The Trap of “I’ll Be Happy When…”
This past weekend, my husband and I went to see Sweeney Todd at UCSB’s student-run musical theater production, where my daughter Chloe had been volunteering endless hours to help put on the show. As we sat there, waiting for the curtain to rise, I had a moment where I realized I felt fully at peace.
Not just in that moment—but throughout the past week, I’ve been feeling truly present, balanced, and at ease. My work has felt good, my personal life has felt full, and I wasn’t caught in the endless cycle of trying to catch up with my many projects, feeling stressed out, or overworking.
And let me be honest… that is not every week.
For years, I operated in survival mode—pushing myself to achieve and constantly second-guessing whether I was doing enough. Even when everything looked successful on the outside, I had this voice inside whispering:
"What if I can’t actually run a business?"
"Am I doing enough?"
"What if I said yes to too many things?"
I kept searching for some kind of reassurance—proof that things were stable, that I was on the right track. I imagined that one day, I’d finally arrive—to a place where I had it all figured out, where the pressure would ease, and I could finally exhale.
And until then? I thought I had to keep pushing.
I told myself I’d focus on my well-being later, after I had “earned” it. Because that’s what everyone does, right? Stress, overwork—even burnout—is so deeply normalized.
One of the biggest mindset traps I see—both in myself and in the leaders I coach—is the belief that “I’ll be happy when…”
When I get that promotion.
When I have more time.
When I hit the next milestone in my career or business.
Here’s what the research shows (and something I learned firsthand when I started researching happiness and personal fulfillment over 10 years ago): we think reaching the next level will finally make us feel happy—but that’s not how our brains actually work.
The Hedonic Adaptation Principle explains that while we believe external achievements will bring lasting happiness, we quickly return to our baseline after each accomplishment.
Which means: if we’re constantly chasing the next thing, waiting to feel at peace later, we miss the opportunity to create fulfillment now.
One of the things that helped me shift? Mindfulness.
A couple of weeks ago, I celebrated with a cohort of nearly 1,000 teachers from all over the world as we completed a two-year mindfulness meditation teacher training, guided by the incredible Tara Brach and Jack Kornfield through the Awareness Training Institute and UC Berkeley’s Greater Good Science Center.
And while I can’t say my practice is perfect (because honestly, whose is?), I now know how to bring myself back when I start spinning out. I don’t shame myself when I fall off track, and I don’t let hours or days go by before I remember to pause and breathe again.
I now know the value of having a calm nervous system so I can make decisions intentionally, not from a place of fight-or-flight. That ability—to reset, realign, and lead from a place of presence rather than pressure—has changed my life.
“Realize deeply that the present moment is all you have. Make the now the primary focus of your life.”
—Eckhart Tolle
I’ve seen firsthand how this shift—from reactive mode to thoughtful response in how we make decisions, work, and communicate—creates ease in every aspect of life.
And it’s one of the reasons I’m so excited to share that I’m offering the Inside-Out Leadership Accelerator (IOLA) again this year—my signature 8-week program that has supported dozens of leaders over the past four years.
This time, it’s even better.
I’ve updated it based on what I’ve learned over the past two years—from coaching high-achieving leaders, teaching workshops, and deepening my own practice through mindfulness training.
Inside IOLA, we’ll cover how to:
Break free from survival mode and self-doubt so you can lead with confidence and ease.
Prioritize what truly matters instead of feeling pulled in a million directions.
Speak up powerfully and navigate tough conversations without over-explaining or people-pleasing.
Set boundaries and delegate effectively—without guilt.
Redesign your leadership rhythms so your work and personal life feel sustainable.
Registration for IOLA Opens Monday, February 17th
To make this an easy yes if you need the support, I’ve dropped the typical price, added a payment plan option, and created a scholarship for those who need it.
I expect this round of IOLA to book up quickly—clients have already been signing up! If you’ve been considering this program, I’d love for you to apply for the program directly on the site or reach out to me with any questions.
And to kick things off, I’m hosting a workshop in two weeks:
Lead & Succeed Without Sacrificing What Matters Most
Friday, February 28th at 9 AM PST
This FREE workshop is designed for leaders who are tired of feeling stretched thin—caught in a constant push-and-pull between work, personal life, and their own well-being. It’s time to step into a new way of leading, working, and living that actually feels good.
We’ll explore:
The 3 biggest mindset traps keeping high-achieving leaders exhausted—and how to shift out of them.
Why presence—not perfection—is the key to feeling fulfilled.
How to set boundaries that honor both your desire for impact and your personal life.
Save your spot below - simply add the workshop to your calendar.
I look forward to seeing you there!
And whether or not you join us, here’s my invitation to you this week:
Reach out to your people. The ones who truly get it. Maybe that’s a friend, a mentor, or a group of women who make you feel safe enough to be honest.
Because when you start talking about what’s actually going on—the self-doubt, the exhaustion, the questioning—you’ll realize you’re not alone.
We’re all struggling and learning and growing every single day.
And you are not failing, no matter what your inner critic says.
The challenge isn’t in doing it all—it’s in creating a way of leading and living that is sustainable, aligned, and fulfilling.
XO,
Ramona
