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Hi, Reader,

Do you have a music artist you’ve been listening to since you were a teenager?

This week, my wife went to see Hilary Duff at Madison Square Garden. If you grew up in the early 2000s, you probably remember her from the Disney show Lizzie McGuire or songs like Come Clean.

I was never a huge Hilary Duff fan myself, but I was pretty amazed by what I saw. More than 20 years after becoming famous, she had sold out Madison Square Garden for two nights in a row. And it wasn’t just that she was still relevant.

She sounded great. She looked fit and healthy. She is married, has four kids, and somehow still seems to be thriving more than two decades into her career.

What’s wild is that toward the end of the show, she brought out a surprise guest I hadn’t thought about in years…Good Charlotte (remember them?). So naturally, I went down a rabbit hole. Turns out, they’re still making music. They have families of their own. They’ve expanded into producing and running a record label. Benji Madden is even married to Cameron Diaz.

And it got me thinking: Why do some people burn incredibly bright for a few years and disappear, while others seem to keep getting stronger?

Not just in their careers. In their health. Their relationships. Their energy. Their overall lives. What does it take to build success that doesn’t just last for a few years, but compounds over decades?

I think there are a few things we can do today to dramatically improve our odds.

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Stop Managing Your Time

I have a confession…and I’m not afraid to admit it.

I’m a workaholic. I love working. Mornings, nights, weekends, even vacations. I’ve mostly accepted that this is just who I am.

But over the last few years, I realized I was optimizing for the wrong thing.

I was optimizing for time.

My calendar was open for meetings whenever I was at my desk. Slack was always on. My inbox was always open. Every day, I’d work my way through a task list until it was time for bed.

Some days I felt invincible. Other days I’d look back and wonder what I had actually accomplished.

What I eventually realized was that managing my time mattered far less than managing my energy.

I came across a great book called The Power of Full Engagement, which breaks our performance into different states based on our energy and mood.

The place we want to spend our time is Peak Performance. High energy, positive mood, strong output, creative ideas, feeling “on.”

But you can’t stay there forever.

Peak performance requires recovery.

Almost everything in life has an ebb and flow. Push, recover, push again. If you ignore the recovery part for too long, eventually your body and mind force it on you in the form of burnout.

My days look very different now.

Instead of letting my schedule run me, I run my schedule. I block time for deep work. I generally take a break every 90 minutes. I shut off notifications when I need to focus. And I have help managing my inbox and calendar.

Not just to save time. To save energy.

The result is that I’m more productive, I enjoy my days more, and when one day ends, I actually have something left for the next one.

But managing your energy can only help you survive the short term. The bigger question is how you keep doing it for decades.

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Built to Last

I come from a family of entrepreneurs. My family immigrated from Afghanistan and Iran with very little, and by the 1970s, many of them were building thriving jewelry businesses. By 1980, diamond prices had exploded. A benchmark one-carat D-flawless diamond that sold for around $10,000 wholesale in the mid-1970s had reached roughly $62,000.

Life was good. My father was part of that world too. But eventually, things changed.

The jewelry business went through a difficult transition, and my father wanted out. My family went through some financially difficult years after that, and as a kid, I grew up with a constant sense that money wasn’t always secure.

But what interests me most looking back isn’t that my father chose the wrong industry. He didn’t. Jewelry had made a lot of people very successful. Plenty of people are still very successful in it today.

The more important detail is that my father never really loved jewelry in the first place. It was a career he had largely been pushed into by the generation before him.

When business was booming, that didn’t matter much. The money was coming in. The opportunity was there. There wasn’t much reason to question it.

But when things got hard, suddenly it mattered a lot.

Because eventually, every career, business, relationship, and pursuit goes through a period where the external rewards aren’t enough to carry you.

And those moments reveal something that success can hide: Do you actually want to keep going?

That’s where the Japanese concept of Ikigai comes in. It’s the idea of building your life around the intersection of what you love, what you’re good at, what the world values, and what you can be paid for.

To me, the question isn’t what will pay the most today. It’s what you care enough about to keep investing in when things get hard, because that’s what has the chance to compound for decades.

I’ve been thinking a lot about what I want my life to look like over the next 10 to 20 years.

It’s a tough exercise. The present is right in front of me, and patience has never exactly been my strength.

But I think about Hilary Duff standing on that stage more than 20 years into her career and wonder: What will people be saying about me when I’m that far into mine?

Last month, I ran my first-ever virtual summit: The Strategic Finance Summit. I didn’t exactly sell out Madison Square Garden, but more than 3,000 people attended live, with the average attendee watching for about 3.5 hours. That stat blew my mind.

More importantly, I probably had more fun doing it than almost anything else in my career.

So what’s my game plan? I’m reaaaaaaally passionate about strategic finance, and I want to spend the next several years building Model Wiz into the #1 financial reporting tool for strategic finance professionals. We have a long way to go. But I genuinely love what we’re building, and I’m in it for the long run.

And when it comes to events, I feel like I’m just getting started. I have some pretty massive ideas for where I want to take them, and hopefully I’ll have more to share soon.

Until then, I want to hear from you:

What are you investing in today that you hope will still be paying dividends 10 or 20 years from now?

Hit reply. I read every response.

Have a great weekend, and make sure you get some recovery in.

Josh

Your CFO Guy