The year I turned 40 and became an entrepreneur
By Kristen Oliveri
Is it a coincidence that the year I turned 40 was also the year I became an entrepreneur? Spoiler alert: I don’t think so.
I’ve been dreaming about building my own brand for years, but something always held me back. And that something? People pleasing. I poured my energy into making others happy, doing great things for other people and companies, while rarely putting myself first.
For the past few birthdays, I’ve done a little exercise: I write down a short list of lessons I’ve learned that year. Recently, those lists have been filled with themes like setting boundaries, saying “no” more often, protecting my time, and valuing my health above all else. Looking back, the trend line is obvious.
Without even realizing it, I had been inching toward this very moment, tuning out the noise, putting myself first, trusting my abilities, and letting go of what no longer served me. So yes, it makes perfect sense that this year, the year I turned 40, is the year I finally said YES to me.
It feels freeing to say no, to scale back, to live with more intention. Sure, men have been doing this for centuries. But for me, and for my people pleasing personality, it took a long time to arrive at this place. I’ve often heard women I admire say that life begins at 40, that everything before was just a dress rehearsal. DAMN, that feels true.
A few musings I’ve learned this year:
• Planning for retirement and for the life I want in my golden years matters to me more now than ever.
• This has been my year of HEALTH. From navigating symptoms to working with healthcare providers, concierge medicine, and even Chinese medicine, I’ve learned that health IS wealth. Period.
• I’m investing my energy in people and relationships who invest back in me.
• “No” is a complete sentence. I continue to set boundaries, stop over explaining, and let go of excuses.
• I’m holding tight to the little moments of motherhood: the way Luca’s hair smells, the way Giuliana delivers a line, the hugs they share. I want to bottle these as core memories.
• I’m documenting my own family’s legacy. While we’re all here, I want to capture our stories and the ways they’ve shaped my own.
Forty feels like freedom. It feels like possibility. It feels like the beginning.