Is It Time to Upgrade Your Operating System?

The companies that win never stop updating. Neither should you.

“So what are you not eating this month?”

My wife asks me this with a little smirk, usually right after I announce I’m tweaking my diet. Again. She’s not wrong. I’ve changed how I eat more times than I can count. In my 20s, I lived on a pantry stocked with pasta, Ragu, and apple juice (it was cheap eating!) and never slowed down. Now if I eat carbs on an empty stomach, I’ll see you in a few hours, because I need a nap.

Here’s what I’ve realized, though. My phone updates itself every few weeks, and I never think twice about it. I let it move the icons, change the layout, rewrite the whole system. Meanwhile, most of us are running our health, money, and relationships on a formula we built ten or twenty years ago.

Our phones get more updates than we do.

The Company That Stopped Upgrading

Do you remember Yahoo? There was a time when Yahoo was the internet, the front door for millions of people going online. At its peak in January 2000, Yahoo was worth about $125 billion. Around 2002, Yahoo had a chance to buy a scrappy little search startup called Google for roughly $5 billion, and Yahoo said it was too expensive.

From there, Yahoo rested on its laurels while Google kept getting better. Faster search, then email, then maps, then phones, then cloud, then AI. Update after update after update. In 2016, Yahoo agreed to sell its core business to Verizon for about $4.8 billion, less than what Google would have cost them fourteen years earlier. Google’s parent company, Alphabet, is now worth over $4 trillion.

One company kept upgrading. The other one drifted.

The Scorecard

Elon Musk is the richest person in the world, worth roughly $900 billion depending on the day. Financial riches aren’t everything, but in business they’re a pretty clear scorecard. How did he get there? He never stops upgrading. Electric cars, self-driving cars, satellite internet, rockets that land themselves. He doesn’t sit back and admire his last win, because he’s already pushing on the next one. You don’t have to like the guy to learn from the pattern.

Now Apply It to You

I’m a big believer that making regular progress is one of the biggest drivers of happiness. Not hitting some finish line, just growing. And if growth drives happiness, then the formula for that growth needs to be reviewed and upgraded regularly, too. What worked at 25 won’t work at 45.

I focus on three big areas of life: health, money, and relationships. They’re the three areas no one else can control for you, and each one needs an occasional upgrade.

Health: Your Body Gets Updates Whether You Want Them or Not

My constant diet tweaks aren’t me being fickle. They’re me paying attention. Your body changes over time, and your metabolism slows down, so you simply don’t burn what you used to. The diet that fueled you at 25 can drag you down at 50.

I monitor my health regularly with bloodwork from my doctor and Function Health. Despite eating healthy, I have elevated cholesterol, and it’s hereditary. Historically, I haven’t eaten much red meat, but last year I decided to eat it more regularly, making sure it was lean and grass-fed. The result? My cholesterol numbers went way up. So my diet now is back to minimal red meat.

I’m also eating bread for the first time in years. It’s homemade sourdough that my wife makes from scratch, and real sourdough without store-bought additives has a relatively low glycemic index, which for me means no carb crash. I’ve been enjoying it dipped in olive oil and pepper. How will my numbers change? I’ll find out in a few months.

Exercise has changed for me too. When I was young, the goal was stronger and stronger. I still want to be strong, but now I have to be smarter about it because injuries take much longer to recover from than they used to. A big part of figuring out what to upgrade is testing. Just as I track my health with bloodwork, I check my body composition with an annual DEXA scan. I just did one last week, and the results show I need to improve my glute strength for a more even distribution of muscle mass. As much as I hate leg day, it’s about to become a bigger focus.

Same goal. Upgraded formula.

Money: Your Relationship With It Should Evolve Too

Money changes over time. Give it enough time and compounding works its magic. But your relationship with money should change too.

When I was younger, I thought being rich was the secret to happiness. As I’ve matured, I’ve learned that money buys freedom. It amplifies who you already are and can feed the values you care about, but money by itself doesn’t make you happy. And the older you get, the more obvious it becomes that you can’t take it with you. As my mom loves to say, “There’s no U-Haul behind the hearse.” So spend it while you can, on experiences with the people you love. I’m constantly thinking about and looking forward to that next vacation with family and friends.

Relationships: Nothing Stays the Same on Its Own

Think about how your relationships with your parents, your kids, and your spouse have changed over the years, from the honeymoon phase to years, even decades, later. Any relationship you don’t act on will slowly drift to a stop. Not because anyone did anything wrong, but because nobody did anything.

So make some tweaks. Text a friend you haven’t talked to in a while just to say you’re thinking about them. Plan something exciting with your spouse to bring back a little of that old spark.

Here’s my tweak. Before I drive anywhere by myself, I ask, “Who can I call during this drive?” Most of my solo drives happen during business hours, since my family is usually with me the rest of the time, so it’s often a work call I’d normally make from the office. It’s a better use of my time. If I don’t have a call to make, I put on a podcast. Recently, though, I made a list of old friends I haven’t talked to in a long time and started reaching out. It’s been great. This week, I caught up with a former employee I hadn’t spoken to in a couple of years, and it was awesome to hear about everything he’s up to these days.

Don’t stick with the routine of hopping in the car and listening to your favorite talking heads. Use that time to make your life better, and the life of a family member or friend. Life is about relationships, so remember to turn them on.

Habits of Upgrading vs. Habits of Drifting

We all get stuck in our daily routines, and habits are amazing. Just make sure yours are habits of upgrading, like the best tech companies, and not habits of drifting through the same routine year after year. Technology evolves. Life evolves. You need to evolve too.

Start Bold

Run a diagnostic. Pick one area (health, money, or relationships) and ask yourself: am I still running the same formula I was five years ago?

Install one update this week. Just one change. Add ten minutes of stretching, bump up an automatic investment, or plan a date night.

Reach out to someone you’ve drifted from. Send the text today. It takes 30 seconds.

Your Turn

What’s one area of your life still running on an outdated operating system? What’s a small tweak you can make today? If you’re willing to share, I’d love to hear about it in the comments.

Minor in money. Major in life.

Don’t drift. Live boldly.

The BOLD Life is for people who want to build wealth without losing themselves in the process - people who want their success to strengthen their health, relationships, purpose, and freedom rather than compete with them. If that’s the life you’re building, you’re in the right place. New here? Start with The Blueprint of a BOLD Life, then read whatever draws your attention. Every post stands on its own.

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