Defining Success at 50
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Jen: I’ve been thinking about how our definition of success changes with each decade. What it meant in our 20s isn’t what it means now.
Theresa: In my 20s, success meant looking the part. I wanted the job title, the business suit, and the credibility that came with both. I spent years trying to prove I belonged in rooms where people thought I was too young.
Jen: Same. I started a business at 19 and thought I was ahead of the game. Then I got my first salaried job, $30,000 a year, and thought I’d arrived. Until I realized a salary just means you get paid the same no matter how many hours you work. I spent most of that decade chasing levels and titles. “Director by 30” was my North Star.
Theresa: I had my version of that too - wanting the next title, the next raise, the next rung. I look back now and realize how much of that drive was about validation.
Jen: Exactly. I don’t regret it, but I see now how success in my 20s was about proving something, mostly to myself.
Theresa: By my 30s, things shifted. I moved to New York, found my footing, but also found anxiety. I was good at what I did, but constantly wondering if anyone could tell I didn’t have it all figured out.
Jen: My 30s were split down the middle: before kids and after. Before, I was obsessed with being in the room where things happened. Afterwards, everything revolved around flexibility. The ability to send an invoice and still make it to soccer practice became my new metric for success.
Theresa: That’s it. It stopped being about achievement and started being about alignment - how work fit into life, not the other way around.
Jen: My 40s were the decade of letting go of proving. I started saying no more often. I stopped trying to earn my worth. I realized that being confident in my expertise didn’t make me arrogant - it made me grounded.
Theresa: I had a similar shift. I left a corporate role after 14 years. It felt like a divorce. But it also gave me clarity about who I am and what I love doing. I rediscovered my “zone of joy” - the intersection of what I’m good at and what lights me up.
Jen: Now, at 50, success feels different again. It’s not about scale or status. It’s about agency - choosing where my time and energy go, and why.
Theresa: Same. It’s not that we care less; it’s that we care more selectively. There’s this freedom in not needing to prove or please.
Jen: I think that’s what confidence at this stage really is. Not louder, just quieter. Steadier.
Theresa: If I could give advice to anyone still figuring it out, I’d say this: write down what your imposter voice tells you, then throw it out. Those old stories don’t deserve a seat at the table.
Jen: And start with joy. If you don’t know what’s next, look for what makes you come alive, not what you think should make you come alive. You might have to give up some of those 'shoulds' you've been carrying around for years.
Theresa: We’ve spent decades proving ourselves. Now we get to define ourselves. I've never felt more settled.
Jen: I love that. New definitions, more joy, all on our own terms. I'm here for it all.