Episode 13: Getting Unstuck with Mark Shrime, CEO of Solving for Why Coaching

Episode 13 Transcript: Getting Unstuck with Mark Shrime, CEO of Solving for Why Coaching

Jim:
Welcome. I’m Jim Marrocco, a financial planner and owner of Thinking Big Financial, a holistic financial planning firm based in New York City.

Mark:
I’m Mark. I’m also in New York City. I’m a surgeon by initial training, but I do a lot of work with clients who are navigating tough decisions: starting or leaving a job, starting or leaving relationships, and other major life transitions. My training is in decision science and the science of decision-making, so I use that work to help people navigate these kinds of choices.  I also have a company called Solving For Why Coaching.

Jim and I got connected through one of the things I think is so unique about living in a city like New York: you just meet the coolest people.

A mutual friend of ours is someone I met who had read a lot of my work around decision-making and also subscribed to Jim’s blog. At one point she texted and said, “You two need to meet each other.”

So we did. We’ve been talking for a few months and eventually started planning around putting something like this together.

Jim:
We thought we would talk today about a commonality we’ve both experienced in our work, but through very different lenses: what happens when people get stuck.

One thing we realized in our conversations is that money and career are really hard to separate. Questions about work quickly become questions about money, identity, purpose, security, and how we want to live.

So I thought we could start by talking about why we get stuck.

In my work, I see a certain version of this. Sometimes people feel stuck in the rat race. They’re doing the same thing over and over again, but don’t feel like they’re actually moving toward anything.

And sometimes it’s almost the opposite. Someone may have enough money that they don’t technically need to keep working, but they still feel a sense of malaise. On paper everything looks good, but something still feels missing.

So, Mark, when people come to you and say they feel stuck, what does that usually look like?

Mark:
That’s such a great question.

“Stuckness” is technically not a word. I get a red squiggly every time I write it. But stuckness and burnout are what bring a lot of people to me too. Finances are obviously a huge part of big career and personal decisions.

Can I make a career change? Can I afford a midlife crisis, so to speak? Can we move the family to New York City? Those are very different decisions from deciding whether you want oat milk or soy milk in your coffee. These decisions affect many different domains of our lives.

I started my life as a physician, and I realized relatively early that being a physician alone wasn’t going to be enough for me. I wanted to do more.  But that immediately becomes a question of identity. Who am I if I’m not the thing I spent 15 years training to do?

These decisions affect identity. They affect finances. They affect other stakeholders. They force us to ask what we’re actually trying to solve for.  I think some of the stuckness comes from the fact that we face these big decisions, we can’t really avoid them, but we don’t necessarily have a framework for thinking through a decision that touches all of these different areas.

When people come to you, Jim, with what sound like financial questions, does it pretty quickly turn into something bigger than money?

Jim:
Absolutely.

Sometimes the financial question is really cover for something else. “Can I stop working?” may actually mean, “I don’t like my job, and I have no idea where to go from here.” And so retirement becomes the default solution. Or someone might say, “I want more money,” or “I wish I had more money saved,” when underneath that is a feeling that they aren’t safe.

They’re hoping a certain amount of money will create a sense of security. And unfortunately, there isn’t necessarily a number that creates security in that way. So I think sometimes people gravitate toward the financial question because it’s tangible. It gives us something concrete to solve when we’re otherwise feeling uncertain or stuck.

And then sometimes life gets upended, and that forces those deeper questions to the surface.

How do you see money interacting with that in your work?

Mark:
Money conversations in my work tend to do two things.

One is exactly what you said: money can be a cover.  “I want more money” may actually mean “I want more safety.”  Or it may mean “I want more freedom.”

Freedom to see my family. Freedom to have hobbies. Freedom to travel. Freedom to have more agency over my time.  A lot of people reach their 30s, 40s, or 50s and say, “I did everything right. I made all the reasonable decisions. I did what I was supposed to do, and I still feel stuck.”

So money becomes tied to the question of, “When can I finally have safety?” or “When can I stop working so much and regain agency over my life?”

But the flip side is that money can also become an excuse for staying stuck.

When someone is considering a big change in jobs, relationships, cities, or something else, one of the first thoughts is often, “I can’t afford it.” So money might have initially represented freedom, but then it becomes the reason you can’t make the change that might give you that freedom.

Does that make sense?

Jim:
It does.

One of the things I learned early in financial planning is that people often come into these conversations believing they don’t have much power or control over the situation. But most financial decisions are, at least to some degree, within our control. We can choose where to live. We can choose how to spend. We can choose what we prioritize.

That doesn’t mean changing those things is easy. It may be incredibly difficult. But we can get caught in this trap of thinking, “I can’t change that,” when that isn’t entirely true. And I’m also picking up on something you said earlier: people can frame work and the rest of life as mutually exclusive.

It becomes, “I can’t have work and the things I want in my life. I have to change work before I can enjoy myself.”

The financial version of that is, “I have to defer all the things I want to do until later because I need to save more money and have enough for the future before I can start enjoying those things today.”

Mark:
That leads into something related.

People often think they know what they’re trying to solve for. “I want more money so I feel safer.”

“I want more money so I don’t have to work as much.” But articulating what a major decision is really trying to accomplish is much harder.  The first time you and I talked, you said something that stuck with me about your philosophy of financial planning.  Instead of saying, “Let’s accumulate enough money so that someday you can retire,” your approach is more about using the money you have in a way that allows you to enjoy your life now too.

I’m butchering it, so maybe I’ll turn it over to you. How would you say that?

Jim:
I think it’s about balancing the trade-offs between the life I want to live today and having a reasonable amount of security for the future.

There’s a distillation that needs to happen around what we’re actually trying to accomplish. Are we trying to create a sense of safety? Are we building a nest egg to make a job change possible? Are we saving for retirement? Whatever it is, I’ve learned that it helps to first get people really clear about their values.

Once you have that framework, things start to open up.  It becomes easier to make decisions because you have something to evaluate them against.

I’m curious how you get there in a non-money context.

Mark:
That’s how I start with my clients too.

Any big decision is trying to accomplish a lot of things at once. Take a job change.  You may want to change jobs because you’re burnt out and desperately want to leave the current one.  But you may also want a higher salary, a better title, fewer days in the office, the ability to live somewhere else, or more time with your kids.  Those are all legitimate reasons.

The problem is that very few jobs are going to accomplish every one of them.  So part of the early work is identifying: what are we actually solving for? Why are you trying to make this change? And how do those priorities balance against one another?  Every major decision involves trade-offs.

The job that pays you an enormous amount of money probably isn’t also going to give you unlimited time with your family.  And part of why people get stuck is that we want to find the one perfect job that solves everything.  But trading off is hard.  Saying out loud, “I am willing to spend less time with my family right now because building a financial nest egg is important to me,” is uncomfortable.

But once you articulate it and hear yourself say it, it becomes easier to make a decision from that place.  I also use the word “values,” although recently I’ve found that word a little insufficient because it can have a moral quality to it. It can sound like values have to be “good.”

But when I’m working with decisions, I try to use values in a more neutral way.  If your value is making a huge amount of money, then we need to structure your decisions around that rather than telling you that you should value something else.  The important thing is removing the “should” from values.

Jim:
Totally.

And I think there’s an important recognition that we don’t all share the same values.

I do values exercises with clients, and when I’m working with a couple, I’ll often have each person do the exercise individually.  Almost every time, they come back with different values.  It doesn’t necessarily mean they disagree. It just means they’re navigating their individual lives with different priorities.

There isn’t one overarching set of values that everybody is supposed to share.  Something else you said made me think about how much pressure we put on work to fulfill so many different things for us.  It has to provide meaning and identity and money and status and fulfillment.  Maybe that’s particularly American or cultural, but I’m curious what connections you see there.

Mark:
One of the things I see with stuckness and burnout is that I think our received approach to burnout is wrong.

We’re often told that the way to get out of burnout is to become more resilient.  Do more wellness. Do more yoga. Breathe better. Go to a retreat.  And all those things can be great. I have a yoga practice. I meditate.

But the evidence suggests they aren’t particularly effective against burnout itself.  It’s not because we’re bad at doing them.  It’s because we’re using the wrong tool for the problem.

Burnout isn’t primarily a failure of resilience.  It comes from a mismatch between our identity, who we thought we would be, what we thought our life would look like, and what it actually looks like.

The friction among those things is what burns us out.  You can’t yoga your way out of a mismatch.  At some point you have to decide your way out of a mismatch.  I think people then approach big decisions in one of two ways.  One is that everything gets placed on that decision.

“This job change is going to solve all my problems.”  But it won’t, because it’s a trade-off. It will solve some things and not others.  The other is that we assume the decision already has a right answer.  I see this a lot with relationships, marriage, divorce, and other choices where people have very strong opinions about what someone is “supposed” to do.  In both cases, we aren’t giving the decision room to actually be a decision.

We need to ask: What are we trying to solve? What matters most? What trade-offs are we willing to make?

Jim:
When you were saying that, it occurred to me that some people may not even realize they’re stuck or burned out.  What are some of the smaller signs people could pay attention to that might suggest something is off.  Because if the issue is misalignment with what you want, sometimes you don’t even know what you want yet.

Mark:
That’s such a good question.

You can go online and look up the formal symptoms of burnout, and they’re real.

But one of the smaller things I notice is what I’d call a counterintuitive hope that something will get in the way of you doing the thing you’re supposed to do.  I was in a terrible job a few years ago that was burning me out, and I would catch myself hoping I would get COVID so I could have six days off.

Or someone might think, “Maybe if I fall off the rock-climbing wall and twist my ankle, I won’t have to go on this business trip.  Those little counterintuitive hopes can be signs that there’s a mismatch between what you’re doing and what some part of you actually wants to be doing.

Jim:
Almost like a fantasy that something outside of you will intervene.

Mark:
Exactly.

It’s like you’re waiting for divine intervention to stop you from doing the thing, because then you don’t have to be the one responsible for deciding not to do it.

Jim:
That makes sense.

Do you find an equivalent when it comes to finances? Something that signals that someone might be more stuck than they realize?  For me, one of the things I think about is avoidance.

There can be a lot behind financial avoidance: money history, shame, fear, all sorts of things.  But it can take many forms.  Maybe someone doesn’t want to look at the numbers.

Maybe they don’t want to talk about money.  Maybe they’re pretending something isn’t happening.  Fortunately or unfortunately, with money, if something is going badly, there’s only so long you can avoid it before you’re eventually forced to deal with it.

Mark:
What are some of the more subtle forms of financial avoidance?

Beyond just saying, “I refuse to talk about my finances.”

Jim:
Sometimes someone has a pretty good awareness of their numbers. They know approximately what they can afford and what they can’t.  And then they make a decision that they know, logically, doesn’t really make sense, but they do it anyway.  It can be a kind of, “I don’t want to fully figure this out, so I’m just going to keep doing what I’m doing,” even though what they’re doing is making the situation worse.

Money is inherently emotional.

None of us are completely logical about it.

But sometimes there’s this gap where someone intellectually understands what’s happening and still acts in a way that runs counter to what they know.

That can be a sign that there’s something deeper going on.

Mark:
How do you counteract that emotional component of money?

Jim:
It’s complicated, but I think the starting point is not immediately jumping to solutions and hitting people over the head with numbers and logic.  It starts with understanding them.

We all have a money history.  Maybe someone was traumatized by money. Maybe they had very positive experiences with money. Maybe they’re terrified of it.

There are countless possibilities.

So part of the work is just beginning to understand that history.

Once people start recognizing where their reactions come from, the guard often comes down.

They start to say, “Okay, I understand myself a little better.”

Then the question becomes: What is the goal? What are we actually planning for?

And is the goal really the goal?

People come to a financial planner and often say, “I want to make sure I’m responsible and doing all the right things.”

One of the first questions I ask is designed to take money out of the equation.

I’ll say:

“Imagine that you are completely financially secure and never have to worry about money again.”

That doesn’t mean you have billions of dollars.

It’s really about imagining the feeling of complete financial security.

I ask people to sit with that for a minute.

What would you change about your life?

What would you do differently?

What would you keep exactly the same?

For some people, it’s affirming.

They realize they’d actually keep much of their life the way it is.

For others, the answer is, “I would quit my job and never look back.”

Either way, it helps us get closer to the real question:

What are we actually solving for?

Do people come to you with a stated goal and you realize pretty quickly that the goal isn’t really the goal?

Mark:
Yes.

I ask a very similar question.

One of the things people are wrestling with when they face a big decision is, “What if it doesn’t work out?”

What if I try this thing and it completely fails?

That’s a very understandable fear.

We’re built to avoid risk and loss, and big decisions threaten us with both.

So I ask:

“If you knew you wouldn’t fail, what would you do?”

For some people, it’s affirming.

They’ll say, “I would absolutely still be a lawyer.”

Great.

Now the decision is no longer, “Should I leave law?”

The decision becomes, “What is it about being a lawyer that you love, and how do we better align your life around that?”

For someone else the answer might literally be, “I would move to Greece.”

Okay. Why?

What is Greece representing for you?

And how do we move you closer to whatever that is?

Those are very different approaches to stuckness depending on the answer.

Jim:
I love that.

When people are facing a big decision and have gotten to the point where they’re genuinely contemplating making the change, I sometimes draw on wisdom from Modern Family.

There was a running joke where something big would be happening, and someone would say, “What’s the worst-case scenario?”

And then you’d hear these ridiculous possibilities.

But there’s something useful about actually saying the worst-case scenario out loud.

Especially in a financial context, you can say, “Okay, if that happened, then here is what we would actually do.”

And often you realize the worst-case scenario isn’t as enormous or terrifying as it felt in your head.

It can help create clarity around the decision.

Mark:
I love that question because we tend to underestimate what, for lack of a better term, you might call our psychological immune system.

We underestimate how resilient we’ll be if the worst-case scenario happens.

And on the flip side, we also overestimate how much the best-case scenario will affect us.

There’s research on something called impact bias.

We predict that we’ll be happier in the best-case scenario than we actually end up being, and we predict that we’ll be more devastated by the worst-case scenario than we actually are.

There was a study where researchers asked college students about dorm assignments.

There was one dorm everyone supposedly wanted and one that nobody wanted.

Before assignments, students predicted they would be dramatically happier if they got the desirable dorm and much less happy if they got the undesirable one.

A year later, researchers went back and asked them how happy they actually were.

The difference was much smaller than people had predicted.

The people who expected the good outcome to be amazing found it less amazing than expected.

The people who expected the bad outcome to be terrible found it less terrible.

We underestimate our ability to adapt to the worst-case scenario.

Jim:
So our emotions are much more extreme when we’re imagining the possibilities than they are once we’re actually living them.

Mark:
Exactly.

And that’s another reason I don’t think burnout is fundamentally a resilience problem.

We are resilient.

We just don’t always trust ourselves to be as resilient as we actually are.

Jim:
That makes sense.

I think about that from a financial and historical perspective too.

There is always something happening in the world that feels terrible or uncertain.

People look at the stock market and say, “This time it’s going to crash and never recover.”

And I’m always cautious about saying, “Just look at history and everything will be fine.”

But there is something reassuring about looking back at all the terrible things people and economies have navigated and realizing that we tend to figure our way through them.

It’s a concrete example of what you’re describing.

When people are worried about money, the economy, the stock market, or other things outside of their control, there’s a long history of people adapting and figuring things out.

Mark:
You take your clients through exercises around what they’re trying to build toward.

I have two related questions.

What exercises do you use to help uncover that?

And then, financially, how do you take someone from identifying what they want to actually changing their behavior in a way that supports it?

Jim:
When we start working with someone, and really throughout the relationship, we spend time talking about their money history.

How do you think about money?

Where did those beliefs come from?

There’s a quote from the philosopher Jacob Needleman that I love. He essentially says that everybody is weird about money.

And I think that’s true.

We all have beliefs about money that we’ve absorbed from our environments, families, culture, religion, and our own experiences.

Simply becoming aware of those influences can be powerful.

You start recognizing, “Oh, that’s that old voice talking.”

We also do a values exercise.

And I try to frame it not as, “How should you live?” but, “What actually matters to you?”

Then we look at how those values show up financially.

Maybe someone thinks other people would find it ridiculous that they spend so much money on a particular thing.

But if that spending clearly expresses something important to them, it may actually be a perfectly reasonable use of their money.

Then we connect that to what we’re solving for.

And I try not to lock people too rigidly into, “This is the exact goal and therefore this is precisely what we have to do.”

I’d rather put someone on the right path.

Instead of, “You must save exactly this amount every year,” it might be, “We want to consistently move money toward this thing that matters to you.”

Once people start doing that, they begin to see progress, and that can be incredibly motivating.

What often doesn’t work is throwing an enormous list of changes at someone and expecting them to implement everything at once. Then people feel like they aren’t making progress, get discouraged, and stop.

I think intention and process are often more powerful than obsessing over a perfect outcome.

Mark:
One of the things that keeps people stuck with big decisions is that we tend to treat too many of them as irreversible.

Jeff Bezos popularized this idea, although it existed before him, of Type 1 and Type 2 decisions.  Type 1 decisions are irreversible.  An amputation is a Type 1 decision. Prosthetics exist and you can adapt, but you cannot undo the amputation.  Type 2 decisions are reversible.

There may be a cost to reversing them, but once you walk through the door, you can walk back through it.  And I like reminding people that the vast majority of decisions are actually Type 2 decisions, including many decisions we experience as Type 1.

I have a tattoo.  A tattoo feels like the epitome of a Type 1 decision. It’s permanently on your body.  But even that isn’t completely irreversible. Lasers exist. Coverups exist.

So I try to shift people away from thinking, “This career decision determines the rest of my life.”

Maybe this career decision is for two years. And that’s okay.

We should spend a lot of time thinking carefully about truly irreversible decisions.

But when we bring that same level of analysis to reversible decisions, we get stuck.

We overthink decisions where we might be better off moving forward with 70% of the information rather than waiting until we have 95%.

Jim:
Totally.  We can work ourselves into believing that we can’t change something.

Mark:
Exactly.  And there are some careers where this is especially difficult.  Medicine. Law. The clergy. Teaching.  These can become identity careers.

You don’t work in medicine. You are a doctor.  You don’t work for the church. You are a priest.

And those careers can make career decisions feel more irreversible because we’ve been told that this identity is who we are.

So sometimes there’s more work involved in helping someone realize, “Your next career decision might only be for two years.”

And that’s okay.

Jim:
Absolutely.

All right, I’m going to ask you our closing reflection question.  We’ve talked about a lot today.  If you could have listeners come away from this conversation remembering one thing, what would you want it to be?

Actually, let me answer first.

For me, I think it’s about going deeper and getting clear with yourself.

Don’t automatically use money as the explanation for why you can’t do something.

Pay attention to stuckness, apathy, avoidance, or whatever else may be showing up.  And then go deeper.

Get clear about the decisions you’re making around money and in your life, and connect those decisions to what is truly important to you, your values, how you want to live, and how you see yourself.

To me, that’s really the heart of the work I do.  What about you? What would you want people to take away from this conversation?

Mark:
I would want them to take away something you said, which is that almost everything is a choice.

Very few things are truly Type 1.  Very few things are completely given to us.

With our careers and our finances, we usually have at least some degree of control.

We can choose to start something.  We can choose to stop something.

There’s freedom in regaining agency over those decisions.

You can work with someone like Jim to intentionally design your finances around the things you want to accomplish, even if right now it feels impossible.

You can make a career decision that balances the things that matter to you now.  The decisions I made at 26 were based on the values I had at 26.

Those values may be different at 46.  They may be different again at 66.

And I have the freedom to make decisions about where I live, what I do, and how I structure my life based on the values I have now.

Not necessarily the values 26-year-old me had.

Not necessarily the values my parents had.

Not necessarily what my culture tells me I’m supposed to value.

But what matters to me now.

Jim:
I love that.

On that note, I just want to say thank you for the conversation.

This was really great.

I hope this blending of our two worlds helps people find a little more clarity around these decisions and gives them a different way to think about money, work, and getting unstuck.

Mark:
I agree. Thank you for this. This was awesome.