On July 30, with just 72 days until my 50th birthday, I decided it was time to make a list. And, in typical Jenn fashion, it was a long one.
50 things I wanted to do before turning 50.
So I sat down and put myself in my future self state of being fifty years old and looked backwards at what I accomplished in the previous 72 days. I wrote some big goals. And some goals that were ridiculously small (this is a great trick to help you stay motivated!).
Some were about my health, business, adventure, relationships, joy, or doing things I’d been putting off.
And yes, looking back, attempting to accomplish 50 things in 72 days while also running a business, speaking, launching a book, and living an actual life may have been slightly ambitious. But that turned out not to be the point.
The list gave me permission to pay attention to what I actually wanted. To mark a milestone birthday with greater intention and focus.
And after sharing pieces of my 50 Before 50 journey on Instagram, I started hearing from people who wanted to make their own. So I’m sharing the whole thing here, including what I did, what I didn’t do, and how you can create your own milestone list at any age.
Why I Created a 50 Before 50 List
Milestone birthdays have a way of making you take inventory. Not just of what you’ve accomplished, but of how you’re actually living.
As 50 got closer, I started to ask:
What would make these next 72 days feel more alive, meaningful, and deeply fulfilling for me?
What had I been putting off?
What did I want to experience?
What would make me healthier?
What would move my business forward?
What sounded FUN?
What would help me enter my next decade feeling strong, healthy, joyful, deeply connected, and excited about the life I was creating?
That’s how 50 Before 50 was born.
My Actual 50 Before 50 List
I divided my list into five areas: Experiences & Adventure, Health & Vitality, Business & Legacy, Celebrate This Chapter, and Joy & Presence.
And because apparently I know myself, I also gave myself two wild cards.
✨ Experiences, Adventure & Self Care
- Go to the ABBA tribute at the Hollywood Bowl ✓
- Go to one more concert ✓
- Get a facial ✓
- Get a massage ✓
- Spend a day at the beach with no agenda ✓
- Host my 50th birthday party ✓
- Eat at Ladyhawk in West Hollywood ✓
- Go whale watching ✓
- See a psychic, intuitive, or healer ✓
- Attend the Dr. Joe Dispenza retreat ✓
- Take my Bellingham trip ✓
- Plan my NYC trip ✓
- Ride a horse ✓
- Go to a movie premiere ✓ (Watched a premiere of my friend, Sharzad Kiadeh’s movie, What Now?)
💪 Health & Vitality
- Strength train three times per week ✓
- Take my Omega-3 + Vitamin D every day ✓
- Increase my daily fiber intake ✓
- Do at least one walking meditation
- Complete at least three virtual Coherence Healing sessions
- Daily red light/face therapy ✓
- Finally get my Function Health bloodwork done after putting it off for a year and a half because I’m terrified of needles ✓
This ended up becoming a much bigger project than I anticipated. I joined Function Health as an ambassador and got a full-body MRI, which gave me an entirely different look at proactive health and longevity as I entered this new decade.
Read about my Function Health and full-body MRI experience here.
🚀 Business & Legacy
This category may have gotten a little out of hand.
- Book at least two speaking engagements for 2026
- Book at least three speaking engagements for 2027
- Book a high-profile podcast
- Receive three high-profile blurbs for Secrets of the Sensei ✓
- Have coffee with someone who inspires me ✓
- Land one dream keynote client
- Reach a new personal best for The Art of Badassery podcast ✓
- Finish the strategy for the next era of The Art of Badassery podcast
- Have one day where I think, “This is exactly the business I want to build.”
- Book at least one 1:1 VIP Retreat Day client ✓
- Plan my next retreat
- Complete my Secrets of the Sensei photo shoot
- Write 10 handwritten notes ✓
- Go to at least one networking event ✓
- Hire a full-time VA ✓
- Complete an SEO project ✓
- Get my coaching page launched ✓
- Upgrade my laptop ✓
One of the biggest milestones on this list wasn’t really one item at all.
It was watching the next chapter of my work begin to take shape.
My new book, Secrets of the Sensei: Emotional Self-Defense for Protecting Your Peace and Reclaiming Your Power, comes out February 23, 2027.
Writing and preparing this book for the world has been one of the biggest projects of my 40s, and watching it become real as I approached 50 felt pretty damn special.
Read more about Secrets of the Sensei and preorder your copy here.
🎉 Celebrate This Chapter
- Wear my new green outfit ✓
- Wear my vintage kimono ✓
- Buy new bedding ✓
- Buy a piece of jewelry to celebrate turning 50 ✓
- Write a letter to my 51-year-old self
I love this category because not everything needs to be about improving yourself.
Sometimes you should just celebrate yourself.
❤️ Joy & Presence
- Spend a day completely offline ✓
- Finish books on nightstand: Sit With Me and Being 40
- Take husband on a surprise date ✓
- Do one thing that scares me, in a good way ✓ (i did at least 10 big asks for my book)
- Watch the sunset with a glass of wine ✓
Looking back, I love this category because what good is building a life you’re proud of if you’re never actually present enough to enjoy it?
Want to Create Your Own Milestone List?
Here’s what I learned: you don’t have to be turning 50.
Make a 30 Before 30.
A 40 Before 40.
A 60 Before 60.
Twenty-seven things before 2027.
Fifty things you want to experience over the next five years. The number doesn’t really matter. The deadline gives it energy. The list gives it intention. Start by asking yourself:
What have I been saying “someday” about for way too long?
- Where do I want to go?
- What do I want to experience?
- What would make me feel more alive?
- What do I want to learn?
- What would make me healthier or stronger?
- Who do I want to spend more time with?
- What have I been putting off?
- What do I want to create?
- What sounds ridiculously fun?
- What scares me in a good way?
- What would my 80-year-old self be thrilled I did?
- What would make this chapter of my life feel meaningful?
Then start writing. Don’t edit yourself too much. And definitely don’t make everything impressive.
Your List Shouldn’t Be Another Way to Pressure Yourself
This may be the biggest lesson I learned from the whole experiment. A milestone list shouldn’t stress you out. Not everything in life needs to be urgent. Some things take more time and that’s OK.
Let this list be a chance to prioritize your self-care and wellbeing. Even when life doesn’t go as planned, you can still find joy, feel fulfilled, and make time for what matters to you. Focus on the things that help you feel your best, so you can step into your next milestone birthday feeling energized, grounded, and more connected to yourself.
Put get a massage on there.
Go see a concert.
Eat somewhere you’ve been wanting to try.
Buy the bedding.
Watch the sunset.
Call someone you love.
Do something simply because it sounds fun.
And give yourself permission to change the list.
That’s why I included wild cards on mine. Life changes. You change.
Did I Finish All 50 Before 50?
Nope. You can see all my checkmarks (and non-existent checkmarks) above as of Oct. 12, 2026. And I’m okay with that. Some things happened exactly as I imagined, while others haven’t happened yet. And that’s okay. I’m still working toward them.
The list did exactly what I hoped it would: it made me pay closer attention to my life and helped pull me out of autopilot.
It pushed me to prioritize experiences I’d been putting off, invest in my health, move important business projects forward, celebrate my wins, make plans, have more adventures, and think intentionally about the woman I wanted to become as I stepped into this next decade.
My theme for 50 was:
I’m stepping into this next decade feeling strong, healthy, joyful, and deeply connected while building a life and business that reflect the person I’m becoming.
I didn’t need 50 checkmarks to do that. I just needed to start living like that woman with more consistency.
So IF this sounds fun and exciting to do, don’t put it off! Trust me, the longer you have before your milestone, the better. 72 days didn’t give me the luxury of putting certain bucket lists items on the list, like “celebrate in an Italian villa”. So, I had to be more realistic.
Now your turn:
Pick a milestone.
Pick a deadline.
Write down what you want.
And then go live some of it.
50 years of badassery. And counting.
Secrets of the Sensei
Is Available for Preorder Now
Secrets of the Sensei: Emotional Self-Defense for Protecting Your Peace and Reclaiming Your Power will be published by Tarcher/Penguin Random House on February 23, 2027.
And you can preorder your copy now at Amazon, Barnes & Noble, Booksellers, Penguin Random House, Books A Million, Walmart, Target or at your favorite local bookstore.
Preorders are incredibly important for a new book. They help publishers, booksellers and the larger book world see that there is demand before publication day arrives. Most importantly to me, every preorder means these ideas have a chance to reach another person who may need them.
So if you’ve ever learned something from me, trained with me, heard me speak, listened to my podcast, read The Art of Badassery, or simply believe that the world could use a little more calm, courage and Big Sensei Energy right now, I’d be incredibly grateful for your support.
PREORDER SECRETS OF THE SENSEI
Thank you for being part of this next chapter.
We can’t control the chaos around us. But we can train for how we meet it.
See you in the dojo. 🥋
Jennifer Cassetta
Keynote Speaker | Author | High-Performance Coach | Third-Degree Black Belt
Looking for a Women’s Leadership Keynote Speaker in California?
Jennifer Cassetta is a California-based keynote speaker, women’s leadership speaker, third-degree black belt, executive coach and author of The Art of Badassery and Secrets of the Sensei.
Her interactive leadership keynotes combine martial arts wisdom with modern strategies for resilience, confidence, wellbeing and high performance. Jennifer speaks at women’s leadership conferences, corporate events, association conferences and professional development events throughout California and across the United States.
Popular keynote topics include women’s leadership, Black Belt Leadership, resilience, burnout prevention, confidence, high performance, boundaries, energy management and leading through change.
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Jennifer Cassetta
Website: jennifercassetta.com
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