I’ve never been good at asking for what I want. My go-to strategy has always been to undervalue my own work while working myself to the bone. In the moment, it felt noble — heroic, even. But over time, it carved out a hollow space in me. A space where the amount of effort and the true value of what I was doing never quite line up.
I started to believe that my worth was measured by how cheaply I could deliver something, not by how much I had to offer.
Of course, that’s where business differs from life. In life, we do things all the time where effort and money don’t correlate— nobody’s going to pay me to mow my own lawn. But in business? It’s different. And over the past few weeks, I’ve been trying to remember that difference.
I sent out three proposals for custom software solutions. I’ll admit: with two of them, the numbers made me uncomfortable. I ran them over and over, making sure they were fair — maybe even a little on the high side. But for the first time in a long time, I didn’t flinch (okay, maybe just a little). I sent them anyway. Because they reflected the real value of my time, the complexity of what I was offering, and the expertise I’ve spent more than twenty-five years building.
One proposal went out then the client ghosted me. By the end of the week, my old instincts kicked in — “slash the price, do whatever it takes to get the work.” But I didn’t do it. I left it alone. Because I’m starting to believe that bravery in business isn’t about cutting your prices in half to be accepted — it’s about holding your ground and trusting that the right people will see what you’re worth.
The second proposal was rejected at first. The client told me flat out: “You can nickel and dime me to death, but don’t send me big invoices.” That stung. But I didn’t cave. And later in the week, he came back — still a little ruffled about it, but he approved the project anyway. My schedule’s full now, so he’ll have to wait a few weeks. But that’s another small case study in not undervaluing myself.
One of the most important lessons I’m learning is that a brave life isn’t about big gestures or public-facing courage. Most of the time, it’s about small, personal decisions that you make:
- Saying no to work that isn’t worth the cost.
- Saying yes to more time with family.
- A big one: noticing when you’re about to give in to old behaviors and choosing not to.
This week, I spent more time with my wife. I went to my youngest daughter’s year-end choir concert (which was, literally, world class). I reached out to my two oldest kids, just to check in. These aren’t the things that show up on a résumé. But they’re the things that make me feel like I’m actually living — not just grinding through another week.
I think we undervalue bravery in everyday life. A brave life, I’m starting to learn, is one that’s intentionally focused on what matters. It’s making decisions that might go against the grain — like saying no to a project that doesn’t value your time, or saying yes to something that doesn’t pay you a dime but fills you up in ways that matter more.
I don’t have this all figured out. I still hesitate. I still worry about money. I still feel that old fear of being forgotten or seen as “less than.” But I’m trying to believe that a brave life isn’t about proving my worth to everyone else.
It’s about finally believing it for myself.
And for now, that’s enough.
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