Realizations Over Resolutions: Ask These 5 Questions to Make 2025 Your Year
Plus the one area of life most people don't plan for at all.
Bless… but honestly, resolutions are overrated.
This morning the fam and I sat in a circle on the beach and we each took a turn and shared some of our goals for 2025. But the conversation was different than I think what most folks talk about when it comes to creating a life you absolutely love.
You know the typical drill: pick a few goals you think are the things that will make you happy if you achieve them, and stick’m on a list. Then, promise yourself this is the year you’ll finally tackle them.
But here’s the thing—most resolutions aren’t designed to make a regular person feel more enlivened or fulfilled. They’re built on what we think we should do. Getting stuff done. Stuff like losing weight. Reading more and scrolling less. Or making more money. An article published in late 2024 even showed that when people focus on happiness as the endgame, they will likely end up feeling less happy. (Which is why I think some people inherently want to vomit when you even mention the word ‘goal,’ and avoid the conversation at all costs)
But here’s what I realize:d:
1. Those goals are often be shoulds in disguise.
2. those goals typically don’t reflect the life you actually want. Or who you need to become to live that life.
3. They reflect someone else’s rules, and are rooted in the idea of pursuing happiness through achievement, instead of pausing to ask: What truly matters?
What if, instead of chasing someone else’s definition of success, we asked questions of quality—questions that guide us toward a life filled with meaning, joy, and authenticity?
I started this process of goal setting in a different way almost ten years ago. Before that, I was living on autopilot, chasing the “next thing” that I thought would make me happy without stopping to reflect. And, most importantly, I wasn’t thinking about where all this goal achieving was even taking me. I was simply climbing a ladder to nowhere, checking off boxes that I thought would compensate for the feelings I had experienced so much of my life that made me feel somewhat not quite enough.
It wasn’t until I met someone in a business mastermind who generously shared with me her approach to goal setting that things began to change. This approach was different from anything I had ever done before because it asked me to pause and reflect, to create a picture of what I wanted my life to look like not just for the next year, but for the long term, and to start asking myself better questions—deeper ones—to start identifying the patterns holding me back and the opportunities waiting to guide me forward.
So today, I thought I would share the five questions I return to every year—questions that have helped me create a life lived with intention, joy, and a deep sense of meaning.
Step 1: Savor the Wins (and the WTFs)
I start with the basics:
What worked this year?
What didn’t?
Here’s why this is so impactful: without reflection, we can’t learn. Too often, we rush forward without pausing to see what actually lit us up, what drained us, or what we’re carrying that no longer fits.
When I look back at what worked, I’m giving myself permission to celebrate—not just the big milestones, but the small moments that brought me joy or ease. And for a person who is consistently battling the negative cognitive bias most of us have to battle daily, realizing what is working feels fucking good.
And, when I ask myself what didn’t work, I’m not beating myself up. I’m seeking wisdom.
This year, what worked for me were things like joining our local small-town synagogue which allowed us to meet new friends and build a sense of community. What also worked was deciding to move out of the small cabin we had been living in and moving into a home that could accommodate the deep joy we have for entertaining and hosting the friends and family we want to visit us. What worked was riding my bike to and from the gym during the summer months. What worked was batching my workflow at work, an experiment I ran hosting a “Connection Cafe,” which was a virtual coffee date with colleagues I wanted to get to know better so that we could support each other.
What didn’t work were things like bottlenecks I discovered while implementing certain projects with my team, less time spent exploring places and things that were new and novel as a result of spending more time in our new town, and because I let go of taking classes and courses as I put all my focus on preparing for my upcoming book launch, I didn’t feel like I learned a lot of new things this year. I missed the community, the learning, and the coaching too.
Step 2: Celebrate the Surprises
Next, I ask:
What were my unexpected blessings and peak experiences?
Here’s the magic: this question shifts your focus away from what you planned to do (and whether you checked it off your list) and toward what actually brought you joy and fulfillment.
The should life teaches us that we have to earn happiness—that joy comes after hard work, or once we’ve achieved something. But blessings and peak experiences often come from the places we least expect: a spontaneous adventure, a deep conversation, or even a quiet moment of connection.
Reflecting on these experiences reminds me of what truly matters. And when I look back at the list, I start to see patterns. For Jeremy and me, five years ago, it was this question that revealed a big ah-ha! Our peak moments all happened outdoors, in nature, with family. That realization guided us to make bold changes, like selling everything and living in an RV for a year to discover more of what truly blew our hair back. This year, the list of peak experiences are still moments we experience in nature, but because we have become so much more social we also had moments with some of our new friends that made the list. One of the best unexpected blessings was in the strange way we met my landlord that not only resulted in us finding a beautiful place to call home, but also work that my hubby does really well and enjoys.
Bottom line: this question is not about big, dramatic moments that cause huge life shifts—it’s about noticing what feels good, what you want more of, and letting those breadcrumbs guide your choices for your future.
Step 3: Reflect on Goals (with Curiosity, Not Criticism)
If you’re someone who loves setting goals, this step is for you. But instead of just asking, Did I hit my goals or not this year? take it a step further:
Which goals felt exciting and aligned?
Which ones felt like a chore—or didn’t happen at all?
What patterns do I notice in the goals I achieved and those I didn’t?
This step isn’t about judgment or keeping score—it’s about understanding yourself. What energizes you? What drains you? What do your goals say about what truly matters to you?
For me, looking back on my goals has been eye-opening. I’ve noticed that the ones I didn’t achieve often weren’t failures—they were red flags, signaling that I wasn’t fully aligned with them. Or, that the timing wasn’t right. Understanding this has been a game-changer in that it gives me space and permission to look at underlying causes that are keeping me stuck. This kind of reflection shifts the focus away from achieving for achievement’s sake. Instead, it helps me pivot easily and design goals that truly support the life I want to create. It’s not about doing more—it’s about doing what feels authentic, meaningful, and aligned with who I am now. And figuring out what is in the way and how to heal parts of myself so that I can become more of who and what I am in this lifetime.
Step 4: Dream Into the New Year
Finally, I ask:
What do I really want my life to look and feel like?
How can I take baby steps toward that vision in 2025?
This is where the should life gets thrown out the window. Instead of asking, “What should I accomplish next year?” I ask, “How do I want to live?”
Seriously, that question alone can change your life.
When Jeremy and I started dreaming into our ideal life, we didn’t have all the answers. In fact, the ideal life we put on paper five years ago was based on simply looking at what other people like us were doing. The dreams we had were vague too, and mostly centered around work and money. And above all, so much of what we thought we wanted was dreamed up in a vacuum of fear and limitation.
But once we started leaning into this process we knew what we wanted more of: connection, adventure, time in nature, and a feeling of ease and simplicity.
This question is about bringing intention into your everyday life. It’s about taking tiny steps toward the big dream—whether that’s writing your book, starting your passion project, or just making your days feel a little more like your peak experiences.
Your Invitation
Now it’s your turn.
Pick one question from this list—the one that feels the most alive for you. Maybe it’s reflecting on your blessings, revisiting your goals, or dreaming into your ideal day.
Give yourself permission to take your time. You don’t need a whole weekend retreat (though if you can, go for it!). A quiet morning with your journal and a cup of coffee is enough.
And as you sit with these questions, remember: you don’t need to wait for “one day” to live the life you want. You can start today—with one tiny step, one small insight, one moment of intention.
Step 5: What’s Missing From Your Dream Life? (Hint: It’s Not Another Goal)
When I sit down to dream about my ideal life, I think about every area—not just the obvious ones like career, relationships, or health, but the deeper layers too.
And….
One area that often gets overlooked in this process is legacy. Most people hear that word and think it only applies if you have kids, or if you’re leaving behind something tangible, like a trust fund or a famous book. But here’s the thing: your legacy is so much more than that.
“Legacy is the ripple effect of how you live your life—the values you embody, the energy you bring into the world, and the impact you leave on others.”
I was reminded of this the past week while I have been in Hawaii, a place that holds so much meaning for my family. My parents started bringing me here 40 years ago. Instead of giving gifts at the holidays, they decided their legacy would be about experiences—time spent together as a family, making memories that would last far longer than anything wrapped in paper.
This year, I found myself reflecting on how that legacy has carried forward. I thought about Max, a man we met here 20 years ago when my oldest daughter, Kloey, was just 8 years old. Back then, they both got certified together for PADI scuba—Kloey, the youngest diver on the boat, and Max, a vibrant 57-year-old who shared his love of the ocean with her.
We’ve stayed in touch ever since, meeting up in Maui almost every year. But this year, something extraordinary happened. We realized that Kloey, now an adult, lives just a few blocks away from Max and his wife. They’re even making plans to share Shabbat together in the coming weeks—a tradition that connects them not just as friends but as part of a larger, spiritual legacy.
And as we watched the kids who are now adults reconnect with friends they’ve grown up with here, we started imagining what it might look like in the future when they have kids of their own. It hit me that this web of connection, tradition, and shared experience is the legacy my parents began decades ago. It’s not just about the place—it’s about the values they passed down: family, adventure, and creating time together that feels sacred.
Areas to Dream About
When I think about building my ideal life, I reflect on every area—not just what’s right in front of me but what I’m shaping for the future. Here’s my list of areas I reflect on, and some of the questions I asked myself to guide me in envsioning my dreams so that I can make what is possible real.
WELL-BEING:
Physical Health: How do I want to feel in my body? What practices will keep me strong, energized, and thriving?
Emotional Health: What helps me stay centered and resilient? How can I create more peace in my daily life?
Spiritual Health: How do I want to connect with my higher self, my values, or something bigger than me?
PURPOSE:
Work: What lights me up? How can I spend more of my time doing work that feels meaningful?
Legacy: What impact do I want to have? How do I want my life to ripple outward and touch the people and world around me?
MONEY:
Financial Freedom: What does security and ease look like when it comes to money? How can I align my financial life with my values?
GROWTH:
Creative Growth: How can I explore my creative side, whether it’s writing, painting, or simply finding new ways to solve problems?
Intellectual Growth: What new things do I want to learn? How can I keep my mind curious and sharp?
EXPERIENTIAL:
Fun and Play: What brings me joy? How can I make space for more laughter, spontaneity, and play?
Travel and Adventure: Where do I want to go? What experiences will expand my horizons and fill my soul?
RELATIONSHIPS:
Family: How do I want to show up for my intimate family and extended family? What traditions or connections do I want to nurture?
Friends: Who do I want to spend more time with? How can I deepen the relationships that matter most to me?
Community: What kind of community do I want to be part of? How can I show up and contribute to something bigger than myself?
PS: Let’s Make 2025 Amazing Together
One thing I have on my list of goals this year is to expand my identity as a writer as well as a builder and member of new communities— and I am excited that Substack is one way I plan to do that in 2025. I am taking two classes in January to get me started; one with the amazing Courtney Kosak creator of the
and , and another with someone I just happened upon here named Sarah Fay, creator of . Finding Courtney was one of my unexpected blessings of 2024, and as a result of taking her class in November I got a byline in the New York Times. (scroll down to see my story called, “Sizzling Through Generations.”)Tonight we celebrated the third night of Chanukah by making the most delicious Latkes in our poorly-equipped timeshare kitchen and s’mores using a BBQ grill. Plus, one of my friends who lives on Maui has let her 9-year-old have a sleepover with my three daughters for the first time ever. I think tonight just might go down in the books as a peak experience. ❤️
Excited to have you back for another round of Pitch Party!