#012: My 50th Birthday Episode: 10 Hard-Earned Lessons on Life, Business & Legacy

I never thought turning 50 would feel like this. There’s something about a milestone birthday that makes you reflect—like, really reflect.

As I sat on a beach in Jamaica, watching the waves roll in, I couldn’t help but think about everything that brought me to this moment. The choices I made. The mistakes I learned from. The pivots, the risks, the lessons that shaped me not just as an entrepreneur, but as a mother, a wife, a woman determined to build something that lasts.

Some lessons I learned the easy way. Most? The hard way. But now, on the other side of five decades, I can say with confidence: these are the lessons that matter most.

So today, I’m sharing 10 of the biggest, hardest, most transformative lessons I’ve learned in 50 years—and trust me, you don’t have to wait until you hit a milestone birthday to start applying them.

If you’re ready for real talk about success, failure, and building a legacy that actually means something, let’s get into it.

1. Family Is the Ultimate Foundation

No amount of business success will ever replace the people who love you at your worst, who cheer you on even when you don’t believe in yourself.

For years, I thought balance meant dividing my time equally. Now, I know balance is about presence. When I’m with my family, I want to be with them. Not half-listening while answering emails. Not brainstorming my next big launch while we’re at the dinner table. Fully there.

This trip to Jamaica was a reminder of that. The sound of the waves, the laughter, the feeling of being present—it hit me hard. We build businesses for freedom, for flexibility, for more time with the people we love. But are we actually taking that time?

If you take nothing else from this post, take this: be present with the people who matter most.

2. The Power of Saying No to Protect Your Yes

When I was younger, I said yes to everything. Every opportunity. Every request. Every collaboration.

I was afraid saying no would make me seem ungrateful. That I’d miss my “big break” if I didn’t say yes. But all that yes-ing? It stretched me thin, burned me out, and left me exhausted.

Here’s what I finally learned: every no is actually a yes to something else.

✔️ When I say no to clients who aren’t the right fit, I say yes to the ones I can serve best.
✔️ When I say no to late-night work, I say yes to my well-being.
✔️ When I say no to projects that don’t align, I say yes to my purpose.

So let me ask you: what do you need to start saying no to so you can finally make space for the yeses that actually matter?

3. You’re Never Too Old (or Too Young) to Reinvent Yourself

There’s this myth that by 30, 40, or 50, you should have life “figured out.” That you should stick to the path you’re on because changing now would be too late.

I call BS.

I left a successful nonprofit career to start an online business in my 40s. I had no roadmap, no guarantees—just a gut feeling that I was meant for something more. And let me tell you, that leap? It was terrifying. But it was also the best decision I ever made.

Maybe you’re feeling that pull too—the one that whispers, This isn’t it. There’s more for you. If so, hear me loud and clear: you are not too late, too old, or too behind. Reinvention doesn’t have an age—it has a decision.

4. Success Is Built on Small, Consistent Actions

We love the idea of overnight success. The viral moment. The big break.

But the truth? Success is the sum of a thousand small, boring, consistent actions.

💡 Sending the emails when no one is responding.
💡 Showing up on social media when you feel like no one is listening.
💡 Selling your offer even when it feels uncomfortable.

I know how frustrating it is when it feels like your hard work isn’t paying off fast enough. But trust me—the work you’re doing now is laying the foundation for the success you’ll see later. Keep going.

5. Your Purpose Isn’t Optional—It’s Non-Negotiable

I used to think purpose was this nice bonus in business—like something extra you could layer in if you had time.

Now I know: your purpose is the foundation of everything.

If you’re feeling lost, stuck, or unfulfilled in your work, ask yourself: Am I actually aligned with my purpose? Or am I just following what I think I “should” do?

The moment I stopped trying to fit into someone else’s mold and started leading from my own mission? Everything changed.

6. Failure Is Just Feedback

For years, I took failure personally. I thought if something didn’t work, it meant I wasn’t good enough.

But the best entrepreneurs I know don’t fear failure—they use it as data.

💡 A launch that flopped? It’s telling you what needs to be refined.
💡 A client that wasn’t happy? It’s showing you where you can improve.
💡 A strategy that didn’t work? It’s guiding you toward what will work.

The sooner you stop fearing failure and start seeing it as a tool for growth, the faster you’ll succeed.

7. Money Is Not the Enemy of Good

I used to believe that making money and doing good were two separate things. That if I really cared about impact, I shouldn’t expect to be paid well for it.

That belief kept me broke.

Money isn’t the enemy—it’s a tool. And when you have more of it, you can do more good. Period.

Charge what you’re worth. Get comfortable selling. Stop apologizing for wanting financial success.

Your mission deserves to be funded.

8. Perfection Kills Progress

If I had waited until I felt “ready” or until everything was perfect, I wouldn’t have a business. Or this podcast. Or this blog.

Done is always better than perfect. The faster you take messy action, the faster you learn, grow, and get better.

9. Ask for Help—You Don’t Have to Do It Alone

The most successful people I know? They aren’t the ones who do it all themselves.

They hire coaches. They join masterminds. They lean on their community.

Stop trying to be a one-woman show. The faster you ask for help, the faster you grow.

10. Legacy Is About More Than Money

At 50, I’m thinking a lot about legacy.

Not just what I build, but how I make people feel. The relationships. The impact. The ripple effect of the work I do.

And I know you feel the same.

So ask yourself: What’s the mark you want to leave? What’s the story you want to be told about you? Because your legacy isn’t in the future—it’s in the way you show up today.

Let’s Keep the Conversation Going

This episode is so close to my heart, and I’d love to hear which lesson resonated with you the most.

💬 Join the conversation in The Business of Good Collective!
📲 Tag me on Instagram @janditchfield.co and share your biggest takeaway!

Here’s to the next chapter—whatever that may look like. 🚀