If you want to grow your wealth faster than the average person, I suggest trying to think in two timelines that move together in unison.

The first timeline is analyzing what’s going on right now. The second timeline is analyzing what could happen in the future, with a consistent spread. It’s like having a dual computer processor always running in your brain.

I’ve been thinking in two timelines since 1999, when I got my first finance job out of college. Thinking this way was key to me building enough wealth to escape corporate America in 2012. I haven’t stopped thinking this way since.

Example Of Thinking In Two Timelines For Greater Wealth

The classic example to explain my suggestion is to people who are currently working.

• Timeline #1: How do you feel about your job now?
• Timeline #2: How do you think you will feel in ten years if you are still doing your same job today?

Most people I talk to never think about question two when they first start their job. They are thrilled to be there and full of optimism. But I want you to think about question #2 because I’m trying to get you to forecast your misery.

If you can approximate when you’ll be miserable at your job, you can take steps to prepare for when that misery comes. But if you don’t think about question #2 consistently in two timelines, by the time you are miserable, you are screwed. You have little-to-no options for getting out of a suboptimal situation.

Saving And Investing Enough To Break Free From Misery

When I was told I had to get in at 5:30 a.m. and stay past 7 p.m. to ensure I got the appropriate research from my colleagues in Asia for clients, I knew I couldn’t last 40 years in a career like my parents did. Instead, I made a more realistic assessment: how long could I conceivably last before burning out completely? The answer I came up with was age 40.

So I calculated how much I would need by then to have the courage to walk away. That number was $3 million. Depending on how the net worth was structured, it could generate potentially $100,000 a year in passive income. From that moment on, saving and investing $3 million became my mission. I constantly visualized what life would look like at age 40, 41, 42, 43, 44, 45, and beyond—free from the grind with that money in mind.

This two-timeline approach—present-day hustle paired with future-day dreaming—kept me focused and motivated. I truly believed that if I didn’t hit that net worth target, I might short-circuit my life from all the stress and hours. I was already beginning to suffer from plantar fasciitis, uncontrollable allergies, and weight gain.

In the end, I left three months before my 35th birthday thanks to an unexpected variable: the ability to keep all my deferred compensation and receive a six-figure severance package after 11 years at my last firm. That severance covered five years of normal living expenses. With that financial cushion in hand, I knew it was now or never—so I took the leap of faith.

Using Two Timelines To Become A Better Investor

Now let’s apply my two-timeline approach to investing.

1) Present Timeline:

Investors have done incredibly well since 2020, especially those who bet on tech. With the S&P 500 up more than 20% in both 2023 and 2024, the investor class has built far more wealth than expected. Real estate has also performed strongly since 2020, although some markets—like Texas and Florida—are correcting. Every investor should look at what their net worth was in 2020 and celebrate.

2) Future Timeline (10–20 Years Ahead):

If you or your parents don’t invest aggressively, life could stay in hard mode indefinitely. The wealth gap has already widened dramatically since 2020, and it’s likely to keep widening. In 10 to 20 years, buying a primary residence might be next to impossible. Finding a job that pays a livable wage could also become increasingly difficult as AI disrupts more industries.

What should we do?

The Plan To Ensure The Future Will Be OK

I’ve developed a general game plan to give my family a fighting chance to compete in an increasingly competitive and uncertain future.

1) Hold onto our primary residence and at least two rental properties to stay long real estate.

Real estate is one of the most reliable ways to build and preserve wealth over time. By holding onto property, we not only benefit from potential appreciation and rental income, but we also protect ourselves from being priced out of housing in the future. Owning one rental property for each child is something you should consider.

2) Build two 529 plans that equal the current four-year cost of the most expensive university today.

College tuition continues to rise faster than inflation, and there’s no sign of it slowing down. Fully funding 529 plans now ensures our kids will have the freedom to choose quality education without being burdened by debt—or burdening us. They will also have the option to attend the best college that accepts.

3) Invest at least the gift tax limit every year in each child’s custodial investment account and Roth IRAs.

By consistently contributing early, we harness the power of compounding. The goal is to build a financial foundation that allows them to pursue careers they enjoy, not just ones that pay the bills or seemed “high status” by society.

4) Aim to invest at least $100,000 a year in risk assets for the next 20 years for ourselves.

To combat inflation and maintain purchasing power, consistent investing in equities, venture capital, and other growth-oriented assets is critical. This aggressive approach is our hedge against stagnation and the rising cost of living. It won’t be easy as a writer, but I’ll somehow find a way through other activities.

5) Build $500,000 in private AI company exposure to hedge against a difficult job market in the future.

AI is both a threat and an opportunity. By investing in private AI companies or funds, we aim to participate in the upside of technological disruption, rather than simply becoming victims of it.

Why a $500,000 Investment in AI Makes Sense

Ever since 2017, I’ve been grappling with the reality of having to pay for college starting in 2036. Based on current projections, we’re looking at around $450,000 for public and $750,000 for private university tuition over four years. That’s a staggering amount—especially considering most of what’s taught in school today is freely available online.

One solution is to guide them toward attending community college for two years before transferring to an in-state university. Another is to educate them ourselves, or at least as much as we possibly can before they are adults.

But perhaps the most compelling solution is to invest in the very technology that’s likely to disrupt traditional education the most: artificial intelligence.

At first glance, allocating $500,000 to private AI investments may seem excessive. But when you compare that to the potential $450,000–$750,000 cost of college in 2036 for each kid, it starts to look like a rational hedge.

The logic goes: if I’m willing to spend $450,000 to $750,000 on college in 2036 per kid, then I should absolutely be willing to invest $500,000 or more in the very companies that might make traditional education obsolete. Heck, I should be willing to invest $900,000 – $1.5 million in private AI companies now that I really think about it.

The Potential Returns On A $500,000 Investment

Here’s a breakdown of how a $500,000 investment grows over 10 and 20 years at different compound annual growth rates (CAGR):

“When you are in uncertainty, when you feel at risk, when you feel exposed, don’t tap out. Stay brave, stay uncomfortable, stay in the cringy moment, lean into the hard conversation, and keep leading.” ~Brené Brown

When you think of someone who’s struggling financially, you might picture someone who’s barely making ends meet, living paycheck to paycheck, just getting by. But money trouble doesn’t always look like that.

I was struggling even though it didn’t seem that way. I had a six-figure salary. I owned a home in one of the most expensive cities in the world, having bought a half-million-dollar property in my late twenties. From the outside, I had it all.

But a year into homeownership, my partner backed out of our financial agreement, leaving me to manage everything alone. Then COVID-19 hit. The government responded to the national deficit by doubling mortgage rates. Suddenly, nearly every penny I earned went toward my skyrocketing payments, insurance, maintenance fees, and property taxes. Selling my home at the right time became an anxiety-inducing gamble.

That’s the thing about financial struggles—they look different for everyone. And at some point in our lives, most of us will experience them.

During those years, the weight of my financial burden crushed dreams I hadn’t even had the chance to imagine. Along with my dreams, my mental and physical well-being and vitality were exchanged with mere survival.

Well-meaning family and friends tried to offer support, but their words often missed the mark. Telling me to “trust the universe” or “just stay positive“ only made me feel more isolated, like I wasn’t truly understood. I struggled to explain why my financial hardships felt like a barrier to my dreams, why I couldn’t simply shake them off and believe everything would work out.

While I did make it through my financial struggles, I have reflected on this period of my life. Maybe easy was never an option, but did it all have to be so hard? I also realized there’s a massive gap between the complex challenges and struggles that can arise from prolonged financial struggles and the solutions, support, and advice that we receive from others in combating them.

What Not to Say to Someone Struggling Financially

“The struggle will end when you learn your lesson.”

This idea—that struggles repeat until we find meaning in them—might be comforting in some situations, but it doesn’t apply to financial hardship. The idea that I was somehow failing to learn my “lesson” only added to my stress.

The truth is, sometimes life throws challenges at us that have no lesson attached. Some things just happen. Our job isn’t to decipher a hidden message—it’s to keep moving forward, however we can.

“You’re strong; you can handle it.”

While meant as encouragement, this statement often feels dismissive. Financial stress is relentless, affecting not just the big picture but the daily grind of survival. Instead of pushing someone to be strong, ask how you can lighten their load. Let them vent. Acknowledge their exhaustion. Strength isn’t the absence of struggle—it’s surviving in spite of it. And even strong people need a break.

“Money is just energy—align yourself with abundance.”

A positive mindset is valuable, but financial hardship isn’t a spiritual failing. People don’t struggle because they’re “out of alignment” with abundance; they struggle because of real-life expenses, job markets, and economic systems. No amount of positive thinking can pay the mortgage.

“When something changes inside you, your external world will reflect it.”

After years of financial struggle, I had no aha moment, no inner transformation or miracle, or even a slight mindset shift before my financial circumstances changed. The only thing that counted was my consistent preparation, planning, and execution of all the logistical tasks that were completed over a very long period of time. In my case, it was hard work that paid off. There was no magical moment of liberation.

“Just work on your passion after your day job.”

When you’re financially drowning, exhaustion is constant. My job required intense mental energy. Coming home and using the same cognitive muscle to work on passion projects was nearly impossible. It’s like telling a personal trainer to do intense workouts morning, noon, and night—they’ll burn out or get injured. Sometimes, survival means setting dreams aside until you can pursue them without harming yourself.

What Actually Helps

Love through Listening

As someone who has gone through a period of financial struggle, it is even impossible for me not to bring my bias, experience, and perspective into the conversation when someone shares their struggles with me. The key is to remind ourselves that we are not an expert on somebody else’s life. They are, but we can be powerful listeners. It is in our listening that we express love.

Get Into the Specifics

One of the most helpful things I experienced was having real conversations about my financial situation. Talking through an overwhelmingly large number of concerns helped me gain clarity and relief. If you want to support someone struggling, ask about their specific plans and course of action. It will help them declutter their mind and ground themselves in something they can actually control.

Provide Resources

Support doesn’t have to be financial. Helping someone find a reputable accountant, connect with another homeowner, or compare mortgage rates were all incredibly useful for me. A friend once helped me break down different bank rates and calculate my options—a simple act that made a huge difference. Another friend helped me with repairs and paints. They helped move the plan along.

Help with Decision Fatigue

Financial struggles come with endless decisions—which bills to pay first, whether to downsize, how to negotiate better rates. The questions are endless. Having someone to talk through those choices with can be a game-changer.

Remind Them of Their Leadership

One piece of advice that truly stayed with me came from Brené Brown:

“When you are in uncertainty, when you feel at risk, when you feel exposed, don’t tap out. Stay brave, stay uncomfortable, stay in the cringy moment, lean into the hard conversation, and keep leading.”

At a time when I felt anything but a leader—let alone a good one—these words resonated deeply. They didn’t focus on what should have been or could have been, but on what was: a whole lot of discomfort. My job wasn’t to crumble under pressure or lose my footing with every new challenge. It was to keep leading—myself and everyone involved—through the uncertainty, no matter how difficult it felt. That was my only job.

—

My financial struggles are now behind me—something I once thought was impossible. If you’re struggling, know that you are not alone. The weight of it may feel unbearable, but the leader inside you, the people who shoulder the journey with you, and a benevolent force greater than you can see will carry you through. As I recently read, “The horrors will persist, but so will you.”

About Kate Pejman

Kate Pejman is an engineer, climate change advocate, and the creator of The Benevolent Series. Through candid interviews and personal stories, she explores life at the intersection of authenticity, relationships, and freedom—examining both what we lose and what we gain in the process. You can find her at thebenevolentseries.com and on Instagram here.

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