Tuesday Email: Your Future Self is Not More Disciplined

Happy Tuesday!

Every Tuesday I'd like to offer strategies for the week ahead and a thought to fuel your action.

It’s been eight months.

And I continue to avoid taking a health test, despite investing a lot into my health.

My functional medicine doctor ordered it last summer.

The box is sitting in my closet right now. I haven't even opened it to read the instructions. And I’ve already had one visit with my doctor where I had to admit not having taken it.

Every few weeks I think, "I should do that test." And then I don't.

My worry is that it will disrupt my “precious” routine. And time will present itself next week for me to do it. Time I don’t have this week.

It was during my research for this very piece that I realized: I'm doing exactly what every human and business owner does when it comes to difficult decisions, situations or challenges. We make up a narrative about how hard it will be. Convincing ourselves that “Future Me” will handle it better. And the whole time, the box just sits there.

In wealth management we all do this in different forms and fashions. We push the CRM migration to next quarter. We defer the equity conversation until "after this market volatility settles." We tell ourselves we'll tackle the service model redesign when we have more clarity, more time, more bandwidth.

But here's what the research shows: Our future self is not more disciplined than we are today. Future us doesn't have more time. Future us isn't better at hard conversations. Future us is just today you with less runway and more urgent problems.

When you think about yourself 10 years from now, your brain lights up the same way it does when you think about a stranger on the street.

This isn't metaphorical. This is actual neuroscience.

It should make us all pause.

Hal Hershfield (who I deem to be the father of the concept of Present You vs. Future You) did research that shows that the neural activity when thinking about your Future Self is nearly identical to the activity when thinking about a complete stranger.

Your medial prefrontal cortex (nerding out a bit here)—the part of your brain that handles self-referential processing—basically shrugs when you imagine Future You.

To your brain, "Future Me" isn't "Me." It's some other guy who'll figure it out.

This explains why you can push off that succession conversation for the 47th time and still sleep at night.

Your brain doesn't register this as screwing yourself over. It registers it as delegating a problem to someone else.

Jerry Seinfeld has a bit about this—Night Guy stays up late, makes a mess, eats garbage, because Morning Guy has to deal with it. Morning Guy wakes up furious: "What was Night Guy thinking?" But Night Guy doesn't care. He's not Morning Guy.

That's exactly what's happening with us. We're Night Guy, pushing problems to Morning Guy, except Morning Guy is you in six months. And he's going to be just as pissed.

But the stranger phenomenon is just the first mechanism working against you. There are four more.

First: Your brain can't weigh immediate pain against future gain. Behavioral economists call this "intertemporal choice," any decision where costs and benefits are spread across time. The cost of a CRM migration is felt immediately: the cognitive load, the weekend work, the staff pushback. The benefits—greater scalability, cleaner data, greater efficiency—are abstract and distant. Your brain discounts the future benefit because it can't really feel it. But it can absolutely feel today's pain.

Second: Hyperbolic discounting. Here's the classic example. If I offer you $100 today or $110 in a year, you take the $100. The extra $10 isn't worth waiting for. But if I offer you $100 in five years or $110 in six years, you'll wait for the $110. Why? Because both options are distant, so your brain's discount rate flattens out. You can be rational about far-future tradeoffs.

This is why "next quarter" never comes. From six months away, starting that succession plan looks reasonable. The delay between "six months" and "six and a half months" feels negligible. But as the date approaches, the immediate pain of doing the work spikes. So you push it again. And again. The math is always against you.

Third: Resource Slack Theory. You assume you'll have more time and more money in the future than you do today. I see this in myself every winter. Things slow down a bit. Fewer outdoor activities, darker evenings, more time at the desk. So I build routines around having that time. I commit to projects assuming winter-level capacity. Then spring hits. We're outside more. Travel picks up. College football season in the Fall. The holidays. And I never have that time I thought I'd have. The calendar I thought was empty just fills with different stuff.

You're doing the same thing when you say "I'll tackle this when things settle down." Things never settle down. The dust doesn't clear—it just accumulates.

Fourth: Construal Level Theory. We perceive distant events in abstract, “cool” terms. Near events in concrete, “hot” terms. When you think about "scaling the business" three years from now, you focus on the vision—the freedom, the wealth, the impact. These are “cool” cognitions. But when you think about the how—the client acquisition necessary, the time investment, the monetary investment—it becomes “hot.” The vision is exciting. The execution is painful.

We have to run through the fire to reach the vision we desire. But we keep pushing the fire to Future Us, thinking they'll handle the heat better. They won't. The hot moment arrives eventually, even if we push it off. You can't avoid touching the hot plate forever.

Sears and Toys R Us both had everything they needed to dominate e-commerce. Brand equity. Resources. Customer relationships. But they underinvested in their Future Selves for years, choosing to milk the declining returns of their physical stores. By the time they attempted to modernize, the technical gap between them and Amazon was insurmountable.

They believed the way things were was the way things would continue to be. That's the End of History Illusion—we acknowledge we've changed in the past, but we believe we've reached our final form. Sears assumed customers would always want catalogs. Toys R Us assumed kids would always want to walk the aisles. Both were wrong.

This plays out in RIAs every single day.

A common version: succession planning and retaining G2. The owner dangles equity for years—"we'll figure it out next quarter." The owner thinks they're being prudent. The G2 advisor sees a leader who won't commit to the firm's future. Eventually, they leave. And the firm that could have been valued as an enduring enterprise gets a 30-50% haircut because it's now just a lifestyle practice with no successor.

The owner who thought they were protecting their equity by not sharing it ends up losing more in valuation than they ever would have given away.

The icing on the cake is that with delaying decisions, the debt compounds. Whether that is technical debt, cultural debt, leadership debt; they all accrue interest. And being in this business, we know the value of eliminating debt.

Just think about it like this. A firm with $200M in AUM can migrate their CRM in a few months. A firm with $2B that's deferred that migration for a decade? Nearly impossible without massive service disruptions. The longer you wait, the harder it gets. The options narrow. The urgency increases.

Your future self isn't getting a cleaner problem. They're getting a more expensive one.

We can’t change the biology we were given. That’s not the goal. The goal is to understand how our biology works and create processes and systems that counteracts the negatives, to help us have more positives in the future.

A tool that Suzy Welch popularized was this concept of the 10-10-10 rule. It’s the idea that when you face a decision you want to defer, stop and force yourself to answer these three questions:

• How will I feel about this in 10 minutes? (Probably stressed, overwhelmed, resistant.)

• How will I feel about this in 10 months? (Probably relieved that the foundation is set.)

• How will I feel about this in 10 years? (Almost certainly: "This was the turning point.")

By explicitly visualizing all three timelines, we activate our brain's planning mode instead of just reacting to immediate discomfort. We're forcing your brain to see Future You as... you.

Another way to help us navigate through fearing what may be to getting an actionable plan of what we need to do is this acronym WOOP.

• Wish: What's a challenging but feasible goal? (Full CRM integration.)

• Outcome: What's the best result? (10 hours saved per advisor per week.)

• Obstacle: What internal barrier holds you back? (My tendency to prioritize small client requests over strategic work.)

• Plan: What will you do when that obstacle shows up? ("If my attention drifts to my inbox, I'll close my browser and set a 25-minute timer.")

Both of these tools require one thing that is necessary not just with these tools, but in order for us to be great advisors: they require empathy. You need empathy for Future You the same way you need empathy for your clients. If you can't put yourself in another person's shoes, you can't put yourself in your own future shoes either. And Future You—according to your brain—is basically a stranger. So you have to practice seeing them as yourself.

So tonight, I'm going to open that box.

Not because I'm suddenly more disciplined.

Not because I magically have more time.

But because I understand that Future Me isn't going to handle this any better. He's just going to be more annoyed that I stuck him with it.

I'm going to open the box and read the instructions. That's step 1. Because the narrative I'm making up in my head about how complicated this is? That might not even be true. But I won't know until I dismiss the narrative and look at what's actually required.

Execution today is a gift to Future You.

What's in your box? What's the thing you keep pushing to next quarter, next year, "when things settle down"? The succession plan you haven't written. The CRM you haven't migrated. The equity conversation you haven't had. The service model you haven't redesigned.

Whatever the reason you're pushing it off today—the fear, the complexity, the disruption—those reasons will still exist in six months. Future You will face the same heat. The same fire. Except with less runway. Fewer options. More urgency.

Either decide you're not doing it at all and delete it from your list. Or figure out step 1 and do it today.

Stop making plans. Start building commitments. Your future self is counting on you.

Actually, scratch that. Your future self isn't counting on you. You are counting on you. Because there is no Future You—there's just You, showing up at different dates with the same problems you're avoiding right now.

The best is ahead!

-Matt