What happens after you leap
Inside my first 90 days of building something new
Three months ago, I was terrified I was making the biggest mistake of my life.
After a year of soul-searching, I finally jumped. On April 1st, I left my job at Pinterest to start something new.
At the time, all I could feel was fear. Fear of failing. Fear of regretting it. Fear of losing the identity I'd built over a decade in tech.
But today, I can't imagine having stayed. The leap didn’t make life easier - in many ways, it’s been the most challenging period of my life. But I feel more alive, more expansive, more whole than I ever have.
Last weekend, my husband and I escaped to wine country for a rare kid-free getaway. Somewhere between the leisurely lunches and long conversations, I took time to reflect on the past three months.
What a season it’s been.
If you’ve ever wondered what happens after you finally leap, this one's for you.
The first thing people ask me is: Do you regret leaving?
The answer is complicated. I miss the simplicity of a clear job description, the stability of a steady paycheck, the familiar validation of promotions and performance reviews. And of course, the amazing people I worked with.
But what I’ve gained is the freedom to define success on my own terms. After a decade of being laser-focused on career achievement, I finally started asking myself: What do I really want?
The first answer that came was simple: rest. So this quarter was intentionally about prioritizing my health, family, and friendships.
During my sabbatical, I did something I hadn’t done in years: nothing.
But this wasn’t a vacation. It was an unraveling. I spent most of April in deep self-reflection, navigating the identity shift that comes with a major life transition. Slowing down forced me to meet myself without the title, the deadlines, or the constant doing. I realized how much of my worth had been tangled up in productivity.
When my energy began to return, I visited family, took a long-overdue girls trip, and started training for a half marathon.
Did I spend more time with my kids? No. I spent better time with them.
I showed up as a more patient, present version of myself. I wasn’t rushing. I was paying attention. I played more silly games, said yes to the extra bedtime book, lingered in the long hugs.
Motherhood started to feel joyful again. And for the first time in a long time, I felt ready to give - not just to my kids, but to the work I’m building.
The second question I get is: What exactly are you building?
I'm still figuring it out, and I've had to get comfortable with that uncertainty.
Professionally, this quarter was beautifully messy. When I officially went back to work in June, I gave myself permission to "follow my nose" and explore different directions I could go.
Now, after some initial testing and learning, I’m gaining real clarity on what I want to build and what needs to be proven out. I'm excited that the vision is finally starting to emerge.
Some highlights from Q2:
LinkedIn follower growth up 58% (9,563 → 15,140)
Substack subscribers grew 68% (1,577 → 2,639) - thank YOU for supporting me!
Landed my first coaching client (shoutout to Katka!)
Hosted a workshop on Navigating the Neutral Zone (100 signups, 56 attendees)
Brought 9 incredible women together for my first Momentum dinner
Recorded a guest episode on the Mothers podcast (airing soon!)
Bought the domain for my business and launched a waitlist (157 signups and counting!)
The metrics feel good, but what matters more is that I'm finally building something that feels aligned with who I am and the impact I want to create in the world.
This quarter taught me that I don't need to have it all figured out. I just need to keep moving toward what feels true.
Then there’s the question I ask myself every day: What if this doesn't work?
Let me be real - it hasn't all been smooth sailing. The fears still show up in different ways.
Now that I'm not getting a steady paycheck, money anxiety is real and relentless. After watching the market volatility earlier this year, I've caught myself wondering: What if this is the worst time to start a company? Will I ever replace my corporate income? How much money is "enough"?
Then there's the strategy fears. After taking a digital detox, I realized I'm feeling completely burned out on LinkedIn. What used to energize me now feels noisy and performative, like shouting into the void. If I can't figure out how to show up authentically there, how will I reach the women who need what I'm building? I've become obsessed with metrics in an unhealthy way and am actively working to reset my boundaries.
And then there's the biggest fear of all: Can I really do this?
Imposter syndrome hits differently when you're building something from scratch. I've questioned whether the market is too saturated, whether my ideas are too "soft," whether I'm really cut out for the uncertainty that comes with entrepreneurship. Some days, it feels like too much.
But here’s what keeps me going: I'm making a bet on me. On my story. On my experience. On the women who keep telling me they're craving exactly this kind of support.
That's the voice I'm choosing to trust, even when the doubt gets loud.
The hardest moment of the quarter came when I least expected it.
My beloved grandmother passed away suddenly, and grief cracked me open in ways I wasn't prepared for. Death and mortality became very real, very present themes in my life.
Her passing brought everything into sharper, more urgent focus. I found myself asking the big questions: What really matters? What kind of life am I building? What legacy will I leave behind?
Her death reminded me that life is devastatingly short. And I realized that if I died tomorrow, my life would feel incomplete. What would I regret most? Not trying this wild idea. Not believing in myself when it mattered.
Yes, I could always go back to working for someone else. Maybe someday I will. The door isn't closed.
But this window - this chance to create something that feels true to who I am - is right now. And I won’t let it pass me by.
Sometimes a leap of faith is the only way forward.
So, where am I heading next?
Looking ahead to Q3, my mantra is simple: focus.
I’m getting ruthless about my priorities and pouring my energy into connecting ambitious moms in meaningful ways. That means:
Going all-in on Substack.
Launching my fall program.
Experimenting with in-person experiences.
I'm refining my offering, putting it out there for the world to see, and practicing the uncomfortable art of promoting myself and asking to get paid for my work.
Most importantly, I'm making a Don’t-Do list. Because protecting my time and energy is just as crucial as what I say yes to.
The quarter gave me space to remember who I am beneath all the striving and achieving. Now it's time to build momentum with clarity, intention, and heart.
Three months ago, I was paralyzed by the fear of making the wrong choice. Today, I know the only wrong choice would have been not trying at all.
If you’re reading this and wondering if there’s something more for you - there is. The question isn't whether you're ready. The question is whether you're willing to bet on yourself.
What's holding you back from taking the leap?
Namaste,
Tamara
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Thank you for your honesty and vulnerability. This is precisely where I am right now, so it's just reassuring to hear that, as uncomfortable as it is, it's just a part of the process 🤍
Hi Tamara! I’m excited about what you’re building even as you figure it out. As you already now, building is the most fun work there is.
I am going to tell you a quick cautionary tale, as a content marketing professor and I suppose as a creator, LinkedIn will steal your soul. I’ve never gotten burned out faster than when I was creating on that platform and I never did figure out what it was for. It’s the only time I questioned being an online person. If you want a quick connect to make sure it’s “worth” it for your goals, I am here for you.