If you’re new here, welcome to The BOLD Life. Each week I write about building wealth in money and in life, because the goal was never just a bigger number in an account. It’s a life that actually feels rich. If someone sent this your way, I’d love for you to subscribe.
I am systematic about my calendar. I optimize nearly every minute of the workday, and most days that means back to back meetings from 8:30 in the morning until 3:30 in the afternoon. I learned a long time ago that I need at least two hours of flex time built into that window, time for emails, phone calls, and the unexpected fires that always show up. It is a simple rule. I know exactly why it exists.
Last week, I broke it anyway. One day I let a last minute meeting pop up and take away one of my flex hours, so I only had a single hour of flex time instead of two. By early afternoon I was already behind, and the stress of being behind made me start moving faster than I should have. Somewhere in that rush, I approved two new tires for my car that weren’t the ones I wanted. I did not catch it until the end of the day, after they were installed, which meant I now had to schedule another appointment to swap them out. Wasted time, wasted money, and a mistake I made because I did not give myself room to think clearly.
But the part that actually stuck with me was not the tires. It was that I walked into my house that night carrying the frustration of a day I had rushed through, and I was short with my family over something that had nothing to do with them. The bad decision did not stay contained to my afternoon. It followed me home.
Why I Get More Upset With Repeats Than With Mistakes
I hate losing. I hate making mistakes. But nothing gets under my skin quite like making the same mistake twice. I know myself well enough to know that when I fail, I do not hide from it or make excuses. I let it sink in, not so I can wallow in it, but so I remember exactly how it felt and make sure it does not happen again. So when I catch myself breaking a rule I already learned the hard way, like my own flex time rule, I do not just get frustrated at the situation. I get frustrated at myself for knowing better and doing it anyway.
That is the part of failure most people do not talk about. It is not just the mistake. It is the argument you have with yourself afterward, the one where you already know the lesson and you still have to relearn it.
A Favor
If you enjoy this content, click the 💚 below. It takes two seconds, and it helps more people find their way to these posts. Thank you.
The Bank Note That Almost Broke Us
When something gets hard enough that most people would walk away, I have found that is often the exact moment right before things turn. My belief is that this is the best time to push forward, to push beyond the uncomfortable and get to the other side. And the other side is where all the riches lie. I have seen this play out in business more than once, but nothing tested it like 2008.
That year, I opened a letter from our bank. We had a construction loan we expected to renew for another year without issue. Instead, the letter said the note was due in full within thirty days. Roughly a million dollars. We did not have anywhere close to that sitting in cash, and no banks were taking on new loans.
I had friends in real estate who walked away from loans that year. They called it “the cost of doing business.” They handed the keys to the bank. I understood why they made that choice, but it was never going to be mine. When I sign my name on a loan, that is my word, and I do not sign my name to something I do not intend to follow through on. We brought in a partner to help carry that loan, and to stay in business through those down years, we got resourceful. We ran the company lean, and because clients could not sell their existing homes to move up into a new build, we shifted into renovation work instead, helping them improve the homes they already had.
Coming out of that stretch, we bought a self storage facility at a price that would have been unthinkable a few years earlier, using a private loan from a former client because banks were still hesitant to lend. We turned the facility around, tripled our money on it, and used that as seed capital to buy more than ten investment properties in the years since. None of that happens if we walk away when the letter arrives. It only happens because we stayed in it past the point where quitting would have been the easier, and more accepted, choice.
The Cost of Holding On Too Tight
Here is the part I have been slower to admit. The same scarcity mindset that got us through 2008 also held me back for years afterward. For a long time, my instinct was to do everything with our own money and keep ownership entirely to ourselves. It kept us lean, and it is a real reason we survived when others did not. But it also meant our growth ramped up much slower than it could have.
It took me the better part of fifteen years to fully shift into an abundance mindset, to bring in more partners, ask for more help, and lean on more mentors instead of insisting on figuring everything out myself. Once I did, I watched something interesting happen. Dividing up the pie did not shrink what I had. It let the whole pie grow so much larger that my slice of it became worth far more than the entire pie ever was when I held onto all of it myself.
Where This Shows Up for You
You do not need a construction company or an investor to feel this. You just need one place in your life right now where you are protecting a small slice instead of growing the whole pie. Maybe it is a coach you know you need but will not pay for. Maybe it is mowing your own grass every Saturday to save a hundred dollars, while your kids are inside wondering when you will finally be done so you can spend time with them. Maybe it is simply refusing to ask for help, at work or at home, because some part of you still equates asking with weakness instead of strategy. The pie only stays small because you are the one holding onto every slice.
The Pillow Test, Updated
I have always relied on what I call the Pillow Test. If I can go to bed knowing I did the best I could with the information I had that day, I sleep soundly, win or lose. I still believe in that. But I have added something to it over the years. The Pillow Test tells me whether I gave my best effort. It does not always tell me whether I was gripping too tight.
Failure is fertilizer, but only if you let it show you both things, the mistakes worth pushing through and the grip you need to loosen. Push through the moment that seems too hard for anyone else to survive. Just do not mistake that same stubbornness for a reason to carry everything alone.
Your Turn
What are you doing yourself right now that you should be handing off or asking for help on?
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.
Don’t drift. Live boldly.
If this one hit home, share it with someone who needs to hear it today. And if you have a minute, tap the heart below. It helps more people find their way to these posts, and it genuinely makes my day.
Letting go and watching people who work for me make mistakes is my challenge. I'm still working in it! Enjoy your perspective....
Love this perspective, and it is so true. Failure is Fertilizer, if we allow it to be the teaching ground. Thanks for sharing this!