence she had that she could weather any instability for a job that good.

And every time, the replays landed on one obvious verdict: She had made a bad decision.

But did she? How could she know?

Wellness programs, resilience training, and meditation apps fail to move the needle on surgeon burnout because they’re treating the wrong thing.

Burnout in surgery is not a wellness problem. It’s not a resilience problem. It is, instead, the predictable collision of three forces: an identity formed before adulthood, a self that keeps changing, and a profession that pretends that neither of those things is true.

You can’t deep breathe your way out of a system built on your back.

Here’s what does work, though →

If you’ve been here for the last few weeks, you’ve heard about Aya, her failing relationship, and the struggle she’s had with whether she should divorce her wife, Priya, to be with Daniel, her new love interest—or whether she should stick that marriage out. (If you haven’t, here’s Aya’s story, and here’s the background science behind today’s post).

Chances are, you have opinions. Aya should leave because she’s already in love with someone else and just leading Priya along. Or, counterpoint, they made a promise till death do them part, and that should outweigh any new relationship energy.

Well today, we’re going to answer Aya’s question a different way. ​Instead of an appeal to authority, we’re going to figure out which of her two choices will, ​with ​A​LL the uncertainties considered, make her the happiest. ​We're going to choose to make Aya as happy as she can be.

Let’s dive in!

Before we get started, a warning: If you’ve ever told yourself “I’m terrible at math,” then this post might be one big trigger to any childhood trauma still hanging around the edges of your brain.

Stick with me, though, because I promise it’s worth the mental lift.

(Also, side note, you are good at math. The problem isn’t you…it’s that you weren’t taught math well).

Remember Aya from last week? Let me (re-)set the scene.

Aya had been married to Priya for a decade and a half.

Unfortunately, like so many marriages, theirs had gotten mired in the mangroves of hurt feelings, mislaid expectations, and the unfortunate friction of familiarity.

Aya was stuck, plagued by all the what-ifs that accompany a break-up. What if I leave and I never find love again? What if I stay and I still don’t find love again?

Should I stay or should I go?

​Today, I'm introducing you to the science that helped Aya make a decision she now describes as the best one she ever made. Let’s go!

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…